From Founder to Leader: Overcoming the Inner Doubt That Comes with Growth
Starting a business is one thing—scaling it is another. Many founders thrive in the early days, wearing multiple hats, making fast decisions, and keeping their hands in every part of the business. But as the company grows, so do the pressures, and suddenly, what once felt like instinctive leadership turns into self-doubt.
At Founded Partners, we work with founders who are in this exact transition. They’re no longer just scrappy entrepreneurs; they’re now leading teams, raising capital, and making high-stakes decisions. But with growth comes new fears—Am I the right person to take this company to the next level? Do I have what it takes to manage a larger organization?
I know this because I’ve been there.
The Growth Paradox: Why Success Breeds Self-Doubt
When I was at HEXO through its meteoric rise, I found myself in situations I had never faced before. Running a startup with a small, tight-knit team was one thing. Steering a public company with hundreds of employees, investors, and board members was a completely different game.
At first, it felt like I had control. I knew the product, the strategy, and the market. But as we scaled, decisions became more complex. More people were depending on me. And for the first time, I started questioning whether I was the right leader to carry HEXO forward.
What I didn’t realize at the time is that this self-doubt isn’t just common—it’s a sign of growth. It means you care. It means you’re stepping into new territory, and it’s your brain’s way of trying to keep you safe. But if left unchecked, self-doubt can become crippling, leading to hesitation, second-guessing, and even burnout.
The Psychology of Self-Doubt in Leadership
There are well-documented psychological reasons why founders struggle with self-doubt when transitioning from operator to leader:
Impostor Syndrome – Coined by psychologists Pauline Clance and Suzanne Imes, impostor syndrome is the belief that you’re not actually as competent as others think you are, despite evidence of your success. This is incredibly common among founders who suddenly find themselves leading a larger company.
Cognitive Load Theory – As businesses scale, the sheer volume of decisions increases exponentially. More decisions mean more room for error, and the mental weight of making them can erode confidence.
Transformational Leadership vs. Transactional Leadership – Bernard Bass (1990) identified two leadership styles: transactional (focused on processes, performance, and rewards) and transformational (focused on vision, motivation, and long-term strategy). Founders often excel in the early transactional phase, but transitioning to a transformational leader requires a mindset shift.
How to Overcome Founder Self-Doubt
Here’s the reality: self-doubt never fully disappears. But the best leaders learn how to manage it, work through it, and even use it to their advantage. Here’s what worked for me—and what we advise founders to do at Founded Partners:
1. Reframe Self-Doubt as a Growth Signal
When you start feeling doubt creep in, pause. Ask yourself:
Is this fear a sign that I’m stretching into new territory?
Am I questioning myself because I’m unqualified—or simply because I’ve never done this before?
Recognizing that self-doubt is part of growth helps shift it from an enemy to a signpost that you’re moving forward.
2. Build a Strong Support System
One of the biggest mistakes founders make is thinking they need to figure it all out alone. You don’t.
At HEXO, I leaned heavily on my co-founder, mentors, advisors, and my executive team. Having trusted people to challenge my thinking and validate my instincts was game-changing.
We see this at Founded Partners all the time—founders who bring in outside advisors or peer groups are more confident, make better decisions, and scale faster.
3. Shift from Operator to Leader
Early on, you are the business. Every decision, every product tweak, every customer interaction runs through you. But to scale, you need to empower others.
This means:
- Delegating decisions to trusted team members
- Letting go of perfectionism
- Creating systems instead of being the system
Ed Catmull (2008), co-founder of Pixar, described how he intentionally built a culture of trust so his team could take ownership of creative decisions without him micromanaging.
The best founders learn to do the same.
4. Set Clear Goals for Yourself as a Leader
Goal-Setting Theory (Locke & Latham, 2006) states that clear, specific, and challenging goals lead to higher performance. This applies to founders too.
Instead of just focusing on company goals, ask yourself:
- What kind of leader do I want to be in 12 months?
- What leadership skills do I need to develop?
- What feedback am I getting from my team?
Write these goals down. Track them. Just as you set metrics for your business, set metrics for your growth as a leader.
5. Get Comfortable with "Not Knowing"
The hardest shift for many founders is realizing they don’t need all the answers. Instead of feeling insecure about this, embrace it.
Great leaders ask more questions than they answer. They surround themselves with experts. They make decisions with incomplete information and adjust as needed.
Gary Pisano (2019) argues that true innovation cultures embrace intelligent risk-taking—meaning the best founders aren’t the ones who avoid uncertainty, but the ones who learn to navigate it.
Final Thought: You’re Not Alone in This Transition
Every great founder faces the same question at some point: Am I the right person to scale this business?
If you’re asking this, you’re already ahead of the game. It means you’re thinking critically about your role, your leadership, and your company’s future. The real challenge isn’t eliminating self-doubt—it’s learning how to lead through it.
At Founded Partners, we help founders make this transition smoother, faster, and with more confidence. If you’re feeling the weight of growth, let’s talk. You don’t have to figure this out alone.