Snippets about: Management
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Before Rolling Out OKRs, Is Your Culture Ready?
When healthcare software startup Lumeris first deployed OKRs, they appeared to be a huge success, but it was mostly theater. People were treating OKRs as a required administrative task vs. a tool for alignment and accountability. The issue was some deep cultural barriers:
- Lack of psychological safety - People feared that honest, public goals would be used against them later. They felt safer sandbagging.
- Directive leadership - The org was used to top-down goals with little autonomy. Following orders was valued over taking risk and ownership.
- Unclear priorities - Absent clear company-level OKRs, teams focused on their local activities vs. broader impact. To address this, Cole and other leaders embarked on a series of interventions:
The lesson: an OKR rollout will struggle if it runs counter to your current culture. Thoughtful change management is key. Meet people where they are and guide them to a better place.
Section: 3, Chapter: 19
Book: Measure What Matters
Author: John Doerr
Checklists Turn Building Projects From Disasters To Marvels Of Consistency
The construction industry's wholehearted embrace of checklists has enabled it to achieve an astonishing record of consistency and success:
- Today, a single builder coordinates an average of 15,000 tasks and 60 types of tradespeople on a project.
- In the US, there are now nearly 5 million commercial buildings and almost 100 million low-rise homes, both types more complex than ever in history. Yet a study found that serious building failures occur in only 2 out of every 10,000 projects per year, a rate of 0.00002%.
- Not only are failure rates extraordinarily low, but building projects are also completed in one-third less time on average than in earlier decades.
Using disciplined systems and checklists, we can augment expert judgment and skill to attain a similar degree of performance and consistency in the complex realms of healthcare, business, government, and beyond.
Section: 1, Chapter: 3
Book: The Checklist Manifesto
Author: Atul Gawande
Culture Is A Byproduct, Not An Objective Itself
You don't install a culture, you cultivate it slowly through your actions and policies. Perks and slogans don't make a culture, they reflect it. Culture is an outcome, not an input. If you encourage sharing, you get a sharing culture. If you reward trust, you develop a culture of trust. If you practice transparency, you build a transparent culture. How you behave as a company determines your culture more than anything you say. Focus on your behaviors and your cultural aspirations will follow.
Section: 1, Chapter: 11
Book: Rework
Author: Jason Fried, David Heinemeier Hansson
Avoid Long-Term Abstractions, Focus On Concrete Daily Needs
Don't agonize over decisions based on imaginary far-future scenarios. What your company might hypothetically need someday is not as important as what it definitely needs now. Borrowing trouble from the future is counterproductive.
Focus on the tangible problems you face today. Make your immediate next step the right one for your current reality and resources. Don't contort your business to fit a theoretical "what if" vision. Concentrate your energies on what you can control now, not what you can speculate about later.
Section: 1, Chapter: 11
Book: Rework
Author: Jason Fried, David Heinemeier Hansson
Vision Leads to Steering
At the core of the Lean Startup model is the Build-Measure-Learn feedback loop. The process goes as follows:
- Build a minimum viable product (MVP) to test fundamental hypotheses
- Measure how customers respond using actionable metrics
- Learn whether to pivot or persevere based on feedback
This cycle of turning ideas into products, measuring customer response, and learning whether to pivot or persevere is at the heart of the Lean Startup model.
Section: 1, Chapter: 2
Book: The Lean Startup
Author: Eric Ries
Building the Right Organization for the Job
To create new capabilities, managers have three options:
Acquisition: Acquire a company with the desired processes and values, but avoid integration that could destroy those capabilities.
Internal Transformation: Attempt to change the processes and values of the existing organization, but recognize the difficulty of altering established ways of working.
Spin-off: Create an independent organization with new processes and values tailored to the new challenge, especially when dealing with disruptive innovations.
Section: 2, Chapter: 8
Book: The Innovator's Dilemma
Author: Clayton M. Christensen
Delivery Managers Eliminate Impediments
In larger organizations, product managers can get bogged down with project management tasks. Delivery managers handle these responsibilities so product managers can focus on discovery and defining the right products. Key functions include:
- Removing obstacles and dependencies holding the team back
- Coordinating with other teams and functions
- Tracking and communicating progress, issues and risks
- Managing the process and facilitating meetings
Delivery managers are sometimes called project or program managers, but the intent is to "servant lead" rather than just track tasks. In Agile organizations, they often play the Scrum Master role.
Section: 2, Chapter: 19
Book: Inspired
Author: Marty Cagan
The Golden Circle - A Naturally Occurring Pattern
The Golden Circle is a naturally occurring pattern grounded in the biology of human decision making. The Golden Circle contains three layers:
- The outside layer is "What" - Every organization knows WHAT they do, the products they sell or services they offer.
- The middle layer is "How" - Some organizations know HOW they do what they do - their unique differentiators, proprietary process or value proposition.
- The innermost layer is "Why" - Very few organizations can clearly articulate WHY they do what they do. WHY is a purpose, cause or belief. It provides a clear answer to: Why do you get out of bed in the morning? Why should anyone care?
Most organizations communicate from the outside-in, telling people WHAT they do, HOW they are better, then expecting a behavior like a purchase. But inspired organizations start with WHY at the center, then flow outward to HOW and WHAT. When WHY is clearly communicated, WHAT you do serves as tangible proof of that belief.
Section: 1, Chapter: 3
Book: Start with Why
Author: Simon Sinek
Relinquishing Authority And Control
One of the biggest blockers to building trusting relationships with direct reports is an unwillingness to give up unilateral authority and control. Using your power and authority to make others do your bidding feels good in the moment but erodes trust over time. A few tips:
- Look for small ways to give your team more autonomy - let them set the agenda for 1:1s, pick their own projects, etc. Show you trust their judgment.
- Delegate decisions - rather than being the decider on everything, empower others to make important calls. Make your role more facilitative than directive.
- Share more context and information - be transparent about what you know and where you're coming from vs. hoarding information to yourself. It enables others to make good decisions.
- Don't micromanage - once you've delegated something, resist the urge to constantly check up on it or override decisions. Let go of control while still being accountable.
Section: 1, Chapter: 5
Book: Radical Candor
Author: Kim Malone Scott
From Brittle Silos to Resilient Networks
Organizations tend to evolve in two major forms:
Brittle, Efficient Hierarchies:
- Siloed units with rigid vertical ties and weak lateral connections
- Centrally planned, narrowly focused action
- Struggle with complexity due to slowness and tunnel vision
Resilient, Adaptable Networks:
- Densely interconnected nodes with strong lateral ties
- Decentralized, autonomous action loosely guided by shared purpose
- Can adapt to complexity by reconfiguring resources and approaches
The former is often a legacy of industrial-era models; the latter is better suited for an information-age world.
Section: 1, Chapter: 6
Book: Team of Teams
Author: Stanley McChrystal
Learning to See Waste
"Learning to see waste and then systematically eliminate it has allowed lean companies such as Toyota to dominate entire industries."
Section: 1, Chapter: 1
Book: The Lean Startup
Author: Eric Ries
Operation Crush: An Intel Story
In 1979, Intel was losing the battle for the 16-bit microprocessor market to Motorola. That's when Andy Grove and other Intel leaders used OKRs to mobilize the entire company behind "Operation Crush" - an effort to reclaim market leadership. The top-line objective was clear and time-bound: "Establish the 8086 as the highest performance 16-bit microprocessor family, as measured by having more than 2,000 design wins by the end of the year."
Every department and person at Intel, from engineering to sales to marketing, set aligned OKRs to support the Operation Crush objective. This connectivity enabled coordination, accountability and focus across all teams. By the end of the year, Intel had exceeded the goal with 2,300 design wins, regained market dominance, and set itself up for industry leadership for decades to come.
Section: 1, Chapter: 3
Book: Measure What Matters
Author: John Doerr
Task-Level Thinking Misses AI's Potential To Drive Organizational Redesign
The authors argue that the predominant "task-level" paradigm for thinking about AI adoption and impact is misguided and limiting. The key points:
- Most leaders and experts focus on identifying specific tasks that AI could perform better than humans and calculating the labor substitution effects
- However, the greatest value from AI comes not from piecemeal task substitution but from reimagining entire systems and processes around AI capabilities
- Focusing on tasks leads to small-scale point solutions, while system-level thinking enables transformative new structures and strategies
- The biggest AI successes to date, like Netflix, Amazon, and YouTube, have come from system-level innovation rather than task substitution
Leaders should adopt a "system mindset" and focus on how AI predictions could enable fundamentally new approaches to delivering value, even if those approaches are inferior on traditional metrics.
Section: 3, Chapter: 8
Book: Power and Prediction
Author: Ajay Agrawal, Joshua Gans, Avi Goldfarb
The Four OKR Superpowers
OKRs, when implemented well, bestow organizations with four powerful benefits:
- Focus and commit to priorities
- Align and connect for teamwork
- Track for accountability
- Stretch for amazing
These "superpowers" enable organizations to operate with focus, alignment, accountability, ambition and transparency - all critical ingredients for executing on what matters most.
Section: 1, Chapter: 2
Book: Measure What Matters
Author: John Doerr
Hiring For Fit, Not Just Skills
Hiring well is one of the biggest levers you have in building a great team. A few tips:
- Create a hiring rubric, not just a job description - Define not just the skills required but the values and behaviors needed for team and cultural fit. Make them specific enough to evaluate against.
- Ask candidates to complete a practical exercise - See their actual work product vs. just trusting a resume. Give them a sample project and evaluate the results.
- Include multiple perspectives - Have a panel do the interviews, not just the hiring manager. Get diverse input on a candidate's potential fit.
- Check references - Ask references specific questions about the person's past behaviors and performance, not just generic info.
- Do informal interviews - Take the candidate to lunch or on a walk. Give them a chance to let their guard down and show their true personality.
Skills are necessary but not sufficient. Drill down on culture and values as much as technical capabilities.
Section: 1, Chapter: 7
Book: Radical Candor
Author: Kim Malone Scott
Can't Apologize Your Way Out Of Being An Ass
Even the most eloquently crafted apology falls flat if you haven't built goodwill with your audience beforehand. Treating people well when things are calm is more important than anything you say after a crisis.
To communicate genuine concern during a fiasco, you must demonstrate genuine concern consistently ahead of time. If people know you care about more than just saving face, they'll extend more patience and forgiveness. But you can't talk your way out of a poor track record. Your response matters, but your reputation matters more.
Section: 1, Chapter: 10
Book: Rework
Author: Jason Fried, David Heinemeier Hansson
Groupthink And Lack Of Innovation In Fixed Mindset Organizations
Fixed mindset thinking at NASA contributed to the Challenger space shuttle disaster:
- Leaders believed NASA's past successes were due to their innate engineering genius rather than careful safety protocols.
- They became overconfident and ignored warnings about Challenger's O-ring safety hazards.
- Dissenters were seen as disloyal and sidelined. Groupthink overtook safety concerns.
- Fixing the O-ring problem was seen as an admission that they weren't the perfect engineers they believed themselves to be.
The fixed mindset culture caused leaders to prioritize protecting NASA's genius reputation over confronting and solving safety problems, with tragic results.
Section: 1, Chapter: 5
Book: Mindset
Author: Carol Dweck
"It Almost Doesn't Matter What You Know"
When explaining the impetus behind OKRs at Intel, Andy Grove stated:
"It almost doesn't matter what you know. It's what you can do with whatever you know or can acquire and actually accomplish [that] tends to be valued here. The key phrases . . . are objectives and the key result. And they match the two purposes. The objective is the direction: 'We want to dominate the mid-range microcomputer component business.' That's an objective. That's where we're going to go. Key results for this quarter: 'Win ten new designs for the 8085' is one key result. It's a milestone. The two are not the same."
Section: 1, Chapter: 2
Book: Measure What Matters
Author: John Doerr
Evaluate Applicants By Testing Them With Real Work
Resumes and interviews are poor predictors of actual work performance. The only reliable way to assess a candidate is to see them in action. So hire them for a mini project first. Give them a small job that's identical or analogous to the real work they'd be doing.
Then evaluate their actual output. It could be a design mockup, a code module, a writing sample - anything demonstrating real skills. What you learn from a little test project is far more useful than what you glean from an interview.
Section: 1, Chapter: 9
Book: Rework
Author: Jason Fried, David Heinemeier Hansson
How Google Embraced OKRs
In 1999, Google was still a fledgling startup. That's when venture capitalist John Doerr introduced founders Larry Page and Sergey Brin to Objectives and Key Results (OKRs).
OKRs provided the scaffolding to help Google scale from 40 employees to over 60,000 and achieve 10x growth and success across products like Search, Chrome, Android, YouTube and more. As Doerr states, "OKRs were a vaccine against fuzzy thinking and fuzzy execution." Google's leadership institutionalized OKRs as a core operating principle and management tool to provide focus, alignment, commitment, tracking and stretching to amazing.
Section: 1, Chapter: 1
Book: Measure What Matters
Author: John Doerr
West Point Cadets And The Grit Test
The author studied West Point cadets and found that those who scored higher on her Grit Scale were more likely to make it through the grueling "Beast Barracks" training than cadets with lower grit scores.
