Should You Sell Your Business or Hire a CEO to Run It?

As a business owner, one of the biggest dilemmas you might face is whether to sell your business or hire a CEO to run it for you. It’s a question I’m asked often as someone who works with founders and operators across various industries. The decision is deeply personal, and there’s no universal formula for the “right” choice. However, by asking yourself some critical questions, you can gain clarity on what’s best for you and your business.

Let’s break this down.

Start With You: What Do You Really Want?

The first and most important thing to consider isn’t the business — it’s you. Don’t frame the question as, “What’s best for the business?” Instead, ask yourself, “What’s best for me?”

Your business is just one part of your life. It shouldn’t overshadow everything else that matters — your health, your family, your community, your sense of purpose. Step back and think about what you truly want. Is it freedom to explore new ventures? More time with loved ones? Financial security? Or maybe it’s the challenge and satisfaction of seeing your vision come to life.

Once you know what’s important to you, you’ll be better equipped to make a decision.

The 8 Questions to Guide Your Decision

When considering whether to sell your business or hire a CEO, ask yourself these eight questions. They will help you evaluate your situation from multiple angles.

1. What’s Your Vision for the Business?

Think about the future. Do you want your business to keep growing until it becomes a market leader? Or are you content with its current size and profitability? Your vision will influence your decision.

If your goal is rapid growth or market dominance, hiring a CEO with the skills and experience to scale the business might be the way to go. If you’re satisfied with the status quo, selling could provide a clean exit and allow you to move on.

2. Are You the Right Person to Achieve That Vision?

It’s okay to admit you’re not the best person to lead your business to the next stage. Many founders excel at starting businesses but struggle with scaling them. Running a larger, more complex organization often requires a different skill set.

If you’re better at building than operating, hiring a CEO might make sense. On the other hand, if you feel like you’ve hit your ceiling and don’t want to bring in external leadership, selling could be the better option.

3. What Is Your Risk Tolerance?

Hiring a CEO is inherently risky. You’re trusting someone else to make critical decisions about your business, and there’s always the possibility they might make mistakes or take the company in a direction you don’t agree with.

Selling, while safer in terms of ensuring a payout, is a one-time deal. You lose the potential upside of the business’s future growth. Consider which option aligns better with your tolerance for risk.

4. What’s the Macro Outlook for Your Business?

Assess the external environment. If your industry is booming and your business has strong growth potential, staying involved (even passively) through a hired CEO might be lucrative. However, if headwinds are on the horizon — increased competition, regulatory changes, or declining demand — selling now could save you from future headaches.

Keep in mind that buyers will also evaluate these factors, so a challenging macro environment might affect your business’s valuation.

5. Are You Ready for the Hassle of Selling?

Selling a business isn’t a quick or easy process. It can take months or even years to find the right buyer, negotiate terms, and close the deal. During that time, your attention will be divided, and the business might suffer as a result. The process is also emotionally taxing, as you’ll need to let go of something you’ve worked hard to build.

If you’re not ready for this level of disruption, hiring a CEO might be a more practical option.

6. Can You Truly Be a Passive Owner?

If you hire a CEO, you need to give them the freedom to lead. This means stepping back, trusting their judgment, and avoiding the temptation to micromanage. Many founders struggle with this transition, especially if they’ve been heavily involved in day-to-day operations.

If you can’t resist swooping in or second-guessing their decisions, it’s better to stay as CEO or sell the business outright.

7. Can the Business Survive Without You?

Take an honest look at your business. Is it heavily reliant on your relationships, expertise, or presence? If so, it may not be ready for a CEO or a sale.

Before you consider either option, work on building systems, processes, and a strong management team that can operate independently. A business that runs smoothly without you is more attractive to both buyers and potential CEOs.

8. What’s Most Important to You?

Ultimately, this decision comes down to your priorities. What do you value most? Financial security? Freedom? The thrill of building something new? Your personal goals should be the guiding force behind your choice.

A Practical Example

Let’s say you own a SaaS business generating $3 million in annual revenue. You’re at a crossroads: should you hire a CEO to scale the business further or sell it and move on?

Here’s how the questions might apply:

• Vision: You want the business to grow into a $10 million operation in the next five years.

• Your Role: You’re great at product development but lack interest in managing a larger team.

• Risk Tolerance: You’re comfortable taking calculated risks, but you’re wary of completely trusting someone else with your business.

• Macro Outlook: The SaaS market is expanding, and your product has strong potential.

• Selling Hassle: You’re willing to go through the process if it means a big payday.

• Passive Ownership: You believe you can step back and let a CEO lead, but you’re not entirely sure.

• Business Independence: The business has strong systems in place and isn’t reliant on your daily involvement.

• Priorities: You want to free up time for new projects but still benefit from the business’s growth.

In this scenario, hiring a CEO might be the better choice. However, if the hassle of finding the right CEO and stepping back feels overwhelming, selling could be a simpler option.

The Bottom Line

Deciding whether to sell your business or hire a CEO is deeply personal. There’s no right or wrong answer — only what’s right for you. By reflecting on your vision, strengths, risk tolerance, and priorities, you can make a choice that aligns with your goals and values.

Remember, as a founder, you’ve already proven your ability to create something valuable. Whether you choose to sell or bring in a CEO, trust that you’ll make the best decision for your future.

What do you think? Are you facing this decision right now? Let me know in the comments — I’d love to hear your thoughts.