This week I found myself having an unusual coaching conversation with an entrepreneur.
Nothing was going wrong.
Quite the opposite.
If things unfold as expected, his business could experience significant growth over the next period. It is the kind of opportunity many entrepreneurs spend years working towards.
We spoke about the opportunity, of course. But our conversation gradually moved somewhere else.
If the business changes significantly over the next few months, what might change for him as its leader?
More customers may mean more people. More people may mean more managers. More revenue can bring more complexity, greater financial exposure and decisions carrying considerably greater consequences.
The business may look very different.
And so might his job.
When the business grows, the leadership job changes
There is a temptation to think of scaling as simply doing more.
More customers. More sales. More staff. More capacity.
But organisational growth research suggests something more complicated happens.
Larry Greiner’s classic work on organisational growth argued that management practices that work effectively during one phase of an organisation’s development can create difficulties as it enters another. Growth doesn’t merely make the existing organisation bigger; it introduces different challenges around leadership, delegation, coordination and control.
The Organisation for Economic Co-operation and Development’s recent work on scaling SMEs makes a similar point from a different perspective. Scaling businesses commonly undergo significant changes in capabilities, structures and the way they operate. Growth and organisational transformation are often intertwined rather than separate events.
Which raises an interesting question for the entrepreneur:
If your business is becoming something different, can you continue leading it in exactly the same way?
That isn’t criticism of what got you here. The way you have led may be precisely why the opportunity now exists. But success can change the context in which that leadership takes place.
The paradox of entrepreneurial success
Noam Wasserman’s research into founder-CEOs gives this idea an uncomfortable edge.
Studying the succession histories of 202 entrepreneurial firms, Wasserman identified what he called the “paradox of entrepreneurial success”. Reaching important business milestones could actually increase the likelihood of the founder being replaced as CEO.
That does not mean successful founders are destined to lose their businesses. It does, however, expose something important.
Creating a successful business and leading the organisation that success creates are not necessarily the same job.
The entrepreneur who once had to be involved in almost everything may find that involvement increasingly difficult to sustain. The person who could personally make most of the important decisions may now have to develop others capable of making them. Informal conversations that once kept everybody aligned may no longer reach everyone. Relationships may become teams. Teams may develop leaders. Decisions may require systems. Culture, previously transmitted simply through proximity to the founder, may have to become far more intentional.
And perhaps hardest of all, the entrepreneur who built their success partly by becoming indispensable may discover that successful scaling asks them to become less indispensable.
What got you here isn’t suddenly wrong
We can easily turn conversations about founder growth into another deficit narrative:
You don’t delegate enough. You’re too operational. You haven’t built enough systems. You need to become more strategic.
Perhaps, but this perspective could also miss something important.
Those behaviours may once have been entirely appropriate. Knowing everything that happened in the business may have been possible when there were eight employees. Personally approving expenditure may have been sensible when cash was scarce. Being involved in every major customer relationship may have helped establish the reputation upon which the business was built. Moving quickly on instinct may have been one of the entrepreneur’s greatest competitive advantages.
The question isn’t necessarily whether those behaviours were wrong. It is whether the context in which they developed is changing.
And, if it is, which behaviours remain valuable, which might require adaptation, and which might eventually have to be released.
Leading consciously through growth
This is where executive coaching can offer something particularly valuable to an entrepreneur approaching rapid growth.
Not because there is a problem to fix. And not because the coach knows how the entrepreneur should run the business.
Rather, coaching creates a confidential space away from the velocity of the business in which the entrepreneur can examine what the emerging reality may ask of them. What might become different if the business doubles? Where could decisions start accumulating? What is the entrepreneur currently carrying that others may have to learn to carry? Where might greater structure protect the business — and where could too much structure destroy something valuable? Which relationships will change? What might their leadership team require from them that the current team doesn’t? What parts of their identity are tied to being the person who knows, fixes, decides or rescues?
And perhaps most importantly:
How might they preserve what made the business successful while allowing both the organisation and themselves to evolve?
These aren’t questions that have a correct answer. They are questions worth exploring before growth answers them on the entrepreneur’s behalf.
Coaching as a developmental partnership
There is growing evidence that coaching has value as a developmental intervention rather than merely a remedial one.
A 2024 pilot study of entrepreneurs who received 5 coaching sessions showed significant improvements in solution-focused thinking, psychological well-being, and progress towards personally chosen coaching objectives..
Perhaps this is where we have historically misunderstood executive coaching.
We often imagine the coach arriving when something has gone wrong. Coaching can certainly support leaders in those circumstances. But why wait?
What is this success calling you to become?
The conversation I had this week was exciting precisely because we weren’t carrying the weight of issues, we could look ahead with clear, uncluttered minds.
We were looking ahead.
There was an opportunity to ask, while things were still going well:
“If the opportunity in front of you becomes reality, who might you be called to become as the leader of that business?”
Not a different person. Not a corporate version of the entrepreneur who originally created it. And certainly not someone following another person’s formula for what a CEO is supposed to look like.
Perhaps simply a more consciously adapted version of the same leader — able to retain the entrepreneurial courage, instinct and energy that created the business while developing the leadership capacity the emerging organisation calls for.
Because sometimes the most valuable time to work with a coach isn’t when everything is falling apart.
Sometimes it is when so much is going right that the world around the leader is about to change.
Success doesn’t always call for the leader to be fixed. Sometimes it calls for the leader to evolve.
References
Cannon-Bowers, J.A. et al. (2023). Workplace coaching: a meta-analysis and recommendations for advancing the science of coaching. Frontiers in Psychology, 14, 1204166.
Chatterji, A., Delecourt, S., Hasan, S. & Koning, R. (2019). When Does Advice Impact Startup Performance? Strategic Management Journal, 40(3), 331–356.
Greiner, L.E. (1998). Evolution and Revolution as Organizations Grow. Harvard Business Review.
Hinkelmann, H., O’Connor, S. & Passmore, J. (2024). Coaching entrepreneurs towards growth: an experimental design study of coaching effectiveness for business leaders’ psychological capabilities. Coaching: An International Journal of Theory, Research and Practice, 17(2), 283–300.
OECD (2025). Unleashing SME Potential to Scale Up: Helping SMEs Scale Up. OECD Publishing.
Wasserman, N. (2003). Founder-CEO Succession and the Paradox of Entrepreneurial Success. Organization Science, 14(2), 149–172.