Getting ahead
Ask for one mentor conversation
A simple exercise to get real guidance from someone who's been there, without asking for a big commitment
Instead of asking someone to be your mentor, ask for 20 minutes of their advice on one specific question.
- 20 minutes
- You and one person
- Every couple of months
- Conversation
Why this can work
Asking someone to be your mentor requests an open-ended commitment that many busy people hesitate to make. A request for 20 minutes on one specific question is easy to say yes to, and tends to get a far better answer. Many of the best mentoring relationships start this way, one good conversation at a time.
Read moreHow to ask for a mentor conversation
You’ll come away with one piece of advice on a question that matters to you, and a door left open.
- Write down the one question you're stuck on.
Make it specific and real: whether to take a role, how to handle a tricky stakeholder, how someone learned a skill you're building. If you can't say it in a sentence or two, narrow it.
Tip: A good test: could they answer it usefully in 20 minutes?
- Pick someone who has faced it.
Someone a few steps ahead of you on the path you're asking about. Not necessarily the most senior person you know; the most relevant one.
- Ask for 20 minutes, with the question in the ask.
Putting the question up front lets them decide quickly and come prepared. Make it easy to say no.
To: someone further alongI've been thinking about your question, in a sentence, and you were the first person who came to mind, because why them.
Would you have 20 minutes in the next few weeks to share your advice? A call or a coffee, whatever's easiest. And no worries at all if the timing doesn't work.
Swap the highlighted parts for your thing. Works on Slack, in email, or said out loud. - Bring context, then listen.
Open with two or three sentences of background, ask your question, and let them talk. Follow-up questions show you're listening.
You“If you were in my shoes, what would you do? And what do you wish someone had told you at this point?” - Follow up with what you did.
Thank them the same day. Then, a few weeks later, tell them what you tried and how it went. That second note is what turns one conversation into a relationship.
Tip: Most people never send the second note. It's the one they'll remember.
Good times to repeat it: whenever you're stuck on a real decisionevery couple of months, with someone newbefore a big career move
Making it work for you
Every workplace is different. Here’s what to think about before you start, and what might get in the way.
Things to think about
A clear, specific question shows you've done your own thinking and respects their time. It's also far more fun to answer than a vague request for guidance.
What might make this harder
Ask a colleague who they'd suggest, or look one step outside your network: a former colleague, an alumni group, someone who has written about it. A warm introduction helps.
Questions people ask
How do I ask someone to be my mentor?
Often it works better not to. Ask for 20 minutes of advice on one specific question instead. If the conversation goes well and you follow up, an ongoing relationship tends to grow on its own.
What should I ask a mentor?
One real question you're stuck on, specific enough to answer in a short conversation. Then: what would you do in my shoes, and what do you wish you'd known at this point?
How do I follow up after a mentoring conversation?
Thank them the same day, then write again a few weeks later with what you tried and how it went. The second note is the one most people skip, and the one that builds the relationship.
Why this works, and where it comes from
“Will you be my mentor?” is a hard question to say yes to. It's flattering, but it sounds open-ended: how often, for how long, about what? Busy people often hesitate, and the ones who say yes may not know what you actually need. Many good mentoring relationships never started with that question. They started with a conversation that went well.
A single, specific question changes the whole ask. It tells the other person exactly what you need, that you've done your own thinking, and that it will take 20 minutes, not a year. It's easy to say yes to and easy to prepare for. It also tends to get a better answer, because they're responding to your real situation instead of offering general wisdom.
Framing it as advice matters too. Asking what someone would do in your shoes invites them to help rather than to judge, and people tend to be more candid when they're helping. Advice looks forward, and it's easier to give well than feedback. A good question also leaves an impression. Someone more experienced now knows what you're working on and how you think, which is a quiet kind of visibility.
The part most people skip is the follow-up. A thank-you the same day is polite. A note a few weeks later saying what you tried and how it went is what turns one conversation into a relationship, because it shows their advice mattered. Do that a few times and you may well have a mentor, without ever having asked for one. If what you need is someone to advocate for you rather than advise you, one good conversation won't get you there. That takes longer.
Other simple things to consider
What to do next
More in Getting ahead
A few minutes that compound
Do it with Truest and it goes on your permanent record, in a Career Vault your employer doesn’t own.
See how Truest worksAlready a member? Log in- A reminder beforePut it on your calendar and Truest reminds you before it starts.
- It comes back if it slipsA missed one comes back around instead of disappearing.
- On your recordWhen it's done, it goes on your record with your priorities and progress.
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An exercise written by Truest, based on our experience. Last updated September 25, 2026. We sell a career membership; where that’s relevant above, we say so.