Questions to Ask Mentor About Career Development Reddit
Questions for a mentor conversation about your own progression: what to stop doing, which skills actually move you a level, how visibility works, what to say in one-to-ones, and how to ask for honest feedback about yourself.
The questions
Open any question for the note
What was your job when you were at my level, and what did the next step actually look like?
Why ask it
Anchors the conversation to a real path instead of general advice. It also exposes how far apart your situations are, since a mentor who moved up in a different decade or a much smaller company is describing a route that may no longer exist.
What did you spend time on early on that turned out not to matter?
Why ask it
Most people can name one thing quickly: a certification nobody asked for, a side project no one saw, hours spent polishing work that was never read. That list is more actionable than any advice about what to add.
Which skill genuinely moved you up a level, and how did you build it?
Why ask it
Push for the how, since the skill itself is usually unsurprising and the method is not. Look for whether they built it through a specific assignment or on their own time, because only one of those is something you can ask for.
How much of your progression came from doing good work, and how much from being visible?
Why ask it
Almost nobody says it was entirely the work, and the ratio they give tells you how their organization actually operated. If they are uncomfortable with the question, ask instead who in the company knew what they were working on.
Who decided your promotions, and how did those people know your name?
Why ask it
Promotion decisions are usually made by people one or two levels above your manager, in rooms you are not in. Push for how those people came to know them: a specific project, a presentation, someone who spoke up on their behalf. That mechanism is the part you can copy; their job title is not.
What separates people at my level who move up from those who stay put?
Why ask it
Mentors have watched a lot of people at your stage and the pattern they name is usually concrete: taking unglamorous work nobody wanted, or being the person who can write clearly. Vague answers about attitude mean they have not thought about it, so ask for two names and what differed.
Looking at how I spend my week, what would you drop?
Why ask it
Requires you to describe your week honestly first, which is half the value. Mentors are far better at spotting wasted effort from outside than you are from inside, particularly recurring meetings and work you have quietly inherited.
What should I be saying in my one-to-ones that I probably am not?
Why ask it
Most people use one-to-ones for status updates that a written note would cover. A useful answer gives you a different agenda, usually asking for specific work, flagging risk early, or naming what you want next.
How do I find out what my manager actually thinks of me?
Why ask it
Formal reviews are usually late and softened. Look for a practical script, for example asking what would have to be true for you to be promoted next cycle, which is harder to answer with reassurance than are you happy with my work.
How do I ask for a bigger project without it sounding like a complaint about my current one?
Why ask it
The framing problem is real and mentors have usually solved it. Good answers tie the request to a need the team already has, rather than to your development, which is the version that tends to get deferred.
How do you decide whether a problem at work is worth raising?
Why ask it
You are asking for their filter, not their politics. The useful part is usually a test they apply, such as whether they would be willing to own the fix, or whether the problem will still exist in six months if nobody says anything.
How did you handle a manager you could not work with?
Why ask it
Nearly everyone has one of these stories and it is more instructive than a success story. Note whether they solved it by leaving, by outlasting the person, or by changing their own behavior, and whether they would choose the same again.
When did you last change jobs, and how did you know it was time?
Why ask it
The signal they describe is the transferable part: stopped learning, a promotion that went elsewhere, a new manager, a number. It gives you something to check yourself against that is not simply how you feel on a bad week.
Was there a point where you should have left somewhere earlier than you did?
Why ask it
Staying too long is the more common regret and the harder one to admit. What kept them, loyalty, a vesting date, an expected promotion, is usually the same thing that will keep you longer than you should stay.
What do you wish someone had told you about money at my stage?
Why ask it
Framing it as what they wish they had known makes it easier to answer than asking what you should earn. Answers often cover equity mechanics, the effect of an early low base on every raise after it, or simply that they never asked.
From what you can see, what should someone at my level be earning?
Why ask it
A mentor outside your management chain is the safest person to ask, and they may know the market better than your manager will admit to. Even a range with a caveat is more use than a published salary survey.
Who else should I be talking to, and would you be willing to introduce me?
Why ask it
Turns a conversation into access, which is what mentors are uniquely able to give. Make it specific, one person and one reason, because open-ended requests for introductions rarely get acted on.
If I worked for you, what about my last six months would concern you?
Why ask it
The hypothetical gives them permission to be critical without it being a verdict. Asked late in a conversation that has gone well, this is the question most likely to produce something you have not heard before.
Is there anything about how I work that you have hesitated to tell me?
Why ask it
Direct, and it only works if you can take the answer without arguing. Expect a pause; if they name something, write it down, say thank you, and resist the urge to explain the context.
What would you like me to come back with next time?
Why ask it
Ends with a commitment, which is what turns a single conversation into an ongoing relationship. It also tells you whether they want to keep meeting, since an unenthusiastic answer here is a polite signal.
Making mentor conversations worth their time
Practical guidance for the conversation itself
Setting it up
Ask for one conversation, not for a mentor
Requests to be mentored are open-ended and easy to decline. A request for thirty minutes about a specific question, with a suggested time, is answered far more often and can become a standing arrangement on its own.
Send two or three questions in advance
It lets them think, and it prevents the meeting turning into their career story followed by an apology about the time. It also signals you have a plan, which is the main thing that makes people agree to a second meeting.
Say what you are actually deciding
Whether to take an offer, whether to change track, whether to raise something with your manager. Advice given without a decision attached is general by necessity, and general advice is why most mentoring conversations feel thin.
Match the mentor to the question
Someone two steps ahead of you is best on tactics: what to say, what to ask for, what a level looks like. Someone much more senior is better on direction and introductions and often out of date on the day-to-day.
In the conversation
- Spend the first two minutes on context and then ask. Long preambles eat the half hour and shift the meeting toward your version of events.
- Ask for stories rather than principles. What did you do in that situation produces something usable; what is your approach to conflict produces a maxim.
- When advice is vague, ask what they would do this week. Specificity is often available and simply not offered.
- Take the criticism without defending it. Explaining the circumstances is the fastest way to teach someone not to be candid with you again.
- Finish early if you have what you came for. Ending a thirty-minute meeting at twenty-five is remembered favorably.
What goes wrong
Asking for a job in the first meeting
It converts a mentor into a referral source and usually ends both. If you do want help with openings, say so plainly when you ask for the meeting rather than arriving under another heading.
Treating their path as the path
One person's route reflects their timing, their company, and a good deal of luck. Ask two or three people the same question and act on what overlaps rather than on whoever spoke most convincingly.
Never reporting back
The single thing that keeps a mentor engaged is hearing what you did with what they said, including when you did the opposite and why. Silence reads as the advice going nowhere.
Only appearing when things are bad
A mentor you contact solely in a crisis has no baseline to advise from. A short note twice a year when nothing is wrong makes the difficult conversation possible when something is.
Afterwards
- Write down what they said within the hour, separating facts from opinions, so you can weigh them differently later.
- Pick one thing and do it before the next conversation. One completed action is worth more than a page of notes.
- Send a short follow-up naming that one thing. It is the most reliable way to get a second meeting.
- If they offered an introduction, make it easy: send a two-line summary they can forward without editing.
- Note anything that surprised you about pay or progression, and check it against another source before acting on it.