10 Questions to Ask a Mentee
Questions to ask a mentee that get past small talk, for mentors paired through a workplace or university program and for those who arranged it between themselves. There are 56 here. Begin with the First Ten, which cover the first meeting and usually spill into the second, then draw on Goals, Work Now, Growth and Check-Ins as the months go on. The last group holds questions to ask potential mentees before you agree to take someone on.
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The questions
Each question, and why to ask it
First Ten
What are your short-term and long-term career goals?
Why ask it
Short term and long term rarely line up. When the two-year answer has nothing to do with the ten-year answer, that gap is the most useful thing you can work on in the first few sessions.
What challenges are you currently facing in your role or career?
Why ask it
Listen for whether the obstacle they name is a skill, a person, or a system. A person tends to come up first, and on a second look it can turn out to be a system they have not learned to work yet.
What skills do you want to develop and why?
Why ask it
The reason matters more than the skill. Wanting to learn data work to get promoted and wanting it because the problems are interesting produce different plans, and the first one collapses when the promotion moves.
What does success look like to you?
Why ask it
Ask this before you start giving advice. A mentee whose definition of success is entirely other people's approval will hear your suggestions as instructions, and you will spend the next year correcting for that.
What kind of support would be most helpful from me as your mentor?
Why ask it
Answers cluster into three types: someone to think out loud with, someone with connections, and someone who will tell them the truth. Deliver the wrong one and the sessions stay pleasant and go nowhere.
Have you had a mentor before, and what worked or did not work about it?
Why ask it
Someone who has been mentored before can tell you what to avoid, often too much of the mentor's own career story or too little challenge, and both are easy to correct once they are said. A first-time mentee will be guessing at what the hour is for, so describe how you like to run it.
How often would you like to meet, and what format works best for you?
Why ask it
Agree a number and a channel now, and set it slightly below what either of you feels ambitious about. Monthly conversations that actually happen beat fortnightly ones that get moved twice and then quietly disappear.
What would you like to know about me?
Why ask it
Mentees often arrive knowing only your job title and guessing at what you can help with. Keep your answer short and include one thing that went badly, since a mentor with a tidy story is hard to bring a messy problem to.
What should stay between the two of us, and is there anything you would rather not discuss?
Why ask it
Say your own side first: what you will keep private, and whether you report anything to a program coordinator or to their manager. In a formal scheme, check what its rules require of you before you promise. People only test how honest they can be once they know where their words go.
Six months from now, what would make you say this had been worth your time?
Why ask it
Write the answer where you can both see it and read it back at the halfway point. A marker you can check, such as a promotion case submitted or a portfolio finished, gives every later session something to be measured against.
Goals
What does your ideal role look like three years from now?
Why ask it
Ask them to describe the day rather than the title. A day full of meetings and headcount points somewhere very different from a day spent building things, and people often chase a title that does not contain the day they just described.
Which parts of your job energize you, and which drain you?
Why ask it
One named task in each direction tells you more than a category does. Somebody flattened by the weekly report and lit up by customer calls is describing a job that could be reshaped, not a career that needs abandoning.
Whose career would you like to have, and what about it appeals to you?
Why ask it
Press on the second half. Two mentees can name the same person, one for the freedom she has and the other for her reputation, and those are different careers to plan for.
What have you ruled out, and what made you rule it out?
Why ask it
Options crossed off early tend to stay crossed off long after the reason has expired: a qualification they lacked then, a city they could not move to, one bad manager in that field. Check with them whether the reason is still true.
What would have to change for you to be happy staying where you are for another two years?
Why ask it
It separates a mentee who needs a new job from one who needs a different version of the current one. A short, fixable list (a project, a pay review, a new manager) is worth raising with their employer before they start applying elsewhere.
What decisions or opportunities are you currently considering?
Why ask it
Someone weighing an offer or a transfer needs a conversation this month, not a development plan for the year. If there is a deadline on it, let that decision take over the session.
What would you try at work if you knew a failed attempt would not count against you?
Why ask it
The answer is the ambition they keep out of their appraisals. Once you have heard it, the useful move is often cover rather than advice: telling them the risk is smaller than they think, or saying so yourself to somebody who matters.
