12 Questions to Ask a Mentor Before and During Your First Call

Bring three questions to your first mentor meeting. Ask what they would focus on given your goal, how they handled a similar decision, and what you could try before you next speak. If you want feedback on something specific, bring one short sample you have permission to share.

A mentor can help you see a tradeoff or spot a weakness in your plan. Give them a decision, a little context and enough time to ask you questions. The prompts below work for a one-off call or the first conversation in an ongoing mentorship.

12 questions to ask a mentor

To decide where to focus

1. Given my goal and the time I have, what would you work on first?
2. What part of my plan depends on an assumption I should test?
3. What could I put aside for now without hurting my chances of reaching the goal?

These work when you have more options than time. If your mentor suggests three priorities, ask which one they would pick if you only had a week.

To learn from their experience

1. Can you walk me through a similar decision you made and what tipped the balance?
2. What did you discover too late the first time you tried this?
3. What was different about your situation that might change your advice for mine?

Ask for a specific example. If their approach relied on a large budget, an established audience or help from a colleague, ask which part you could still apply with the resources you have.

To get feedback on your work

1. Where did you first get confused when you looked at this sample?
2. What would you change first, and what would you keep?
3. What would convince you that my next version is better?

Give them a small piece of work they can review during the meeting. A single slide, opening paragraph or portfolio page is easier to discuss than an entire project.

To leave with a next step

1. What is the smallest thing I could try this week to test your advice?
2. What result would tell me to keep going or change direction?
3. If we meet again, what should I bring so we can review what happened?

Close by repeating the action you plan to take and when you will review the result. A next step like rewriting an opening paragraph by Thursday gives you something concrete to discuss later.

Turn a vague question into a useful one

• Career change. Turn “How do I get into design?” into “I have time for one portfolio project this month. Which skill would you show in it, and what would make the work credible?”
• Skill practice. Turn “How do I take better photos?” into “These three indoor photos look flat. Which lighting change would you test first using the equipment I already have?”
• Starting a service. Turn “How do I find customers?” into “Two people asked me for feedback on their slides. What would you include in a first review session, and where would you draw the line on revisions?”

Copy this first mentor meeting brief

• Goal. What do I want to achieve and by when?
• Decision. What do I need help choosing or improving?
• What I tried. What did I do, and what happened?
• Constraint. What time, budget or resource limit matters here?
• Sample. What one item can I share safely?
• Three questions. Which answer would make the biggest difference? Put that question first.
• After the call. What will I do, by when, and how will I check it?

Worked example for a portfolio review

In this fictional example, Maya has one weekend to improve a design case study. She brings the first screen of her portfolio, with client details removed. Her goal is to make it easy for a reader to understand the problem and her contribution.

She asks where the reader got confused, what she should rewrite first, and how she can tell whether the rewrite worked. Her possible next step is to revise the opening and ask two readers to summarize the project in their own words. If both can identify the problem but neither can describe her contribution, she knows which part needs another pass.

Use the time you booked

For a 20-minute conversation, try three minutes on the context, twelve on the main question and five on the action you will take. This is a sample agenda. Adjust it to the actual meeting length. Cornell’s guidance for a first mentorship meeting likewise recommends preparing questions and agreeing on a goal and first steps.

If you want to try a focused conversation on Cash For Chat, open Users from the site menu and look for experience relevant to your question. Check what the session covers, its price and its length before booking. If you want ongoing mentorship, ask what follow-up the person offers and agree on expectations separately.