Are You Still the Right CEO for Your Business?

In This Article: I tackle the tough question every founder faces sooner or later: are you still the right CEO to scale your company? We’ll explore the Founder’s Paradox, where your greatest strengths can become your biggest obstacles, and introduce the “Five Mirrors”, a framework for honest self-assessment. Discover whether your path forward is reinvention or a thoughtfully planned succession.

The market has never been more demanding of its leaders. In 2024 alone, a record number of CEOs departed their roles in less than three years. I don’t see this as a story about failure. On the contrary, it’s a clear signal that the playbook that got a company to where it is today is rarely the one that will get it to its future. The pressure is immense, and the timeline to prove yourself is shrinking. For founders, this reality hits even harder.

This brings us to a question every founder hits at some point, but not every founder has the courage to ask: Am I still the best person to lead this version of the business?

The Founder’s Paradox

The very traits that make you a brilliant founder can become the primary obstacles to scaling your business. I’ve seen it time and again in my 20 years of coaching executives. That intense, single-minded focus on the product that got you off the ground can make it difficult to transition your focus to managing the people who now manage the product. That fierce loyalty to your founding team can make it painful to admit when the company’s needs have outgrown their skills.

The paradox is this: your greatest strengths as a builder can become your biggest challenges as a scaler. As the company grows, the CEO’s job fundamentally shifts from doing the work to leading the people who do the work. It’s a role you may not be equipped for, may not enjoy, and which may ultimately be holding your company back.

The Five Mirrors: A Framework for Honest Self-Assessment

If you’re feeling this tension, it’s probably time to take an honest look in the mirror. Here are five reflections I ask my clients to consider. I think of them as the canary in the coal mine indicators for identifying that it may be time for a leadership evolution.

1. The Focus Shift: Is your primary role now centered on operational efficiency, financial discipline, and structured processes rather than the high-growth innovation you love? If you find yourself disengaged from or struggling with the demands of a more mature organization, that’s a sign the role has outgrown your passion.
2. The Boardroom Shift: Are your investors or board members subtly – or perhaps openly – pushing for leadership changes? This probably isn’t personal; it’s often pattern recognition. Boards are increasingly seeking to de-risk the next phase of growth. In fact, a 2024 analysis showed that the share of externally hired CEOs surged to 44% among S&P 1500 companies, with that number jumping to an incredible 58% for mid-cap firms. The market is actively voting for proven scalers.
3. The Energy Shift: Are you feeling burnt out? Do you find yourself pulled away from the parts of the business that give you energy and bogged down by the parts you endure, like HR management or regulatory compliance? When your passion fades, it’s a clear signal that your role needs to be redefined.
4. The Skills Gap: Does scaling the company require specific expertise you simply don’t have? This could be experience in global expansion, complex mergers and acquisitions, or sophisticated financial structuring. No one is an expert in everything. The key is to know what the business needs and when you are not the one to provide it.
5. The Growth Ceiling: Has your leadership style become a bottleneck? Signs of this can include high employee turnover, difficulty attracting top-tier senior executive talent, or persistent internal conflicts that are hindering strategic decisions.

Your Strategic Crossroads: Reinvention or Succession?

Seeing yourself in these mirrors isn’t failure. It’s maturity. It’s the ultimate act of putting the business first. This moment is a strategic crossroads, presenting you with two powerful paths forward: reinvention or succession.

For some, the answer is reinvention – a conscious effort to upgrade your skills and leadership style to meet the new demands. This is where targeted executive 1-to-1 coaching can help you evolve into the leader the company needs for its next chapter. Others find a peer advisory setting like what I do though Vistage more ideal. As Vistage members, leaders can present their raw, unfiltered challenges to a group of non-competitive executives who have faced similar battles. This gives space and opportunity to learn from one another and build up each other based on shared experiences and visions. For others, the answer is succession – thoughtfully planning a transition to a new leader while you move into a role that better suits your strengths, like Executive Chairman. A well-crafted exit strategy can ensure this transition maximizes the value of what you’ve built. It’s something I’ve written about a lot and I’d love to tell you more about how much of an impact is has had on the CEO’s I’ve worked with.

You owe it to the company you built – and to yourself – to answer this question with clarity and confidence. You don’t have to do it alone. An objective view, culled from over 20 years of experience, can make all the difference.

Schedule a complimentary, confidential consultation with me today and let’s map out your next chapter.

Frequently Asked Questions for Identifying Whether You’re Still The Right CEO for Your Business

Q: What are the key signs a founder should step down as CEO?
A: A founder should consider transitioning their role when the company’s needs shift from innovation-led growth to operational efficiency. Key signs include feeling personally burnt out or disengaged, recognizing that scaling requires expertise they don’t possess (like in global expansion or M&A), persistent pressure from the board for more experienced leadership, and evidence that the founder’s leadership style has become a bottleneck to growth, often seen in high employee turnover or an inability to attract top executive talent.

Q: Is a founder-led company more successful?
A: Research shows that founder-led companies can significantly outperform their peers. One study of Fortune 500 companies found a median cumulative return of 1,129% for founder-led businesses, versus just 57% for those with non-founder managers. However, this success is highly dependent on the company’s stage. A founder’s vision is invaluable early on, but as a company scales, the required skill set often shifts toward professional management and operational expertise that a professional CEO may be better equipped to provide.

Q: How can a founder CEO successfully evolve as their company grows
A: A founder CEO can evolve by strategically shifting their role from being the primary “doer” to becoming the chief visionary and culture-keeper. This requires mastering delegation, empowering a trusted leadership team, and establishing clear decision-making frameworks to avoid becoming a bottleneck. The founder’s focus must move from the daily details of execution toward high-level strategy, long-term innovation, and talent development. This is a significant challenge that often requires self-awareness and the support of an objective third party, like an executive coach, to build the necessary leadership capabilities.

Q: For a CEO who isn’t a tech expert, what’s a simple way to start using AI for strategy?
A: Start by focusing on questions, not technology. Begin by asking your data or analytics team one predictive question per week. Instead of asking “What were our sales last month?” (historical), ask “Based on current trends, what customer segment is most likely to churn in the next 90 days?” (predictive). This shifts the team’s focus toward future-oriented insights and trains the CEO to think like a strategist using AI, without needing to understand the underlying code or algorithms.