Grit mattered more for retention than things like SAT scores, high school rank, leadership experience or athletic ability. The Grit Scale was a better predictor of who would make it through the intensive 7-week training program than any other factor. This was true even when controlling for things like physical fitness and aptitude test scores. It demonstrated that inner traits like passion and perseverance can be more important than raw talent.
Section: 1, Chapter: 1
Book: Grit
Author: Angela Duckworth
Red Balloons And Red Faces
In 2009, DARPA launched the Network Challenge, a nationwide hunt to find ten red weather balloons that had been secretly placed in various locations. The winning team would receive $40,000. The contest featured two very different collaboration strategies:
- Most teams used a "hub and spoke" model where a central authority directed the search and offered to share the prize money with anyone who provided useful information. This approach created a lot of activity and competition, but also a lot of noise and inefficiency.
- The winning team, from MIT, used a "cascading incentive" model where anyone who contributed to finding a balloon (directly or indirectly) would share in the reward. This approach essentially turned every participant into a recruiter and problem-solver; the network grew organically as people invited their friends and family to join.
The MIT team's decentralized, non-hierarchical strategy was incredibly effective - they located all ten balloons in under nine hours, shocking the challenge organizers who had expected it to take days or weeks. The key was that every participant had skin in the game and could take initiative without waiting for orders or permission.
Section: 2, Chapter: 8
Book: The Culture Code
Author: Daniel Coyle
Entrepreneurship is Management
Contrary to popular belief, a startup is not just about developing a product, coming up with a brilliant idea, or being in the right place at the right time. A startup is a human institution designed to create a new product or service under extreme uncertainty. This means entrepreneurs are everywhere, in companies big and small. Entrepreneurship requires a managerial discipline geared towards handling extreme uncertainty.
Section: 1, Chapter: 1
Book: The Lean Startup
Author: Eric Ries
The Advantages of the Fabless Model
The success of fabless companies like Nvidia and Qualcomm highlights the advantages of specializing in chip design and outsourcing manufacturing. This approach allows companies to:
Reduce Capital Expenditure: Avoid the massive costs associated with building and maintaining fabs.
Focus on Core Competencies: Concentrate resources on design and innovation rather than manufacturing intricacies.
Access Cutting-edge Technology: Leverage the expertise and advanced processes of leading foundries.
Increase Flexibility and Agility: Respond quickly to market demands and technological advancements.
Section: 6, Chapter: 36
Book: Chip War
Author: Chris Miller
Apple And The Celery Test
Apple not only communicates from the inside out, starting with WHY, but everything they do - their products, packaging, advertising, stores, etc - all serve as further proof of their WHY. Let's apply The Celery Test - if you're buying celery and rice milk at the grocery store, it's clear that you value health. Everything you say and do "proves" that you believe in healthy eating.
Similarly, Apple believes in challenging the status quo and thinking differently. Every product they release, from computers to iPods to iPhones, challenges the conventional thinking in that industry. Apple's marketing and messaging is aspirational and iconoclastic. Even their stores, with open layouts and approachable staff, aim to make technology less intimidating. Regardless of WHAT Apple makes, it always starts with WHY - and that clear sense of purpose inspires loyalty from customers and employees alike.
Section: 1, Chapter: 3
Book: Start with Why
Author: Simon Sinek
Failure Is Not A Rite Of Passage
Business folklore romanticizes failure as an essential step on the path to success. But the authors argue this is misguided logic. Failure is not a prerequisite for success. The goal is to succeed, not fail first. While you can learn from mistakes, you can also learn from successes - both your own and others'. Focus on what works, not what doesn't. Studying and replicating success is more constructive than mythologizing failure as a required rite of passage.
Section: 1, Chapter: 3
Book: Rework
Author: Jason Fried, David Heinemeier Hansson
The Alternative To Roadmaps Focuses Teams On Outcomes
Instead of a prescriptive roadmap, empower product teams by giving them clear business objectives (e.g. improve onboarding conversion from 30 days to 3 hours). Let them figure out the best way to solve the problems. Leadership's role is to:
- Set the right business objectives for each team
- Provide business context through a clear product vision and strategy
- Ensure teams aren't just delivering features but solving underlying problems
- Hold teams accountable to results
When specific commitments are truly needed, rather than false certainty from a roadmap, have product teams make high-integrity commitments based on validated solutions. This gives you both the predictability to run the business, and the right products for your customers.
Section: 3, Chapter: 23
Book: Inspired
Author: Marty Cagan
The Must-Have Product Prerequisite for Growth
Chapter 2 explains that before focusing on rapidly scaling growth, companies must first ensure they have achieved product-market fit and are delivering a "must-have" experience to users. Ways to assess:
- Conducting a user survey asking how disappointed users would be if they could no longer use your product. If over 40% say "very disappointed", that indicates the product is must-have.
- Analyzing user retention data to see if retention stabilizes over time, ideally showing increased retention the longer users stay with the product. Declining retention is a red flag.
Making your product a must-have comes before growth tactics. Otherwise you risk scaling up a product that ultimately fails to retain users.
Section: 1, Chapter: 2
Book: Hacking Growth
Author: Sean Ellis
Teams Of Forecasters Beat Prediction Markets
Prediction markets are often hailed as the gold standard of forecasting. These markets harness the "wisdom of crowds" by having people bet on the likelihood of future events. But teams of superforecasters did even better. Across a two year forecasting tournament, superforecaster teams bested prediction markets by 15-30%.
Why did teams do so well? The ability to share information and perspectives was key. Forecasters could share ideas, challenge each other, and collectively dig deeper into problems.
Diversity also played a big role. Teams with a variety of backgrounds and thinking styles generated more creative solutions. As long as discussions remained friendly and focused, diversity led to better accuracy.
Section: 1, Chapter: 8
Book: Superforecasting
Author: Philip Tetlock
WHO's Safe Surgery Checklist Proves Remarkably Effective Across The Globe
Gawande describes his experience leading the World Health Organization's initiative to reduce surgical complications globally. His team developed a 19-item safe surgery checklist that could be applied in operating rooms worldwide:
- Before anesthesia, to confirm the patient's identity, allergy status, airway risk, etc.
- Before skin incision, to ensure all team members are introduced, antibiotics are given, critical steps reviewed, etc.
- Before the patient leaves, to ensure instrument/sponge counts are complete, specimens are labeled, equipment problems addressed, etc.
Eight hospitals tested the checklist with a combined 4,000 patients. The impact was remarkable:
- Major complications fell 36% on average, from 11% to 7%.
- Deaths fell 47%.
- Infections fell almost 50%.
- The percentage of procedures with missed safety steps fell from 6% to 1%.
Despite the checklist taking only 2 minutes to complete, it significantly improved surgical outcomes in a wide range of settings.
Section: 1, Chapter: 5
Book: The Checklist Manifesto
Author: Atul Gawande
Divorcing Compensation From OKRs
One of the most important decisions an organization can make is to separate OKRs from compensation and promotions.
- Tying OKRs to comp incentivizes sandbagging and risk aversion. People set goals they know they can hit.
- It diminishes the healthy stretch and learning that comes from aspirational OKRs. Suddenly 70% = failure.
- It turns conversations about goal setting and reflection into arguments about money. The focus shifts from growth to defense.
- It penalizes people who choose the most ambitious, business-changing OKRs. The safer path gets rewarded. u
Section: 3, Chapter: 15
Book: Measure What Matters
Author: John Doerr
Keys To WHO's Surgical Checklist Implementation
Gawande outlines several key decisions that enabled the WHO surgical checklist to be so effective:
- Requiring complete buy-in from surgical leadership. Hospitals were required to have surgical department leaders champion the checklist to their teams, not just impose it.
- Piloting before broad rollout. Teams implemented the checklist initially with just a couple providers, to work out kinks before expanding.
- Encouraging modification. Teams were urged to customize the checklist to their setting, increasing their ownership of it.
- Tracking impact. Hospitals carefully measured complication rates before and after introduction, so they could see the checklist's value.
Section: 1, Chapter: 6
Book: The Checklist Manifesto
Author: Atul Gawande
Three Skills For Channeling Transcendent Desire In Your Organization
- Shift gravity: Don't insist on being the model that everyone revolves around. Redirect attention to transcendent goals and ideals. Stand shoulder-to-shoulder with your team, not above them.
- Increase the speed of truth: Make unvarnished truth-telling normal and expected. Reward people who surface hard realities quickly, even if they're inconvenient. Ask: how fast does critical info reach key decision-makers?
- Filter feedback: Don't over-index on pleasing audiences. Stay anchored in your thick desires and values. Pursue the long-term good, not short-term approval. Remember: the customer isn't always right.
Section: 1, Chapter: 7
Book: Wanting
Author: Luke Burgis
Use Transparency To Build Trust And Achieve Excellence
Some key tips Dalio gives on using radical transparency:
- Share hardest things - increases trust long-term even if uncomfortable short-term
- Make things public so justice prevails; integrity matters more than privacy
- Be extremely open; don't let fears of judgment prevent getting in sync
- Explain reasoning openly; have integrity to be honest with all Used well, radical transparency reduces politics, exposes harmful actions, and keeps an organization aligned and performing with the highest standards.
Section: 3, Chapter: 1
Book: Principles
Author: Ray Dalio
The Perils Of Over-Cascading OKRs
A common mistake organizations make is cascading OKRs too rigidly from the top. This "waterfall" approach has several downsides:
- Rigidity: If the top-line OKRs take weeks or months to cascade down, it makes the org slow to adapt to change. Managers resist adjusting OKRs mid-cycle.
- Marginalized contributors: Frontline employees have little autonomy or ability to influence the direction of their work. It becomes a one-way commandment vs. a two-way conversation.
- Tunnel vision: Focusing only on vertical alignment neglects important lateral networking across teams and functions.
- Employee disengagement: People feel like OKRs is a "check the box" exercise vs. a useful tool. OKRs should be transparently shared so people can quickly align their work to org priorities in an agile way.
Section: 1, Chapter: 7
Book: Measure What Matters
Author: John Doerr
Management Is Emotional Labor
At the core of being a good boss is building trusting relationships with each direct report. This is hard, emotionally-draining work, not just logistical or administrative. It requires a substantial amount of emotional labor.
Early in her career, the author made the mistake of viewing this emotional labor as a distraction from "real work." But her coach admonished her: "It's not babysitting...It's called management, and it's your job!" Over time, she realized that having 1:1 conversations, getting to know people personally, and being emotionally present was some of the most valuable and important work she did as a leader. It wasn't a distraction from the job, it was the essence of the job. Bosses have to embrace, not begrudge, the emotional labor of leadership.
Section: 1, Chapter: 5
Book: Radical Candor
Author: Kim Malone Scott
Trust Is Maintained When Values And Beliefs Are Actively Managed
Trust is not born out of the rational calculations of costs and benefits - it comes from a belief that another person or organization shares your values and beliefs.
For that trust to be maintained, the values of an organization must be actively managed. The WHY must be clearly communicated, and everyone must be held accountable to living those values.
Consider Walmart - Sam Walton built a retail empire on the belief in service to people and the community. But after Walton passed, Walmart lost sight of its WHY and has become embroiled in scandals as its culture suffered. On the other hand, Costco has actively managed its culture of service, generosity and providing a living wage - and has seen the benefits in loyalty and performance.
Section: 3, Chapter: 6
Book: Start with Why
Author: Simon Sinek
How Small Teams Achieve Coordinated Adaptability
Small teams like Navy SEAL units can achieve remarkable feats of coordinated adaptation without detailed central planning. This adaptability emerges from extensive training that builds trust and common purpose among members. With shared consciousness and strong lateral ties, team members can autonomously make smart decisions that align with the team's goals. They don't need to wait for orders. While this agility is common in small teams, it's rare in large organizations, which default to top-down command structures.
Section: 1, Chapter: 5
Book: Team of Teams
Author: Stanley McChrystal
Career Conversations - Helping People Achieve Their Dreams
Beyond regular 1:1s, it's important to have periodic "career conversations" to understand what really motivates and inspires your direct reports. Recommend doing these annually and focusing on three key areas:
- Life story - What have been the high and low points in their life and career? What are they proud of and what was challenging? Look for patterns in what drives them.
- Dreams - If nothing was holding them back, what would they want to achieve in the next 5-10 years? Have them describe 3-5 different dream scenarios.
- 18 month plan - Based on their dreams, what skills and experiences do they need to gain in the next 18 months? Make a concrete action plan. The goal is to really listen and draw out what matters to the person, not impose your own view of what their career path should be. Then look for ways to align their work with their long-term aspirations as much as you can.
Section: 1, Chapter: 7
Book: Radical Candor
Author: Kim Malone Scott
Make People Glad to Do What You Want
People are more likely to do what you want when you frame it so it is aligned with what they want. Here is a summary of how to do this effectively:
- Be sincere. Don't make promises you can't keep or offer incentives you can't provide.
- Know exactly what you want the other person to do.
- Be empathetic. Consider what it is the other person really wants out of the situation.
- Consider what benefits the other person will get from doing what you suggest. How will it advance their goals and desires?
- Match the benefits you offer to the other person's wants.
- When making your request, put it in a form that shows how the other person will personally benefit.
