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Most business owners don’t start out dreaming of becoming a CEO.

It’s a role you grow into—or one you’re thrown into—when the stakes get high and the responsibilities stack up.

In The Leadership Series: An Operator’s Guide, we’re breaking down what it takes to lead well. Today, we’re focusing on the CEO role — the challenges, the mistakes, and what separates good leaders from great ones.

This post is for anyone who’s felt in over their head while running a business.

Leadership doesn’t come with a manual, but mastering the CEO role can transform both your business and your confidence as a leader.

Let’s explore what the role really requires — and how to grow into it.

Why The CEO Role Matters More Than Ever

When I was 19, I started my first business. By 22, I had raised over $1M in capital and was managing a team across multiple states.

I was in over my head — and I didn’t even know it.

I thought I understood what leadership meant. But I didn’t. I micromanaged. Then I over-delegated. I struggled to communicate effectively and failed to inspire confidence.

My impatience drove decisions that should have been carefully considered.

Without a business degree or seasoned mentors, I had to learn the hard way — thrown into the deep end with no choice but to swim.

Slowly, painfully, I improved. Every misstep taught me something new about leadership and what it means to truly step into the role of a CEO.

That’s why I’m writing this post.

I’ve spent years trying to figure this out, and I know I’m not alone.

This article is part of The Leadership Series: An Operator’s Guide, where we break down the qualities that define great leaders and how to develop them in your business. If you missed the last post, Ruthless Prioritization, it’s worth revisiting to see how what you spend time on is one of the most important things you think about as a leader.

The CEO role stands apart.

It’s where operational maturity and leadership collide — your ability to manage this tension defines your success.

The CEO sets the tone. You’re responsible for defining the vision, aligning the team, and driving execution. More importantly, you’re the one making the tough calls — decisions that ripple across your organization and impact the lives of the people who work with you.

If you don’t fully understand the CEO role, you’re likely not playing it well.

You might be too hands-on, too distant, or focusing on the wrong priorities. That misalignment can hold back your team, your growth, and your potential.

In this post, we’ll demystify the CEO role — what it truly entails, how it evolves over time, and the pitfalls many leaders encounter along the way. By the end, you’ll have a clearer understanding of what it takes to lead effectively—whether you’re running a small business or scaling a company. Let’s dive in.

CEO: The Leadership Apex

The CEO role is the pinnacle of leadership. Your responsibilities define the trajectory of your business and the experience of everyone in it. Fred Wilson, in his classic blog post What a CEO Does, distills the role into three essential pillars:

1. Set the vision and strategy. 

   Define the company’s goals and chart the course to achieve them.

2. Recruit, hire, and retain exceptional talent. 

   Build and maintain the team that will execute the vision.

3. Ensure the financial health of the company.

   Without cash in the bank, nothing else matters.

Matt Blumberg, in Startup CEO, expands on these ideas with a more tactical breakdown:

1. Lead by example and hold yourself accountable.

2. Set and clearly communicate vision and strategy.

3. Build and inspire a world-class team.

4. Maintain the financial resources to sustain the company.

5. Advocate for customers while balancing short-term demands.

6. Drive execution and evolve operational systems.

7. Champion the company and its mission externally.

The CEO role extends into the intangible.

You’re the chief decision-maker, managing risk and making calls no one else can. You’re the Chief Evangelist, rallying employees, investors, and customers around your vision. And critically, you’re the cultural architect, shaping values through what you prioritize and tolerate.

In short, the CEO role is more than a job — it’s a craft. And like any craft, it requires continuous refinement to master.

Small Business CEOs: Leader or Just Owner?

Small business owners often feel like they have to do it all — and for a while, that’s true.

You’re the one closing sales, running payroll, and handling customer service all in the same week. But if you stay stuck there, you risk holding your business back.

Here’s the thing:

It’s not about abandoning the trenches — it’s about solving problems at their root and leading with intention.

Here’s how the small business CEO role is unique:

• Operational Involvement: 

  You’re deeply hands-on, giving you unmatched insight into day-to-day operations. Use this vantage point to spot inefficiencies and opportunities, but don’t let it prevent you from thinking strategically.

• Personalized Leadership: 

  Small teams allow for closer relationships with employees. This is a unique advantage — you can directly influence team culture, morale, and alignment.

