Why I Hired My First Executive Coach Over 20 Years Ago

Many years ago I hit a wall.

I had read the books on success and personal development. I had spent tens of thousands of dollars on seminars and programs. My income moved a little. My life moved a little. But I was not seeing the kind of shift I felt was possible.

I was doing a lot.

I was not changing much.

At some point it became clear that reading and thinking were not enough. I needed a different kind of help. I decided to hire a coach.

What I thought I was buying

At the time, I saw coaching as a way to get an objective view of my life and work. Someone who was not inside my head and not inside my story.

I wanted someone who could see my strengths and weaknesses more clearly than I could. Someone who could put a finger on the patterns that kept repeating, even when I promised myself I would do things differently next time.

I told myself it was a smart investment. I was paying for:

An outside perspective I could not generate on my own

Strategies that were tailored to me instead of generic advice

Accountability and support so I did not drift back into old habits

All of that turned out to be true.

But it was not the whole story.

The real issue was simple and uncomfortable

Underneath all the books, seminars, and plans there was one basic problem.

I could not see myself clearly.

I had blind spots in how I operated, how I made decisions, and how I reacted under pressure. I had stories about who I needed to be in order to be successful. I had ways of protecting myself that also kept me stuck.

I could not fix what I could not see.

Self awareness is the foundation of any real change. Not as a slogan, but as a lived experience of recognizing what actually drives you, what you avoid, and how you impact people around you.

The problem is that true self awareness is hard to build alone. By definition, you cannot see your own blind spots. You can journal, reflect, and think deeply. Those tools are useful. But they all happen inside the same system that created the problem.

You are judging your own thinking with the same thinking that is in the way.

Where a coach became essential

This is where my coach made the difference. Not by delivering a magic framework, but by acting as an honest mirror.

He noticed the patterns I normalized. How I overextended myself to avoid disappointing others. How I distracted myself with new strategies instead of staying with the discomfort of one simple commitment. How I told myself certain ceilings were about the market when they were really about fear.

He reflected those things back without blame.

He asked questions I would not have asked myself.

Sometimes the insight was a single sentence that landed hard. Sometimes it was a pattern he pointed out after watching me repeat the same thing three times.

From there we could work on practical changes. He helped me set clear commitments, try small experiments, and stay with them long enough to see what was actually true. He offered tools and structures. He also held me accountable when I slipped back into old habits.

The value was in the combination of perspective, honesty, and support.

What changed for me

The impact showed up in both obvious and subtle ways.

My income grew, yes. But more importantly, my relationship with work shifted. I stopped chasing every new “solution” and started building from a clearer sense of what actually mattered to me.

I learned to see where I was getting in my own way. Perfectionism. Avoidance. Needing approval. Overcommitting to prove something. Once I could see those patterns, I had options.

I could say no when I needed to.

I could focus on one thing and let other things go.

I could make decisions from a place that was a little quieter and a little less reactive.

Over time, that changed how I led, how I sold, and how I built companies. It gave me a different kind of confidence. Not the loud kind. The kind that comes from knowing you can meet what shows up because you know yourself better.

Why this still matters for leaders now

Fast forward to today, and the context is different. The pressure is higher. The pace is faster. The tools are more advanced. But the core issue has not changed.

Most leaders are drowning in information and starving for honest reflection.

They know the latest frameworks. They can list ten ways to improve a funnel or a culture. What they do not have is a place where someone is laser focused on how they show up, what they avoid, and what that costs them and their teams.

That is the real work of executive coaching.

It is not about fixing broken people. It is about helping capable people see the difference between strategy problems and self created constraints. Between what is happening in the business and what is happening in them.

What you are actually choosing when you hire a coach

On the surface, hiring a coach is a professional development decision. You are choosing to:

Accelerate your learning instead of waiting for painful lessons to repeat

Get structured support instead of trying to white knuckle your way through every challenge

Have a confidential place to talk about the things you cannot say to your board, your team, or sometimes even your family

Underneath, you are making a deeper choice. You are admitting that you cannot see yourself fully on your own. You are acknowledging that there are parts of your pattern you are too close to. You are willing to let someone in.

That is not weakness.

That is maturity.

You are also buying back time. The time you would have spent circling the same questions. The time you would have spent trying one more tactic instead of confronting the real issue. The time you would have spent alone in your head when you could have been in an honest conversation that moves something.

A different way to think about “return on investment”

People often ask about the return on investment from coaching. It is a reasonable question.

You can measure it in numbers. New roles. Better compensation. More stable growth. Clearer decisions that prevent expensive mistakes.

You can also measure it in things that are harder to quantify and more important over a career.

Being able to make a hard call without spinning for weeks.

Having the courage to say what is true in a boardroom.

Leading a team in a way that does not quietly burn you out.

In my own case, the money I paid my first coach was significant. At the time, it felt like a stretch. Looking back, it is hard to imagine where I would be if I had not made that decision.

The cost was real.

So was the cost of staying stuck.

If you see yourself in any of this

You may be at a point where the strategies you know how to run are not the issue. The gap may be self awareness. The ability to see how your beliefs, fears, and patterns are shaping every decision you make as a leader.

If that is true, you do not need more information. You need a different kind of conversation.

I hired my first coach over twenty years ago because I knew something had to change and I could not get there alone. That decision started a process that still unfolds in my life and work today.

If you are reading this and recognize that same tension in yourself, it might be time to do the same.

Not because you are broken.

Because you are ready to see more of yourself, and to lead from that place.