Section: 4, Chapter: 9
Book: How to Win Friends and Influence People
Author: Dale Carnegie
Deciding How To Decide - Elevating Key Debates And Decisions
Not every decision needs to go through the full GSD wheel - that would take too long. As a leader, your job is to "decide how to decide" - identify decisions that need more discussion vs. those that should be made quickly by an individual. To do this:
- Push decisions into the facts wherever possible - empower those closest to the work to make the call
- For bigger, high-stakes decisions, pull the facts into the decision - make sure there is clarity on the situation before deciding
- Separate "debate" meetings from "decision" meetings to allow enough time for input without rushing to consensus
- Explicitly clarify who the "decider" is on key decisions - is it you? Someone else? A group vote? Empower others to decide while breaking ties yourself when needed.
Section: 1, Chapter: 4
Book: Radical Candor
Author: Kim Malone Scott
Hallmarks of effective OKRs
- Urgency: When a crisis arose, Intel's leadership responded within weeks to set and communicate a clear, focused objective to the entire company.
- Clarity: From the CEO down, everyone knew exactly what the objective was and how their work connected to it. No ambiguity.
- Alignment: Every team, from engineering to marketing to sales, set their own OKRs in service of Operation Crush. While the key results differed, the overarching objective unified everyone.
- Tracking: Regular check-ins and grading enabled leaders to monitor progress, identify obstacles, and make adjustments as needed.
- Stretching: The 2,000 design win goal was hugely ambitious. But it motivated people to rethink old approaches and deliver amazing results.
Section: 1, Chapter: 3
Book: Measure What Matters
Author: John Doerr
Use OKRs To Drive Organizational Clarity
When Atticus Tysen took over IT at Intuit, he faced a big challenge. His 600-person org was operating in silos, pursuing disparate objectives. There was little visibility into how different sub-teams' work laddered up (or didn't) to Intuit's strategic priorities. To address this, Tysen rolled out OKRs across his entire org. Through the OKR process, Tysen and his leadership team:
- Defined 3-5 clear, aspirational objectives for IT as a whole
- Translated these into measurable, time-bound key results
- Had each sub-team and individual define their OKRs to support the top-line goals
- Made everyone's OKRs visible across IT
- Established frequent check-in points to track progress, identify dependencies and remove barriers
Section: 2, Chapter: 9
Book: Measure What Matters
Author: John Doerr
What, How, When - The Anatomy of Effective OKRs
Effective OKRs clearly define the what, how and when:
- What are you trying to achieve? This is the objective - significant, action-oriented, and ideally inspiring.
- How will you get there? These are the key results - measurable, time-bound milestones.
- When do you need to achieve them by? OKRs should have a clear deadline, typically quarterly.
Section: 1, Chapter: 4
Book: Measure What Matters
Author: John Doerr
Without Tracking, Goals Are Just Wishes
To drive disciplined execution, you have to continuously track and score them. As Doerr puts it, "Ideas are easy. Execution is everything."
- Make sure OKRs are visible and always up-to-date.
- Have a regular cadence of check-ins to review progress. These should be forward-looking conversations, not postmortems.
- Scoring is critical. Be honest about what % of each key result was achieved.
- Celebrate wins, but also openly examine "misses." Extract lessons learned. Don't penalize teams for transparency.
Teams that diligently track and score OKRs not only execute better - they accelerate their collective learning. You can't improve what you don't measure.
Section: 2, Chapter: 10
Book: Measure What Matters
Author: John Doerr
Using Premortems To Stress-Test Plans
One way to harness the power of dissent is to conduct a "premortem" on important decisions. A premortem involves imagining a future where your plan failed, then working backwards to figure out why.
Have the team brainstorm as many paths to failure as possible - imagine competitors' responses, think through operational snafus, consider external risks. Then update your plan to mitigate the identified issues. This "creative dissent" makes the final plan much more robust. Premortems give permission to express doubts in a productive way.
Section: 1, Chapter: 6
Book: Thinking in Bets
Author: Annie Duke
Identifying "Rock Stars" Vs. "Superstars" On Your Team
To identify who are the "rock stars" (gradual growth trajectory) vs. "superstars" (steep growth trajectory) on your team, plot each team member on a 2x2 matrix with performance and growth trajectory as the two axes.
- People who are excellent performers and on a gradual growth trajectory are your rock stars. Think about what you can do to recognize and reward them in their current role.
- People who are excellent performers and on a steep growth trajectory are your superstars. Think about how you can keep challenging them and create opportunities for them to grow.
- People who are poor performers and on a steep growth trajectory need coaching, training, and role adjustment. Perhaps they have been miscast in their current role.
- People who are poor performers and on a gradual growth trajectory may need to be let go. If they aren't doing well now and show no signs of improving, they are dragging the team down.
Section: 1, Chapter: 3
Book: Radical Candor
Author: Kim Malone Scott
The Limits of a "Command of Teams" Structure
The U.S. Task Force's original structure was a "command of teams" - while individual SEAL, Ranger, etc. units were adaptable, the overall hierarchy was rigid. Units were highly independent and only loosely coordinated. This worked for limited, linear missions, but failed against the interdependent complexity of the Iraqi insurgency. Silos led to poor information flow between teams, and centralized decision-making couldn't keep up with the speed of events. The Task Force realized it needed to become a "team of teams," with rich linkages between its parts and the ability to combine efforts seamlessly.
Section: 1, Chapter: 6
Book: Team of Teams
Author: Stanley McChrystal
Match Organizational Structure to the Environment
Taylorist management and rigid organizational structures work well when tasks and environments are predictable. But in fast-changing, complex environments, adaptability is key. Leaders must recognize when old models no longer fit and be willing to drastically change organizational structures, trading some efficiency for agility. Just as the industrial revolution demanded a management revolution, the information revolution demands new ways of organizing.
Section: 1, Chapter: 2
Book: Team of Teams
Author: Stanley McChrystal
The Importance Of Focusing On What Matters Most
As Grove wrote, "The art of management lies in the capacity to select from the many activities of seemingly comparable significance the one or two or three that provide leverage well beyond the others and concentrate on them."
- Limit to 3-5 objectives per cycle. More dilutes focus.
- Choose objectives with the most leverage for outstanding performance.
- Be willing to say no and make hard choices about what not to do.
- Communicate choices clearly to the entire org to reduce ambiguity and create alignment.
Section: 1, Chapter: 4
Book: Measure What Matters
Author: John Doerr
How OKRs & CFRs Reshape Culture
When implemented well, OKRs and CFRs don't just clarify goals and boost performance - they transform an organization's culture:
- Transparency & openness - Everyone's OKRs are visible. Conversations about priorities, progress, and problems happen out in the open.
- Healthy risk-taking - Aspirational OKRs make it okay to try big things and sometimes fail. The focus is on learning and iterating.
- Intrinsic motivation - Stretch goals tap into people's desire to grow and master new skills. They take more pride in their work.
- Customer-centricity - OKRs often align to key customer metrics. Teams are more attuned to evolving user needs.
- Bias for action - Regular OKR/CFR cycles create a cadence of shipping, learning, and improving. Decisions get made promptly.
Section: 3, Chapter: 18
Book: Measure What Matters
Author: John Doerr
Meetings That Don't Suck
Meetings are one of the biggest drains on time and energy at most companies. A few tips to make them more productive:
- Have a consistent agenda - For staff meetings, focus first on learning (key metrics), then listening (progress updates), then clarifying next steps. Don't mix everything together.
- Don't solve problems in the room - The staff meeting isn't the place for deep problem-solving. Identify issues, then spin them off to separate "Big Debate" or "Big Decision" meetings with the right stakeholders.
- Time-box everything - Give each agenda item a time limit and move on when you hit it. Don't let conversations meander just to fill the hour.
- Empower the meeting owner - Make it clear who is running the meeting and give them authority to keep things on track. Rotate owners to build skills. Meetings should be a place to get in sync, make decisions, and clarify next steps - not a free-for-all conversation.
Section: 1, Chapter: 8
Book: Radical Candor
Author: Kim Malone Scott
The Power of Cross-Functional Growth Teams
Chapter 1 discusses the importance of building cross-functional growth teams to drive rapid experimentation and growth.
- Growth teams should include members from marketing, engineering, product, and data analysis. This breaks down organizational silos. The team focuses relentlessly on a singular goal - driving growth through rapid experimentation and analysis.
- Growth teams work best when they have strong executive sponsorship and authority to work across normal organizational boundaries.
- Two common growth team structures are the independent model reporting to a growth lead, and the functional model embedded in product teams. The right structure depends on the company.
Section: 1, Chapter: 1
Book: Hacking Growth
Author: Sean Ellis
OKRs And CFRs - The Dynamic Duo Powering High Performance
Continuous performance management has two key components that work in tandem:
- Structured goal setting with Objectives and Key Results (OKRs)
- Continuous, high-quality communication with Conversations, Feedback, and Recognition (CFRs) Some key benefits of this dual approach:
- OKRs provide clarity of purpose and priorities to guide CFRs. You know what to talk about and why it matters.
- CFRs provide the day-to-day fuel for achieving OKRs. They surface issues, build commitment, and keep everyone aligned.
Section: 2, Chapter: 15
Book: Measure What Matters
Author: John Doerr
Governance Is the Secret Sauce
Good governance, especially at the top of the organization, is critical for an idea meritocracy to function well. Some key principles:
- Make sure no one individual is more powerful than the governance system itself. Power must be distributed, not concentrated.
- Institute strong checks and balances on power, especially at the top. No one should be beyond scrutiny.
- Ensure that decision rights are clear. Everyone should know who has what authority.
- Carefully define the scope and mechanics of voting. Not all decisions should be made by simple majority rule.
Section: 3, Chapter: 16
Book: Principles
Author: Ray Dalio
Checklists Are Powerful Tools, But Not Foolproof Panaceas
While a strong proponent of checklists, Gawande offers some important caveats:
- Checklists are not cure-alls. They don't supplant the need for skill, judgment, and teamwork. Rather, they enhance those abilities by ensuring teams get the basics right.
- Checklists must be well-designed to be effective. Good checklists are precise, efficient, and easy-to-use.
- Checklists require cultural change to work. Teams must be committed to using them consistently and correctly.
- Simply mandating checklists is not enough - they must be built into the team's culture.
Section: 1, Chapter: 9
Book: The Checklist Manifesto
Author: Atul Gawande
Manage The Person, Not Just The "Talent"
"For many bosses, 'recognition' means 'promotion.' But this is a big mistake in most cases. Promotion often puts these people in roles they are not as well-suited for or don't want. The key is to recognize their contribution in other ways. It may be a bonus or a raise. Or, if they like public speaking, get them to present at your all-hands meetings... If they like teaching, get them to help new people learn their roles faster. Or if they are shy, make sure you and others on the team thank them privately for the work they do. Consider, carefully, tenure awards."
Section: 1, Chapter: 3
Book: Radical Candor
Author: Kim Malone Scott
The Allen Curve
In the 1970s, MIT professor Thomas Allen set out to discover why some engineering teams were more productive and innovative than others. What he found - the best predictor of team success was not skill level, resources, or experience, but simple physical proximity.
- When people sit within 8 meters of each other, communication and collaboration skyrocket, with an exponential increase the closer you get
This pattern is known as the Allen Curve. It reveals the huge impact of proximity on behavior and output. The simple act of being able to see and talk to people in an instant, without barriers or formality, is an incredible accelerator of trust and creative problem-solving. To apply this principle:
- Organize your physical space around an open central area that enables "collisions" between people
- Designate team spaces for informal hangouts (couches, snacks, games, etc.)
- Reduce private offices and increase shared spaces
Section: 1, Chapter: 5
Book: The Culture Code
Author: Daniel Coyle
The "Get Stuff Done" (GSD) Wheel - A Framework For Collaborative Execution
To drive results collaboratively, use the 6-step "Get Stuff Done" or GSD Wheel framework:
- Listen - Hear the ideas and concerns of your team. Create space for people to share their views without fear.
- Clarify - Make sure everyone is on the same page about what ideas actually mean. Don't let ambiguity linger.
- Debate - Critically examine ideas from all angles. Encourage a culture of debate and information-sharing.
- Decide - Commit to decisions and communicate them broadly and clearly. But don't rush to consensus if there isn't one.
- Persuade - Once a decision is made, explain the rationale in a way that gets buy-in, even from those who disagreed. Make it safe to disagree but not to opt out.
- Execute - Get the decided-upon work done. Remove barriers and hold people accountable. Ensure there is time and space to execute.
Section: 1, Chapter: 4
Book: Radical Candor
Author: Kim Malone Scott
Efficiency Versus Adaptability in Organizations
Many organizations pursue efficiency, trying to execute known processes as well as possible. But when the environment is uncertain, the ability to adapt is more important.
Efficiency:
- Doing things optimally based on predefined criteria
- Relies on prediction and planning; vulnerable to the unexpected
- Well-suited for complicated, knowable environments
Adaptability:
- Able to change to meet new circumstances
- Continuously evolves based on new information; tolerates the unexpected
- Needed in complex, unknowable environments
The key is matching the organizational approach to the environment. Too often, organizations default to chasing efficiency even when adaptability is needed.
Section: 1, Chapter: 4
Book: Team of Teams
Author: Stanley McChrystal
Stretch Goals Require Stretching Yourself
When Sundar Pichai set Chrome's 20M user goal, he wasn't sure how they would get there. Some lessons he learned about leading through a stretch goal:
- Acknowledge the uncertainty, but exude optimism.