• Resource Constraints: 

  Limited budgets and smaller teams mean you can’t delegate as freely as a large-company CEO. This makes prioritization and smart decision-making even more critical.

• Transitioning as You Scale: 

  As your business grows, your role must evolve. Build systems and hire leaders so you can focus on strategy and culture.

Even in a small business, you’re still the CEO — and that means you have to do more.

It’s harder, frankly. Sometimes, you’ll need to set the title aside and step into an individual contributor role to keep the wheels turning. But don’t forget: if you’re not leading, no one is.

Two Tips to Lead Like a CEO, Even in the Trenches

1. Schedule CEO Time: 

   Block off 1-2 hours a week to step away from day-to-day operations and think about the bigger picture. Use this time to review goals, identify bottlenecks, and plan for the future. Protect this time as if it were your most important meeting.

2. Delegate in Phases: 

   Start small. Identify one recurring task that drains your time and document the process for it. Assign it to someone on your team with clear expectations. Over time, build on this by handing off more responsibilities as you grow trust and confidence.

Delegation isn’t easy — it’s a skill that takes practice. In fact, it’s such a common challenge for small business owners that we’ll dive deeper into the topic in a future post in The Leadership Series. Stay tuned for actionable advice on how to delegate effectively without losing control.

Your business looks to you for direction. Every decision you make, every action you take, shapes the future of your company. Leadership isn’t just about doing—it’s about deciding what matters most and making sure it happens.

Micromanaging? Over-Delegating? Avoid These CEO Traps

First-time CEOs often fall into predictable traps.

These aren’t failures — they’re part of the learning curve. But the faster you can identify and address them, the sooner you can lead effectively.

Here are the most common pitfalls — and how to fix them:

Micromanaging: Struggling to let go of tasks you’ve always done.

🛠 Fix: Delegate outcomes, not just tasks. Provide clear expectations, support your team, and let them own the results.

Poor Communication: Assuming people understand your vision or priorities without clarity.

🛠 Fix: Over-communicate until you feel repetitive. Clarity is your greatest leadership tool.

Short-Term Thinking: Getting caught up in the day-to-day can blind you to long-term opportunities.

🛠 Fix: Set regular intervals for stepping back, reviewing progress, and planning ahead.

Avoiding Tough Decisions: Postponing difficult conversations or decisions to avoid conflict.

🛠 Fix: Face challenges head-on. Use a decision-making framework, gather input, and act decisively to prevent issues from festering.

Burning Out: Working unsustainable hours and setting an unhealthy example for your team.

🛠 Fix: Prioritize self-care and model work-life balance. A rested leader makes better decisions and inspires a healthier team culture.

Being Too Reactive: Constantly putting out fires instead of proactively planning.

🛠 Fix: Implement a weekly planning process to focus on proactive priorities. Limit distractions by batching reactive tasks like emails or meetings.

Failing to Adapt: Sticking to old strategies or habits despite changing circumstances.

🛠 Fix: Stay curious and open to feedback. Regularly evaluate what’s working, and don’t be afraid to pivot when necessary.

Ignoring Metrics: Leading without a clear understanding of your business’s key performance indicators.

🛠 Fix: Identify 3-5 core metrics that reflect your company’s health. Review them weekly, and use them to guide your decisions.

Every misstep is a chance to refine your craft. Great leadership isn’t about avoiding mistakes — it’s about learning from them quickly.

Conclusion: Leadership Is a Craft

The CEO role demands clarity of vision, decisiveness, and humility to learn from mistakes. Whether you’re leading a small business or a larger organization, your ability to master this role will shape your company’s success.

Reflect on your leadership. Are you thinking strategically, or stuck in the weeds? Are you shaping culture intentionally, or letting it evolve by accident?

Leadership isn’t about titles. It’s about responsibility, action, and growth. By mastering the craft of leadership, you’ll not only build a stronger business—you’ll also become the kind of leader others want to follow.

Want to explore the other posts in The Leadership Series? Find them here.

And stay tuned — we have many more posts in the Leadership Series ahead. Thanks for reading.

That’s a wrap.

That’s it for this week — thanks for following along. I enjoy reader feedback + ideas on what to write about next. Just hit reply.

As always, you can find me here:

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Have a great week ahead 🤙 

Chase Murdock