How to Make Better Decisions as a Founder

One of the harder (and rarely talked about) parts of being a founder is this: No matter how thoughtful, experienced, or committed we are, some of our decisions will be wrong.

Not because we’re careless. Not because we’re inexperienced. But because decision-making at the founder level often happens under pressure, with uncertainty or limited information, and without guarantees.

It’s not just about probability. It’s about patterns — in how we think, how we feel, how we react (especially when the stakes are high). It’s about what remains invisible to us as we work inside complex, fast-moving systems where every choice we make affects people, culture, capital, and time.

For most of the founders who fail, it’s not because they lack intelligence, effort, or even ethics. They fail because they don’t truly understand why they make the choices they do. Even though I deeply believe failure is essential to long-term growth, that’s only true if we actually learn from it. Because if we don’t do the work of understanding our own personalities, patterns, and motivations, who will?

Let’s talk about why we make bad choices (in my view, there’s at least four root causes) and explore how we can be better for our own good and for the good of our companies.

4 Reasons Founders Make Bad Choices

The truth is, we all make questionable calls. When you’re juggling decisions related to strategy, relationships, and ethics (often all in the same week), it’s hard not to fumble sometimes. But to understand how to make better choices in the future, we need to understand why we’re making bad choices in the first place.

In my experience, there are four patterns that tend to trip us up the most:

1. The Confidence Trap

I’ve seen this one play out more times than I can count, and to be honest, I’ve lived it, too: You’re smart. You’ve done the research. You’ve built the model. You can see ten moves ahead. And because of that, it becomes dangerously easy to assume you’re right. 

But that’s not clarity. That’s confidence without reflection.

We’ve all been there — seeing what we want to see and jumping to patterns that aren’t really there. We start to mistake our early insights for universal truths and ignore the data that contradicts our vision. And worst of all, we stop asking the hard question: What might I be missing?

This is why we talk so much about Focus Filters. Because clarity doesn’t come from being intelligent — it comes from being anchored. That means having a compelling vision, a set of Forever Agreements, and a defined sense of who you serve, why you exist, and where you’re going. Those things create the context that gives your thinking meaning and direction.
And when you build that kind of clarity into your company, it becomes a lot harder to fool yourself.

2. Lack of Discipline

Most founders I know aren’t short on vision. (That’s what got us here in the first place, right?) We usually have a pretty good sense of where we’re going or where we want to be. The real struggle is doing what needs to be done when the moment arrives.

We know what we should do, but instead of following through, we react — emotionally, impulsively, socially. We rationalize, overcommit, delay hard calls (telling ourselves we’ll circle back later). And before we know it, that clarity we worked so hard to build doesn’t have any traction.

This happens a lot in the early stages, when ambition is high but systems and resources are limited. We confuse energy and momentum with progress. We assume that being inspired is the same thing as being prepared. But building a great company isn’t about one brilliant sprint — it’s about a thousand small things done consistently well, especially when no one’s watching. It requires intentional and consistent energy.

As I’ve said before, occasional brilliance is appealing but unreliable. The founders who build lasting companies show up every day — not just when it’s exciting, but when it’s repetitive, uncomfortable, or dull. That’s how you win the long game.

3. Losing Sight of Your Values

You don’t just wake up and decide to abandon your values. That’s not how it works.

It happens slowly, with one small compromise. And then another. A decision justified because “we’re not ready yet” or “just this once.” And before you know it, the gap between what you say you care about and how your company actually operates starts to widen.

We tell ourselves we’re being flexible, adaptive, realistic — that we’re being pragmatic. But there’s a line we all have to draw between adjusting our strategy and compromising our principles. Because once you’ve crossed it a few times, it gets harder and harder to see where the line was in the first place.

I’ve seen this wreck otherwise promising companies. Cultures that were once built on trust and respect start to fray because they’ve strayed too far from the very values they were built on. And once trust is gone, momentum doesn’t matter anymore.

