82 essays
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- The 18-Month Rule and the Small Business Problem
I talk about this so often in coaching that I sometimes forget whether I ever wrote it down. I don’t think I have, so here goes… The 18-Month Rule Yesterday I asked a founder whether we
- The Three Confidences of a Volunteer
A volunteer is a leader who does the work only because it is Right (for the customer, for the team, and for the world) and who could walk away tomorrow without fear.
- Locate Yourself: The Path to AI Native
In May I helped a major medtech company jumpstart its internal AI efforts. In the process I came up with a way of thinking about the journey a company takes to fully embrace AI. I keep
- Hiring First. Everything Else Second.
Excellence in organizations starts and ends with hiring. Most leaders agree in principle. Very few behave as though they believe it.
- Load-Bearing Terms
Effective leaders master the skill of choosing memorable terms, defining them precisely, and using them with unreasonable consistency. I call these load-bearing terms: words and phrases that hold up part of the structure. Remove one and something falls down.
- No-Look Coding and the Five Stages of Grief
This week the argument found a name. Uncle Bob Martin, who started coding in the late 60s and wrote the book on clean code, posted that his current strategy is to not read any of the
- The Most Dangerous Lie In Project Plans: “We’ll Hire”
If you want help writing a 5Ps, use the 5Ps app. It’s a prompt you paste into an agent. It writes a first draft and revises it.
- You Are Behind in Using AI. Here’s How to Catch Up
Updated July 2026. The original March version of this post is below, revised. The biggest changes: my credentials for giving this advice got stronger (I stopped reading the code entirely; see No-Look Coding and the Five Stages
- Program: You Keep Using that Word, I Don’t Think You Know What it Means
I’ve heard “program” used to mean everything from a team to a project plan to a portfolio to lines of code. At some point, someone has to stop and say: you keep using that word—I don’t
- Mechanisms In Action: How Tech Giants Scale “Good Intentions”
Mechanisms are complete processes—owned by a leader, built around a tool or ritual, broadly adopted, and continually inspected and improved—that make the right behavior the default. Rather than hoping people do the right thing, great leaders engineer processes that guarantee it.
- Leading by Fitness Functions
You don’t scale excellence by inspecting outcomes—you scale it by designing systems that send the right signals. These are called Fitness Functions.
- The Secret to Giving Feedback Without Triggering Defensiveness
The right kind of feedback can transform teams, while the wrong kind erodes trust and performance. SBI, which stands for Situation–Behavior–Impact, is a structured way to give feedback that’s clear, non-defensive, and actionable.
- Your Leadership Priorities Are Probably Backwards (And How to Fix Them)
Here’s a simple yet powerful exercise, the CBTO Stack Rank, designed to force you into uncomfortable clarity about where you really stand as a leader.
- Your Org Is Sinking in Silo Gravity. Build a Damn Rocket
Organizational Silos Are Like Gravity. You Don’t Hope Them Away. You can’t culture-doc them into nonexistence. You Engineer Around Them.
- Exorcise the Ghost of Mediocrity
Every great org starts the same way: a handful of people with conviction, urgency, and the energy of a shared mission. The best ones are driven by clarity of purpose, crisp principles, and a team that
- How We Scaled Alexa: One Problem, One Leader
The Single-Threaded Leader (STL) model was born inside Amazon and became foundational to how we scaled and delivered customer-obsessed innovation—especially in the early years of Alexa. I wrote the original doc that helped crystalize the model,
- People Management Is Not a Hobby
There are three states a leader can be in relative to people management: 🔧 The Builder This is the Individual Contributor (IC) track. Builders go deep on the T, C, and B parts of Customer, Business,
- The First Rule of Skills
The first rule of skills is simple: know the skill exists. That sounds obvious, but most people—especially growing leaders—aren’t intentional about skills. They focus on outcomes. Goals. KPIs. But they don’t stop to ask: What specific
- Send in the Wolfes: Why Hard Problems Need Fixers, Not Just Leaders
When an organization hits a wall (be it a product failing in the field, a critical project slipping off the rails, or a big customer walking away) the knee-jerk reaction is often to lean on the
- Stop Answering the Wrong Question: Unlock Your True Work Happiness
Let’s start with a simple question: What kind of work do you like doing? Go ahead, answer it in your head. I’ll wait. … Did you just describe what you like working on? Or who you like working with? Or maybe
- How To: Write a Working Backwards Doc
This post introduces the concept of Working Backward (WB) narratives and formalizes the mechanism through which a company can drive product development. The WB mechanism is a complete process designed to create a “virtuous cycle” that
- No Starving Children? The Shocking Truth About Prioritization.
