The Three Mistakes That Even Good Mentors Make

In front of you is someone who’s confused, frustrated, and seeking guidance. Here’s what not to do.

The Three Mistakes That Even Good Mentors Make
[Photo: Charlie Foster via Unsplash]

“One of the best ways to elevate your character immediately,” wrote the Stoic philosopher Epictetus, “is to find worthy role models to emulate.” These days, we think of personal development and mentorship a little bit differently. The best mentors aren’t remote paragons of excellence. They’re more like experienced collaborators, people who see you, hear you, and believe in you–in addition to offering their counsel.


That takes a certain amount of emotional labor; empathizing, understanding, and asking tough questions can be really hard work. At best, that process not only transforms the person you’re mentoring, it can help you grow as well.

When it doesn’t, it’s usually because our approaches are off-kilter, despite the best intentions and top-notch expertise. These are some of the most common mistakes that otherwise effective coaches and mentors make, and how to get around them.

1. They Don’t Reframe The Problem

Perception–the way we comprehend events and challenges, people and ideas–comes down to the stories we tell ourselves. What good mentors do, then, is help their students tell themselves a different story. Here’s what Rosamund and Benjamin Zander said on that subject in their book The Art of Possibility:

The frames our minds create define—and confine—what we perceive to be possible. Every problem, every dilemma, every dead end we find ourselves facing in life, only appears unsolvable inside a particular frame or point of view. Enlarge the box, or create another frame around the data, and problems vanish, while new opportunities appear.

Helping someone through an obstacle is about helping them look at the problem differently. Tackle perception by asking students to reflect on the way they’re looking at the problem, not the particulars of the immediate challenge itself. This way they can learn over time to look at new obstacles in multiple ways, no matter what they consist of.


2. They Give Away The Answers

Which brings us to the second, related error that mentors tend to make. We tend to believe that having a mentor or a coach is about getting the best solutions to a problem on demand—a kind of guardian angel that ensures we avoid failure.

That isn’t the case—in fact, it can be counterproductive. Great coaching is about helping the student find the right path independently.

When we share what feels like the right decision, we actually steal our students’ opportunity to think it through critically on their own. Don’t rob them of that experience, which is actually your job as a mentor to provide. Instead, nudge them by asking tough questions so they can figure it out on their own. The reward is twofold: You don’t steal their revelation, and they hone a necessary life skill.

When one of my students asked me which topics to write about on his new blog, I simply reflected the question back to him: “What do you think you should write about first?” Of course, he didn’t know right away–that’s why he’d asked for my advice. But for the next 10 minutes, he emptied his brain and devised a strategy right there in front of me.

Was his answer correct? Who knows. The purpose of my coaching wasn’t to affirm that he was focused on the right topics. Rather, my goal was to get him to just start writing, because that was the real roadblock–not, as he thought, which specific subjects to write about.

3. They Assuage Fear Rather Than Look For It

In front of you is someone who is a little bit lost and confused, seeking clarity and guidance. They don’t know if they should quit their job, start a company, or move across the country. As their mentor, what should you do?


In most of my experiences, the person already knows the answer. What they’re afraid of is taking ownership of that decision. It’s charged with uncertainty and a fear of change. Seeking information and others’ perspectives helps alleviate some of that anxiety. It may feel good to shop for affirming views, but it’s like walking on a treadmill–you delude yourself with the illusion of forward progress.

The first step is pointing at the fear. Why aren’t they starting that new company? Why aren’t they shipping their project? Why are they delaying the move?

When you find the fear, you can get to work.

That’s where real progress is made—when we acknowledge our fears, reframe them, and then construct a new narrative that allows us to take action.


“Good advice is priceless,” writes Seth Godin. “Not what you want to hear, but what you need to hear. Not imaginary, but practical. Not based on fear, but on possibility. Not designed to make you feel better, designed to make you better. Seek it out and embrace the true friends that care enough to risk sharing it. I’m not sure what takes more guts—giving it or getting it.”

The truth is, everybody could use a coach. There’s no one who doesn’t benefit from having someone who sees them, listens to them, believes in them, and pushes them to explore their boundaries and embrace news narratives to live and work better. What a gift—to be the pusher and the one who’s being pushed. We just need to shake some bad habits first.

Paul Jun is the founder and editor of Motivated Mastery, a blog where he connects the dots on mastery, creativity, and change. He does marketing at Help Scout and coaches for the altMBA.