On Mentoring Without a Manual
We’re rarely taught how to be a good mentor – we’re all just figuring it out as we go.
There’s something I’ve been thinking about for a while, and I’m not sure I’ve got it fully figured out – but it’s on my mind enough that I wanted to share where I’ve landed so far.
When I became a leader for the first time, I remember thinking I’d somehow get a manual. Or at least some targeted training. Some kind of “here’s how to mentor another human being” download that would calibrate my instincts before I started having weekly meetings with people who were now reporting to me.
I did not get that manual. (Did anyone??)
I got the title, the team, the calendar – and I was expected to figure it out.
Which I did, eventually, but with a lot of stumbling and a lot of awkward moments where I wasn’t sure if I was helping or overstepping or coming across the way I meant to. (Not to mention constantly second-guessing myself thanks to my Turbulent personality trait.)
This month, our entire series has been about specific moves to help you master 1:1 meetings. But underneath all of those moves, I keep coming back to a bigger question:
What does it actually mean to mentor someone – and how do we do it well when no one taught us how?
Here are three things I’ve been working through. I don’t really have a clean, definitive answer for any of them, but I’ll share my thoughts, and I welcome discussion in the comments.
I Made Something I Wish I’d Had as a New Leader
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It’s called 27 Questions Every Leader Wishes They’d Asked Sooner – a practical guide packed with the questions I wish I’d known when I was leading my first team and stepping into management.
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1. Most mentees have to learn how to be mentees
This one took me a while to see.
I used to assume that when someone showed up to a 1:1 with me, they already knew what to do with the time. They’d come with questions, raise the things that needed raising, ask for the help they needed.
But that’s not actually how most people show up – especially earlier in their careers, or the first time they’ve ever had a real mentor.
Most of them just answer the questions I ask. They show up, they’re polite, they leave. The relationship doesn’t really get used.
I was the same way at the beginning of my career. I had managers and mentors who I never actually used as mentors.
What I’ve noticed helps, is asking deeper questions like:
How do you work best?
Is doing this actually helpful for you?
Where would my involvement be most helpful for you?
What’s the best way to share my feedback with you so you absorb it?
The signal I’m trying to send is: this is something we’re shaping together. You can ask for things. You can tell me what’s not working.
2. The instinct to help can overshadow what they actually need
I struggle with this one, but I’m getting better.
When someone I’m mentoring brings me a problem, my instinct is to solve it. I have the experience. I can usually see the answer. The fastest path from “they have a problem” to “they don’t have a problem anymore” is just for me to tell them what to do.
And sometimes that’s exactly right. If I have specific information they don’t, and the stakes are high, just answering is the kindest move.
But a lot of the time, it isn’t.
A lot of the time, what they need is to think it through themselves – and my answer, however good, replaces the thinking they were going to do. They walk out with my decision instead of theirs. And the next time something similar comes up, they’re going to bring it to me again, because they didn’t actually solve anything. I did.
I’m still not great at the pause. I still get the urge to fix things. But I’ve started noticing the moments when what do you think? would serve them more than here’s what I think.
3. I don’t have to have all the answers
This one has been the most freeing.
For a long time, I had this assumption that if someone was looking to me for guidance, I should know more than them about whatever they were bringing to me. That’s the implicit deal of mentorship, right? You’re the one with experience.
Except a lot of the time, I don’t know more.
I have my own experience, sure, but they have theirs. And the situations they’re navigating now aren’t always the situations I navigated then.
I’ve learned it’s okay for me to say “I don’t know either – let me think about it” or “I’m not sure, what’s your read?”
I think this also gives the people I’m mentoring permission to grow into leaders who don’t have all the answers, either. People who know how to think out loud, ask for help, and sit with uncertainty.
Where I’ve landed (so far)
I don’t think mentoring is something we become qualified for. I think it’s a practice we grow into through repetition, through getting it wrong, and through showing up and trying again the next week.
I’m sure my thinking will evolve here again, as I grow in my career and gain even more experience. We’ll see.
If you’ve been mentoring people for a while, I’d love to hear what you’ve figured out – or what you’re still figuring out. Let me know in the comments.







