How to Ask for Mentorship

How to ask for mentorship

In the previous post in this series, I told you I’m not the best mentor for everyone. Then I told you how to identify the attributes in a mentor that will get you to take action.

“OK, Coop,” I imagine you saying. “I picked Jocko Willink. Now what?”

Or maybe: “I picked my old drill sergeant. But he doesn’t know anything about business!”

Or maybe: “It’s my dad!” or “It’s my wife!” (I get both of those a lot.)

Identifying the best mentor is easier than asking for help.

Knowing that your dream mentor might say no can create a barrier—we say “no” a lot, and here’s why. Two other barriers: You might not be able to afford their help or you’re not really clear what they’re going to do for you. These are the barriers most people face, and I’ve come up against all three. Here’s what to do about them.

Obtaining Mentorship: Step by Step

Step 1

Interact with the prospective mentor first. Let the person hear from you. A simple “thank you!” email goes a long way.

In 2020, I wanted to rescue our annual Summit event. The purpose of the Summit is to inspire entrepreneurs and bring gym owners together. In 2020, I knew that gym owners needed it more than ever, but I couldn’t bring people together in Chicago. We set up 30 regional events worldwide, but I knew we’d need a huge leader to draw people together. I picked the biggest: Seth Godin.

I started the conversation with a “thank you” email. It was long and specific.

He replied with two words:

“You’re welcome.”

But we had a conversation.

Step 2

Explain exactly how you think the prospective mentor can help you.

My next email to Seth briefly laid out the problem: that microgyms—especially CrossFit gyms—needed to tell a new story. I remembered that Seth had written about CrossFit in his book “Tribes” and asked if he would tell a different story now.

He said he’d think about it.

Step 3

Think about what you’d pay to solve the problem forever.

Measuring ROI in mentorship is tough because it snowballs. Avoiding one bad hire is easily worth $50,000. Saving your gym is worth well over $1 million in the next five years.

The problem I had to solve was a huge one: Gym owners needed to create a new brand around their own gyms. Some had dropped the CrossFit affiliation; most hadn’t—but they still needed to tell their story, over and over. That’s a massive pivot. Knowing I’d pay at least $3,000 to rebrand my gym, I knew Seth would bring a minimum of $30,000 in value to the Summit. (As it turns out, he brought far more.)

Instead of asking “What’s the immediate ROI?” ask “What’s the value of this over the next five years?”

Step 4

Ask yourself, “What value do I bring to the mentor?”

Sometimes, the value is money. That’s the simplest exchange of value: You pay to buy the mentor’s success without paying for his or her mistakes.

If the answer is “I’ll pay for expertise,” then it’s simple. All you have to do is show up and be a sponge.

Sometimes, the value is different. My current mentor is paid but doesn’t need the money. He gets to “stay close to the pain of entrepreneurship” by working with me. That will help him write more books and give more speeches.

Step 5

Lay out the terms of mentorship. It’s really easy to ask a buddy for help. But if there’s no exchange of value, it will quickly dwindle out. You’ll start with monthly lunches for a while, but you won’t act on advice. Or the person will eventually become busy and your relationship will sputter.

You need to exchange value with a mentor. But more than anything, you need to set an appointment schedule, a communication plan (how the mentor will hold you accountable) and some boundaries. Is it OK to call in a crisis? Is text better? Should you bring up the mentor’s name or not?

Step 6


Be prepared for prospective mentors to say “no” or “you’re not a good fit.”
When they do, ask for a recommendation to someone else.

I own a mentorship practice. We do a free consultation. But we don’t invite everyone to join. Even with a huge team of diverse mentors, we refer people elsewhere more than 50 percent of the time.

How do you know if we can work well together? How do I know if we can help you? Well, you put your hand up. We get on a call. And then we decide, together. Click here to raise your hand.

Other Media in This Series

“How to Choose a Mentor”
“Who’s the Best Mentor?”
Video: “How to Choose a Mentor”


One more thing!

Did you know gym owners can earn $100,000 a year with no more than 150 clients? We wrote a guide showing you exactly how.