Questions to Ask a Mentor
For anyone who has a mentor or is about to meet one: at work, at school, in a trade, or anywhere someone further along has agreed to help. The questions are grouped by moment, from the first meeting and their story through your direction, skills and feedback, and hard situations to keeping the relationship going. Each has a note on what to listen for, what to ask next, or when to hold it back.
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The questions
Each question, and why to ask it
First meeting
How did you get to where you are today?
Why ask it
Ask for the turning points, not the list of titles: the offer they nearly refused, the year that went sideways, the person who opened a door. A path that sounds tidy has usually been tidied in the telling, so ask which step was luck. It is also the easiest question for a mentor to answer, which makes it a good one to start with.
What do you wish you had known when you were where I am now?
Why ask it
Say where you are first, in a sentence or two, or you will get advice for a stage you have already passed. The answers worth keeping are the specific ones: 'keep copies of your best work as you go', 'ask for help in the first week, not the sixth'. If it comes out as a slogan, ask what happened that taught them it.
What made you decide to be a mentor, and what do you hope to get out of it?
Why ask it
Some want to pass on what they were given, some like explaining things, and some were asked by a program and said yes. None of those is a bad answer. Each tells you what will keep them interested: hearing how things turned out, a good argument, or a plain thank you. Whatever they hope for, you now know what to give back.
What do you expect from me as a mentee?
Why ask it
Most mentors have two or three things in mind and wait to be asked: turn up on time, come with a subject, report back on what you did with the last piece of advice. Hearing them in the first meeting is far cheaper than discovering in the fourth that you have been missing one. Then say what you are hoping for from them.
How often should we meet, and for how long?
Why ask it
Let them answer first, then say what you can keep up. An hour a month that happens is worth more than a weekly slot that keeps getting moved. Settle who sends the invitation and who sets the subject as well, and assume both are your job.
A year from now, what would tell us both this had been worth doing?
Why ask it
It gives the two of you a finish line you can see: a decision made, a skill you can demonstrate, an application sent. Without one, meetings drift into pleasant catch-ups. Offer your own answer as well, and note both down so you can look at them again halfway through.
What did your own best mentor do that you would want to repeat with me?
Why ask it
The answer is their working model of mentoring: regular meetings, blunt feedback, introductions, or simply a door left open. If they never had a mentor, ask what they wish someone had done for them.
Here is the one thing I most want help with. Is that something you can speak to?
Why ask it
Name one thing, concretely: getting a first client, choosing between two courses, becoming easier to work with. A mentor who says 'not really, but I know who can' has saved you both several months.
Have you mentored someone before, and what did the people who got the most from it do?
Why ask it
You are asking for the manual. Expect answers like 'they came with a real problem' or 'they told me what happened afterwards', and then do those things. If it is their first time too, say so and agree to work it out as you go.
If you think I'm about to make a mistake, will you tell me straight?
Why ask it
Nearly everyone says yes. The value is in having asked: it gives them permission now, and you can remind them of it later if they start being polite. Offer the same in return for the times their advice doesn't fit your situation.
Do you think better out loud, or should I send you something to read before we meet?
Why ask it
Some mentors give their best advice off the cuff and others need a day with a page. A short written summary gets a reader's hour off to a running start. Sent to a talker, it goes unread and you both feel awkward about it.
What do you already know about me, so I don't repeat it?
Why ask it
If you were matched or introduced, they have probably been sent a paragraph about you, and hearing their version shows what stuck. Fill in only the gaps, in a couple of minutes, then get to what you came for.
What is the best way to reach you between meetings, and what is worth a message?
Why ask it
A two-line text suits one mentor and irritates another who wants everything saved for the next meeting. Ask for an example of something that should not wait, so you are not left guessing on the day it happens.
Is there anything I might tell you that you would have to pass on?
Why ask it
In a workplace or school program the mentor may know your manager or answer to a coordinator, and the rules differ from one program to the next. Ask how it works in yours before you bring up anything you would not want repeated.