- Proactively seek ideas and resources from other teams. Stretches often require cross-functional collaboration.
- Break the big goal into sub-milestones to make it feel more achievable.
- Celebrate progress and small wins along the way. Stretches can be a long slog - people need encouragement.
- Be willing to course-correct as you learn. If one approach isn't working, explicitly pivot and try another.
Section: 2, Chapter: 13
Book: Measure What Matters
Author: John Doerr
Andy Grove - The Architect Behind OKRs
Andy Grove, Intel's pioneering CEO, was the main architect behind OKRs. Grove wanted to create an environment at Intel that valued and emphasized output rather than activities.
He sought to create a system where managers didn't have to tell people what to do through command-and-control. Rather, he aimed to create a culture of discipline and self-management where there was clarity on objectives and people could determine the best approach themselves.
Grove eschewed traditional, private goal-setting in favor of transparent OKRs where everyone's goals, from the CEO down, were openly shared. Objectives were significant, concrete and action-oriented. Key results were measurable and verifiable milestones for achieving the objective.
Section: 1, Chapter: 2
Book: Measure What Matters
Author: John Doerr
Manipulative Insincerity - What Happens When You Neither Care Nor Challenge
The opposite of Radical Candor is Manipulative Insincerity - this is what happens when you neither care about a person nor challenge them directly. It's praise that is insincere and not specific, or criticism that is neither clear nor kind. People give praise or criticism from a place of Manipulative Insincerity when they are too focused on being liked, or when they are too tired to care or argue anymore. But guidance that comes from this place tends to be confusing and unhelpful for the recipient.
Section: 1, Chapter: 1
Book: Radical Candor
Author: Kim Malone Scott
Use Of Surgical Checklist Spread Rapidly Worldwide
After the results of the WHO surgical checklist study were published, showing a 36% reduction in complications and a 47% reduction in deaths, its use spread rapidly:
- Within 18 months, 2,000 hospitals worldwide had adopted the checklist
- Countries from the UK to Jordan to Thailand mandated the checklist in all hospitals
- 20 U.S. states saw 25% reductions in post-surgical death rates after statewide checklist implementation
The demonstrated power of the checklist to save lives and prevent harm led to enthusiastic embrace by many health systems globally.
Section: 1, Chapter: 7
Book: The Checklist Manifesto
Author: Atul Gawande
Good Teams and Trust
"Great teams consist of individuals who have learned to trust each other. Over time, they have discovered each other's strengths and weaknesses, enabling them to play as a coordinated whole."
Section: 1, Chapter: 5
Book: Team of Teams
Author: Stanley McChrystal
Google's 10X Mindset For Moonshot Goals
Google is famous for setting audacious goals. Underpinning Google's outsized ambition is a philosophy they call "10x thinking" - the idea that you should aim for a 10X improvement versus incremental gain.
As Larry Page explains: "If you set a crazy, ambitious goal and miss it, you'll still achieve something remarkable."
By systematically stretching for 10X gains, Google believes you can achieve outsized results over time. You create a culture where the question is never "can this be done?" but rather "what would it take to make this happen?"
Section: 2, Chapter: 12
Book: Measure What Matters
Author: John Doerr
Manipulation Through Promotions, Fear, Aspirations And Peer Pressure
Many companies rely on manipulations to motivate customer behavior and drive sales. Typical manipulations include:
- Dropping prices through promotions and rebates
- Using fear-based messaging like "your health is at risk unless you buy our product"
- Aspirational messages that play on fantasies and insecurities
- Leveraging peer pressure by claiming "experts agree" or "everyone else is buying it"
While effective in the short term, manipulations do not breed loyalty and trust. Costs keep increasing as bigger and bigger carrots and sticks are needed over time. It's an unsustainable and stressful strategy for both companies and consumers in the long run.
Section: 1, Chapter: 2
Book: Start with Why
Author: Simon Sinek
Startups Require Three Structural Attributes
To apply Lean Startup principles in an established company, Ries argues you need to create a platform for experimentation with three key attributes:
- Scarce but secure resources - The startup needs to be assured long-term budgetary security from cancellation but not so much that they become complacent or bloated
- Independent authority - The startup needs complete autonomy to develop and market new products within their limited mandate without excessive approvals
- Personal stake - Teams need to have a personal stake in the outcome, either through bonuses tied to success or a strong sense of ownership and autonomy
Section: 3, Chapter: 12
Book: The Lean Startup
Author: Eric Ries
Keeping A "Finger On The Pulse" As You Scale
As your team grows, you can't be in every meeting or every room. A few ways to keep your finger on the pulse as you scale:
- Walk around - Block time each week to walk the floor and check in with people beyond your direct reports. Ask them what they're working on and how it's going.
- Actually use the products - Don't just read reports about customer experience. Use your own products and see what the experience is really like. Compare it to competitors.
- Read raw feedback - Review raw survey data, support tickets, and other feedback directly. See problems as they come in vs. in aggregate.
- Keep coding/selling/designing - Stay close to the actual work of your team vs. just managing.
The closer you are to the front lines, the more you'll understand. Your goal is to "smell the smoke" of problems when they're still small vs. waiting until they become full-blown fires. The more directly you experience the work, the faster you can sense when things are off track.
Section: 1, Chapter: 8
Book: Radical Candor
Author: Kim Malone Scott
Why Can-Do Companies Can't
Digital Equipment Corporation (DEC), a dominant player in minicomputers, struggled to enter the personal computer market despite having ample resources. Its processes, designed for complex minicomputers with long development cycles and direct sales, were ill-suited for the fast-paced, modular, and retail-driven PC market. Similarly, DEC's values prioritizing high-margin products clashed with the lower margins of PCs.
Section: 2, Chapter: 8
Book: The Innovator's Dilemma
Author: Clayton M. Christensen
Product Objectives and Key Results Align Teams
Objectives and Key Results (OKRs) is a technique for setting clear, measurable business goals and empowering teams to achieve them. The key elements are:
- Objectives are qualitative, key results are quantitative and measurable
- Key results measure outcomes (e.g. customer usage) not output (e.g. features)
- Each team has 1-3 objectives with 1-3 key results each
- Teams are accountable for achieving objectives, with regular check-ins
- Objectives don't cover everything, but the most important items
- Some key results are committed, others are more aspirational
- Shared transparently across teams to coordinate work
OKRs replace roadmaps by aligning teams towards common product objectives.
Section: 3, Chapter: 28
Book: Inspired
Author: Marty Cagan
Success Can Be The Greatest Challenge To Maintaining Your WHY
It's a great irony that achieving success can often be what causes an organization to lose sight of the very purpose, cause and belief that made them successful in the first place. As organizations grow, several things happen:
- The founder can no longer be involved in every decision, so the clarity of WHY starts to dilute as others make choices
- Outside pressures from shareholders, media, competitors, etc. can distract from the original purpose
- Early passion fades as success feels less exciting and more like "business as usual"
Section: 5, Chapter: 11
Book: Start with Why
Author: Simon Sinek
Impromptu Guidance - The Best Feedback Is In The Moment
The most effective feedback isn't the formal review or scheduled 1:1. It's the in-the-moment, impromptu guidance that happens in real time. When you see someone doing something well, tell them right away. The more continuous and less episodic your feedback is, the more natural and effective it will be.
There are a few keys to impromptu guidance:
- Timing - Give the feedback as close to the observed event as possible. The fresher, the better.
- Specificity - Point to specific actions and impacts you observed vs. vague generalities. The more concrete your feedback, the more actionable it is.
- Brevity - Don't belabor the point or make it a long discussion. Just say what you observed and the impact, check for their reaction, and move on.
Section: 1, Chapter: 6
Book: Radical Candor
Author: Kim Malone Scott
Safety Is The Foundation Of Strong Culture
The overarching insight from Chapter 1 is that psychological safety is the foundation on which all strong cultures and successful groups are built. People's brains are constantly assessing their environment and asking "Are we safe here? What's our future with these people? Are there dangers lurking?" When people feel safe and connected to others in a group, it unlocks neural pathways that enable cooperation, creativity and high performance. Conversely, when safety is absent, people become anxious, guarded and self-protective, and group performance suffers dramatically. Building safety is therefore the leader's top priority and essential for group success.
Section: 1, Chapter: 1
Book: The Culture Code
Author: Daniel Coyle
You Can't Predict What Information Matters, So Share Widely
In a complex environment, it's impossible to know in advance what information will be important. The most effective approach is broad transparency, so people can access the data they need when they need it. This means:
- Investing in knowledge sharing technology and processes
- Shifting culture from "need to know" to "duty to share"
- Encouraging people to pull information from other teams, not just push what they think matters
- Focusing on the accessibility of raw data, not just final analyses
When unexpected needs arise, a transparent information environment allows teams to quickly adapt rather than getting bogged down in requests and approvals.
Section: 1, Chapter: 7
Book: Team of Teams
Author: Stanley McChrystal
Obscurity Helps You Improve Without Scrutiny
When you're unknown, you can try new things without expectations or pressure. No one is watching, so you're free to experiment out of the spotlight.
Obscurity protects you from criticism as you find your voice and vision. You can iterate boldly without fear of public failure or ridicule. So be glad no one has heard of you. Enjoy the freedom to make mistakes, learn, and improve. Once you're established, that flexibility to experiment diminishes. Use obscurity to evolve your idea safely.
Section: 1, Chapter: 8
Book: Rework
Author: Jason Fried, David Heinemeier Hansson
Three Elements Necessary To Handle Extreme Complexity Successfully
Gawande proposes three common elements are required to handle extreme complexity:
- Acceptance of our inadequacy. We must recognize that our memory, knowledge and skills are inherently inadequate in the face of the immense complexity of modern systems. We need tools and processes to support and enhance our abilities.
- Belief in the possibility of finding a solution. When failure is common in complex systems, it's easy to become resigned and fatalistic. Success requires maintaining the conviction that solutions can be found despite the complexity, if we are disciplined enough.
- Discipline to apply systematic approaches, even when they seem simplistic. Applying a simple checklist to an immensely complex problem can seem silly, irrational, and a waste of time. But in complex systems, disciplined use of even simple tools is essential and cannot be skipped, even by experts. Consistent success depends on it.
Section: 1, Chapter: 1
Book: The Checklist Manifesto
Author: Atul Gawande
"Pull, Don't Push"
Traditional mass production systems use a "push" model - they produce large batches of products based on forecasts and push them to the next stage of the supply chain. Toyota revolutionized this by using a "pull" model - each step only produced what the next step needed and "pulled" materials as needed.
The same concept can apply in startups. Instead of building massive features and pushing them to customers, Lean Startups need to let their experiments and validated learning "pull" work from product development based on what needs to be learned next. Essentially, avoid large batch development and only build what is needed to test the next assumption. Any other work is waste.
Section: 3, Chapter: 9
Book: The Lean Startup
Author: Eric Ries
From Clockwork to Complexity in Modern Warfare
In Iraq, the U.S. military confronted an environment that was not just complicated, but complex. A complicated environment, like the battlefields of the World Wars, still had a basic, underlying clockwork logic. But by 2004, the speed and interdependence enabled by new technologies had pushed things over the edge into complexity. Small events could spiral outward with disproportionate impacts. Insurgent tactics and civilian reactions seemed to shift constantly in unpredictable ways. Cause and effect were no longer straightforward. Precision plans quickly became irrelevant. The U.S. Task Force realized that rather than just doing complicated operations more efficiently, it would have to fundamentally transform to become an adaptable, complex system itself.
Section: 1, Chapter: 3
Book: Team of Teams
Author: Stanley McChrystal
Hire The Right People
When hiring, it's critical to be extremely discerning and have a systematic process:
- Think through the values, abilities and skills you need for the role
- Don't just look at resumes - hear how candidates think and visualize if they will succeed
- Check references thoroughly and don't assume someone who succeeded elsewhere will succeed in your company
- Look for people you want to share your life with, not just fill a job
Bridgewater (Dalio's company) looks for people who think independently, embrace truthful reflection and improvement, and value excellence and the community.
Section: 3, Chapter: 8
Book: Principles
Author: Ray Dalio
The AI Canvas For Redesigning Decisions And Systems
The authors present an "AI Canvas" framework for mapping how AI predictions could enable businesses and organizations to redesign their decision-making systems. The key steps:
- Define the core objective or "north star" of your organization
- Identify the key decisions required to achieve that objective, assuming the availability of perfect predictions
- For each decision, specify the prediction required as an input and the judgment required to act on that prediction
- Analyze how the decision-making roles and processes would need to change to incorporate AI predictions
- Redesign the overall system to maximize the value of AI predictions while preserving necessary human judgment
The authors apply the framework to an extended case study of the insurance industry, showing how AI could transform insurers' decision-making from underwriting and claims processing to customer acquisition and retention.
Section: 6, Chapter: 17
Book: Power and Prediction
Author: Ajay Agrawal, Joshua Gans, Avi Goldfarb
Avoid The "Peter Principle" When Promoting
The "Peter Principle," based on the book by Laurence J. Peter, is the concept that in a hierarchy, people tend to rise to "their level of incompetence." In other words, people keep getting promoted as long as they are competent in their role. But there eventually comes a role they are no longer excellent at - and they stay stuck there. This happens frequently when excellent individual contributors are promoted into management roles they may not be well suited for or truly want.