Prioritization means making decisions that focus energy and resources on a few things that are at the top of the list, and starving things that are lower in the list. The most important aspect of prioritization
- Don’t Sell Ideas – Debate Them
The practice of selling ideas in meetings can lead to misalignment and superficial agreement. When the focus is on persuasion rather than understanding, team members may agree without fully grasping the implications or having their concerns
- The Secret to Delivering Outsized Results
In 35+ years of building companies and organizations in multiple industries, I’ve concluded most leadership books are great examples of survivorship bias. I’ve learned a lot from many of these books. But none of them really
- Biases and Fallacies Lead to Smol Thinking
All human beings are prone to cognitive biases and fallacies that influence our thinking and decision-making processes. These biases and fallacies can be sneaky and hard to detect, but it’s important that we are aware of
- Engineer the Sh*t out of Errors – Everywhere
Errors. They’re everywhere, but they don’t have to spell disaster. In fact, they’re an opportunity for improvement, if you Engineer the Sh*it out of them. By everywhere, I mean in all functions of a company, not
- Make the Routine, Routine – Blow up Dunbar’s Number
As fast-growing organizations approach Dumbar’s number, they either become forever mediocre or they adapt and become excellent at scaling (in addition to being excellent at delivering customer value). The key differentiator is making the routine, routine by implementing cadence-based mechanisms, which I call Routines.
- Breaking Down Innovation & Invention
A friend recently asked me if I had a Lexicon & Taxonomy for Innovation and Invention. While I do, I realized I’ve never written it down. Here’s my first stab; using the Customer, Business, Organization, and
- Be A Volunteer
Once you get to the point in your career where you realize a) you’ll be just fine financially (because your resume kicks ass), b) your company doesn’t give a sh*t about you, and c) you know what the Right Thing to do is, act like a volunteer.
- Virtuous Cycles, Platforms, Flywheels, Snowballs, and Tidal Waves
I’m working on writing down my thoughts on space. I’ve learned a ton since deciding space would be my next mission. Some pretty clear thoughts are forming, and whenever that happens, I’ve trained myself to write,
- Find the Crux by Debating Excellence
No, don’t debate excellence; become excellent at debating. “It is better to debate a decision without settling it than settling a decision without debating it.” – Joseph Joubert Vigorous debate is critical to clear thinking in
- How to be a Secret Agent (of Change)
Great leaders don’t let changes happen to them. Instead, they become skilled at driving change. Leaders effective in driving change are known as agents of change or change agents. This post documents a tool called D x V x F > R that will enable you to become a great agent of change.
- Do Your Job – Don’t Use Placeholder Text
If you are a UX designer, Software Developer, or Product Manager, and you use placeholder text anywhere but where it’s impossible to know what the content will be (user supplied) then you are doing it wrong.
- Broken Windows – Right Idea, Bad Analogy
It is well understood that no product is perfect and small issues will always exist. Without an ongoing mechanism to fix those issues, not only do they not get fixed, they pile up. Having a clear
- Mechanisms
Mechanisms are complete processes built around a tool, owned by a leader that gets adopted broadly and regularly inspected and improved to ensure things get done, not because everyone has good intentions, but because the mechanism’s elements structurally force the desired behavior. “Good intentions never
- Path To Green
A Path To Green (PTG) is a clear, crisp, and complete statement describing a team’s plan for getting a project or task from red or yellow status to green. Organizations that routinely deliver results on time hold
- Tenets
Tenets are a few carefully articulated guiding principles for any endeavor. They act as a guide to align on a vision and simplify decision-making. Tenets are the written-down rules that distinguish good behavior from behavior that
- Work Backwards From The Customer
At the 1996 Microsoft Professional Developer Conference (PDC) I stood up in front of 8,000 customers and announced what I’d been working on for the previous two years: the Distributed Component Object Model (DCOM). On stage, in front of
- Have Specific Conversations, not General Conversations
If you are discussing a topic with colleagues, it’s almost always better to have a specific conversation instead of a general conversation. General Conversation Specific Conversation “We need to figure out how to scrub all open
- Taxonomy and Lexicon
How many times have you been in a heated discussion only to find out that the two sides were talking past each other because they were reading from two different dictionaries? I bet you can also
- One-Way and Two-Way Doors
Effective decision-making starts with understanding; in the long-term, very, very few things actually matter. The vast majority of the decisions made day-to-day are either minutia or easily reversible and can be made quickly. However, a small number
- Mental Models
A secret to clear thinking and decision-making is to learn, invent, and adopt mental models. You’ve probably noticed effective leaders can frame complex ideas simply. They’ll lead conversations like this: “Well, I think there are three
- Lead Without Authority
There are two forms of influence in the world: Influence by authority Influence without authority When a ‘boss’ (a manager or someone with a big title) attempts to influence change or drive action using only their
- Focusing on users is not Customer Obsession
Let’s talk Customer Obsession and how it is different than user obsession. My definitions: Customer: An individual (or entity) that pays you, directly or indirectly, for value you provide. User: An individual that is forced to use something
- Debate Tenets
I’ve long thought having a set of guiding principles for any project is important (see my blog post “the 5Ps”; Purpose, Principles, Priorities, People, Plan). At Amazon I learned there was a synonym to the word principle: Tenet.