Is there anything you would rather I didn't ask you about?
Why ask it
What they earn, a former employer and people you both know are the usual ones. Most mentors will say 'ask me anything', and that helps too, because you can hold them to it when a harder question comes up.
How much room do you realistically have for this, with everything else you have on?
Why ask it
It lets them be honest about their time before either of you is disappointed. A mentor in the middle of a launch, a house move or a new baby will answer slowly, and knowing that stops you reading the silence as lost interest.
Could we try this for a few months and then decide whether to carry on?
Why ask it
A check-in point makes it easier for a busy person to say yes and painless for either of you to stop. If a program sets the length, ask what usually happens when it ends.
Their story
What is the best advice anyone ever gave you?
Why ask it
Ask who said it and what was going on at the time, because advice without its occasion is a poster on a wall. Then ask whether they acted on it straight away. Sometimes it sat unused for years, and the reason it finally landed is the half you can use.
What is the biggest mistake you have made, and what did it teach you?
Why ask it
Give them room to choose a real one. The first offer is sometimes a mistake that flatters, like working too hard. If they name something that cost money, a client or a friendship, ask how they found out and what they did first. That sequence is what you will want on the day it is your turn.
What were you doing at the stage I'm at now, and what worried you most?
Why ask it
The worry is the useful half. If theirs was the same as yours, ask how it resolved. If it was something you have not thought to worry about, write it down.
What are you proudest of in your work so far?
Why ask it
The answer shows what they count as success, and it may not be the title or the prize: a person they trained, a job done properly when nobody was checking, something they built that is still standing. Ask what it took that nobody saw. It is a generous question as well as a useful one.
Who took a chance on you before you had earned it?
Why ask it
Most people can name one, and the story shows what a real opening looks like: who offered, what they risked, and why. The follow-up is what your mentor did afterwards to justify it.
What advice from your own mentors did you end up ignoring, and were you right to?
Why ask it
Good advice for one person is bad advice for another, and this gets them to say so. It also gives you standing permission to set aside their advice when it doesn't fit, which makes the rest of it easier to hear.
What part of your work looks easy from the outside and is not?
Why ask it
Whatever they name is usually the thing that took them years: reading a room, pricing a job, knowing when a piece is finished. Ask how they got the practice, because it will not be in any course description.
How did you know you were actually good at this, and not only getting by?
Why ask it
The answer tends to be a moment: someone trusted them with something that mattered, or a problem that used to frighten them became routine. That gives you a marker to watch for in your own work.
How do you define success now, and is that different from when you started?
Why ask it
Listen for what moved. A definition that began with a title, a salary or being picked may have shifted toward who they work with, how much say they have over their time, or the work itself. Ask what caused the shift. You need not adopt their version, but it tells you what their advice is aimed at.
Was there a point where you nearly gave this up, and what kept you in it?
Why ask it
Listen for whether it was a person, money in the bank, stubbornness or plain luck. If the answer is short, leave it there. Some stories are not for a second meeting.
What is a risk you took that you would advise me against, even though it worked out?
Why ask it
People tend to recommend whatever happened to work for them. This separates a good decision from a lucky result, and a mentor who can tell the two apart is one whose other advice deserves more weight.
What would you do differently if you were starting today, with things as they are now?
Why ask it
Their route ran through a world that has changed: how people get hired, what training costs, which tools exist. A mentor who says 'I'm not sure my path still exists' is being more useful than one who tells you to follow it.
How much of your week is the work you set out to do, and how much is everything around it?
Why ask it
A title hides the week. If you are aiming at something like their position, the share of it spent in meetings, on the road or on paperwork tells you whether you want the job or only the idea of it.
How did you meet the people who ended up mattering most to your work?
Why ask it
Expect ordinary settings more often than events with name badges: a shared project, a class, a favor done for a stranger. Those are situations you can put yourself in, which a list of names is not.
