What are good conversation starters for mentoring?

Good mentoring conversation starters are open questions tied to where the pair is in the relationship: getting to know each other in the first meeting, goals and career direction early on, skills, feedback and obstacles in the middle, and reflection at the end. They invite a story or an example rather than a yes or no.

What should I talk about with my mentor?

Talk about what you are actually working on: a goal you want to reach, a decision you are weighing, a skill you are building, a situation at work you are unsure how to handle, or feedback you want on how you come across. Bring one real example to each meeting; it makes every conversation more useful than a general catch-up.

How many conversation starters should we use in one mentoring session?

Two or three is enough for a 45 to 60 minute session. One good starter followed by real follow-up questions can fill half a meeting. Choosing more than three usually turns the session into an interview and leaves no time to agree on next steps.

Who should start the conversation in a mentoring meeting?

In most programs the mentee owns the agenda and opens with the topic they most need help with, while the mentor asks the questions that deepen it. In the first meeting the mentor often goes first to put the mentee at ease. The template marks which side usually asks each starter, but most work both ways.

What topics should you avoid in a first mentoring meeting?

Avoid asking for a job or a referral, salary details, and personal topics such as health, family plans, religion or politics unless the other person raises them. Also hold back on big decisions like whether to quit; the mentor does not have enough context yet. Those conversations go better once trust is built.

Mentoring Conversation Starters: 72 Prompts by Session

Mentoring conversation starters are short, open prompts that a mentor or mentee uses to open a topic in a session, so the conversation reaches something real in the first five minutes instead of drifting into small talk. This template gives you 72 of them, grouped by stage and theme, with the side that usually asks each one.

Use it as a session-by-session prompt sheet: print it, keep it next to your notes, and pick a few before each meeting. It is deliberately short per topic. For deeper question banks, mentees can use the questions to ask a mentor guide and mentors the questions mentors ask guide.

How do you use these conversation starters?

Pick two or three per session, not more. One good starter with honest follow-up can fill half an hour.
Choose by stage. The session map below shows which sections fit which point in the mentorship.
Split the choice. The mentee picks one starter, the mentor picks one. Agree on them in the message that confirms the meeting.
Follow up before moving on. “Tell me more”, “What happened next?” and “What would you do differently?” turn a prompt into a conversation.
Tick what you used. Write the date next to each starter you used so you do not repeat yourselves, and so you can return to a good one later.
Close every session with section 9. One reflection prompt at the end makes the next meeting easier to plan.

Point in the mentorship	What the pair is doing	Pull starters from
Session 1	Getting to know each other, agreeing how to work	Sections 1 and 2
Sessions 2 to 3	Setting direction	Sections 2, 3 and 4
Middle sessions	Working on goals	Sections 4, 5, 6 and 7; section 8 now and then
Midpoint review	Checking progress, adjusting goals	Sections 2, 5 and 9
Final session	Closing and looking ahead	Section 9

The template

Mentoring conversation starters sheet

Mentor: ________
Mentee: ________
Program (if any): ________
Start date: ________

Who usually asks: Mentor = usually asked by the mentor. Mentee = usually asked by the mentee. Either = works both ways. Treat these as defaults, not rules.

1. First meeting: getting to know each other

#	Conversation starter	Usually asked by	Used (date)
1	“What does a good week look like for you right now?”	Either	________
2	“What are you working on that you genuinely enjoy?”	Either	________
3	“What is the short version of how you got to where you are?”	Either	________
4	“What made you sign up for this program?”	Either	________
5	“What kind of help is most useful to you: advice, questions, introductions or a sounding board?”	Mentor	________
6	“What is something about you that would not show up on your CV?”	Either	________
7	“How do you like to get feedback: direct, gentle, in writing, on the spot?”	Mentor	________
8	“Six months from now, what would make this feel worth the time?”	Either	________

2. Goals and direction

#	Conversation starter	Usually asked by	Used (date)
9	“If this mentorship goes well, what will be different for you in six months?”	Mentor	________
10	“Which of your goals would you work on even if nobody asked about it?”	Mentor	________
11	“Which of my goals do you think matters most right now?”	Mentee	________
12	“What have you already tried toward this goal?”	Mentor	________
13	“What would a small win look like before our next meeting?”	Either	________
14	“Is this goal yours, or one someone else expects of you?”	Mentor	________
15	“What would make you change or drop this goal?”	Either	________
16	“How will we both know you are making progress?”	Either	________

3. Career path

#	Conversation starter	Usually asked by	Used (date)
17	“Where do you want to be in two to three years, and how sure are you about it?”	Mentor	________
18	“Which roles around you look interesting, and what do you actually know about them?”	Mentor	________
19	“What did you consider doing instead of your current path?”	Either	________
20	“Which turning point in your career would you walk me through?”	Mentee	________
21	“What kind of work gives you energy, and what drains it?”	Mentor	________
22	“If you stayed in your current role two more years, what would you want from it?”	Mentor	________
23	“What do people at my stage tend to get wrong about career moves?”	Mentee	________
24	“Apart from me, whose career would you like to learn from?”	Mentor	________

