The Biggest Obstacle in Your Business May Be Sitting in Your Chair
Issue #31 | Sep 2026
Hello Reader,
There is a stage in every successful business where the question changes.
In the beginning, the business needs the founder to be more involved: more decisions, more relationships, more problem solving, more control.
But then the business grows.
And something strange happens.
The very behaviours that built the business can start limiting the business.
Because there comes a point when your greatest contribution to the next stage of growth may be becoming less necessary to it.
Meet Rajiv, founder and MD of a successful manufacturing business.
For 25 years, Rajiv had been the engine of the company. He knew the customers, the products, the numbers, and could walk into almost any problem and find a solution.
His people admired him for it.
And he had earned that admiration.
The business had grown from a small family enterprise into a professionally managed organization with multiple divisions and a strong leadership team.
But something wasn’t quite right.
The more the business grew, the more Rajiv seemed to be involved.
Every major decision came to him. Every important customer wanted to speak to him. Every senior leader wanted his view.
And every time someone asked him why he was still so involved, his answer was simple:
“I just want to make sure things are done right.”
It sounded like responsibility.
But underneath it was something else.
He didn’t fully trust the organization to do it as well as he could.
Sometimes the biggest barrier to leadership growth is too much support.
During a leadership review, I asked Rajiv a deceptively simple question:
“If you disappeared from the business for six months, what would stop working?”
Rajiv initially laughed.
Then he started listing things.
Customer relationships. Major approvals. Strategic decisions. Certain operational issues. Key people.
The list kept growing.
And suddenly the realization hit him.
He hadn’t just built a successful business.
He had built a successful business that still needed him too much.
Then came the harder question:
“Are you building a business that depends on your brilliance… or an organization that multiplies it?”
That changed the way Rajiv looked at leadership.
Rajiv didn’t suddenly step away.
He started stepping back intentionally.
In leadership meetings, he began speaking last.
When someone brought him a problem, he stopped giving the answer immediately. Instead, he asked:
“What do you think we should do?”
He started delegating decisions, not just tasks.
He allowed leaders to make decisions differently from how he would have made them.
Some decisions weren’t perfect.
But they became learning opportunities rather than reasons to take control back.
And Rajiv introduced a new personal measure of leadership:
“How much can my team handle without me?”
Over time, something remarkable happened.
His leaders became more confident. Decisions moved faster. People started challenging ideas. The organization became less dependent on one person.
And Rajiv finally had the space to focus on the things only he could do: direction, strategy, relationships, and the future.
He hadn’t become less important.
He had become more valuable.
Because he had stopped being the organization’s best problem solver…
and started becoming its capability builder.
🧩 Our Solution: The CEO Ego Check – 5 Questions
Before stepping into a decision, ask yourself these 5 Questions.
The Leadership Shift
From: “I need to be involved.”
To: “I need to build people who can lead without me.”
Coach’s Note
The hardest thing for a successful founder isn’t building the business.
It’s accepting that the next version of the business may require a different version of you.
Your experience built the organization. Your judgment helped it grow. Your involvement may have been essential.
But eventually, your greatest act of leadership is to create an organization where your presence is no longer required for everything to work.
The goal isn’t to become indispensable.
The goal is to become unnecessary to the things others can now do.
Because when your team no longer needs you to solve every problem…
that’s not a loss of control.
That’s leadership success.
Previous Newsletters:
The Conversation You’re Avoiding Is Costing You the Most