Which habits or routines have made the most difference to your work?
Why ask it
Ask for the ones they still keep, not the ones they admire in other people. A weekly review, the hardest task before the inbox, a notebook of things that went wrong: small and dull is a good sign. Try one for a month before you ask for another.
How do you keep the work from taking over the rest of your life?
Why ask it
Listen for the rule they actually keep: no email after supper, one day fully off, a practice night that does not move. If the honest answer is 'I didn't, for years', the story of what changed that is the part worth hearing.
What do you still find hard?
Why ask it
It is a relief to hear that the difficulty changes shape and does not disappear. This is also often the point where the conversation stops being an interview and becomes two people comparing notes.
Which of your strengths did someone else have to point out to you?
Why ask it
People rarely see their own, so there is usually a story about who said it and when. It sets up a later meeting where you ask them to do the same for you.
Who do you go to for advice these days?
Why ask it
Experienced people keep advisers too: a former boss, a peer in another city, a blunt friend. You learn what kind of counsel they value. Do not turn it into a request for an introduction on the spot.
Direction
What would you do next if you were in my position?
Why ask it
A fair question with one safeguard: ask for the reasoning as well as the answer. They would be making the move with their savings, their nerve and their contacts, and you have yours. Hear what they would weigh, make the decision yourself, and tell them afterwards what you chose.
Do my goals for the next couple of years look realistic to you?
Why ask it
Bring them written down, with dates. Spoken aloud, a goal can stay vague enough for anyone to agree with. A mentor can say which one is too timid, which depends on things outside your control, and which has a step missing in the middle. Ask what they would move to the top.
What would I need to show to be ready for the next step up?
Why ask it
Name the step: a promotion, a first paying client, a harder course, a bigger stage. The answer is more often evidence than time served, such as a project you ran yourself or a result somebody else can vouch for. Ask who decides, and whether that person has seen any of it yet.
Here are the directions I'm weighing. Which would you look at harder, and why?
Why ask it
Bring two or three real options, not 'what should I do with my life'. The 'why' is worth more than the pick, because it shows what they are weighing. You can disagree with the weighting and still use the reasoning.
What do you think I'm underestimating about the path I've described?
Why ask it
This asks for the cold water directly, so they do not have to decide whether you can take it. If they name a cost you have already counted, good. If it is new to you, the meeting has paid for itself.
From what you have seen, what am I suited to that I haven't mentioned?
Why ask it
You edit your own options before you say them out loud, and an outsider doesn't. Weigh the answer by how long they have known you: after two meetings it is a guess, after a year it is evidence.
Does this goal sound like mine, or like something I think I'm supposed to want?
Why ask it
Someone who has listened to you for a few meetings can often tell from which subjects make you talk faster. Save it until they know you a little, and be ready for the answer to be the second one.
What would you want to find out before committing to something like this?
Why ask it
It turns their experience into a list of homework: who to talk to, which numbers to see, what the contract or the course really requires. Come back next time with what you found.
Is there a cheap way to try this out before I'm committed?
Why ask it
One class before the degree, a weekend stall before the shop, a day shadowing someone before the switch. Mentors tend to know the small experiment because they have watched people skip it.
What does this path look like ten years in, for the people who stayed on it?
Why ask it
Your mentor has watched a cohort grow older, which you cannot do from the start line. Ask what the ones who are glad they stayed have in common, and what the others say about it now.
How do I know whether to stay where I am or move on?
Why ask it
Tell them what is prompting it: boredom, a difficult manager, an offer, a plateau. Each of those has a different answer. A mentor who has stayed too long in one place and left another too soon can describe what each felt like beforehand. Ask what they would try changing before they left.
If I change nothing for the next year, where do you think I end up?
Why ask it
Staying put is a choice too, and the one people examine least. Sometimes the honest answer is 'somewhere perfectly fine', which is worth hearing before you turn your life over.