What does your life outside work need your career to make room for?
Why ask it
Care for a parent, a child's school years, a sport, a faith, a second income: plans that ignore these get agreed in the session and dropped at home. You do not need the details, only the shape of the constraint.
If you could make real progress on only one thing this year, what would it be?
Why ask it
A mentee with six priorities is usually moving slowly on all of them. A single choice shows what they would protect, and it lets you sort everything else they bring you into help or distraction.
Work Now
How did you end up in the role you are in now?
Why ask it
The route says more than the CV: what they chose, what they fell into, and who gave them a chance along the way. A student can answer for their course instead, and the pattern of choices reads the same.
What does a normal week look like for you right now?
Why ask it
Have them walk you through it day by day. How the hours split between meetings, their own work and other people's emergencies is often news to the mentee as well, and it keeps your suggestions tied to the job they have instead of the one you picture.
What have you done or learned in the last few months that you are proud of?
Why ask it
A mentee who cannot think of anything has still told you something. It can mean the job has become maintenance, or that nobody around them is naming what went well.
What are you good at that people do not give you credit for?
Why ask it
Out comes the work that no review form has a box for: calming the difficult client, writing the document everyone quietly relies on, keeping a project honest. Often your most useful contribution is helping them get it counted.
How would you describe your relationship with your manager?
Why ask it
You are hearing one side, so collect facts as well as feelings: how often the two of them meet, whether feedback arrives, who decides the next assignment. If you know the manager, say so now and keep what you hear to yourself.
Who else is in your corner at work, and where are the gaps in your support?
Why ask it
Get them to draw the map out loud: a manager, a peer they trust, somebody senior who knows their name. The empty box is usually the senior sponsor, and that is a gap you may be able to close with one introduction.
Which unwritten rules at work are you still trying to figure out?
Why ask it
Every workplace has unwritten rules about who speaks in meetings, how fast to reply and what counts as ambitious. A mentee new to the field or the country may be guessing at them, and you can often supply in five minutes what took you years to notice.
Which working relationship would you most like to improve?
Why ask it
Get the last conversation with that person described, not their general character. The detail shows whether this is a clash of styles that a different approach could ease, or something that belongs with their manager or HR and not with a mentor.
What is taking more of your time than it should?
Why ask it
Often it is work that was handed over informally and never handed back: the rota, the meeting minutes, showing every new starter around. Help them work out who could release them from it and what the request would sound like.
What have you been avoiding, and what makes it hard to start?
Why ask it
What makes it hard to start is the part to listen to. Avoidance often turns out to be a missing skill, a conversation they dread, or a brief nobody has made clear, and each of those needs a different response from you.
Growth
What areas do you feel less confident about?
Why ask it
Expect a hard skill first, then ask again. The real gap is usually social, such as speaking in a room full of senior people or saying no to a request from someone they like.
What feedback have you received recently that stuck with you, and why?
Why ask it
The word stuck is doing the work, because it catches praise and criticism they are still carrying around. If they reach for a comment from three years ago, that deserves more of your attention than anything written on their development plan.
How direct do you want me to be when I think you are getting something wrong?
Why ask it
Nearly everyone says 'very direct', so offer a real choice: stop you mid-sentence, or raise it at the end of the session. Once the manner is agreed, the first hard comment arrives as something they asked for.
What did you last learn the hard way?
Why ask it
A recent mistake told plainly shows how they handle being wrong, and that matters more to the mentoring than the mistake does. Notice whether the blame lands entirely on themselves or entirely on others, and remember it when you give feedback.
When did you last ask for something at work, and how did it go?
Why ask it
A raise, a day off, a place on a project, more time on a deadline: any example will do. Someone who cannot remember one may be waiting to be noticed, and rehearsing a small request with you is a safe place to begin.
What would you like the people you work with to say you are known for?
Why ask it
Compare the answer with how their week is spent. When someone wants to be known for strategy and fills every day fixing other people's spreadsheets, the reputation they want and the one they are building have come apart.
What do you do when you are stuck on a problem?
Why ask it
Some push on alone for days and some ask at the first obstacle, and both habits cost something. Which one they are tells you whether to nudge them to ask sooner or to stay with a problem longer before bringing it to you.
