It seems like these days everyone is selling a coaching or a mentoring service that promises to make you a better leader, employer, lawyer, or whatever. In the sea of options, it can be easy to distrust the validity of the ads, become cynical of them, or even think that you’re above the level of needing a coach.
But the truth is, a good mentor is invaluable no matter your standing.
The best performers in the world are the best because they know they can always improve. They know there’s something they don’t know and they want to learn it. Tom Brady had multiple coaches throughout his entire career (and last I checked, it worked out pretty great for him).
I didn’t always believe in coaching either. I thought it was a scam that made promises it couldn’t possibly live up to. But one day in the early days of Crisp, when we had just grown to $1 million, I found myself stuck. Not failing, but not growing either.
That’s when I read a book written by a business coach and liked it enough to reach out to the author and inquire about his coaching services. He quoted me a price of $5,000 a month, which included just two phone calls. The amount was so shocking I had to take multiple walks around the block.
But after a lot of reflection, I decided to pull the trigger.
What I learned was that I was paying for far more than just clear-cut, yes/no advice. I was paying for a new way to think and approach problems.
Every time I got on the phone with my coach, he didn’t tell me what to do. Instead, he asked me questions that forced me to examine how I was thinking until I came up with the answer myself. He helped me clarify the real problem, not just the symptoms.
Instead of giving me a fish, he taught me how to catch one.
We’d lay out a plan together, and on the next call there was an accountability check. I was paying $5,000 a month, so I made sure to do every single thing we came up with as soon as I hung up the phone. I wasn’t going to be slacking off. I took all his advice in and acted on it.
At the end of that year, our company grew five-fold, from $1 to $5 million.
As amazing as those results sound, the real value wasn’t numerical growth. It was clarity. It was confidence. It was having someone I could call when I was stuck, uncertain, or facing a challenge I hadn’t seen before, knowing his advice made me more capable of handling it in the long run.
That’s what great coaches do. They don’t make you dependent on them. They sharpen your judgment, raise your level of thinking, and help you become a better decision-maker — not just in one situation, but in every situation after that.
Leadership can be isolating. The higher you go, the fewer people you can be fully honest with. A great coach gives you a place to think out loud, pressure-test ideas, and challenge your assumptions without ego, politics, or hidden agendas.
The idea that you’ve “made it” so you don’t need help is one of the fastest ways to stall out. The best leaders don’t avoid coaching because they’re weak. They seek it out because they’re serious about getting better.
So if you’re at the top of your game, you may still want to look into getting a mentor — not because you need someone to think for you, but so someone can help you think better.