Which of my goals do you think pull against each other?
Why ask it
Freedom and seniority, a new field and the same income, going fast and going deep. Collisions like these are easier to see from outside. Ask which one they would give up first in your place.
What does this choice make harder to do later?
Why ask it
Every direction closes something off. Someone further down the road knows which ways back are open in practice and which only look open. If the answer is 'nothing much', you can commit with less fretting.
When have you seen someone change direction late and make it work?
Why ask it
Worth asking if you fear you have left it too long. A real case tells you what the person carried over from the old life and what the change cost, which is more use than being told it is never too late.
Who is doing what I want to do in a way you admire, and what do they do differently?
Why ask it
A named example gives you something to study: how that person works, what they refuse, where they spend their time. If your mentor cannot think of anyone, ask whether the thing you are aiming at exists in the form you imagine.
Skills and feedback
Which skills should I be building at this stage?
Why ask it
Say what you are aiming at first, or you will get a general list. Push for an order: the one skill that would make the others easier, and one you can stop worrying about for now. Then ask how they would practice it in your place, because 'get better at presenting' is no use without somewhere to present.
Where do you think I most need to improve?
Why ask it
Hold it until they have seen some of your work or heard you talk a problem through. Before that it is guesswork. Ask for one thing, and for the occasion when they noticed it. Thank them, skip the defense, and come back in a month with what you changed, since that is what earns the next honest answer.
Would you look at something I've finished and tell me what you would have done differently?
Why ask it
Bring one finished thing: a report, a pitch, a portfolio page, a recording. Comments on a real piece of work are specific in a way that comments on you as a person never are. Keep it short enough to take in within ten minutes.
What is one thing I do well that I should be doing more deliberately?
Why ask it
Feedback on what you do well tends to come less often than feedback on faults, and it is easier to act on. Ask for the occasion they saw it, so you know exactly what to repeat.
What do you notice about the way I talk about my own work?
Why ask it
Your mentor hears you describe yourself at more length than most people do. Underselling, hedging, taking five minutes to reach the point, blaming other people: these are audible to a listener and nearly inaudible to you.
How could I get my ideas across better?
Why ask it
Give them something to judge: an email you sent, a slide, two minutes of you explaining your project. The findings are often small and fixable, such as a request buried in the third paragraph or an answer to a question nobody asked. Ask them to redo one of your messages the way they would have sent it.
How did you practice the thing you are best at?
Why ask it
You are after the routine: how often, with whom, and who corrected them. If the answer is 'I just did it a lot', ask what the first hundred attempts looked like and where they found the chances to make them.
How do you keep your own skills up to date?
Why ask it
You are asking for sources and for the habit: what they read, which colleague they ring, the hour they block out for it. Ask what they gave up on as well, because that saves you time. If the answer is 'not as well as I should', ask what they would do with one free afternoon a month.
What is the quickest way to find out whether I'm any good at this yet?
Why ask it
It is hard to judge your own level early on, and people miss in both directions. A mentor can name a test: enter the competition, submit the piece, try teaching it to someone, show it to a particular person. Then take the test.
Can I tell you exactly what I said, and hear how you would have put it?
Why ask it
Repeat a real exchange as close to word for word as you can, then ask for their version. Hearing the sentences an experienced person would use teaches more than the principle behind them, and you can borrow the wording next time.
Can I rehearse this with you before I do it for real?
Why ask it
A difficult conversation, a pitch, an interview answer, the first two minutes of a talk. Ten minutes of practice with someone who will stop you beats an hour of advice about it. Ask them to play the difficult version of the other person.
Is there a time I could watch you do the part of this I find hardest?
Why ask it
Sitting in on a client call, a critique or a tricky repair shows the small moves they would never think to mention. If it can't be arranged, and where clients or confidences are involved it often can't, have them talk you through the last one from the first minute: what they said, what they noticed, what they let pass.
