Questions to ask your mentor
Most first calls with a mentor die the same way. Someone asks “so, any advice?” It’s too big a question for anyone to answer, so small talk fills the rest of the hour and you both leave polite and empty.
Good questions fix that. They give the other person something real to hold on to, and they show you’ve already thought about your own situation. That’s the whole trick. There’s nothing clever about it.
You don’t need perfect questions. You need honest ones. Pick two or three from below, ask them in your own words, and let the conversation wander where it wants to go.
Questions for a first meeting
You are not trying to impress anyone. You are trying to find out who this person is and how they can actually help you. These questions do that without turning the call into an interview.
1.“What made you say yes to mentoring someone?”
Why this works: Warm way in, and you learn what they care about in the first two minutes.
2.“What do you wish someone had told you when you were at my stage?”
Why this works: Pulls out their best advice before you've had to explain your whole life story.
3.“How did you actually get to where you are - not the tidy version?”
Why this works: Real paths are messy. Hearing a messy one makes your own feel normal.
4.“What are you really good at that I could learn from you?”
Why this works: Points you both at the thing they can genuinely help with, instead of guessing.
5.“How do you like to work with people - quick messages, or longer calls?”
Why this works: Agreeing on this in week one saves months of awkward guessing.
6.“How honest do you want me to be about the things going badly?”
Why this works: Gives you permission to bring real problems, not just the wins.
7.“What would make this a good use of your time too?”
Why this works: Mentoring goes both ways. Knowing what they get keeps them showing up.
8.“Is there anything you'd rather I didn't ask you about?”
Why this works: Shows respect early and makes the space safe for both of you.
9.“What should we talk about next time?”
Why this works: Ends the call with a plan, which is the easiest way to make sure there is a next time.
Questions when you feel stuck
Stuck usually means you can't name the problem yet. A good mentor can help you name it in one conversation - but only if you ask straight questions instead of hinting.
1.“Here's where I am. If you were me, what would you do?”
Why this works: A direct question gets a direct answer. It stops you both from circling for an hour.
2.“Have you ever been stuck like this? What got you out?”
Why this works: You get a real story instead of general advice, and stories are easier to copy.
3.“What am I not seeing here?”
Why this works: Blind spots are the main thing another person can give you. Ask for them directly.
4.“Is this a me problem, a job problem, or a timing problem?”
Why this works: Naming which one it is decides everything you do next.
5.“What's the smallest thing I could change this month?”
Why this works: Big moves feel impossible when you're stuck. Small ones don't.
6.“Am I being patient, or am I just scared to move?”
Why this works: Hard to answer alone. Much easier to say out loud to someone who won't judge you.
7.“What would you stop doing if you were in my job?”
Why this works: Most advice adds things to your plate. This one takes something off it.
8.“How long is too long to stay in a spot like this?”
Why this works: Turns an open-ended wait into a deadline you can hold yourself to.
9.“If nothing has changed in six months, what should I do then?”
Why this works: You leave with a plan for the bad case, which makes today much less frightening.
Questions when you're thinking about a change
Every job looks better from the outside. Before you jump, find out what the other side really looks like and what you'd be giving up to get there.
1.“What should I know about this kind of work that people outside it don't?”
Why this works: Gets you the inside view, which is the only reason to ask a person instead of the internet.
2.“What parts of my current job would I actually miss?”
Why this works: Stops you running away from something you'd want back a year later.
3.“What would I have to give up to make this change?”
Why this works: Money, title, time, comfort - far better to know the price before you pay it.
4.“Do you know anyone who made a move like this? How did it go for them?”
Why this works: One real example beats ten guesses, whether it went well or badly.
5.“What's the smallest way I could test this before I commit?”
Why this works: A side project or three conversations can save you two wasted years.
6.“Does it sound like I'm running toward something, or away from something?”
Why this works: Both can be fine. You just need to know which one you're doing.
7.“Which of my skills carry over, and what would I be starting from zero on?”
Why this works: Turns a scary leap into a list you can actually work through.
8.“How do I explain this change so it sounds like a plan and not a panic?”
Why this works: You'll need this story in every interview. Practise it on someone kind first.