Pushing people into roles they aren't suited for just for the sake of promotion does both them and the organization a disservice. Managers need to be thoughtful about what roles people will truly thrive and excel in vs. just what seems like the logical "next step."
Section: 1, Chapter: 3
Book: Radical Candor
Author: Kim Malone Scott
Committed And Aspirational Goals Are Both Essential
In any given quarter, YouTube (and Google more broadly) aims for a 60/40 split between committed and aspirational OKRs:
- Committed OKRs: Challenging goals you fully expect to achieve, barring unforeseen circumstances. You should hit these 90-100% of the time. Failing to do so requires explanation.
- Aspirational OKRs: Ambitious "stretch" goals that push beyond your current capabilities or knowledge of how to achieve them. The target is ~70% achievement. Lower is fine as long as you learn something useful.
The balance of the two keeps people motivated. They get dopamine hits from regularly achieving hard things, while still feeling challenged to grow. If your committed goals are consistently harder than your aspirational ones, your aspirations aren't aspirational enough!
Section: 2, Chapter: 14
Book: Measure What Matters
Author: John Doerr
"Shared Consciousness" as an Organizational Goal
To achieve "team of teams" adaptability at an organizational scale, the Task Force pursued "shared consciousness" - a holistic, ever-updated understanding of the entire mission shared by all. Key elements included:
- Extreme transparency of information across units, enabled by technology
- Rich lateral ties between units to build trust and awareness
- Instilling common purpose beyond just unit goals
- Leader emphasis on the "why" behind missions, not just the "what"
When every team understands the whole system and how their choices impact others, they can combine fluidly and adapt in sync. While never perfect, shared consciousness makes the "team of teams" approach viable even in very large organizations.
Section: 1, Chapter: 6
Book: Team of Teams
Author: Stanley McChrystal
Committing To The OKR Process
For OKRs to drive focus and execution, leaders need to:
- Actively demonstrate their own commitment to OKRs by regularly tracking and discussing them
- Consistently communicate the importance of OKRs for the company's success
- Ensure their executive team bought into and modeled the process
- Hold people accountable for following through on their OKRs
Jini Kim advises other leaders: "The OKR process takes discipline, commitment and iteration to work. Don't get discouraged if it feels hard at first. Stick with it and make it your own."
Section: 1, Chapter: 6
Book: Measure What Matters
Author: John Doerr
The Perils of Over-Analysis: Millennium Challenge '02
Gladwell recounts the story of Millennium Challenge '02, a massive military war game conducted by the U.S. military. The exercise pitted a high-tech Blue Team (representing the U.S.) against a low-tech Red Team led by retired Marine Corps general Paul Van Riper.
Despite Blue Team's technological superiority and extensive planning, Van Riper's Red Team managed to outmaneuver them by using unconventional tactics and quick, adaptive decision-making. Van Riper's approach:
- Relied on decentralized command structure
- Encouraged rapid, intuitive decision-making
- Avoided over-analysis and information overload
Section: 1, Chapter: 4
Book: Blink
Author: Malcolm Gladwell
How To Spur People On To Success
Praise is more effective than criticism in getting people to change and improve:
- Be specific. Instead of saying "You did a good job", say "You did a good job in getting that report out under a tight deadline. I appreciate your extra effort."
- Act as if the trait or achievement you are praising is already one of the person's outstanding characteristics. This gives them a reputation to live up to.
- Refer to a person's good traits or reputation when asking them to make an improvement. "You're always so conscientious, could I ask you to take on this additional task?"
- Phrase your suggestions as questions or requests, not demands.
Section: 3, Chapter: 6
Book: How to Win Friends and Influence People
Author: Dale Carnegie
Recruit People Who Are Excited To Work With You
When recruiting early employees for a startup, look for people who are genuinely excited to work with you and believe in the mission of the company. Some tips:
- Hire for both aptitude and attitude. Raw talent is great but a shared sense of purpose is essential.
- Communicate a compelling mission that attracts like-minded people who will fit the culture.
- Favor highly motivated people over highly experienced people early on.
- Be wary of people who are more excited about the general idea of a startup than the specific mission of yours.
- Design a culture where everyone is rowing in the same direction, even without top-down direction.
Section: 1, Chapter: 10
Book: Zero to One
Author: Peter Thiel
How Leaders Can Amplify Cultural Change
Changing a large organization's culture is never easy. But when leaders visibly embrace OKRs and CFRs, it sends a powerful signal.
When making a key decision, connect it explicitly to a company OKR. Show how priorities guide actions. Essentially, make OKRs and CFRs an integral part of how you manage. Through your example, you give your team permission to embrace the new normal. Culture change is a marathon, not a sprint. Stay the course with OKRs and expect some resistance early on. But know that each cycle brings you closer to operating excellence.
Section: 3, Chapter: 18
Book: Measure What Matters
Author: John Doerr
"You Don't Hire For Skills, You Hire For Attitude. You Can Always Teach Skills."
Southwest Airlines co-founder Herb Kelleher had a knack for hiring people who embodied Southwest's WHY. His famous quote, "You don't hire for skills, you hire for attitude. You can always teach skills" embodied Southwest's approach. They figured out that the people who were the best cultural fit were those who had been cheerleaders or mascots - they had an attitude of exuberance and positivity that matched Southwest's WHY of freedom and fun in air travel.
Section: 4, Chapter: 8
Book: Start with Why
Author: Simon Sinek
Balancing Urgent Action With Careful Analysis
Effective leaders face a perennial dilemma: How to balance the need for decisive action with the need for careful deliberation. Superforecasters offer a way to resolve this dilemma by rapidly generating accurate probability estimates. Leaders can use these forecasts to make smarter bets, faster.
Leaders must proactively shape how forecasts are made. Some key steps:
- Meticulously breaking down big strategic issues into specific, forecastable sub-questions
- Assigning clear owners to each sub-question to gather information and generate estimates
- Encouraging a culture of creative friction, where forecasts are carefully debated and challenged
- Making final decisions that coherently synthesize the wisdom in the various forecasts
By balancing foresight with decisive action, leaders can get the benefits of anticipation without the inertia of excess caution. Organizations can act with "enlightened boldness" - an elusive but invaluable capability.
Section: 1, Chapter: 10
Book: Superforecasting
Author: Philip Tetlock
Create Space For Open, Honest Communication
Many workplaces unintentionally stifle honest communication, especially when there is an imbalance of power or status. Junior employees don't feel safe raising concerns or taking risks. Sandberg argues that leaders should actively create space for open, authentic conversations:
- Explicitly invite dissenting opinions in meetings
- When someone criticizes you, thank them for their candor
- Share your own fears, mistakes, and areas for growth
- When you hear a valid criticism of the company, repeat it to signal you welcome the honesty
These actions, especially when modeled by leaders, create a culture of psychological safety where people can be their true selves.
Section: 1, Chapter: 6
Book: Lean In
Author: Sheryl Sandberg
The Emerging "Goal Science"
In the 40+ years since Andy Grove first developed OKRs at Intel, an entire field of "goal science" has emerged. Some of their key findings from research reinforce the core tenets of OKRs:
- Specific, challenging goals drive higher performance than vague exhortations to "do your best"
- Connecting goals to a larger purpose stimulates intrinsic motivation and persistence
- Involving people in setting their own goals leads to greater engagement and achievement
- Personalizing goals based on someone's past achievement, personality profile, and current circumstances
- Gamifying goals to make them more engaging and enjoyable to pursue
The underlying insight is that goals, like any powerful technology, are evolving rapidly. What seemed advanced a decade ago may soon be table stakes. As Doerr writes, "My ultimate 'stretch OKR' is to empower people everywhere to achieve the seemingly impossible together, to create new realities, and in doing so make the world a little bit better."
Section: 3, Chapter: 21
Book: Measure What Matters
Author: John Doerr
Resource Realignment: From Cold Spots to Hot Spots
Instead of focusing on acquiring more resources, tipping point leadership emphasizes maximizing the value of existing resources. This involves identifying and redirecting resources from "cold spots" (activities with high resource input but low performance impact) to "hot spots" (activities with low resource input but high potential for performance gains). Additionally, "horse trading" – exchanging underutilized resources between departments – can further optimize resource allocation.
Section: 3, Chapter: 7
Book: Blue Ocean Strategy
Author: W. Chan Kim and Renee Mauborgne
Constantly Train, Test, Evaluate, and Sort People
Managing people at Bridgewater is a constant process of training, testing, evaluating, and sorting. Training focuses on helping people develop the skills and abilities required for their role. Testing gives them opportunities to succeed or fail in applying their training. Evaluation is a constant process of openly and objectively assessing people's performance, getting in sync on their strengths and weaknesses, and planning next steps for training or reassignment. Sorting means moving people into roles that best fit their abilities, or out of the organization if they're not a good fit. It's all about matching people to the right roles at Bridgewater.
Section: 3, Chapter: 9
Book: Principles
Author: Ray Dalio
The "Um" Story - How Direct Feedback Can Be An Act Of Caring
Early in her career at Google, the author's boss Sheryl Sandberg pulled her aside after a presentation. She complimented the author's intellect and ability to see both sides of an argument. But then Sheryl told her very directly "you said 'um' a lot in there. Were you aware of it?" The direct feedback made the author aware of how much she was saying "um" and motivated her to work with a speech coach to improve. This demonstrated how giving direct, even uncomfortable, feedback can be an act of caring when done with good intent.
Section: 1, Chapter: 1
Book: Radical Candor
Author: Kim Malone Scott
Identify The "Slowest Hiker" And Remove The Obstacle
In the business parable The Goal, the protagonist Alex faces the challenge of improving his factory's output. His mentor teaches him to find the bottleneck or constraint in the system - the "slowest hiker." This one bottleneck is holding up the entire production line. Alex learns that instead of trying to maximize the efficiency of every single element in the system, he should focus on alleviating the chief constraint, which then has a domino effect on overall throughput. We can apply this to our own work and life:
- Clarify your essential intent - what's your goal?
- Identify the obstacle - the "slowest hiker" - that is holding you back the most
- Remove that obstacle before worrying about optimizing anything else
Sometimes what is standing between us and our goal is just one key constraint. Remove it and execution becomes far easier.
Section: 4, Chapter: 16
Book: Essentialism
Author: Greg McKeown
The Price You Pay For The Money You Make
Manipulations like price drops, promotions, fear tactics and peer pressure marketing can certainly drive short-term transactions and sales. But there is always a price to pay for the money you make using these techniques:
- Costs keep increasing as you rely more and more on manipulations
- Loyalty and trust are eroded over time as customers feel tricked
- Stress increases for both company and customer in an unending struggle
- The pattern repeats in a downward spiral as manipulations are the only way forward
If you're just focused on short-term gain, manipulations can work. But to build an enduring and loyal customer base, a deeper sense of purpose and trust is needed beyond carrots and sticks. Starting with WHY provides an alternative path.
Section: 1, Chapter: 2
Book: Start with Why
Author: Simon Sinek
Intellectual Humility
The most effective problem-solving groups share a common trait - they prioritize intellectual humility over individual status or ego. Intellectual humility is the willingness to admit what you don't know, to welcome new and contradictory ideas, and to change your mind in the face of compelling logic or evidence. To model intellectual humility as a leader:
- Frame questions neutrally: "What am I missing?" vs. "Does anyone disagree with my idea?"
- Give people permission to challenge your thinking: "I could be wrong, so tell me if you see it differently"
- When someone raises a contrary view, thank them for it: "I'm so glad you brought that up; it made me rethink my assumptions"
- Call out groupthink: "I'm worried we're getting too bought into this plan - who can poke holes in it?"
- Reward people not just for being right, but for successfully changing the group's mind
Section: 2, Chapter: 7
Book: The Culture Code
Author: Daniel Coyle
The Difference Between Complicated and Complex Systems
Understanding the difference between complicated and complex systems is key to managing in the modern world:
Complicated systems:
- Are rule-bound with predictable cause-and-effect relationships
- Consist of many parts, but connections between parts are fixed and straightforward
- Respond in expected ways to change - Optimal solutions can be planned in advance Examples: an assembly line, a Swiss watch
Complex systems:
- Consist of many interdependent parts with unpredictable, nonlinear relationships
- Produce emergent behaviors and effects that cannot be predicted just by looking at individual components
- Defy attempts to "solve" with reductionist planning and control Examples: the weather, a rainforest ecosystem, the global economy
Section: 1, Chapter: 3
Book: Team of Teams
Author: Stanley McChrystal
CTO Responsibilities Go Beyond Engineering
The head of engineering or CTO role is about much more than just managing developers. The six key priorities are:
- Building and retaining a high-caliber engineering team
- Representing technology in the company strategy and planning
- Delivering quality products rapidly, reliably and repeatedly
- Defining a product architecture that supports current and future needs
- Contributing to product discovery and innovation
- Evangelizing the technology organization externally
Engineering leaders must partner closely with their peers in product and design to create an environment where engineers are motivated and empowered to build great products.
