Questions to Ask a Mentor: 30 Questions, Sorted by What You Want

Before you ask anything

Mentors give you two things: their lived experience and their honest judgement. Every question should spend one of those. If the answer is already on a website, in a course catalogue or in a salary survey, asking it costs you minutes you can't get back.

So before the conversation, write down the one decision you're actually trying to inform. Not 'I want advice about my career' — 'I'm choosing between a big firm and a startup internship by the end of the month.' Everything you ask should connect to it, at least loosely.

• Name your decision in one sentence before you write any questions.
• Do the solo research first: their path, their company, the basics of the field.
• Ask for a fixed, short slot and end it on time — it's the single best way to be invited back.

Career exploration questions

These help you understand the path — how people actually end up in this work, and what the branch points were. Paths look inevitable in hindsight and almost never were, so push on the forks.

• What were you doing two years before this role, and how did you get from there to here?
• Was there a moment you nearly took a different direction? What tipped it?
• What did you apply for and not get — and did it matter in the end?
• Which parts of your education turned out to matter, and which never came up again?
• What does the first year in this field actually feel like?
• If you were graduating now, what would you do differently?

Skill-building questions

These turn admiration into a plan. The goal is to leave knowing what to practise, read or build next — not just that their job sounds nice.

• What skill separated the people who did well in your field from the ones who stalled?
• What could I build, write or try this term that would teach me that skill?
• What's something students usually over-prepare for, and something they under-prepare for?
• What should I read or follow to keep up — and what's overrated?
• How did you get your first break, and what did you have to show for it?

Questions for a decision you're facing

If you're weighing a real choice — a course, an offer, a move — bring it to the conversation directly. A mentor's judgement is worth most when it's applied to something specific. Ask for their reasoning, not their verdict.

• Here's my situation and my two options — what would you want to know before choosing?
• What have you seen happen to people who took the option I'm leaning away from?
• What's the downside of the safer choice that people don't notice until later?
• What would you do in my position this term, and why?
• What would make you change your answer?

Questions that get honest answers

Ask these late in the conversation, once the relationship has a little weight. Frame them about the field rather than about them personally, and don't press if they deflect.

• What's the most common reason people leave this field or team?
• What surprised you most in your first six months?
• What do you wish someone had told you before you started?
• What's the realistic pay range for someone entering at my level?
• What does progression actually look like, and how long does it take?

Questions about the mentor relationship itself

If the first conversation goes well, these keep it going. Mentorship usually grows out of one good conversation, not a formal request to 'be my mentor' — which puts a strange weight on both of you.

• Is there something I should read, try or build before we speak again?
• Would it be alright if I checked back in when I've made progress on that?
• Given what you've heard, is there anyone else whose path I should hear about?
• What's the most useful way for me to keep you updated — a short email, or a message when something changes?

Closing the conversation

The last three minutes decide whether this becomes a relationship or a one-off. Don't fill them with thanks — be concrete.

Then follow up in writing within a day: short, and naming the specific thing that changed your thinking. That detail is what makes people remember you and reply next time.

• Say back one thing you'll do differently because of the conversation.
• Ask if there's anyone else they'd suggest you speak to.
• Send a short thank-you within a day that names the specific thing that helped.

Finding someone to ask on Weave

Weave was built around one honest 30-minute conversation — not long-term mentoring and not a job pipeline. You describe where you are and what you're deciding, and you're introduced to a student, graduate or early professional whose path overlaps yours.

It goes both ways: everyone who joins agrees to answer questions from people a step behind them as well as asking their own, and each person sets a cap on how many introductions they take. Many of the best mentor relationships start exactly there — with one good question, asked well.

Frequently asked questions

What are the best questions to ask a mentor?

The best questions are specific to where you are now. Ask about branch points in their path ('what nearly went differently?'), the ordinary texture of the work ('what did last week actually look like?'), and decisions you're facing ('if you were me this term, what would you do?'). Avoid anything you could look up yourself.

How many questions should I prepare for a mentor meeting?

Prepare eight to ten and expect to ask five. Thirty minutes moves quickly once answers get specific, and the most useful moments usually come from following up on something they said rather than marching down your list.

What should you not ask a mentor?

Don't ask them to make the decision for you, to get you a job or referral in a first conversation, or anything you could have researched — what their company does, what a course covers, what a salary is 'on paper'. Those questions waste the one resource a mentor gives you: their lived experience.

How do I start a conversation with a mentor?

Say who you are in one line, name the single decision you're trying to inform, and ask for a fixed short slot — 20 to 30 minutes. Specific, bounded requests get answered; open-ended 'can I pick your brain' requests get ignored.

What's the difference between a mentor and an informational interview?

An informational interview is one conversation to understand a path. A mentor is someone you return to as your situation changes. The first meeting looks the same either way — start with the informational-interview style questions and let a return relationship grow if it fits both of you.

How do I find a mentor as a student?

Start one or two steps ahead of you — a final-year student, a recent graduate, someone two years into the job you're considering. They remember the details and are far more likely to reply. Weave introduces you to exactly one person whose path overlaps yours, for a single honest 30-minute conversation.