- The Tension is Intentional
It is no accident many of the Amazon Leadership Principles seemingly contradict each other: they were carefully selected and crafted to encourage leaders to be thoughtful about the gray area. Bias for Action vs. Think Big
- Good Intentions are Never Enough
Everyone has good intentions… Everyone WANTS to do the right thing. But good intentions are never enough. Stuff doesn’t get done based solely on people’s good intentions. Change can’t happen based only on good intentions. What
- Have Strong Opinions, Weakly Held
The Are right, A Lot Amazon Leadership Principle reads: Leaders are right a lot. They have strong business judgment and good instincts. They seek diverse perspectives and work to disconfirm their beliefs. A great mnemonic for
- Everyone’s a Leader
The word leader is not a synonym for manager. Everyone can be a leader. Leader is defined as: leader noun a person or thing that leads. It’s entirely possible for a people manager to be a
- Have a Plan (With Dates)
I’ve written a lot on the importance of having a plan. This week’s Leadership Principle tip doubles-down on that. Consider a status update: Bad: “The team will investigate the issue.” Good: “The team will complete the
- How Meeting/Not-Meeting Goals relates to Earn Trust and Insist on Highest Standards
This week’s Leadership Principle tip is about how setting goals, and holding yourself accountable, relates to Earn Trust and Insist on Highest Standards.
- Dive Deep != Micromanaging
You’ve said it. You’ve heard others say it. You are not quite sure how you feel about it. “So-and-so is a micro-manager. He/she’s always in my shorts and doesn’t let me just do my job.” This
- Just Right Porridge and Leadership Principles
Last week I wrote about Have Backbone, Disagree and Commit. This week the topic is about how to get the balance right when living Leadership Principles. Just as it is possible to not live a leadership
- Have Backbone, Disagree and Commit
Have Backbone, Disagree and Commit Leaders are obligated to respectfully challenge decisions when they disagree, even when doing so is uncomfortable or exhausting. Leaders have conviction and are tenacious. They do not compromise for the sake
- A FAQ About Frequently Asked Questions
A list of questions with answers written in English are a great way to drive clear thinking on all the stuff that surround the central idea presented in a narrative. This ‘stuff’ includes things like strategy, execution, technology, business, and resources.
