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Mentorship & guidance

20 questions to ask a mentor about your AI career

By TechlyUpUpdated 2 min readMentees

Quick answer

The best mentor questions are specific to a decision or piece of work. Organise them around what you're figuring out — direction, skills, projects, job search, and growth — and send them before the session so your mentor can prepare.

Direction

Clarify where you're heading.

  1. Given my background, which AI-related roles would use my strengths?
  2. What do people in that role actually do week to week?
  3. What would you choose if you were in my position?
  4. What misconceptions do newcomers have about this path?

Skills and projects

Focus your learning.

  1. Which skill should I learn next, and which can wait?
  2. Does this project demonstrate what employers need?
  3. What's missing from my portfolio?
  4. How would you evaluate this piece of work?

Growth

Longer-term questions.

  1. What habits helped you grow fastest?
  2. How do you keep up with changes in AI?
  3. What mistakes should I avoid?
  4. Who else should I talk to?

Questions to avoid

These rarely produce useful answers.

  1. “What's the best AI course?” without your goals or level.
  2. “Can you get me a job?” — it puts mentors in an awkward position.
  3. “Is AI going to replace everyone?” — too broad to be useful.
  4. Questions you could answer with a quick search.

Turning answers into action

After each session, write down the two or three actions you'll take and when. Share progress with your mentor before the next session. This shows you value their time and gives them context to give better advice.

Over several sessions, your notes become a record of decisions and progress — useful for your own reflection and for future mentors.

Try it yourself

Choose five questions relevant to you now and send them to your mentor (or potential mentor) before your next conversation.

Frequently asked questions

How many questions should I bring?

Three to five focused questions per session is usually plenty.

Should I share my work before the session?

Yes — reviewing real work makes advice much more specific.

What if my mentor doesn't know the answer?

Ask who might; good mentors connect you to others.

Want a suggested next step for your situation?

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Sources and further reading

Examples are authored practice material, not measured learner outcomes. Tool behavior can change. Found an error? Contact TechlyUp with the page URL and correction.

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