4. Skills and learning

#	Conversation starter	Usually asked by	Used (date)
25	“Which skill, improved this quarter, would make the biggest difference?”	Mentor	________
26	“How do you learn best: reading, doing, or watching someone else?”	Either	________
27	“Can we look at a real piece of my work together next time?”	Mentee	________
28	“Which skill took you longest to learn, and what finally helped?”	Mentee	________
29	“Where could you practice this at work in the next month?”	Mentor	________
30	“What feedback have you already had on this skill?”	Mentor	________
31	“What would good enough look like for this skill, for now?”	Either	________
32	“Which resource or person helped you most when you were starting out?”	Mentee	________

5. Feedback

#	Conversation starter	Usually asked by	Used (date)
33	“What feedback would be most useful to you today?”	Mentor	________
34	“How did our last conversation land? Was anything unhelpful?”	Either	________
35	“Can I share what I noticed just now, honestly?”	Mentor	________
36	“What recent feedback did you disagree with, and why?”	Mentor	________
37	“How well do I prepare for these meetings, from your side?”	Mentee	________
38	“What is one thing that would make these sessions more useful?”	Either	________
39	“Which piece of feedback changed how you work?”	Mentee	________
40	“What did you do with the feedback from last time?”	Mentor	________

6. Challenges and obstacles

#	Conversation starter	Usually asked by	Used (date)
41	“What has been the hardest part of the last two weeks?”	Mentor	________
42	“What is in your way that you have not said out loud yet?”	Mentor	________
43	“Where do you feel stuck, and since when?”	Mentor	________
44	“How have you handled something like this before?”	Either	________
45	“Which part of this problem is actually in your control?”	Mentor	________
46	“How would you approach this if you were in my position?”	Mentee	________
47	“What is the worst realistic outcome, and could you live with it?”	Mentor	________
48	“Who else could help with this, besides me?”	Either	________

7. Navigating the workplace or organization

#	Conversation starter	Usually asked by	Used (date)
49	“Who has to say yes before your work moves forward?”	Mentor	________
50	“Whose support would make your next step easier?”	Mentor	________
51	“What unwritten rules did you have to learn where you work?”	Mentee	________
52	“How visible is your work to the people who decide on your next role?”	Mentor	________
53	“How is it going with your manager, honestly?”	Mentor	________
54	“Is there a conversation coming up that you would like to rehearse?”	Mentor	________
55	“How do you say no to extra work without hurting your reputation?”	Mentee	________
56	“What do you wish you had understood about this industry earlier?”	Mentee	________

8. Wellbeing and balance (light check-ins)

#	Conversation starter	Usually asked by	Used (date)
57	“How is your energy compared with last time we met?”	Mentor	________
58	“What are you looking forward to outside work this month?”	Either	________
59	“Is your workload realistic right now?”	Mentor	________
60	“What do you do when you notice you are close to overloaded?”	Either	________
61	“What is one thing you could take off your plate?”	Mentor	________
62	“How do you protect time for the things that matter to you?”	Mentee	________

These are check-ins, not counseling. If something serious comes up, listen, and point to the right support: the program coordinator, HR, or a professional service.

9. Reflection and closing

#	Conversation starter	Usually asked by	Used (date)
63	“What will you try before our next meeting, and by when?”	Mentor	________
64	“What was the most useful moment of today’s conversation?”	Either	________
65	“What do you know now that you did not know when we started?”	Mentor	________
66	“Which of our earlier conversations do you still think about?”	Either	________
67	“What should we spend more time on, and what less?”	Either	________
68	“What has changed since our first meeting?”	Either	________
69	“What will you keep doing after this mentorship ends?”	Mentor	________
70	“How would you like to stay in touch, if at all?”	Either	________
71	“What would you tell the next mentee in this program?”	Mentor	________
72	“What did you get out of this mentorship, as the mentor?”	Mentee	________

Session planner

Session	Date	Starters chosen (#)	What we agreed to do next
1	________	________	________
2	________	________	________
3	________	________	________
4	________	________	________
5	________	________	________
6	________	________	________

Questions to avoid early on

Save these until trust is built, or leave them out entirely:

“Can you get me a job or refer me?” Introductions follow trust. Asked in session one, it turns the mentor into a recruiter.
“How much do you earn?” Ask how pay is structured in the field instead, if it matters to the goal.
Health, family plans, religion, politics, relationships. Only if the other person raises them. In many countries these are also sensitive topics at work.
“Should I quit?” In the first meeting the mentor has no context. Ask what they would weigh, later.
Gossip about named colleagues or the mentee’s manager. Talk about situations and patterns, not people who are not in the room.
Interview-style questions such as “What is your biggest weakness?” They put the other person on trial.
Yes or no questions. “Do you like your job?” ends the topic. “What do you like most about your job?” opens it.

How should you adapt the template?

Fit it to the program type.

Employee programs: keep section 7, and add starters about internal moves and cross-team projects. If you run one at scale, employee mentoring software can put the right starters into each session for every pair.
Students and early-career mentees: swap part of section 3 for starters about internships, first jobs and choosing a specialization.
Founders and accelerator programs: rewrite section 7 around the team, customers and investors instead of a manager.
Peer and reverse mentoring: mark everything “Either”. Both sides teach, so both sides ask.

Adjust the tone. Formal cultures may need “Could you tell me about…” where informal ones use “What’s…”. Keep the open structure; change only the wording.

Give each session a theme. If you run a program, assign two or three starters to each planned session and add them to the meeting brief. The mentoring meeting agenda template has a slot for them.

Keep it to one page per session. Pairs use what they can see at a glance. A long list read aloud is an interview, not a conversation.

More templates and step-by-step guides for every stage of a program are in the guides library.