July 24, 2024


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Eight years ago, I was coaching a girl’s softball team. We were in the fifth inning, down by one, and one of my rising star batters stepped up to the plate.

She swung, connected with the ball — and was promptly called ‘out.’ She asked why, but the umpire wouldn’t explain. Feeling confused and frustrated, she came to me. I explained that her foot was outside the box when she swung, which was why she had been called out.

This story illustrates a key difference between coaches and referees (or umpires): the coach is there to help people improve; the referee points out all the problems. Their job isn’t to make people better.

But as a manager, I’ve always believed that your role is to be a coach, not a ref. Too many managers fall into the trap of sitting back and observing — but while being observant is useful in management, it’s not enough.

If you want to help your team succeed, you need to be genuinely invested in their success. Below, I’ll explain how thinking of mentorship from a coaching perspective has informed my approach and how it can do the same for you.

What great mentors and coaches have in common

Coaching a mentee is a lot like coaching a player on a team. In both cases, you want to:

  • Encourage self-reflection: Help the person you’re coaching develop the tools to take inventory of their own actions. Ask, “What can you do to improve the outcome?”
  • Foster accountability: create an environment where the person you’re coaching can be honest with themselves and others about what they notice while self-reflecting. Ask, “How will you measure your progress?”
  • Promote incremental improvements: motivate the person to move forward. They don’t need to make the NFL draft; they need to do a little better than before. It adds up over time. Ask, “How have you improved since last we spoke?”

The main difference between all of this is what you’re trying to accomplish. When I coached girls’ softball, I was trying to improve the way my team played. But when I coach a mentee in a business setting, I want to improve their thinking.

Related: 6 Effective Coaching Strategies for Your Team

The goal of mentorship is to make people think

I’ve mentored a lot of people at different levels and in different disciplines, and I’ve noticed some common threads. In my experience, a good mentor always sets out to make the people around them think — ideally in a certain direction.

This is one of the main reasons why mentors need to be more than mere observers. To make someone think, you need to provide feedback, and you can only provide feedback based on what you know about your mentees.

That means you must encourage them to open up and verbalize their honest opinions, needs, and feelings. You have to communicate actively enough to learn about them instead of making assumptions based on what you notice from a distance.

In other words, you have to be a coach.

Related: How to Get People to Think Differently

Asking the right questions as a mentor

Asking the right questions is one of the best ways to become more actively involved as a mentor.

Here’s an example: I used to teach a class called “Being a Leader” when I worked at Square. Time and time again, I’d ask my students: what’s the one question you never ask your kids at the dinner table?

It’s “How was your day?” because the answer is always “Fine.” That’s not a conversation; it’s an excuse for both parties to tune out and go through the motions instead of engaging with each other meaningfully.

Instead, try asking, “What was the most exciting part of your day?” or “What did you learn?” or “Did you make any new friends?” Questions like these encourage detailed responses, and asking also encourages you to listen more closely to the answers.

It’s the same when you’re a mentor. You have to ask the right questions to spur the conversation forward.

Other coaching techniques to apply to mentorship

Asking questions is one of the best things you can do as a mentor, but successful coaches also need to do a few other things. I will close this article with three reminders that I believe can help mentors in any organization.

Firstly, earn the trust of your mentees. People only respond honestly and openly to questions when they know they can trust you. Use language that lets them know you’re on their side.

I would never ask the softball players I coached or the people who reported to me at Square questions like “Why did you fail,” when something went wrong. That would create an antagonistic relationship and make it harder to provide future feedback. Instead, I’d ask, “What could you have done better?”

Secondly, help your mentees analyze. Just as I always sat down with my softball team for a post-game analysis about what went right and what went wrong, mentors should meet with mentees after each major project or milestone and help them examine their choices.

Write down a quick retrospective on what went right, what went wrong, and what questions still need to be answered. Then, examine these writings with your mentee and have them identify patterns or areas to optimize.

Finally, see everything that doesn’t go as planned as a learning event. Remember that growth mindsets aren’t just for employees or players but also critical for people in leadership roles.



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