What piece of your work would you like me to look at?
Why ask it
A slide deck, a CV, a draft email to a difficult client, a recording of a talk: comments on something real do more than an hour of general advice. Settle what kind of comments they want first, since big-picture and line-by-line are different jobs.
Where do you think you are harder on yourself than you need to be?
Why ask it
It lets a self-critical mentee say so without having to perform confidence. Hold back the reassurance and find out whose standard they are using, because it is often a rule from an old boss or a school that no longer applies.
Check-Ins
What did you do with what we talked about last time?
Why ask it
Opening here tells them the sessions connect. If nothing happened, treat it as information and not as a failing: the step was too big, the week was too full, or the advice did not fit.
What do you want to walk away with today?
Why ask it
A decision, a plan, a rehearsal of a hard conversation and a chance to think out loud each need a different kind of hour. Hearing which in the first five minutes saves you from solving a problem they only wanted to describe.
What is on your mind today that was not on the agenda?
Why ask it
Agendas get written days ahead, and the thing that happened yesterday afternoon is not on them. Leave a real pause afterwards, because the honest answer takes a few seconds to arrive.
What is the one thing you will do before we meet again?
Why ask it
Close on it, and have them say it in their own words instead of agreeing to yours. A step small enough to finish in a week, with a day attached, gets done; a resolution to work on their confidence does not.
How would you like me to hold you accountable between our conversations?
Why ask it
Letting them pick the mechanism is what makes it hold, whether that is a message on Friday or simply knowing you will ask first thing next session. If they say they need nothing, open the next meeting with last time's commitments anyway.
Is there a door I could open for you, such as an introduction, a project or a recommendation?
Why ask it
Offer it, because asking a senior person for a favour is hard and politeness keeps many mentees from doing it. A name or a project in reply turns your goodwill into something you can act on this week.
What has changed in your goals since we started?
Why ask it
Goals stated in a first meeting are partly a guess and partly what the mentee thought you wanted to hear. Come back to them every few months, and treat a change as knowing themselves better, not as inconsistency.
What have I suggested that turned out not to fit your situation?
Why ask it
This gives them permission to say your advice missed, which few mentees do unprompted. The reason it missed (money, family, a manager you have never met) is usually something you needed to know anyway.
What could I do differently to be more useful to you as a mentor?
Why ask it
Ask this in the first month rather than saving it for the end, then wait out the polite answer for the second one. The less senior person in the room is unlikely to say first that the sessions are not working, so raising it has to be your job.
Has this mentoring done its job, or is there more you want from it?
Why ask it
Formal programs end on a date, and informal ones drift on unless somebody asks. If it has done its job, finish well: look back together at where they started, and offer one introduction to whoever should come next.
Potential Mentees
Why do you want a mentor, and why now?
Why ask it
A trigger such as a new role, a stalled application or a decision with a deadline means there is real work to do together. 'Everyone says I should have one' is not a reason to refuse, but it tells you the first job will be finding the question.
What made you ask me in particular?
Why ask it
You are checking whether what they want is something you have. If they are after your employer's name or a field you left ten years ago, say so kindly and point them to somebody closer to it.
What is the first thing you would want my help with?
Why ask it
A potential mentee who can name one concrete thing, even a small one, has thought about how to use your time. Students and career changers often cannot yet, and a single trial conversation is a fair way to find out more before you decide.
What have you already tried on your own?
Why ask it
The answer shows effort and saves you from suggesting the obvious. It also shows where they got stuck, which can be a more exact description of the help they need than the request they opened with.
How much time can you give this each month, including what you do between meetings?
Why ask it
Good intentions on both sides do not survive a full calendar. Have them name a number, give yours, and agree on the lower of the two.
How do you take it when someone tells you something you did not want to hear?
Why ask it
Nobody describes themselves accurately here, so get the last time it happened and what they did next. You are deciding whether you can be honest with this person, and a mentor who has to tread carefully is not much use to anyone.
Do you have other mentors, and what do you go to each of them for?
Why ask it
Several is healthy, and it tells you which gap you would be filling. If you would be the only one, encourage them to find a second voice so that yours does not become the only opinion they hear.