Is there one book, course or person that taught you more than all the rest?
Why ask it
Asking for one forces a ranking. A list of ten is a shelf you will not get through. When you have finished it, come back with what you disagreed with, because that is the part they will want to talk about.
What was hardest to learn about leading other people?
Why ask it
Worth asking before you are in charge of anyone, and urgent once you are. Listen for the particular thing: handing work over and leaving it alone, telling someone their work is not good enough, being liked a little less. Ask who was on the receiving end while they learned it, and what they would say to that person now.
How do I get honest feedback from people who would rather be polite?
Why ask it
Your mentor has been on both ends of this. Expect tactics: ask about one piece of work, ask for a single thing to change, ask the same day while it is fresh. Try one before you next meet and report what you got.
How do I build a network when I don't know anyone yet?
Why ask it
Expect the unglamorous version: be useful to someone, turn up to the same thing more than once, follow up when you said you would. Ask which one room, group or event they would choose in your position, and how they would introduce themselves there. One specific place is something you can act on this month.
What are the standards in this line of work that nobody writes down?
Why ask it
Every field and workplace has them: how fast to reply, how finished a draft should be before anyone sees it, what counts as late. Insiders stop noticing them, so ask for the ones newcomers trip over.
Where am I being too hard on myself, and where too easy?
Why ask it
It is common to be off in both directions at once, strict about something that doesn't matter and lax about something that does. Ask for one example of each, and expect the second to sting more.
Is there something you have held back from telling me because you weren't sure I wanted to hear it?
Why ask it
This one is for once there is trust, not for a first meeting. Then stay quiet and take it without arguing, because how you react decides whether they ever do it again.
Hard situations
Can I describe a situation and have you tell me what you think is really going on?
Why ask it
You are inside it and they are not. Give the facts before your reading of them, and include the part that makes you look bad, or the advice you get will fit a different situation from the one you are in.
I made a mistake. How would you go about putting it right?
Why ask it
Bring it while it is fresh, not as a tidy story a year later. The two things to come away with are who to tell first and in what words. How calmly your mentor takes it is a fair measure of how big it is.
How should I ask for a raise or a promotion?
Why ask it
How this is done differs by employer, field and country, so ask how it works where you are: who decides, at what time of year, and what they need to see. Your mentor can hear your case before your manager does and tell you where it is thin. For the going rate, check published figures too, since one person's memory of pay is a single data point.
How do you work with someone you just don't get along with?
Why ask it
The useful version is about one specific person from their past and what they changed: their approach, the amount of contact, or their expectations. 'Rise above it' is not an answer, so ask what they did the next morning.
How do you disagree with someone more senior than you?
Why ask it
Ask for a time it went well and a time it did not. The difference tends to lie in the setting and the wording: in private or in the meeting, as a question or as a verdict, before the decision or after it. Borrow the opening sentence they used.
What do you do when you have taken on too much?
Why ask it
You want the mechanics: what they drop, who they tell, and the words they use. If the answer is that they simply work longer, ask about the time that stopped working.
How do you get back on your feet after something goes badly in front of people?
Why ask it
A talk that fell flat, a lost client, a rejection everyone heard about. What they did the following week, and how long it took to stop stinging, is the part to get. Knowing their timescale helps when you are on day two of your own.
Have you ever felt you didn't belong in the room, and what did you do about it?
Why ask it
Hearing it from someone you respect changes how you read your own doubt. Ask whether the feeling went away or whether they learned to work alongside it, since those lead to different advice.
How do you say no to someone you can't afford to annoy?
Why ask it
Ask for the actual words. A mentor who has turned down a boss, a client or a relative has a sentence that worked, and a borrowed sentence is easier to say than one you invent under pressure.
I've been turned down again. Is that a reason to change something or to keep trying?
Why ask it
Bring the detail: what you applied for, how many times, and any feedback you were given. One rejection tells you very little. Someone who has sat on the other side can say whether three of them point at the same thing.
