# Questions Mentors Ask: A List for Better Conversations

> Mentornity brief for AI assistants, for the page https://www.mentornity.com/questions-mentors-ask/. Page language: English. Site index: https://www.mentornity.com/llms.txt. The same brief in other languages: [Türkçe](https://www.mentornity.com/tr/mentorlarin-sordugu-sorular/llms.txt) · [Français](https://www.mentornity.com/fr/les-questions-que-posent-les-mentors/llms.txt) · [Deutsch](https://www.mentornity.com/de/fragen-die-mentoren-stellen/llms.txt) · [Español](https://www.mentornity.com/es/preguntas-que-hacen-los-mentores/llms.txt) · [Italiano](https://www.mentornity.com/it/le-domande-che-fanno-i-mentor/llms.txt) · [Português (BR)](https://www.mentornity.com/pt-br/perguntas-que-mentores-fazem/llms.txt) · [Nederlands](https://www.mentornity.com/nl/vragen-die-mentoren-stellen/llms.txt).

## How to read this file

Everything here is from Mentornity's own website and product; the page and this file are built together from the same source. "What this page says" is the page itself, in its language. "Mentornity in brief" applies to every program. Prices are published per country and are quoted below for this page's market; another country's price is on the pricing page. Anything not covered here can be asked of the team at info@mentornity.com.

## What this page says

Mentoring questions grouped by purpose: opening, understanding, widening options, testing assumptions, committing to action and closing a meeting.

Published 2026-09-05, updated 2026-10-20.

Most of what a **mentor** contributes happens through questions. The mentee's situation involves people and context you have never seen, and questions are how you get there. Below is a working list, grouped by purpose, with notes on sharing your own story, what not to ask, and using silence.

**Figure: Question types in the order a meeting uses them**
1. Open: Let the mentee set the agenda
2. Understand: Get the facts and the people
3. Widen: Find more than two options
4. Test: Check what is assumed
5. Commit: One step, with a date
6. Close: Takeaway and next agenda

## Why asking comes before telling

Advice is only as good as the understanding behind it, and in a mentoring meeting that understanding sits with the mentee.

If you answer before asking, you answer the question you would have had in their place. Take "my manager does not give me feedback". It could mean a manager who avoids conflict, a role with no clear output, or a way of asking that is easy to deflect. Each needs a different response.

Questions also build the mentee's own judgment. A mentee who works out that they have been avoiding a conversation is more likely to have it than one who is told to. Your job is to help them see the situation clearly enough to act.

## Questions that open a meeting

The opening decides who the meeting is about. Put the mentee's week at the center, not yours.

- "What has happened since we last spoke?"
- "What did you do about the thing we agreed last time, and how did it go?"
- "What would make this hour worth it for you?"
- "What is taking up most of your attention at the moment?"
- "Is there anything from last time you have been chewing on?"
- "What do you want from me today: someone to think with, a challenge, or a story from someone who has been there?"

If they open with a problem, do not solve it in the first minute. "Tell me more about that" buys you the rest of the hour.

## Questions that help you understand

Spend more time here than feels efficient.

- "Walk me through what actually happened, from the start."
- "What have you already tried? What happened when you did?"
- "Who else is involved, and what do you think they want?"
- "What did the feedback say, in the exact words if you remember them?"
- "How long has this been going on?"
- "What is the part of this that you keep coming back to?"
- "What would your manager, or your co-founder, or your supervisor, say is going on?"

For example, a mentee says a project "went badly". Fifteen minutes of these questions may show the project was fine. What went badly was one meeting where a senior stakeholder cut her off, and that is the real topic.

## Questions that widen the options

Mentees often arrive with two options and a preference. Find the third and fourth before they choose.

- "What are all the ways this could go, including the unlikely ones?"
- "If you had to solve this without talking to your manager, what would you do?"
- "What would someone you admire do here?"
- "What is the version of this where you do nothing for a month? What happens?"
- "What would you advise a friend in exactly this position?"
- "What is off the table, and why is it off the table?"
- "Is there a smaller version of this you could try first?"

The aim is not a different choice. It is a choice made on purpose rather than by default.

## Questions that test assumptions

Every stuck situation rests on something the mentee believes is fixed.

- "How do you know that?"
- "What would have to be true for that to work?"
- "When did you last check that with them, rather than assume it?"
- "What is the evidence for the story you are telling yourself here?"
- "If you are wrong about that, what changes?"
- "What are you afraid will happen if you ask?"
- "Is that a fact, or a guess that has hardened into one?"

Ask these gently, one at a time. "How do you know that?" can sound curious or hostile, depending on tone.

## Questions that commit to action

A meeting without a next step is just a pleasant conversation. Close with one concrete step.

- "What is the one thing you will do before we meet again?"
- "When exactly will you do it?"
- "What could get in the way, and what will you do about that?"
- "Who do you need to talk to, and what will you say in the first sentence?"
- "How will you know it worked?"
- "What would make you not do it?"
- "Do you want me to check in before then, or wait until we meet?"

