Enough people have asked me for career advice over the years that I’ve started to notice a pattern in how those relationships go. Some of them turn into real mentorships that last years. Most fizzle out after one or two conversations. The difference rarely comes down to how smart or capable the person is.
It comes down to what they did with what I told them.
I’ve written before about finding a mentor and the broader role mentorship plays in a leader’s development. Both of those posts are about the first half of the process: how to find someone, how to approach them, how to get the relationship started. Today’s post is about the second half: how to ensure you stay worth that person’s time once they’ve said yes.
The Pattern I Keep Seeing
When a relationship fizzles out, this is usually how it goes. Someone reaches out with a question. I answer it, usually in more detail than they asked for, because I like being helpful. A few weeks later, they’re back with a new question, or several questions at once, often a scattered mix of things that have been bothering them since we last talked. We never circle back to the first thing, they never share any updates with me. We just keep adding new open loops.
After this happens a few times, I stop being as generous with my time. I still answer. I’d never turn someone away. But my responses become less personal and more perfunctory. If I can’t tell whether someone acted on the last thing I told them, whether my last piece of advice did anything, I have no real signal that the next piece will either. Eventually I start treating the conversation as a favor instead of an investment.
Here’s the version I like much more, the version that doesn’t fizzle. Someone reaches out, and before they ask anything new, they tell me what happened with the last thing: “You told me to stop giving my team lead the answer and start asking her what she’d try first. I did that for three weeks. It was slower at first, and then it wasn’t — she handled two escalations on her own that she definitely would have brought to me before.” Then, and only then, do they ask the next question.
That person gets more of my time, even though they ask for it less often. I find myself thinking about their problems between conversations. I start mentioning them to other people. It’s more rewarding for my because I can see that my advice is actually being followed and making a difference.
Why Mentors Say Yes in the First Place
There’s a line I came across a few months ago that’s stuck with me since: a mentor is just someone who answers more than one question.1
That framing is useful because it strips away the formality most people assume mentorship requires. You don’t need a title, a standing meeting, or a signed agreement. You just need someone willing to keep answering your questions.
Most advice about finding a mentor focuses on the first question: how do you get someone to help you once? But a mentor isn’t someone that just helps you out once, it’s someone willing to answer your second, third, and fourth questions. And often, their willingness to do that depends on what you did with the answer to the first one. Mentors aren’t running a help desk. They’re investing attention in watching someone put their advice to use, and that investment only keeps paying out if they can actually see it work.
A mentor is just someone who answers more than one question. The whole relationship depends on staying worth a second answer.
The Protocol: Act, Report, Ask Again
The fix is incredibly simple. Three steps, in this order, every time:
Act on what you were told, before you ask anything else.
Report back specifically: what you were told, what you did with it, and what happened. Not a generic “it went well,” but the actual result.
Ask the next question, now that you’ve earned the right to.
Notice what this protocol does to the conversation. It turns every interaction into evidence instead of a request. A mentor who hears a concrete report doesn’t wonder whether the relationship is working or is worth their time. They can see it. And once they can see it, continuing to invest in you stops being pure generosity and starts being an easy, obvious call.
This also solves the “too many questions” problem on its own, without you having to deliberately ration yourself. If you can’t report back on something yet, you haven’t finished acting on the last round. And if you haven’t finished acting on their last advice, it usually means you’re not ready for more. The protocol paces you automatically.
How to Be a Good Mentee
I wrote a while back about what makes someone worth sponsoring, the three things that make someone’s manager comfortable vouching for them:
Work that survives without them there to defend it
Visibility outside their daily weeds
Trust that doesn’t require a favor to sustain
Being a good mentee follows the exact same pattern.
Work that survives without you there to defend it, as a mentee, is following through on advice without needing to be checked up on. Visibility is following up and telling your mentor what happened, instead of just letting the results sit in your own head. And trust that doesn’t require a favor is a mentor who keeps answering your next question because doing so has consistently been worth their time, not because they feel obligated.
None of this requires impressing anyone. It requires being, in a very literal way, helpable — someone whose problems actually move when you hand them good advice, which makes handing you good advice worth doing again.
Space Is Fine. Disappearing Isn’t.
There’s an important piece here I want to address directly, because it goes counter to what most people believe about mentorship. The relationships that work well aren’t necessarily the ones that meet the most often. You don’t need to have a pre-scheduled monthly meeting. In some of the best mentoring relationships I’ve been part of, we only had a conversation every few months, sometimes closer to once a year. That’s fine. What makes it fine is that every single conversation is substantive — there was real action taken, a real report, a real next question — instead of a vague catch-up.
Relationships that fizzle out are not simply those where you meet infrequently. They’re the ones with no real conversation ever closing the loop on the last one. Silence after giving advice comes across as nothing happened. A bit of space followed by a real report comes across as someone actually doing the work and coming back when there’s something worth discussing. A mentor can feel the difference, even if they can’t explain it.
From Theory to Action
Nobody teaches this because it sounds too obvious to need teaching: act on what you’re told, tell your mentor what happened, then ask the next thing. But almost nobody actually does it, which is why the people who do stand out immediately. Being a good mentee isn’t about asking better questions. It’s about becoming the kind of person whose results make answering those questions worth someone else’s time.
Before you ask your mentor anything new, write down what you actually did with the last thing they told you. If the honest answer is “nothing yet,” that should be your next step, not a new question.
The next time you reach out, lead with the report, not the request. One or two sentences: what they told you, what you did, what happened. Ask your question after, not before.
Cut your question list down to the one or two that actually matter. If you’re showing up with five scattered concerns, you haven’t finished processing the last conversation yet.
Pick one piece of advice you got months ago and never closed the loop on. Go back to that person, even if it feels late, and tell them what you did with it, or admit you didn’t do anything. Both are more useful to them than silence.
Don’t treat infrequent contact as a sign the relationship is fading. If your last few conversations were substantive, space is a feature, not a problem. Don’t manufacture an unneeded check-in just to stay “active.”
The framing that "a mentor is mostly just somebody that answers questions more than once." comes from the Stay SaaSy blog: https://staysaasy.com/career/2021/10/16/mentorship.html?ref=commoncog.com