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Business consultant & CEO advisor Jane Gentry lends her expertise in these articles on strategy and leadership.

Is It Time to Fire Yourself?

A Guide for Mid-Market CEOs

When should a ceo step down?

As CEO of a mid-market business, you’ve taken your business from an idea or a passion to a thriving entity. You have been driving most if not all of the important decisions about the future of the business. But there comes a time in every leader’s journey when they must ask themselves a difficult question: “Is it time to fire myself?”

The thought of stepping back as the CEO can be daunting. It’s not just about relinquishing control; it’s about acknowledging that the organization might benefit from a change in leadership. So, when should a CEO step down?

Recognizing the Signs

1. Stagnation in Innovation

If your company is no longer at the forefront of innovation, it might be a sign that fresh vision is needed. A new leader can bring new perspectives and drive the company forward.

2. Lack of Passion

Passion is contagious, and if yours is waning, it can have a ripple effect throughout the company. Recognize when your heart is no longer in it and consider passing the torch to someone whose passion burns bright.

3. The Company Has Outgrown Your Skillset

It’s not uncommon for a CEO to excel in the startup phase but struggle in the scale-up phase. If the company’s needs have outgrown your expertise, it’s time to step aside for someone with the necessary skills.

4. You’re Resistant to Change

The business world is ever evolving, and adaptability is key. If you find yourself resisting new ideas or technologies, it might be time to let someone else lead the charge.

5. Succession Planning

A good leader always has an eye on the future. If you’ve groomed a successor who is ready to take over, it might be the perfect time to make the transition.

“I knew that to meet our goals of doubling the size of our firm, I would need to bring in someone who could scale and give them the freedom to make decisions that I might not agree with. Letting go of the reigns was challenging, but we are aligned around vision and it is exciting to see how the company is growing."

- CEO, Flooring Company

Making the Decision to step down as CEO

Deciding to step down as CEO is not an admission of failure; it’s an act of courage and self-awareness. It’s about putting the company’s interests above your own. Here are some steps to help you make this critical decision:

Consult with Trusted Advisors

Speak with mentors, board members, and trusted colleagues. They can provide an outside perspective on your performance and the company’s direction.

Reflect on your goals

Consider your personal and professional goals. If they no longer align with the company’s path, it might be time for a change.

Evaluate the Market

Look at the market trends and the competitive landscape. A new CEO might be better equipped to tackle the challenges and opportunities ahead.

Consider the Timing

Timing is crucial. Plan your exit during a stable period to ensure a smooth transition and minimal disruption to the business.

“Our market had begun to change rapidly and I got caught flat footed. I brought in a new President who changed us from an introspective organization to one that was leading innovation.”

- CEO, Media Company

The Transition

Once you’ve made the decision to step down as CEO, it’s important to handle the transition gracefully:

Communicate openly

Be transparent with your team about your decision. This will help ease uncertainty and maintain trust.

Ensure a smooth handover

Work closely with your successor to transfer knowledge and relationships. Your goal should be to set them up for success.

Stay Involved

If appropriate, offer to stay on in an advisory role. Your experience can still be a valuable asset to the company.

Embrace the Future

Look forward to new opportunities. Your journey as a leader doesn’t end here; it simply takes a new direction.

“Having a long-term communication plan in place as we transitioned the new leader was one of the smartest moves I’ve made. Painting a picture for our team as to why the change was necessary, how it would grow our company and what their roles were in our success enabled them to be completely enrolled. We barely missed a step in the transition.”

- CEO, Marketing Agency

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So, When should a ceo step down?

The decision to step back is deeply personal and requires introspection. Remember, leadership is not just about leading; it’s about knowing when to let others lead. For mid-market CEOs, asking “Is it time to fire myself?” is not just a question—it’s a testament to your commitment to the company’s success and your own growth as a leader.

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Meet Jane


Jane Gentry has had a successful 30-year career as a CEO, Business Consultant, Executive Coach, and Keynoter. Jane formed her practice in 1999 and since then has partnered with her clients to improve growth, profitability, client retention, employee retention, leadership capabilities and business value.

Jane leverages strategies including the proprietary Value Blueprint to enable business owners and leaders to successfully create healthy organizations, plan for succession or sell their businesses for the highest possible market value. Jane is considered one of the top voices in leadership and sales.