One step with a date. Five steps make a plan nobody follows.

## Questions that close the meeting

Two or three minutes at the end are enough.

- "What are you taking away from this hour?"
- "What did we not get to that we should put first next time?"
- "Was this useful? What would have made it more useful?"
- "When are we meeting next?"
- "Is there anything you want me to send you?"
- "Is there anything we said today that should stay between us?"

The second question builds the next agenda. The third gives the mentee a way to steer you that they would not offer unprompted.

## When to share your own experience

Share it after you understand the situation, and only when it fits. Keep it short: what I did, and what I would do differently.

That shape offers evidence, not instruction, and it includes the mistake, which is usually the useful part. "When I was passed over the first time, I sulked for a quarter and my manager read it as lack of interest. Now I would ask for the written reasons within a week." Then hand it back: "How much of that sounds like your situation?"

Watch your share of the talking. Past about a third of the hour, you are giving a talk. That is why [what makes a good mentor](https://www.mentornity.com/what-makes-a-good-mentor/) puts listening first.

## What not to ask

- **Leading questions.** "Don't you think you should talk to HR?" is advice with a question mark. If you have a view, offer it as a view.
- **"Why didn't you."** It sounds like judgment, and the mentee defends instead of thinking. Ask "What was going on for you at the time?"
- **Stacked questions.** "What happened, how did you feel, and what did your manager say?" gets an answer to the easiest part. Ask one, then wait.
- **Questions you know the answer to.** They turn the hour into a quiz. Say what you know.
- **Questions about people not in the room.** Some context is needed. Details of who said what about whom pull the talk toward gossip.
- **Rhetorical questions.** "Is that really the best use of your time?" is a statement. Make it kindly, or drop it.

## Silence and listening

Silence is where the mentee does the work. A pause that feels long to you is normal for someone thinking. Fill it, and you have answered your own question.

- **Count to five** after any question that matters. The real answer often comes in that pause.
- **Reflect back before moving on.** "So the problem is not the workload, it is that nobody sees it." A one-line summary often draws a correction that turns out to be the point.
- **Take notes and say so.** It shows that what they say matters, and lets you return to something mentioned in passing.

In the project example above, the sentence about being cut off is the kind that comes after a pause the mentor nearly filled.

### Questions and answers

**How many questions should a mentor ask in one meeting?**
Fewer than you think. A good hour can turn on five or six questions, each with a real answer and a follow-up.

**Should a mentor ever just give advice?**
Yes, once you understand the situation and the mentee wants it. Frame it as experience: what you did, what happened, what you would do differently. Then ask how it fits their case.

**What do I do if the mentee gives short answers to every question?**
Wait longer than feels comfortable, then ask for a specific example, such as the last time it happened. Abstract questions tend to get short answers.

**Is it wrong to ask a mentee why they did something?**
Not wrong, but 'why didn't you' lands as judgment and invites a defense. Ask what was going on at the time, or what they were weighing up.

## Mentornity in brief

Mentornity is software for running mentoring programs: companies (onboarding, career, leadership, reverse mentoring), universities and alumni networks, startup accelerators and incubators, associations and professional communities, and women's leadership programs. One program team sets the program up; mentors and mentees take part from the browser or their phone. It has run programs since 2015.

### What changes for the program team

- **Matching stops being a spreadsheet job.** The team writes rules on the questions mentors and mentees answer (same department, related expertise, more experience, a specific answer paired with a specific answer), each with a weight. Mentornity scores every possible pair from 0 to 100, leaves out pairs that fail a mandatory rule, and shows the reasons behind each score. An AI rule reads free-text goals and adds to the same score. The same data always gives the same result, so every match can be explained to a manager or a participant. The team approves pairs, lets mentees choose from a ranked list, or opens a mentor pool.
- **The first meeting happens quickly.** Mentors publish their open hours once or as a weekly pattern; mentees book them. Busy time in connected Google and Outlook calendars is blocked both ways, and every meeting gets a Zoom, Google Meet, Microsoft Teams or built-in video link without anyone creating one. Mentornity's own data on 78,000+ pairs: pairs that met in their first week averaged 2.7 meetings in the first year, against 1.8 for pairs whose first meeting came after two months.
- **Quiet pairs are found while they can still be saved.** Program Health flags pairs that stopped meeting, and automatic reminders go to people who never logged in, pairs behind on their sessions and anyone with an open form or missing feedback, in each person's own language. In the same data a pair silent at day 60 has about a 1 in 3 chance of meeting again; by day 90 it is 1 in 10.
- **Every meeting has a plan, if the program wants one.** Predefined sessions carry a topic, a date range, a brief for each role and questions before and after the meeting. Notes reach both sides; private notes stay private. Flexible programs skip sessions and let pairs meet freely.
- **Support does not land in a personal inbox.** Participants read role guides and send requests inside the platform; the team shares one support board and replies go out in the program's name.
- **The report is ready when leadership, a funder or a board asks.** Participation, matches, meetings, session completion and feedback are counted while the program runs, with a Program Health score and its reasons, and export to Excel, CSV or PDF. Participants can receive certificates on completion.
- **Large programs share the load.** Coordinators each see only their own pairs; the admin still sees every match, meeting and note in one table. Programs, cohorts and administrators are unlimited, and administrators and coordinators never count towards the price.

