The Paradox of Growth: Why Great Companies Need Imperfect Leaders
Greatness has nothing to do with perfection.
I used to believe that being a great CEO meant being flawless. I chased perfection relentlessly, convinced that any mistake would undermine my leadership.
I’m glad I was wrong.
Here’s the truth I’ve discovered: Great leaders are powerful precisely because they’re imperfect.
Let me show you the difference:
The “Perfect Leader” operates out of fear.
Obsessed with control, they push perfectionism into every corner of the company. This leads to micromanagement, fear of delegation, and avoiding healthy risks. Instead of thriving, their companies stagnate. They build inflexible and inefficient companies.
The Imperfect Leader embraces flaws.
They recognize their strengths and lean on their team to fill in the gaps. By prioritizing trust, experimentation, and reflection, these leaders build companies that adapt, innovate, and grow.
I know better than anyone how hard it is to let go of perfection. Trusting yourself - and your team - takes courage. But when you do, real growth follows.
Today we’ll explore how to take that essential leap.
Perfection Creates Anxiety, Not Confidence
I once believed perfection would shield me from anxiety and failure. In reality, it amplified both.
When building my first business, I remember the enormous pressure of it. I started to default to a “battle-ready” approach. Rather than empowering my team, I sought control in every corner.
My worth became dangerously entangled in the company’s success. Every setback felt personal and huge.
Worse, my battle with perfection spread to the company.
It felt like everything could fall apart, so I hung on tight. I wanted to control everything, so I didn’t trust my team with anything.
I was exhausted. My team was demoralized. And my company had stalled. The harder I tried to be perfect, the farther away I got from control.
My perfection, not my imperfection, was my biggest liability.
Here’s what perfectionism can look like in leaders:
Avoiding delegation because mistakes feel personal.
Micromanaging instead of building effective systems.
Choosing safety over growth.
Becoming a bottleneck by failing to trust others.
Letting Go: The Turning Point
Letting go of perfection doesn’t happen overnight, it’s a disciplined practice.
It starts with recognizing perfectionism’s impact. Which of the symptoms above do you resonate with?
Overcoming perfectionism requires action across three areas: yourself, your team, and your entire company.
Yourself
Separate Your Worth from Business Success: When your identity is tied to your business, setbacks feel personal. Create space between who you are and your business outcomes. Mistakes become lessons, not existential threats.
Build Resilience: Every morning, list your wins and progress, no matter how small. It trains your mind to focus on growth rather than perfection.
Create a Mistake Log: Track your “failures,” how you overcame them, and what you learned. This log serves as tangible proof that setbacks aren’t fatal - they’re opportunities.
Your Team
Delegate Regularly: Start small. Delegate one task per week, then increase the number as your comfort grows. Each delegated task builds trust and empowers your team.
Make Explicit Agreements: Create clear, explicit agreements with your team about decision-making. I might give a team member 51% decision-making power, but with the agreement that (1) if anything goes wrong, they come to me immediately and (2) I get to veto anything that doesn’t align with company values or goals.
Implement Weekly Updates: I like team members to send me an end of week update that highlights what’s top of mind for them, along with anything blocking their progress. This prevents micromanagement throughout the week and builds trust.
Your Company
Perfect companies are rigid; great companies are resilient and adaptable.
Build Your Risk Muscle: Perfectionism stops us from taking any risk, even the necessary ones. Categorize potential risks as low, medium, and high. Celebrate both success and failure to normalize innovation.
Strategic Thinking Time: Schedule 30 minutes each week for strategic reflection without judgment. Give yourself permission to think freely and openly - imperfections welcome.
The Real Perfection: Trust
Trying too hard to let go of perfection can itself become another perfectionist trap. Remember, this process will feel messy - and that's exactly right.
One of the values I include in my User Manual in working with me is that I am human first and CEO last.
Rather than striving for perfection, I strive for excellence. I want to do the best work of my life, and I want to do that with people who want that, too.
Perfectionism isolates. Trust builds community. A team that trusts is confident, innovative, and collaborative. Greatness emerges not from individual perfection, but collective strength.
When you stop micromanaging and worrying, you finally have the time to do what you’re great at - leading.
This is the cycle you want to be in.
Putting It All Together
Imperfect leaders build extraordinary companies. They scale faster, innovate more boldly, and foster teams that drive sustainable growth.
When you embrace imperfection, you create:
Space for creativity
Empowered, confident teams
Better decisions and stronger strategy
Resilience across your company
Only by letting go of your need to be perfect can you build something truly exceptional.
See you next week! 👑
Looking For More In-Depth Help?
Here's four ways I can help you:
⚫️ The 20 Hour CEO: Two-week live cohort where you'll learn how to scale yourself and your business, with 1:1 coaching from me. I share my exact methods, playbooks, and actionable strategies for building 3 businesses to $200M. Limited spots - join waitlist.
⚫️ The 20 Hour CEO Video Replay: Created for greater accessibility, this is the exact same course without the 1:1 coaching or community. You'll get instant access to all the video replays, templates, frameworks, and playbooks included in the live course.
⚫️ The CEO Delegation Mastery: Learn how to make delegating your superpower. Master how to work with an executive assistant to create leverage in both your business and personal life. You’ll get instant access to my systems, templates, and frameworks to become a delegating Jedi.
⚫️ CEO Coaching: Private coaching for early and growth-stage entrepreneurs who want to lead more effectively while increasing their resiliency. See if we're a good fit here.
Special thanks to Julie Rogers for help editing this piece.