Section: 2, Chapter: 18
Book: Inspired
Author: Marty Cagan
Thriving in a "VUCA" World Requires New Mental Models
The challenges the Task Force faced in Iraq are a microcosm of the Volatile, Uncertain, Complex, and Ambiguous (VUCA) world facing many organizations today. To thrive in this environment requires new ways of thinking and operating:
- From predictive planning to rapid adaptation and experimentation
- From siloed execution to transparent collaboration across boundaries
- From centralized control to decentralized initiative within a common framework
- From brittle efficiency to resilient networks able to respond to change
- From leaders with all the answers to leaders who empower others to find answers
While uncomfortable, these new mental models are essential for organizations to make the leap from 20th century bureaucracy to 21st century adaptability.
Section: 1, Chapter: 12
Book: Team of Teams
Author: Stanley McChrystal
Build A Business, Not Just A Client Portfolio
Avoid the trap of doing client work to fund your product business. This makes you a consultant, not an entrepreneur. Your efforts go into serving clients, not building something scalable that can thrive without you. It's a tempting compromise, but it splits your focus.
You wind up with a viable portfolio but not a viable product. If you want a product business, make that your main focus from day one. Use your own resources and find a way to start generating revenue directly.
Section: 1, Chapter: 4
Book: Rework
Author: Jason Fried, David Heinemeier Hansson
At Apple, A Culture Of Criticism Coupled With Deep Respect
The author observed the culture at Apple involved intense, direct debate and criticism, but always done with a foundation of deep respect. Steve Jobs invited people to tell him when he was wrong, insisting they challenge his ideas. He wanted people's genuine opinions, even if they disagreed with his.
But while the criticism was very direct, it was coupled with real personal caring and respect. Jobs would explain why someone's work was not good enough and articulate why, but would also emphasize that any criticism was not fundamentally calling their abilities into question. This demonstrated a culture of Radical Candor - direct challenge coupled with real personal caring. The respect and personal caring made the direct criticism and debate possible.
Section: 1, Chapter: 1
Book: Radical Candor
Author: Kim Malone Scott
Rethinking Ambition - Not Everyone Wants To "Climb The Ladder"
Too often as managers, we assume that everyone on our team wants to be on a steep growth trajectory and be promoted as quickly as possible. But the reality is that not everyone wants the next bigger job right now. At different phases of life and career, people may be very content and fulfilled in their current role. Pushing them toward promotions they don't want leads to unhappiness.
The author calls this the difference between "rock stars" and "superstars." Superstars are always gunning for the next big role. Rock stars are excellent at their current job and find fulfillment there. Organizations need both. If you promote a rock star into a role they don't want, you lose them. If you fail to keep giving a superstar new challenges, you lose them.
As a manager, you have to get to know each individual, understand what their current ambitions and motivations are, and manage them accordingly. Don't impose a one-size-fits-all idea of ambition.
Section: 1, Chapter: 3
Book: Radical Candor
Author: Kim Malone Scott
How to Criticize - and Not Be Hated for It
A manager at a department store in New York had to deal with a young salesperson who was causing customer complaints due to poor service. Instead of criticizing her directly, he called her into his office and had a conversation:
"Mary, I understand you had trouble with a customer yesterday... [Explains the situation] I'm on your side and I know you were trying your best to handle a difficult customer. However, in future situations like this, it may help to... [Provides suggestions] That way we can ensure the customer leaves satisfied and you have a positive interaction. What do you think?"
By empathizing with Mary and framing his critique as a suggestion rather than a condemnation, the manager was able to correct the behavior without Mary getting defensive. She left feeling supported rather than attacked.
Section: 4, Chapter: 2
Book: How to Win Friends and Influence People
Author: Dale Carnegie
Data, Not Wishful Thinking
"Setting a goal is fine, but if you don't know how you did against it, it's like running a race without a stopwatch and a finish line. Having a good mission is not enough. You need a concrete objective, and you need to know how you're going to get there." - Bill Gates
Section: 2, Chapter: 11
Book: Measure What Matters
Author: John Doerr
Maintaining Your WHY Takes Consistent Effort And Accountability
It's one thing to have a clear sense of WHY at the outset, but the true challenge is maintaining that clarity and consistency of purpose as the organization grows and evolves.
- Put your WHY into writing. Make it a mantra that is communicated over and over from leadership.
- Codify your HOWs into guiding principles that align to the WHY. Make them actionable and hold everyone accountable to them.
- Build the WHY into the hiring process. Hire people who believe what you believe and will be culture adds, not just skill adds.
- Celebrate and showcase actions that exemplify the WHY. Reinforce the behaviors you want to see more of.
Section: 5, Chapter: 12
Book: Start with Why
Author: Simon Sinek
How To Grow Your Reach Without Growing Your Team
For companies of one, the key to sustainable growth is implementing scalable systems that increase output without a proportional increase in costs or headcount. Some examples:
- Email marketing allows you to communicate with thousands of leads for the same effort as emailing one
- Webinars let you present to a global audience without travel costs
- Chatbots handle basic customer service inquiries 24/7
The goal is to automate and templatize repeatable processes so you're not always trading time for money. Look for opportunities to provide one-to-many value at every stage of your funnel. Could that sales demo become an on-demand video? That onboarding call a self-guided tutorial?
Scalable doesn't mean impersonal. Use technology to enhance, not replace, human connection.
Section: 2, Chapter: 8
Book: Company Of One
Author: Paul Jarvis
The AI Innovator's Dilemma Favors Startups Over Incumbents
The authors argue that AI presents an "innovator's dilemma" that makes it difficult for incumbent firms to adopt the technology in a timely and effective manner. The key challenges:
- Incumbent firms are optimized for their existing systems and metrics, while AI often requires new systems and metrics to deliver value
- Adopting AI may cannibalize incumbents' existing profitable businesses, while startups have no such conflicts
- Incumbents' organizational structures and processes are "glued" together in ways that resist the changes required to fully exploit AI
AI systems often decouple prediction from judgment in ways that disrupt incumbents' existing decision-making structures and power dynamics As a result, the authors expect AI to be more rapidly adopted by startups than incumbents, leading to significant disruption as new entrants scale up AI-powered systems that incumbents struggle to match.
Section: 4, Chapter: 10
Book: Power and Prediction
Author: Ajay Agrawal, Joshua Gans, Avi Goldfarb
Belonging Cues Light Up The Brain
MIT's Human Dynamics Lab, led by Professor Alex Pentland, used sociometric badges to measure the behavioral signals exchanged in successful groups. They found that high-performing groups consistently displayed a set of subtle cues that generate feelings of belonging and safety:
- Close physical proximity (often in circles)
- Profuse amounts of eye contact
- Lots of short, energetic exchanges (no long speeches)
- High levels of mixing; everyone talks to everyone
- Few interruptions
- Intensive, active listening
- Humor, laughter
Pentland found that belonging cues were the single greatest predictor of group performance, more important than all the individual skills and intelligence of the group's members. These cues trigger the release of oxytocin and activate neural pathways of trust and cooperation, enabling the group to sync their behaviors and act as one.
Section: 1, Chapter: 1
Book: The Culture Code
Author: Daniel Coyle
Standard Operating Procedures Provide Reliability But Stifle AI-Enhanced Decisions
The authors present a framework for understanding the role of rules and standard operating procedures (SOPs) in organizations:
- SOPs reduce individual cognitive load by providing pre-specified actions
- SOPs enable reliability and predictability across an organization by ensuring different people/groups take consistent, coordinated actions without extensive communication
- SOPs "glue" different parts of an organization together in an interdependent system resistant to change
- Replacing SOPs with AI-enhanced decisions reduces reliability and predictability, unsticking the organizational glue
- Transforming rules into AI-enhanced decisions often requires systemic change to re-establish coordination in new ways
Section: 2, Chapter: 6
Book: Power and Prediction
Author: Ajay Agrawal, Joshua Gans, Avi Goldfarb
The Power Of Heuristics In Complex Environments
Danny Meyer is the CEO of Union Square Hospitality Group, which owns and operates some of the most acclaimed restaurants in New York City. How does Meyer ensure that his teams are always on their game, no matter what challenges they face?
The answer lies in what cognitive scientists call heuristics - simple, memorable rules of thumb that guide behavior in complex situations. Heuristics make it easy for his employees to do the right thing, even under pressure. Some examples:
- "The Excellence Reflex": Treat every customer interaction, no matter how small, as an opportunity to create a memorable experience.
- "Athletic Hospitality": Anticipate customers' needs before they ask, and go the extra mile to exceed their expectations.
- "The 51% Solution": If a customer is unhappy with their experience, it's the restaurant's responsibility to make it right, even if the customer is partly to blame.
- "Writing a Great Last Chapter": The last few minutes of an interaction are disproportionately important in shaping a customer's overall impression and likelihood to return.
Section: 3, Chapter: 15
Book: The Culture Code
Author: Daniel Coyle
Use Tools and Protocols to Shape How Work Is Done
Bridgewater heavily leverages tools and protocols to help shape behavior and steer the company toward principles-based decision making. From the "Dot Collector" that facilitates open feedback to the "Pain Button" that encourages learning from mistakes, these tools reinforce desired mindsets and practices. The tools both teach and facilitate the desired behaviors. Over time, they help the right behaviors become more automatic and embedded in the culture. Dalio believes an idea meritocracy can't function on good intentions alone - proper tooling and reinforcement is needed to make it real.
Section: 3, Chapter: 15
Book: Principles
Author: Ray Dalio
Avoidable Failures Are Common Across Fields
"Avoidable failures are common and persistent, not to mention demoralizing and frustrating, across many fields—from medicine to finance, business to government. And the reason is increasingly evident: the volume and complexity of what we know has exceeded our individual ability to deliver its benefits correctly, safely, or reliably. Knowledge has both saved us and burdened us."
Section: 1, Chapter: 1
Book: The Checklist Manifesto
Author: Atul Gawande
Organizational Culture Can Be Intentionally Designed To Promote Grit
While individuals can cultivate grit from the inside out, grit can also be powerfully shaped by the environment and culture in which we operate. Leaders and organizations can create a "culture of grit" that encourages passion and perseverance.
Organizational culture includes the shared language, norms, and values of a group. It's "the way we do things around here." A strong culture makes certain behaviors and mindsets feel expected and normal. Leaders like Pete Carroll of the Seattle Seahawks and Jamie Dimon of JPMorgan Chase have fostered grit in their organizations through consistent messaging, role modeling, and systems that promote and reward effortful practice, resilience, and purpose.
Section: 3, Chapter: 12
Book: Grit
Author: Angela Duckworth
Bias, Gender, And The "Abrasive" Trap
Studies have shown that the more competent a woman is perceived to be, the less likeable she is found to be. This plays out in performance reviews, where women tend to get much more critical feedback about their personality and communication style than men do. Women are much more likely to be labeled as "abrasive", "judgmental" or "strident" when they assert themselves or challenge others directly. As a manager, it's important to be aware of this bias. A few tips:
- Evaluate your feedback for gendered language - are you using words like "abrasive", "bossy", or "aggressive" with women more than men?
- Consider the individual's context - is this a woman in a role/field where she is a minority? Is she being held to an unfair double standard?
- Focus on actions and impacts, not personality - give feedback on specific behaviors and results rather than vague judgments of character. Base assessments on facts.
Section: 1, Chapter: 6
Book: Radical Candor
Author: Kim Malone Scott
How Pixar Builds A Culture Of Rethinking
Pixar, the studio behind beloved films like Toy Story and The Incredibles, is known for its culture of creativity and constant improvement. A big part of that stems from making rethinking a regular practice:
- The Braintrust - a group of the studio's top creative minds - meets regularly to give candid feedback on work in progress. The focus is on identifying problems, not proposing solutions.
- Employees are encouraged to be "candid and constructive" in their critiques. Managers emphasize that a rigorous critique is a sign of respect, not disregard.
- Teams engage in "plussing" - building on each other's ideas rather than tearing them down. The goal of feedback is to maximize potential, not minimize errors.
- Directors actively seek input from colleagues throughout the production process, normalizing iteration. Early mock-ups are presented specifically to spark rethinking.
Section: 3, Chapter: 10
Book: Think Again
Author: Adam Grant
An Organization Is A Machine With Two Major Parts
Dalio explains that an organization is like a machine consisting of two major parts - the culture and the people. A great organization needs both a great culture that solves problems well and loves building new things, as well as great people with excellent character and capabilities. The key is to cultivate meaningful work and relationships through radical truth and transparency.
Section: 3, Chapter: 1
Book: Principles
Author: Ray Dalio
Covid-19 Illustrates The High Costs Of Managing Uncertainty With Crude Rules
The authors use the example of blanket social distancing rules during the Covid-19 pandemic to illustrate the economic costs of managing uncertainty with rules rather than predictions.
- Social distancing was a crude but effective rule for limiting virus spread in the absence of information on who was infectious
- However, it came at an enormous economic and social cost, disrupting work, education, and social connectivity for everyone rather than just the infectious
- Better predictive tools for identifying infectious individuals, like rapid testing, could have enabled more normal life to continue safely for the majority. Realizing this would have required an "oiled" system able to flexibly adapt based on new information, rather than a "glued" system locked into rigid rules
Section: 3, Chapter: 7
Book: Power and Prediction
Author: Ajay Agrawal, Joshua Gans, Avi Goldfarb
Transparency and Information Sharing as a Foundation for Adaptability
To become an adaptable "team of teams," the U.S. Task Force had to fundamentally change how it shared information. Instead of hoarding intelligence in silos, it needed to make data widely accessible. This meant shifting from a "need to know" mindset to a "duty to share" one.