- Tools to Achieve Clarity of Thought
This post is an inventory of tools I use to drive clear thinking. I update it regularly as I learn new tools, or gain new insights about existing tools as I use them. I am available
- Ownership
Organizations thrive when leaders think like owners—not just of their teams, but of the whole company and its customers. Yet, many mistake ownership for simply crushing their individual goals. How can you encourage true ownership culture
- Clear Narratives Show Instead of Tell
This is yet-another-post on the topic of Amazon-style “six-page memos,” aka Narratives. This post focuses on the mantra: “Great narratives show, they don’t tell.” When writing things you believe to be facts, ask yourself: How do
- Be a Great Reader
When an organization has a culture where the written word is valued, being a great reader is just as important as being a great writer. Over time, I’ve tried to have a very high-bar for my
- Customer, Business, Technology, Organization (CBTO)
CBTO = Customer + Business + Technology + Organization
- Details Matter in Presenting Narratives
Narratives are written documents used to present clear thinking. Narratives enable readers to quickly understand the author’s ideas in order to drive robust conversations and decisive decision making. Details matter when it comes to printing narratives
- Merit Badges – A Mental Model for Success
The concept of a Merit Badge comes from the Boy Scouts. The idea is that a scout can only earn a particular merit badge (actually a patch that gets sewn onto a vest) by demonstrating mastery
- What it Means to Be Great Product Manager
A Tweetstorm of mine from earlier in the week: https://twitter.com/natbro/timelines/611337333711843330 Piling on a comment @natbro made about PMs: Besides customers, there are two groups of people involved in building tech products: Engineers and everyone else. Only
- Attention is the Currency of Leadership
Great leaders optimize how they spend their attention. They are skilled at turning up the heat to get others to focus their attention on the right things at the right times. Attention is the currency of
- Find Work That Does Not Feel Like Work
The first thing I ask people who are looking for a new job is “What work do you want to do in your ideal job?” It is interesting how few people answer this question. Almost everybody
- Have a Plan
Yesterday someone asked me to share my thoughts on the secret to building excellent things. I summarized what I know as: “Put the customer first, have a plan, create a shared mission, get early victories, remove
- Businesses Buy Differently
My post on Why Nobody Can Copy Apple has become one of the most read posts I’ve ever written (thanks @gruber). Commenters are asking me “Can you describe more what the behaviors are that are different
- "Write Once…" is Anti-Customer
Just as in the ’90s, there’s a bunch of hype these days around solving the cross-platform development problem. Mobile platform fragmentation is killing developers, and if only every device supported some common language or technology engine
- Why Nobody Can Copy Apple
Horace Dediu has written another brilliant piece titled “Why doesn’t anybody copy Apple?”. As he points out, Apple is fairly unique in its command of vertical integration and many people point to that as the “why”.
- Don’t Make Your Team Say No To You
Leaders are often visionary “idea people”. The difference between success and failure is how good these leaders are at training their teams to say No. Idea People often forget they are disrupting their own teams by
- Be as Excellent at Saying No as Saying Yes
While in Amman Jordan last month, I had the opportunity to speak at Amman Tech Tuesdays, a local startup event held every month there. I was asked to talk about what I’ve learned in my career
- Apps are Dead. Long Live Experiences.
I like to get people’s attention by asserting “apps are dead”. I do this because it causes people to pause and think about what “apps” really are. After Apple started the app explosion in 2008 most
- Paying Developers is A Bad Idea
The companies that make the most profit are those who build virtuous platform cycles. There are no proof points in history of virtuous platform cycles being created when the platform provider incents developers to target the
- Wanna Compete with Apple? Focus on Experiences.
TL;DR Apple’s insane profitability has the other big guys jealous and freaked out. None are stupid enough to try to compete with Apple on Apple’s terms. The way to beat Apple is to redefine the game
- The Job Decision Matrix
A Job Decision Matrix will help identify what is actually important to you in your career (and life). Gaining clarity on what is important to you, right now, will help you identify new job opportunities, avoid
- Don’t Build APIs…
My first job at Microsoft was providing developer support for the early Windows SDKs. To do my job well, I spent hours studying the Windows SDK documentation, the Windows source code, and writing sample applications. I
- You are Thinking of Your Career Trajectory Wrong
Most people think about their career trajectory as being like a bell-curve or that of a cannon ball fired from a cannon. Something like this: For 99% of all successful people, this is completely the wrong
- Experience = Stuff / Time
The real value in creating new businesses is in delivering customer experiences. The ubiquitous nature of the web, devices, and social networks means successful companies in the future will understand this. The question is “what do
- Brand is a Critical Part of the End-to-End Experience
A commenter on another of my posts asked me to explain further why I think “brand is as much a part of the end-to-end experience as the user interface, device, OS, apps, and services.” I took it
- Be Either an App or a Platform, Not Both
If you think the thing you are building is both an “app” and a “platform” you will fail. Oh, and if you think it’s going to be a just a platform, you will fail too. (Update:
- 90% of the Decisions You Make Don’t Matter
In my post The 5 Ps: Achieving Focus in Any Endeavor, I noted that “90% of the decisions you make don’t matter; real success comes in being able to identify the 10% that do and focus
- The 5Ps: Achieving Focus in Any Endeavor
Always have a plan. Always. A great, simple, framework for any plan is the 5Ps: Purpose, Principles, Priorities, People, and Plan. This framework applies to software development projects, job searches, building a garden, or a phase
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