9.“If I do this and hate it, what's my way back?”
Why this works: Knowing the exit exists makes the jump much easier to take.
Questions when you're new in a job
The first three months quietly decide how people see you for years. Ask these early, while not knowing things is still completely normal.
1.“What do people usually get wrong in their first three months?”
Why this works: A cheap way to skip the mistakes everyone else makes.
2.“How do I find out what my boss actually cares about?”
Why this works: The job description and your boss's real priorities are rarely the same thing.
3.“What's a good first win for me to aim at?”
Why this works: One early win buys you trust for everything that comes after.
4.“How much should I be asking questions versus working it out myself?”
Why this works: New people worry about this constantly. A straight answer settles it for good.
5.“How do I get to know people here without being annoying about it?”
Why this works: Relationships are the real onboarding, and most people are too shy to start them.
6.“What should I write down now that I'll have forgotten in a month?”
Why this works: Fresh eyes notice the confusing parts. In eight weeks you won't see them at all.
7.“I think something here is done badly. Do I say anything yet?”
Why this works: Being right early is worth nothing if the timing is wrong. Ask before you speak up.
8.“How do I tell if I'm doing well before my first review?”
Why this works: Six months of quietly wondering is a long time to feel unsure.
9.“What did you do in your first months somewhere that really paid off?”
Why this works: Copy what worked for someone who has already done this a few times.
Questions about growing to the next level
Nobody gets promoted for being busy. These questions get you the specific gap between where you are now and where you want to be.
1.“What does the next level actually look like, day to day?”
Why this works: Job titles are vague. Days are specific, and you can prepare for a day.
2.“Where's the gap between what I do now and that?”
Why this works: Straight feedback you almost never get anywhere else.
3.“What do people at that level do that I'm not doing yet?”
Why this works: Turns 'work harder' into a real list you can start on Monday.
4.“Who decides this, and what do they need to see from me?”
Why this works: Promotions are decided by people in a room, not by how tired you are.
5.“What should I stop doing to make room for bigger work?”
Why this works: You usually can't grow by adding more. Something has to come off first.
6.“Is there work here that nobody is doing that I could pick up?”
Why this works: The fastest way up is often the job nobody has claimed yet.
7.“How do I talk about my work without sounding like I'm bragging?”
Why this works: Good work nobody sees doesn't count, and almost everyone needs help with this bit.
8.“Honestly, how long does this usually take?”
Why this works: A real timeline stops you quitting one month before it would have happened.
9.“If it can't happen here, where else could it?”
Why this works: Sometimes the ceiling is the room you're in, not you.
Questions when you're starting to lead people
Leading people is a different job, not a bigger version of your old one. Ask someone who has already made that switch and remembers how strange it felt.
1.“What surprised you most when you first led a team?”
Why this works: The surprises are exactly the part no course or book warns you about.
2.“How do I stop doing all the work myself?”
Why this works: This is the hardest habit for a new leader to break, and the most expensive one to keep.
3.“How do I give hard feedback without wrecking the relationship?”
Why this works: You'll need this in month one. It's a skill you learn, not a personality you're born with.
4.“What do I do when someone on my team is better at the work than me?”
Why this works: Very common, very uncomfortable, and almost never talked about out loud.
5.“How do I know if my team trusts me?”
Why this works: Nobody will tell you directly. You have to learn what the signs look like.
6.“What's worth stepping in on, and what should I let go?”
Why this works: Saves you from turning into the boss who checks everything and slows everyone down.
7.“How do I say no to work coming from above me?”
Why this works: Protecting your team's time turns out to be most of the job.
8.“What mistake did you make as a new leader that I could skip?”
Why this works: A free lesson from someone who already paid for it.
9.“How do I keep getting better at my craft while I'm managing?”
Why this works: Nearly every new leader worries about this, and nearly none of them ask.
One last thing about asking
Don’t read these off a list like a form. Ask one, then actually listen. The best part of the answer usually comes after the pause, when they say “although, thinking about it more…” That bit is the reason you asked.
Good questions are step one.
The real thing is having someone who’s still around to answer them next year. That’s what we do.
Answer 10 honest questions