The best books about building startups aren’t really about startups. They’re about people — how they work together, why they fall apart, and what it takes to lead through the mess.
Here are three that I keep coming back to and recommending to founders. They’re all short reads. They’ll all change how you think about your job.
1. Leadership Without Easy Answers — Ronald Heifetz
This is the book that rewired how I think about leadership. I took Heifetz’s class at the Kennedy School, and his core idea has stuck with me ever since: the hardest leadership problems aren’t technical — they’re adaptive.
Technical problems have known solutions. Someone has the expertise, you apply it, done. Adaptive challenges are different. They require people to change their beliefs, habits, or identity. And that’s where everything gets hard, because change means loss — and people resist loss even when the change is right.
Sound familiar? Every pivot, every reorg, every “we need to rethink our strategy” conversation is an adaptive challenge. Heifetz gives you the framework to understand why your team pushes back even when they intellectually agree with you, and what to do about it.
The key insight: your job as a leader isn’t to have the answers. It’s to manage the rate of change your organization can absorb — enough heat to force progress, not so much that people break. He calls it the “productive zone of disequilibrium.” I call it the most useful idea I’ve ever encountered for running a startup.
Read this if: You’ve ever been frustrated that your team “just won’t get on board” with a decision that seems obviously right.
2. The Five Dysfunctions of a Team — Patrick Lencioni
This one reads like a novel — literally, it’s written as a fable — and you can finish it in an afternoon. Don’t let that fool you. The framework underneath is sharp.
Lencioni lays out five dysfunctions as a pyramid:
- Absence of trust — people won’t be vulnerable with each other
- Fear of conflict — so they avoid honest debate
- Lack of commitment — because without real debate, there’s no real buy-in
- Avoidance of accountability — without commitment, nobody holds anyone to anything
- Inattention to results — and eventually people optimize for themselves, not the team
The pyramid matters because each layer depends on the one below it. You can’t have healthy conflict without trust. You can’t have commitment without conflict. It’s sequential — and most founding teams are stuck at layer one or two without realizing it.
I think about this framework every time I see cofounders who are “nice” to each other in meetings but clearly not aligned. Niceness without trust isn’t harmony — it’s avoidance. And avoidance kills startups slowly, in ways that don’t show up in your metrics until it’s too late.
Read this if: Your founding team “gets along great” but somehow never resolves the hard disagreements.
3. The Hard Thing About Hard Things — Ben Horowitz
If Heifetz gives you the theory and Lencioni gives you the framework, Horowitz gives you the war stories. This book is what it actually feels like to lead a company through near-death experiences — the layoffs, the pivots, the moments where everything is falling apart and you still have to show up on Monday.
What makes this book different from most CEO memoirs is that Horowitz doesn’t sanitize it. He talks about the loneliness, the self-doubt, the physical toll. He’s honest about how many of his decisions were made with incomplete information under extreme pressure — and how that’s not a bug of the job, it’s the job.
Two ideas from this book I think about constantly:
“The Struggle.” Horowitz names the emotional reality of building a company in a way that most startup literature doesn’t. The Struggle is when you wonder why you started the company. When the easy answer is to quit and nobody would blame you. Naming it doesn’t make it easier, but it makes you feel less alone.
Peacetime CEO vs. Wartime CEO. Different situations require fundamentally different leadership styles. Peacetime is about expanding advantages and building culture. Wartime is about survival — and the skills that make you great in one mode can make you terrible in the other. Most founders don’t realize when they’ve crossed from one to the other.
Read this if: You’re in the middle of something hard and need to know that other founders have been there and survived.
How They Connect
These three books aren’t usually grouped together, but I think they form a complete picture:
Heifetz explains why leading people through change is so hard — because change requires loss, and loss triggers resistance. This is the theory of what’s happening beneath the surface.
Lencioni shows you where teams break down — the specific layers of dysfunction that prevent people from doing hard work together. This is the diagnostic tool.
Horowitz shows you what it feels like to lead through it anyway — the emotional reality that no framework fully prepares you for. This is the field guide.
Together, they give you the vocabulary to understand what’s happening in your team, the framework to diagnose where you’re stuck, and the reassurance that the struggle is the job — not a sign you’re doing it wrong.
If you only read one, read Heifetz. If you need motivation to get through next week, read Horowitz. If you think your team is fine but somehow nothing is getting decided, read Lencioni.
Or read all three. They’re short. What books have shaped how you think about leadership? I’d love to hear — drop me a note.