This is why anchoring your company in clear, consistent Core Values is so critical. And why we emphasize agreements at Ninety. When values are specific, shared, and regularly reinforced, they guide how people act, especially when things get tough.

It isn’t one big decision that pulls you off course — it’s all the small ones you don’t notice. And just like it takes time to drift, it takes time to realign. That means being intentional about the decisions you’re making and whether your actions still reflect what you care about.

4. Low Self-Awareness

This is the one that drives all the others. Because if you don’t know yourself, every other effort starts to unravel. Self-awareness isn’t just knowing what you believe — it’s also having a deep understanding of how you operate.

I’ve seen founders stuck in the same vicious cycle of rinse and repeat. They continue to make the same kinds of hires that don’t work out, get into the same kinds of conflicts, and burn out over and over again for the same reasons. And in most cases, the problem isn’t strategy or execution. It’s that they haven’t done the work of understanding their own patterns.

Without reflection, it’s easy to confuse your instincts with truth. To assume that if something’s not working, the issue is always out there: in the market, in the team, in the product. Not in you.

This isn’t about being hard on yourself. It’s about being honest. Because the things you avoid, the reactions you repeat, the way you show up under pressure — all of that shapes the culture you’re building. And if you don’t see it, you can’t change it.

As founders, our own self-awareness is foundational for building something that lasts. If we’re serious about building great companies, we have to be just as serious about understanding the person building it.

The Path to Better Decision-Making

So how do we move forward, learn from our mistakes, and make different (better) decisions next time?

It starts by asking a different question. Not “How do I make better choices?” but:

How do I build a system where truth, integrity, and clarity shape decisions at every level, even when I’m not in the room?

That’s the real shift — moving from relying on personal performance to building systems that hold up without you. Here are five principles that have helped me build that kind of foundation:

1. Rewire how you think, not just what you know: Reading more books, listening to more podcasts, chasing the next insight — it only makes a difference if you’re changing how you think, decide, and lead as a result. That means upgrading your mental models. Challenging your assumptions. Evolving your worldview. It means surrounding yourself with people who stretch you, not just validate you, and staying relentlessly curious.
2. Build feedback loops: Feedback should be a built-in part of how your company runs. If the people around you are hesitant to tell you the truth, you’re leading blindly (and you have a culture problem). The best founders make space for feedback. They ask hard questions and actually listen to the answers. And when your team is aligned with your vision and Core Values, the feedback gets better (not easier) because your people are just as invested in winning as you are.
3. Turn values into action: When your values don’t shape how you hire, build, and lead, they’re not really values — they’re just words. People watch what you do. If your actions don’t match what you say matters, that disconnect becomes the culture. So make your values clear, refer to them often, and use them as a guide for every decision.
4. Slow down: If you’re always reacting, you’re not leading — you’re just moving. I get it, we often feel pressure as founders to act fast, but speed without direction leads to avoidable mistakes and wasted efforts. The best leaders pause and take a step back to make sure they understand the situation before they commit to a decision. Because once you move, your team follows. So make sure your next move is the right one.
5. Do the inner work: You can’t lead others well if you don’t understand yourself. The patterns you don’t face (triggers, insecurities, overreactions) show up in how you build, how you lead, and how you make decisions. Whatever helps you see yourself more clearly (whether it’s therapy, coaching, meditation, or reflection), do it. Because leaders who truly know themselves build cultures that trust themselves.

What Your Decisions Say About You

Our decisions don’t just move things forward — they define what our companies become. Every call we make influences how our team thinks and how our company operates. And the impact doesn’t stop with us. It echoes through our people, our processes, and our culture.

So when you’re about to make a tough call, slow down and ask:

Is this decision coming from a place of clarity, character, and courage?

You won’t always get it right. No one does. But asking that question, consistently and honestly, is the beginning of better leadership. It’s how you build something that not only works, but endures.

Remember this: Every decision you make leaves a mark. Make sure it’s one you’re proud of.