At 28, I became the reluctant CEO of my family’s business, a 100-year-old company that was losing $3.5 million a year and about six months from running out of cash.
No succession plan was handed to me. The team was shaky, the market was brutal and everyone was watching to see whether the kid would sink it.
My instinct was the one most driven leaders have: work harder. Longer hours. More decisions funneled through me. More weight on my shoulders. It nearly broke me, and it didn’t fix the business.
What actually turned fortunes around wasn’t effort. It was focus, and having someone in my corner who could see what I couldn’t.
My mentor, Frank, never handed me a playbook. He asked better questions than I was asking myself. That experience is why, years and one successful exit later, I coach CEOs for a living… and why I’m blunt about what executive coaching really is.
It is not a crutch for leaders who are failing. It’s what stops capable leaders from making the expensive mistake I made: Confusing motion with progress.
The job has only become harder
If you feel the pressure mounting, the data backs you up.
PwC’s 2026 Global CEO Survey found that confidence in revenue growth has fallen to a five-year low, with just 30 per cent of CEOs feeling very or extremely confident about the next 12 months, down from 38 per cent a year earlier and a 56 per cent peak in 2022.
AI, tariffs, cyber risk, and geopolitical noise are all landing on the same desk. Yours.
Here’s what the survey doesn’t capture: it’s lonely at the top and isolation is where good judgment goes to die. The higher you climb, the fewer people will tell you the truth, and the more your blind spots cost.
That’s the gap a good coach fills. Not with theory. With three specific shifts.
1. It restores the judgment that isolation erodes
When you’re too close to a problem, you can’t see it clearly and no one on your payroll is fully incentivized to tell you where you’re wrong.
A coach is the one person in your world with no agenda except your success. Their job is to surface the biases, blind spots, and pet habits quietly costing you, and to ask the questions your team won’t. Better questions produce better decisions.
That’s the whole game.
2. It gets you working ON the business, not just IN it
The single biggest trap I see in owner-led and family businesses is a CEO who has become the bottleneck… every decision, every approval, every fire routed through one person. It feels like control. It’s actually a ceiling.
Coaching forces the harder work: Knowing your role and doing only what only you can do, building a bench of A-players you genuinely trust, and reducing the company’s dependence on you.
That’s what makes a business scalable and, eventually, worth leaving on your terms rather than out of exhaustion.
3. It protects the one asset you can’t replace — you
DDI’s 2025 Global Leadership Forecast found that 71 per cent of leaders report rising stress and, of those, 40 per cent have considered walking away from leadership altogether.
I understand the impulse. I lived a version of it.
A company can replace almost anything faster than it can replace a burned-out founder who’s lost the plot. Coaching reduces the isolation, protects your work-life balance before it collapses, and keeps you resilient enough to lead through the next crisis instead of becoming one.
Your wellbeing isn’t a soft perk… it’s a business-continuity issue.
How to know it’s working
Good coaching isn’t a warm chat that leaves you fired up for a day.
Within a few months you should see it in the operation: decisions made faster and further down the org chart, fewer things bottlenecked on you, a leadership team stepping up instead of stepping back, and your own week with more room to actually think.
If a coach only ever agrees with you, find a different coach.
The bottom line
I resisted getting help because I thought asking for it meant I wasn’t up to the job. I had it backwards. The leaders who scale without burning out are almost never the ones who did it alone — they’re the ones who found a clear-eyed outside partner sooner.
If you’re carrying too much and moving too fast to step back and see clearly, that’s precisely the moment to do it.
Talk with Richard for a straight conversation about where your business is stuck and whether coaching is the right lever. No pitch, and no playbook you’ve already read
