Entrepreneur
When I coach water polo, one of the first things I tell my team is, “Success doesn’t always end in a goal.” Players forget their fundamentals — not to mention teamwork and good sportsmanship — when all they think about is scoring. In the long run, this actually makes the whole team less effective. I want them to focus on the process instead of fixating on the end result.
The result doesn’t actually change my central responsibility as a coach. Win or lose, my job is still the same: to facilitate an open and honest analysis of what happened, including what went well and what didn’t. Winning a few games doesn’t mean the team is finished growing.
I take the same view when I mentor employees at FutureFund, my SaaS company that provides a free fundraising platform for K-12 schools. In either case, I’m pushing people towards developing expertise in their field — showing them how to find the wins and identify areas for improvement no matter what outcomes they achieve.
But expertise isn’t something that can just be given to you — it’s something you earn, which requires the ability to self-reflect. So, as a coach or business mentor, I don’t provide answers. Instead, I lead people toward finding answers for themselves.
That means my greatest tool as a mentor is the ability to ask questions. Here are the ones I find most effective.
Related: Be a Coach, Not a Referee — How to be a Good Mentor and Manager from a Coaching Perspective
“How do you think that went?”
This is one of the first questions I ask when I’m coaching or mentoring someone new. It shows me what a person is able to observe on their own.
Once I know what someone can see for themselves, I better understand the skills and knowledge they’ll likely apply to other endeavors. Let’s say a water polo player scores their first goal in three games — if they can’t tell me what they started doing differently, I have no way of knowing whether or not it’s a fluke. But if they can identify the tactics that helped them score, I know I can count on them to use them again.
Here’s another example: when I ask an engineer how fixing a bug went, they might tell me they think it was successful because the bug got fixed. But when I ask them if they went back and looked for the same error in other code, they often say no.
Again, results don’t always indicate progress. If you want a better idea of your capabilities, ask people to tell you about the journey they went on to achieve those results.
“What would you do differently?”
Once people understand how to assess themselves, you can encourage them to make positive changes. After I ask someone to reflect on their past performance, I always ask them to think about what they would do differently the next time a similar situation arises.
A player might know they were sluggish during a game because they slept poorly the night before — but why weren’t they well rested? Did they drink alcohol or stay up too late? If so, would they do these things again before the next game? What do they think might happen if they avoided drinking and got a full eight hours of sleep instead?
A mentor guides people through answering questions like this and helps keep them honest. Just remember, you don’t want to sound like you’re scolding, which makes people afraid of judgment and shuts them down. Mentorship is not about dictating actions; it’s about encouraging people to take ownership of their growth. That means you need to build trust with people so they feel comfortable opening up to you.
Sometimes, it’s helpful if a person’s mentor isn’t their direct supervisor but someone who can ask questions from an impartial place instead — like an outside consultant. But when you’re mentoring one of your own employees, I’ve found the best way to get an honest answer to this question is to demonstrate some vulnerability yourself.
Try leading by example. Share a story about a similar learning experience you went through so that they feel like you’re relating to them and not putting them under the microscope when you ask questions.
Related: Stop Trying to Manage Employees Without Understanding Them — How to Build Relationships for Leadership Success
“How have you changed over time?”
Giving instant feedback after a game or project helps people grow by reflecting on experiences while they’re still fresh. But you also want them to be aware of long-term trends in their development — so I always like to ask questions that make people think about their performance over time.
If we’re playing baseball and I give instant feedback every time a batter is up, they’ll grow — but I should also take them aside at some point and ask them to reflect on their previous 10 at-bats. This helps them spot patterns or habits that go beyond their actions during a single game.
This is also great for helping people recognize the progress they’ve made after months or years of growth. Some changes take much longer than others — like breaking lifelong habits, attitudes or addictions. Over time, it’s easy to get discouraged and feel like incremental change isn’t enough anymore — but when someone asks you to look back at who you were when you started, you get a much different sense of how far you’ve come since then. And that can inspire you to keep moving forward.
Mentorship is like that too — ideally, you evolve alongside the people you coach or manage. Keep learning how to mentor the people in your life effectively by learning about the different stages of mentorship in the article below.
Related: The Importance of Mentors
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