How do you make a decision when you can't wait and don't know enough?
Why ask it
Listen for a method: who they call, what they write down, how long they let themselves go back and forth. A good second question is about a decision made that way that went wrong, and whether they would make it again knowing only what they knew then.
What is a conversation you put off for too long, and what did the delay cost?
Why ask it
Few people get far without one, and telling the story tends to make them generous with advice. It is also the natural opening to describe the conversation you are putting off yourself.
When life outside is affecting your work, how much do you tell people?
Why ask it
This varies a great deal by workplace, school and culture, so ask what is normal where you are and who is safe to tell. A mentor who shares what they once disclosed, and how it was received, has given you a real example to go on.
I've agreed to something and I think I'm out of my depth. What would you do?
Why ask it
The usual answer is to say so early, to the right person, with a suggestion attached. Press on the details: how early is early, and how do you word it so that it reads as responsibility and not panic.
What would you do if you were treated unfairly and could not prove it?
Why ask it
A mentor cannot fix this, but can tell you how such things tend to be handled where you are, what to write down, and who else to speak to. If it is serious, ask who has real authority to act. A mentor is a sounding board, not a complaints process.
Keeping it going
I tried what you suggested last time, and here is how it went. What would you change?
Why ask it
Hearing that their advice was acted on is what keeps a mentor invested. Report it honestly when it did not work, since a failed attempt gives them more to go on than a polite 'that was helpful'.
What is one small thing I could try before we next meet?
Why ask it
Asking for one small thing gets you something you will do. Write it down in front of them, and open the next meeting with how it went.
What haven't I asked you that I should have?
Why ask it
Good at the end of any meeting, and better after a few. It hands them the agenda for a minute, and what they pick is often the subject they have been waiting for you to raise: money, a habit of yours, a decision you keep circling. If they say you have covered it, ask what they would be asking in your place.
Is there something you expected me to follow up on that I haven't?
Why ask it
Mentors notice a dropped thread and rarely chase it. If there is one, either pick it up or say plainly that you decided against it and why. Left hanging, it tends to make their next piece of advice shorter.
Have I been asking too much of you, or too little?
Why ask it
Worth raising every few months. Politeness pushes people toward asking too little, which a mentor can read as fading interest, so if that is the answer, find out what they would be glad to be asked for. 'Too much' is their easy opening to say shorter or less often.
What have you noticed change in me since we started?
Why ask it
Slow progress is invisible from the inside. The answer also shows what they have been paying attention to. If they struggle to name anything, the meetings may have been too general, and that is worth fixing.
What could I do that would be useful to you?
Why ask it
Do not assume the answer is nothing. You may know a tool, an audience or a piece of news that they don't, and some mentors only want to hear how things turned out. Mean it when you ask, and follow through if they name something.
Who else do you think I should be learning from?
Why ask it
Asking for a name is lighter than asking for an introduction, so it is fine in the early meetings: someone whose writing to read, a group to join, a person whose route resembles the one you want. Once your mentor has seen how you handle advice they may offer to connect you. If they do, send a few lines about yourself that they can forward.
Is there someone who would give me the opposite advice to yours?
Why ask it
One mentor is one view. A confident one will name the person and may offer to connect you. Hearing both sides of a real disagreement in your field teaches you more than hearing the same view twice.
Is it all right if I use your name when I contact someone you know?
Why ask it
Using a mentor's name without asking spends their reputation without their consent. Ask each time, say what you plan to write, and afterwards tell them how the conversation went.
Would you be a reference for me, and what would you feel able to say?
Why ask it
Raise it before you list them anywhere. The second half matters: it shows how they would describe you, and it lets them decline gracefully if they cannot speak to what the application needs.
As I get further along, how should what we talk about change?
Why ask it
The questions of the first year stop fitting. They may suggest meeting less often, moving to bigger decisions, or finding a second mentor for the things they cannot help with. None of that is a demotion for either of you.
