Sometimes the company grows—and the leader should grow with it.
Imagine a founder who started a business from scratch.
When the company was small, she did everything. She knew every customer. She interviewed every employee. She approved every major expense. She knew what was happening in sales, operations, and finance. And she was really good at it.
The company grew from $5 million to $20 million and eventually to $50 million. But something changed. She was exhausted. Her leadership team was frustrated. Decisions were backing up. And she couldn’t understand why running the company had become so difficult.
The problem wasn’t that she had become a worse CEO.
The job had changed.
The Company Changed. Did You?
Every stage of growth requires something different from a leader.
When your company is small, it may need you to be the rainmaker, problem solver, decision maker, customer relationship manager, and keeper of virtually all institutional knowledge.
As the organization grows, your role has to change. Instead of making every decision, you need to develop people who can make decisions.
Instead of knowing everything happening today, you need to be thinking about where the company needs to be three years from now.
Instead of solving problems, you need to build a leadership team capable of solving them without you.
The skills that helped you build the company aren’t necessarily the skills you’ll need to scale it.
Success Can Become the Trap
Ironically, the behaviors that made you successful can be the hardest ones to give up.
If you built the company by personally solving customer problems, stepping away can feel irresponsible.
If you’ve always been the best salesperson, letting someone else lead sales feels risky.
If every major decision used to come through you, delegating can feel like losing control.
But eventually, what made you invaluable can make you the bottleneck.
Sometimes your greatest strength becomes your biggest limitation when you don’t know when to let it go.
What Are You Doing to Grow?
CEOs spend a lot of time thinking about how to develop their people. But who’s developing the CEO?
One of the best things you can do is intentionally put yourself in situations that challenge your thinking. That might mean enrolling in an Executive MBA program or an executive leadership program at a university. Maybe it’s joining a CEO peer group, attending an industry program outside your normal circle, finding a mentor, working with an executive coach, or serving on a board.
You don’t necessarily need another degree. You need exposure to people, ideas, and perspectives that make you think differently.
An executive education program can put you in a room with leaders from completely different industries who approach strategy, technology, finance, culture, and growth differently than you do.
A CEO peer group can expose you to problems you haven’t encountered yet.
A coach or mentor can ask the questions your employees may be reluctant to ask.
The important thing is to keep expanding your world rather than assuming your years of experience have given you all the answers.
Ask a Different Question
Most CEOs ask:
“What does my company need to do differently to get to the next level?”
Try turning that question around:
“What do I need to do differently?”
- Do you need to delegate more?
- Become a better coach?
- Listen more?
- Learn more about technology or AI?
- Strengthen your financial knowledge?
- Spend less time solving today’s problems and more time thinking about tomorrow?
- Or surround yourself with executives whose strengths complement your weaknesses?
Leadership maturity includes being able to say:
“Someone else can do this better than I can.”
Three Things to Remember
- Your role should change as your company grows. If you’re doing essentially the same job you were doing five years ago, ask yourself why.
- Your development shouldn’t stop because you reached the top. Take a class. Attend an executive program. Join a peer group (Young Presidents’ Organization, Entrepreneurs Organization, Vistage to name a few). Find a coach or mentor. Put yourself around people who challenge how you think.
- Letting go isn’t losing control. It’s creating capacity for yourself and opportunity for others to grow.
Here’s a question I’ll leave you with:
If your company doubled in size over the next three years, could you lead it the way you’re leading today?
If the answer is no, that’s not necessarily bad news.
Maybe the question isn’t whether you’re still the right leader for your company.
Maybe it’s:
Who do you need to become to remain the right leader for the company you’re building?
Because your company isn’t the only thing that needs to grow.
You do, too.
Onward and upward,
Karen Caplan
Executive Coaching and Consulting for Business CEOs, Owners and Presidents