By making information transparent across the organization, frontline teams could act on intelligence faster, recombine data in creative ways, and avoid decisions that helped one unit but hurt the mission overall. While uncomfortable at first, this shift to "shared consciousness" proved crucial to success against Al Qaeda.
Section: 1, Chapter: 7
Book: Team of Teams
Author: Stanley McChrystal
To Get Things Done, Don't Tell People What To Do
A common mistake bosses make is thinking their job is to tell people what to do. But unilateral decision making without input and buy-in doesn't work well, especially with today's knowledge workers. People need to be influenced and inspired, not just ordered around.
The author learned this the hard way when she first joined Google and tried to reorganize her team without getting their input first. Her directives were met with resentment and pushback, and several people left the team. She realized she had to shift to a more collaborative approach.
Even leaders known for top-down authority like Steve Jobs succeeded not by ordering people around, but by engaging in debate, soliciting input, and convincingly explaining decisions. Telling people what to do doesn't work, even if you're the boss. Bosses have to learn to influence and facilitate rather than dictate.
Section: 1, Chapter: 4
Book: Radical Candor
Author: Kim Malone Scott
Artificial Culture Is Useless, Real Culture Emerges From Consistent Behavior
You don't create a corporate culture by proclaiming abstract values in a mission statement or manifesto. Culture emerges organically from how a company operates day to day. If a company claims to value transparency but makes decisions privately, the real culture is one of secrecy, not openness. To shape culture, focus on practicing the behaviors you want consistently over time.
Section: 1, Chapter: 11
Book: Rework
Author: Jason Fried, David Heinemeier Hansson
Four Key Lessons From Construction On Making Checklists Actually Work
Gawande distills four key lessons about how to make checklists work in practice:
- Simple checks are essential, but often overlooked. It's easy to dismiss basic checks as being too "stupid" and "ineffective" to matter. But in complex environments, they are crucial to catching the obvious-but-essential things that are so frequently missed, leading to catastrophe.
- Checks must be explicit and mandatory, not vague advice. The construction manager's new checklist explicitly spelled out which teams had to talk, about what, and when. The steps were mandatory for all.
- Checks must generate buy-in and investment from the team, not just compliance. The construction manager achieved this by having the checklist system designed by the builders themselves, so they felt ownership over it.
- Checks must feel streamlined and pragmatic, not cumbersome. It was designed to fit efficiently into their existing workflows.
Section: 1, Chapter: 4
Book: The Checklist Manifesto
Author: Atul Gawande
Transactive Memory: How Groups Think Together
Small, close-knit groups can develop a kind of shared memory system called transactive memory. Over time, members unconsciously divvy up and specialize in remembering different types of information based on their unique skills:
- Bob becomes the go-to for tech help and fixes everyone's computer issues
- Alice is the expert on company history and institutional knowledge
- Charlie knows all about their clients' businesses and needs
The group's memory becomes a division of cognitive labor, not just a sum of individual minds. They can collectively store and process far more knowledge than any one person.
This works through intimate social bonds, not org charts. Transactive memory is why small, tight-knit teams are often more efficient than large bureaucratic divisions.
Section: 1, Chapter: 5
Book: The Tipping Point
Author: Malcolm Gladwell
The Enduring Legacy of Frederick Winslow Taylor's Scientific Management
Frederick Winslow Taylor pioneered the concept of "scientific management" in the early 20th century, seeking to optimize industrial efficiency through time-motion studies, process optimization, and centralized planning. His reductionist approach of breaking work down into specialized, repetitive tasks boosted productivity tremendously and left an enduring mark on management thinking across business, government and the military. However, the rigidity and top-down control inherent in "Taylorism" has limitations in environments with greater complexity and unpredictability.
Section: 1, Chapter: 2
Book: Team of Teams
Author: Stanley McChrystal
Doing the Right Thing
"Efficiency Is Doing Things Right; Effectiveness Is Doing the Right Thing"
"If you have enough foresight to know with certainty what the 'right thing' is in advance, then efficiency is an apt proxy for effectiveness. In the wayward swirl, however, the correlation between efficiency and effectiveness breaks down. The Task Force had built systems that were very good at doing things right, but too inflexible to do the right thing."
Section: 1, Chapter: 7
Book: Team of Teams
Author: Stanley McChrystal
The MyFitnessPal Story
When MyFitnessPal hit product-market fit, growth took off like a rocket ship. But this hypergrowth came with a cost. Co-founders Mike and Albert Lee found it increasingly difficult to keep everyone rowing in the same direction. Different teams were pursing competing priorities. Inefficiencies and duplicative work crept in. The engineering team, in particular, felt torn between different product managers.
As Mike puts it: "If you put two people in a boat and have one row east and the other row west, they'll use up lots of energy going nowhere. Before you know it, they're working on two different things. It doesn't help to push them harder. If two nails are even slightly misaligned, a good hammer will splay them sideways."
Section: 2, Chapter: 8
Book: Measure What Matters
Author: John Doerr
Symbols Are Powerful Communicators Of Belief
Symbols are a tangible representation of a company or cause's beliefs. They can be much more than just a logo - they are any image, object, slogan, cultural touchpoint, etc. that captures the meaning behind WHY an organization does what it does.
Apple's famous "Think Different" ad campaign served as a symbol of Apple's belief in championing rebel thinkers who pushed boundaries. It was making a statement about its own identity and worldview.
Symbols don't get their meaning from the organization; rather the meaning comes from what the believers put into it. Harley-Davidson tattoos are earned symbols of belief in Harley's WHY - a sense of independence and American freedom.
Section: 4, Chapter: 10
Book: Start with Why
Author: Simon Sinek
To Build Culture, Start With Shared Language
The author profiles how Pete Carroll established a culture of grit after becoming head coach of the Seattle Seahawks. One of his first moves was developing a shared vocabulary, including mantras like:
- Always compete (compete with yourself to get better every day)
- Practice is everything (give max effort in training, not just in games)
- Finish strong (maintain focus and intensity all the way)
- Team first (put the mission and your teammates before yourself)
Critically, Carroll focused more on process than outcomes. His core ideas emphasized things that were repeatable and controllable - competing with oneself, finishing practices strong, putting the team first. By keeping the language on effortful mastery rather than winning, Carroll made grit the bedrock of Seahawks culture.
Section: 3, Chapter: 12
Book: Grit
Author: Angela Duckworth
How Checklists Empower Heroes In The Modern Era
"What is needed, however, isn't just that people working together be nice to each other. It is discipline. Discipline is hard—harder than trustworthiness and skill and perhaps even than selflessness. We are by nature flawed and inconstant creatures. We can't even keep from snacking between meals. We are not built for discipline. We are built for novelty and excitement, not for careful attention to detail. Discipline is something we have to work at."
Section: 1, Chapter: 8
Book: The Checklist Manifesto
Author: Atul Gawande
The Rule Of 150: The Magic Number For Groups
There seems to be a tipping point in the size of social groups:
- Below 150 members, a group can rely on informal social norms, peer pressure and personal relationships to maintain cohesion
- Above 150, rules, hierarchy, and formal authority are needed to keep order. Things become impersonal and unwieldy.
The dynamics of a group change fundamentally when it exceeds 150 people. This number shows up again and again:
- Hunter-gatherer societies around the world have average village sizes of 148
- Offices tend to max out around 150-200 employees
- The Hutterite religious communities always split when they exceed 150
"At 150, the Hutterites believe, something happens - something indefinable but very real - that somehow changes the nature of community overnight."
By keeping groups under 150, an organization can exploit the bonds of memory and peer pressure to maximize cohesion and trust. Going over that threshold makes an epidemic vulnerable to tipping in the wrong direction.
Section: 1, Chapter: 5
Book: The Tipping Point
Author: Malcolm Gladwell
Pare Down To The Essence, But Don't Remove The Poetry
"Pare down to the essence, but don't remove the poetry. Keep things clean and unencumbered but don't sterilize."
Simplicity is essential, but it requires careful judgment. The goal is to pare down to the essence, but not overshoot into sterility. Too much removal makes a product lifeless. So as you simplify, don't just cut - refine. Keep the essential core but also retain the poetic touches that make your product engaging, memorable, and human. The right details make simplicity sing.
Section: 1, Chapter: 7
Book: Rework
Author: Jason Fried, David Heinemeier Hansson
U.S. Airways Flight 1549 Illustrates How Checklists Enhance Teamwork Amid Complexity
The successful water landing of U.S. Airways Flight 1549 demonstrated how checklists can help teams navigate extremely complex situations:
- By having the pilot and co-pilot methodically go through their checklists together before takeoff, they developed a shared mental model and readiness to work as a seamless team.
- When both engines failed after hitting a flock of birds, the pilots immediately retrieved the checklist for that situation. Each executed their defined roles - one flew the plane, the other went through the engine restart steps.
- The flight crew referenced checklists for passenger preparation and evacuation, allowing them to get all 155 people off the plane in 90 seconds after landing.
- Checklists helped the crew function as a coordinated unit, ensuring the right steps were taken at the right time, and empowering each member to do their part with precision.
Section: 1, Chapter: 8
Book: The Checklist Manifesto
Author: Atul Gawande
People Don't Buy What You Do, They Buy Why You Do It
Consider an advertising message from Apple if they started with their WHAT: "We make great computers. They're user friendly, beautifully designed, and easy to use. Want to buy one?" It's not very compelling.
But Apple actually communicates from the inside out, starting with their WHY: "With everything we do, we aim to challenge the status quo. We aim to think differently. Our products are user friendly, beautifully designed, and easy to use. We just happen to make great computers. Want to buy one?"
The second version is more compelling because it starts with WHY - a purpose or belief. The products (WHAT Apple makes) serve as tangible proof of the WHY. For people who share those beliefs, Apple products become a symbol of their own values and desires.
Section: 1, Chapter: 3
Book: Start with Why
Author: Simon Sinek
Small Batches Yield Big Benefits
Working in smaller batches has surprising benefits. Imagine two projects:
- Project A delivers 100 units all at once at the end of 4 weeks
- Project B delivers 1 unit every day and finishes 100 units in 4 weeks
Both take 4 weeks and deliver 100 units, but Project B has significant advantages:
- You get value from Project B from Day 1 vs waiting 4 weeks
- If a design flaw is discovered, Project B loses 1 unit, Project A loses 100
- Project B gets customer feedback 100 times faster than Project A
The ideal goal is to achieve small batches all the way down to single-piece flow along the entire supply chain.
Section: 3, Chapter: 9
Book: The Lean Startup
Author: Eric Ries
Guidance - The Atomic Building Block Of Management
Radically Candid relationships enable good guidance - praise and criticism that is kind, clear, specific and sincere. Guidance is the "atomic building block" of being a good boss. To be successful:
- Bosses have to want to give guidance
- Bosses have to be able to give it effectively
- Employees have to be eager to receive guidance
If any of these three are missing, an organization will collapse.
The chapter explores how to get guidance as a boss, give it to your employees, and encourage it across the whole team.
Section: 1, Chapter: 2
Book: Radical Candor
Author: Kim Malone Scott
Vanity Metrics vs Actionable Metrics
Vanity metrics are dangerous because they give a rosy picture of the business, even if no real progress is being made. Examples include total registered users, raw pageviews, and number of downloads. These metrics tend to go "up and to the right" regardless of the actual business performance.
Actionable metrics, on the other hand, clearly demonstrate cause and effect. They focus on the parts of the product customers interact with and tie them to business results. If a change is made to the product, an actionable metric will immediately reflect any positive or negative impact. Actionable metrics are the foundation for learning what's working and what's not.
Section: 2, Chapter: 7
Book: The Lean Startup
Author: Eric Ries
Value vs Waste
In manufacturing, value is providing benefit to the customer; anything else is waste. But in a startup, who the customer is and what they might find valuable are unknown, part of the uncertainty of a new venture.
Ries came to realize they needed a new definition of value: The real progress they made was the discovery of what creates value for customers. Anything they did that did not contribute to their learning was a form of waste. Could they have learned the same things with less effort? The answer is yes. Unnecessary features, chasing the wrong metrics, delays in getting feedback from customers - all these are waste.
Section: 1, Chapter: 3
Book: The Lean Startup
Author: Eric Ries
Hire Managers Of One
"Managers of one are people who come up with their own goals and execute them. They don't need heavy direction. They don't need daily check-ins. They do what a manager would do - set the tone, assign items, determine what needs to get done, etc. - but they do it by themselves and for themselves."
Section: 1, Chapter: 9
Book: Rework
Author: Jason Fried, David Heinemeier Hansson
The Daily O&I Briefing as an Adaptability Engine
The Task Force's daily Operations & Intelligence (O&I) briefing became the key mechanism for driving transparency and pushing decision-making down.