What would you expect from me, and what should I be able to expect from you?
Why ask it
Give your own list too: who books the meetings, who sets the subject, how much notice to cancel. If the two sets of expectations are far apart, it is kinder to find out before either of you has committed.
Mentoring Without Wasting Each Other's Time
Practical guidance for the conversation itself
Choosing Which Questions to Ask
The First Ten are a first meeting, and probably a second
Ten questions with real answers will not fit in one hour. Take the first four for the opening meeting (goals, obstacles, skills and what success means to them), and keep the six about how the two of you will work for the end of that session or the start of the next. If the meeting is short, question 5, the one about what kind of support they want, is the one not to skip.
Match the group to how long you have known them
Goals and Work Now suit the second and third sessions, when you still need the facts of their job and their plans. Growth works once they have seen you keep a confidence, because those questions ask them to admit a weak spot. Check-Ins is for every session after that: one question to open with and one to close on is plenty. With a student, read tutor or supervisor wherever a question says manager.
Potential Mentees comes before all of it, if you have a choice
When a program has already matched you, skip that group. When someone has asked you directly, or you are choosing among applicants, a first coffee built on three or four of those eight questions tells you whether you are the right person and whether they have the time. Saying no after it, with a name to try instead, is a fair result.
Three or four questions fill an hour
The list is 56 questions long so that you can choose, not so that you can get through it. A mentee who is asked twelve questions in a session gives twelve short answers and leaves feeling interviewed. Pick a few, and let the follow-ups come from what they say.
An Example of Asking a Mentee the Right Questions
Start with a question from the list
Say you open with 'What challenges are you currently facing in your role or career?' and the mentee answers, 'Mostly workload. There is just too much.' That is a true answer and a safe one, and if you respond with tips on managing time, the session ends there.
Ask for the particular case
The right next question is small: 'Which piece of it would you hand back tomorrow if you could?' Now the answer has an object in it, such as a monthly report they inherited from someone who left. One named task can be worked on, where 'too much' cannot.
Find out what has been tried
'Have you raised it with anyone?' often gets 'No, I did not want to look like I could not cope.' The problem has changed in three questions from workload to a conversation they are avoiding with their manager, and that is the one a mentor can help with.
Give your view last, and ask before you give it
'Would it help to work out how you might put that to your manager?' leaves the decision with them. If they say yes, draft the opening sentence together and agree when they will say it. The pattern is the same for any question on the page: wide question, particular case, what has been tried, then an offer.
The First Two Sessions
Spend the first session on scope, not advice
Agree what the mentoring is for, how long you are both committing, how often you will meet, and what is out of bounds. Pairs that skip this drift apart after a few agreeable meetings, because neither person ever decided what progress would look like.
Resist the first answer
The first problem a mentee raises is usually the safest one. Ask the same question again in different words later in the session, and treat whatever surfaces in the final ten minutes as the real agenda.
Say plainly what you do not know
If they ask about a path you have not walked, say so and offer to find them somebody who has. Guessing costs you credibility the first time it is exposed, and it can send them the wrong way for a year.
End with two small commitments
One thing they will do, one thing you will do, both finishable inside a week. Vague homework such as think about your positioning is why the next session starts from nothing.
Keeping It Useful Over Months
- Ask before you tell. Your experience only helps once you know which of their constraints it applies to, and mentees rarely interrupt a story to say it does not fit.
- Watch for advice they nod at and never act on. That pattern usually means the advice ignores something they have not told you, so ask what you are missing rather than repeating yourself.
- Keep notes between sessions: the goal they stated, the names of the people in their story, what they promised. Remembering the detail is most of what makes a mentor feel trustworthy.
- Do not drift into being their manager. Feedback on their work is fair. Assigning them work, or negotiating on their behalf without being asked, is not.
- Guard confidences carefully, especially if you know their manager. One remark repeated in the wrong room ends the honest part of the relationship permanently.
- Say something when the relationship has run its course, and offer to introduce them to the next person. Mentoring kept on the calendar out of politeness costs you both an hour a month.
- If they are being treated badly rather than struggling, name it, and help them find out who handles that where they work or study. Coaching someone to work harder inside a broken team is one way mentoring does harm.