Should I be mentoring someone myself yet?
Why ask it
Explaining something to a person one step behind you shows up the gaps in what you know. Your mentor can say whether you have enough to offer, and often knows who is looking.
Would you be willing to stay in touch once the formal part ends?
Why ask it
For programs with an end date. Suggest something light, such as a short note with your news twice a year, since a small and specific request is easy to agree to. If they would rather not, thank them and let it end well.
Getting more out of a mentor
Practical guidance for the conversation itself
Choosing what to ask
Three questions fill a meeting
A good answer, with its follow-ups and your side of the story, can run fifteen minutes. Pick three for an hour: one about them and two about your own situation. Arriving with twelve turns the meeting into a survey, and the mentor starts giving short answers to get through it.
Match the group to how well you know each other
First meeting and Their story belong to the first conversation or two. Direction and Skills and feedback work once they know enough about you to have an opinion. Hard situations is for when you are in one, not for the abstract. Keeping it going is worth a question every few months.
Put your own case in front of the question
'How do you say no?' gets a general answer. 'My coach has asked me to run the junior sessions and I don't have the evenings' gets one you can use on Thursday. One or two sentences of your situation is enough.
Leave out what you could look up
Entry requirements, typical pay and application dates are quicker to find elsewhere. A mentor's hour is for judgment and experience: what they would weigh, what they have seen go wrong, what they would say in your place.
Different kinds of mentor
Matched through a program
The program usually sets the length, how often you meet and what gets reported, so ask the coordinator and the mentor how it works. The First meeting questions about what gets passed on and when to review matter most here. The first conversation may feel arranged, because it was.
Someone you asked yourself
There is no structure unless you supply it. Propose the date, the length and the subject each time, and make each request easy to decline. Suggesting a trial of a few months takes the weight off a yes.
Inside your own workplace or school
They know the people you will be talking about. That makes their advice specific and your candor riskier. Settle what stays in the room before you name names, and remember they may sit in meetings where you are discussed.
Outside work altogether
A coach, an elder, a tradesperson, a business owner, someone further along in a craft. Their story and Hard situations carry over unchanged. In Direction, read 'path' as whatever you are building: a practice, a business, a body of work.
Someone you rarely see
If you talk a few times a year or only by message, send a short update first so the time is not spent catching up. By message, ask one question at a time. Three in one email usually gets the easiest one answered.
What to do with the answers
Ask for the example
When advice arrives as a principle, ask about the last time they did it themselves. The story holds the detail you need: who they called, what they said, how long it took, what went wrong first.
Write down their words
The phrase they used to refuse a client or open a hard conversation is the thing you will want three weeks from now. Your own summary of it will have lost the wording. Note it during the meeting, or straight afterwards.
Treat advice as one person's experience
It worked for them, in their time and place. Take what fits, and tell them what you did with it, including when you chose differently and why. A mentor can work with disagreement. Silence about what happened gives them nothing to work with.
Let the pause run
After a hard question, wait. The first answer is often the one they have given before. What comes after a few seconds of quiet is more likely to be about you.
Habits that wear a mentor out
Asking them to decide for you
'Should I take it?' hands over a responsibility they never agreed to carry. Ask what they would weigh and what they would want to know, then decide yourself and tell them what you chose.
Only turning up when something is wrong
If every meeting is a crisis, the mentor never sees your ordinary work and has nothing to compare the bad week with. Meet when things are going well too. Those are the meetings where Direction and Skills and feedback get proper attention.
Asking for favors before there is a relationship
Introductions and references come out of a mentorship that is going well. Asked for in the second meeting, they tell the mentor what you came for. Wait until they have seen how you handle advice.
Bringing what needs a different kind of help
A legal question, a health problem or a formal complaint needs someone qualified or someone with authority. A mentor can help you work out who that is and what to say to them. They should not be asked to stand in for that person.