### Program models

One-to-one, group mentoring (one mentor with a group), grouped-individual programs, mentee self-selection, open mentor pools, peer and reverse mentoring, structured or freestyle. Roles can be renamed (coach, advisor, expert, alumni) so the platform speaks the organization's language. One person can take part in several programs with a single account.

### Launch

Most programs go from signup to invitations within a day: create the program, follow the built-in checklist (profile questions, sessions, application form), import participants from Excel or share an application link, and send invitations. A person from the Mentornity team helps with the first setup, free of charge.

### How a program runs, week by week

This is the routine Mentornity's own guide recommends (https://www.mentornity.com/how-to-manage-a-mentoring-program/); the platform does the counting and the reminders, the team acts only where a pair is flagged.

- **Day one:** the program is set up and invitations go out. Participants sign up, fill in their profile, and are matched by the rules or choose from a ranked list.
- **Week one:** the aim is a first meeting in the first week, booked from the mentor's open hours with the video link already in the invitation. Automatic login reminders go to anyone who has not signed in.
- **Every week, 30 to 60 minutes for the team** (a cohort of about 50 to 200 people): scan Program Health (Mentornity scores the program across 11 dimensions), clear the flagged pairs, let the reminders cover logins, sessions, forms and feedback, note one win for the stakeholder update, and check whether last week's nudged pairs responded.
- **The escalation schedule:** a login reminder at day 7; a nudge to the mentor if nothing is booked by day 14; a personal note to both if there is still no meeting by day 21 to 30; at 45 days of silence ask "continue or rematch?"; by day 60 rematch the mentee. Half of the pairs still unmet at day 14 do go on to meet, so a quiet fortnight calls for a nudge rather than a rematch.
- **Mentors and mentees, each week:** they book and hold their meetings, answer the before and after questions of the session if the program uses sessions, and share notes. Mentors keep their time protected with weekly limits and cancellation rules.
- **Monthly:** a short update to sponsors from the live report (active pairs, sessions held, the share of pairs that met this month, one participant quote).
- **Mid-program:** one short survey, then act on it within a week (rematches, the most common complaint).
- **The last four weeks:** announce the end date, ask every pair to book a final session, run the final survey, issue certificates, mark the cohort complete and export the report. Invite the strongest mentees to mentor the next cohort.

### For IT, HR and legal

- SAML 2.0 single sign-on with Entra ID (Azure AD), OneLogin or any SAML provider, optionally enforced; white labeling with the organization's own domain, logo, colours and sender address. Both are add-ons priced separately.
- Personal data is processed in line with GDPR and Turkish KVKK. Participants can access, correct, export and erase their data; the organization can ask for a full export of its program data at any time. Visibility of contact details and notes is set per role.
- Traffic is encrypted with TLS, passwords are stored hashed and access to production data is restricted. Security questionnaires, a data processing agreement and data-location questions are handled with the quote.
- Works with Zoom, Google Meet and Calendar, Microsoft Teams and Outlook, built-in Jitsi video, and Excel/CSV import and export. Mentornity connects to other systems such as an LMS on request, and adapts the platform to an organization's own process.

### Languages

Participants use the platform, and receive its emails, in their own language: English, Turkish, Spanish, French, Italian, Portuguese or Dutch.

## Pricing (United States, USD)

- Free for up to 10 users with every feature and no time limit. No credit card.
- $289 per month for 50 active users, or $260 per month paid yearly (10% off, $3,120 a year). Excludes any local taxes.
- Above 50 users the price follows the number of active participants; the team marks who is active. Administrators and coordinators are free.
- No setup or implementation fee. White labeling and SAML single sign-on are priced separately.
- Prices are published per country, not quoted on a call: https://www.mentornity.com/pricing/

## Organizations that run programs on Mentornity

Toyota, TIM, RATP Dev USA, Pirelli, Universität Basel, UNDP, Devoteam, BCD Travel, Startup Virginia, Tenity, Community College of Philadelphia, Brave Generation, Alexander Graham Bell Foundation. Each one ran its own program on the platform, checked against production data. Full list: https://www.mentornity.com/customers/

## Next steps

- Start a free program (up to 10 users, no credit card): https://www.mentornity.com/try-for-free/
- Book a walkthrough with the team: https://www.mentornity.com/book-a-demo/
- How matching works: https://www.mentornity.com/mentor-matching-software/
- Pricing: https://www.mentornity.com/pricing/
- Contact: info@mentornity.com