Key aspects included:
- Broad participation across units and ranks via technology
- Conversational format encouraging questions and debate
- Focus on surfacing diverse views vs. formal presentations
- Senior leader modeling of curiosity and humility vs. asserting rank
- Tying individual updates to whole-system view of the mission
Over time, the O&I created a shared consciousness, empowered frontline troops to make quick decisions, and fostered a "we're in this together" ethos.
Section: 1, Chapter: 8
Book: Team of Teams
Author: Stanley McChrystal
Speaking With Clarity And Authenticity
For a WHY to have impact, it must be communicated with clarity and authenticity. An organization amplifies its WHY through everything it says and does.
Walmart lost sight of Sam Walton's original WHY of service to people and community as it grew. Its actions (WHAT) no longer matched its intended purpose (WHY), and scandals and poor treatment of employees ensued. Virgin Atlantic, on the other hand, maintains a clarity of purpose that shines through in every product and customer touchpoint. Stunts like Richard Branson driving a tank down 5th Avenue work because they align with Virgin's WHY of shaking up established industries.
If your WHAT doesn't match your WHY, your message will be muddy and inauthentic. When WHAT and WHY are aligned through a disciplined adherence to HOW, your organization's purpose will come through loud and clear in everything you do.
Section: 4, Chapter: 10
Book: Start with Why
Author: Simon Sinek
The Best Teams Balance Speaking And Listening Equally
Google spent years studying what made some of its teams perform better than others. The key factor was "equality in distribution of conversational turn-taking" - in high-performing groups, members spoke in roughly the same proportion. The worst teams had a few people who dominated while others rarely got a word in. Equally important was "average social sensitivity," the ability to intuit how others felt based on nonverbal cues. Good listeners notice and respond to subtle social signals. The best teams, in short, were the best listeners.
Section: 1, Chapter: 9
Book: You're Not Listening
Author: Kate Murphy
Inspiring Leaders Embody Their Company's WHY
For an organization to maintain its WHY, the leader must embody that belief and keep it at the center of everything they do. Leaders like Steve Jobs at Apple, Bill Gates at Microsoft, Herb Kelleher at Southwest Airlines - they all served as a personification of their company's WHY.
By staying true to their WHY in every decision and communication, these leaders provided a constant reminder to everyone inside and outside the organization of WHY the company exists. They inspired by example, not just by words alone.
However, when a leader departs, it can create a dangerous vacuum if the company has not codified its WHY beyond just the leader. The key is to ingrain the WHY into every level of the organization, so the mission lives on beyond any single leader.
Section: 4, Chapter: 8
Book: Start with Why
Author: Simon Sinek
Trust and Purpose Allow Teams to Handle Complexity
For small teams to handle complex environments, they need two things:
- Trust: Faith in each other's reliability and commitment, often forged through shared experience and allowing autonomous action
- Common Purpose: A deep, shared understanding of the team's goals and context, so choices align without explicit coordination
When both are present, remarkable "emergent intelligence" is possible, with the team able to creatively solve problems no leader could have foreseen. But building this trust and purpose takes extensive, focused effort - it can't be shortcut. And without them, autonomy fails.
Section: 1, Chapter: 5
Book: Team of Teams
Author: Stanley McChrystal
Intellectual Humility In The Cockpit
In the 1970s, a series of high-profile plane crashes revealed a disturbing pattern - in many cases, the crash was caused not by mechanical failure or bad weather, but by human error and dysfunction in the cockpit. To address this issue, the NTSB (National Transportation Safety Board) developed a new training protocol called CRM (Crew Resource Management). CRM was designed to break down the communication barriers between pilots and crew:
- Captains were taught to proactively invite input and feedback from their crew, especially in high-stress situations. They practiced using inclusive language like "What do you think?".
- Crews were given explicit permission to challenge the captain's decisions if they had safety concerns. They practiced using assertive language like "I'm not comfortable with that" and "I suggest we consider another option."
- Debriefs focused not just on technical skills but on communication and decision-making processes. Crews were rewarded for admitting mistakes and identifying areas for improvement.
CRM represented a radical shift in mindset for an industry built on strict obedience to authority. It wasn't easy or comfortable for pilots and crews to adopt, but the airline industry's safety record has improved dramatically, with human error accounting for a much smaller share of accidents and incidents.
Section: 2, Chapter: 10
Book: The Culture Code
Author: Daniel Coyle
Balancing Efficiency and Autonomy for Adaptability
Decentralized decision-making can feel chaotic and inefficient compared to centralized control. But in complex environments, some inefficiency is a price worth paying for adaptability. To find the right balance:
- Make information transparent so edge teams have context for smart choices
- Communicate a clear Commander's Intent so subordinates understand the "why"
- Push resources and authority to the edge so frontline teams can act quickly
- Set "boundaries" on autonomy based on risk and competence, not hierarchy
- Focus senior leaders on strategic decisions, not tactical micromanagement
The result is "eyes on, hands off" oversight - leaders who can see what's happening, but trust subordinates to steer the ship.
Section: 1, Chapter: 10
Book: Team of Teams
Author: Stanley McChrystal
Build A Culture Of Winning AND Losing
"It's not enough to create a culture where people love what they do and love the people they work with. If you do all that without achieving results, it's not just pointless, it's dangerous. You'll attract people who are comfortable, not people who want to do something great. On the flip side, if you have a culture where achievement comes at the expense of human connection, you won't get the best results, because fear and loathing don't drive collaboration, creativity, or excellence. The trick is to marry cultural health and business excellence."
Section: 1, Chapter: 8
Book: Radical Candor
Author: Kim Malone Scott
Decisions Are Progress, So Make Lots Of Them
When you put off decisions, they pile up. Unmade decisions accumulate and complicate each other, creating stress and stagnation. The solution is to decide early and often, even when information is incomplete.
Don't treat decisions as permanent. Make the best call you can now with the information you have. You can revisit it later if things change. The important thing is not to sacrifice momentum. Keeping the decision train rolling, even if imperfectly, maintains your pace and morale.
Section: 1, Chapter: 7
Book: Rework
Author: Jason Fried, David Heinemeier Hansson
Product Framing Techniques Align The Team
Product discovery starts by framing the problem to be solved and aligning the team on the approach. Three effective techniques are:
- Opportunity Assessment - Succinctly articulate the target customer, problem, business goals, and success metrics. Have the team review and buy-in.
- Customer Letter - Describe the customer's pain points and the impact the new product will have from their point of view. Include a response from your CEO.
- Startup Canvas - For new products, list your key assumptions about the customer problem, target market, value proposition, solution, revenue model, and competition. Identify the riskiest assumptions to test first.
The key is to align the team on the desired customer and business outcomes before jumping into solutions. Take the time to frame the problem from multiple angles.
Section: 4, Chapter: 35
Book: Inspired
Author: Marty Cagan
Gaining Clarity Of WHY, Discipline Of HOW And Consistency Of WHAT
For an organization to function at its best, The Golden Circle needs to be in balance:
- Clarity of WHY: The WHY must be clearly defined within the organization. It's the leader's responsibility to make sure everyone understands WHY the company exists.
- Discipline of HOW: The guiding principles and values need to be manifested in HOW things are done. Systems, processes, and operations need to be aligned with the WHY.
- Consistency of WHAT: Everything the organization says and does has to prove what it believes. WHAT you do is the proof of WHY - the reason to buy from the company, work for the company, or invest in the company. Authenticity happens when WHAT and WHY are in balance.
Section: 1, Chapter: 5
Book: Start with Why
Author: Simon Sinek
The Origins Of The WHY
An individual or organization's WHY is not something that's created or invented - it's discovered. Your WHY is a product of your upbringing, your influences, your life experience.
Some find their WHY early in life, like the Wright Brothers' belief in flight and Bill Gates' belief in the democratization of computers. Others discover it through the ups and downs of their career journeys and life experience, like Southwest Airlines co-founder Herb Kelleher realizing his passion for championing the common man.
Regardless of when you find it, authenticity to your WHY will always come from looking at the sum total of where you've been and what has shaped you. You can't fake your WHY or try to co-opt someone else's. Authenticity to purpose can only come from an honest examination of the experiences and beliefs that made you who you are.
Section: 6, Chapter: 13
Book: Start with Why
Author: Simon Sinek
You Shouldn't Score 100% on Stretch Goals
When YouTube first deployed OKRs in 2012, they set their product & engineering teams a goal of going from 3 to 5 hours of watch time per monthly active user (MAU). They thought this was the maximum achievable through optimizing the existing experience. But halfway through the year, they were pacing to 6 hours per MAU. The goal was too easy.
Susan Wojcicki, SVP at the time, reflects: "Even in a well-intentioned stretch goal, it can be hard to find the right degree of difficulty. Make it too hard, and people will give up or feel fearful. Too easy, and you'll get tactical progress but not real breakthroughs. I think the 70% rule is about right: if you're consistently scoring 100%, you aren't aiming high enough. But much lower than 70%, and you risk creating a culture of burnout and failure. Of course, you have to consider the context - newer teams that are still developing their OKR muscle may need more achievable goals to build confidence."
Section: 2, Chapter: 14
Book: Measure What Matters
Author: John Doerr
To Lead Adaptable Teams, Focus on Conditions and Context
For leaders looking to build more adaptable teams, the key is to focus on creating the right conditions for success:
- Communicating clear priorities and intent, but avoiding micromanagement
- Making information transparent so teams have context for smart decisions
- Shaping culture and incentives to encourage smart risk-taking and initiative
- "Eyes on, hands off" - monitoring execution, but resisting the urge to jump in
Shifting from hero to gardener means seeing leadership as an ongoing process of enabling, not a series of decisive interventions.
Section: 1, Chapter: 11
Book: Team of Teams
Author: Stanley McChrystal
People Change, So Should Your Management Of Them
An important nuance is that individuals will likely move between gradual and steep growth trajectories over the course of their career as their life circumstances and priorities change.
For example, the author describes having an aspiring Olympic athlete on her team at Google. Right out of college, this woman was training intensely and so wanted a more gradual growth trajectory at work. But a few years later, when her athletic goals changed, her career ambition kicked into high gear and she started seeking much more challenge and growth from her job.
As a manager, you can't put a person into a category of "rock star" or "superstar" and expect them to stay there permanently. Check in frequently, look for signs that priorities are shifting, and adjust your management style accordingly. Be responsive to the individual in front of you, not who they used to be or who you assume they should be.
Section: 1, Chapter: 3
Book: Radical Candor
Author: Kim Malone Scott
Averages Hide Individual Fit
Designing standardized systems around an average person is an alluring but misleading approach. Averages mask the variation between individuals. Whether for cockpits or diets or schools, one-size-fits-all solutions underperform compared to adjustable ones. Adapting to individual diversity, rather than suppressing it, unleashes potential. Don't force conformity to an arbitrary standard - make the system adapt to the person.
Section: 1, Chapter: 6
Book: Rebel Ideas
Author: Matthew Syed
The Prisoner's Dilemma and the Need for Trust in Organizations
Even when information is widely shared, people still face incentives to "defect" rather than cooperate. In the classic game theory scenario of the Prisoner's Dilemma, two crime suspects are better off collectively if they stay silent, but as individuals they're tempted to betray each other for shorter sentences.
The same dynamics play out in organizations under pressure - without trust, people hoard resources, fail to coordinate, and make choices that hurt the overall mission. Building trust, so that people instinctively cooperate instead of defect, is key to organizational effectiveness.
Section: 1, Chapter: 9
Book: Team of Teams
Author: Stanley McChrystal
Sustaining vs Disruptive Technologies
Technological advancements can be categorized as either sustaining or disruptive. Sustaining technologies enhance the performance of existing products, aligning with the values of established markets and customers. Disruptive technologies, however, introduce products with inferior performance initially, often targeting niche markets with different values.
Despite possessing the capabilities for innovation and execution, well-managed companies often falter when faced with disruptive technological changes. Their downfall can be attributed to their adherence to conventional management principles that prioritize customer demands and invest in sustaining technologies, neglecting the potential of disruptive innovations.
Section: 1, Chapter: 1
Book: The Innovator's Dilemma
Author: Clayton M. Christensen
Break Big Time Frames Into Tiny Intervals
Estimates, especially long-term ones, are always wrong. The solution is to break big tasks and time frames into the smallest possible units. Instead of one 12-week project, frame it as 12 one-week projects.
By planning one week at a time, your estimates get more realistic. Your assumptions are regularly tested. You avoid investing heavily into plans that prove misguided later. When timeframes or tasks prove bigger than expected, you can adjust tactically without derailing the whole project.
Section: 1, Chapter: 5
Book: Rework
Author: Jason Fried, David Heinemeier Hansson
Achievement Versus Success
There is an important distinction between achievement and success:
- Achievement is about hitting a goal, milestone, metric. It's focused on WHAT you attain or accomplish.
- Success is a feeling or state of being. It's about WHY you do what you do and feeling fulfilled by it.
Many high achieving people are surprised to realize they don't feel successful despite their outward accomplishments. That's because achievement alone doesn't satisfy our deeper desire for meaning and purpose.
Achievement comes from pursuing and attaining WHAT you want. Success comes from clearly knowing and staying true to WHY you want it. Organizations that drift away from their WHY may continue to achieve, but they will cease to inspire the success that comes from a clarity of purpose.
Section: 5, Chapter: 11
Book: Start with Why
Author: Simon Sinek
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