Career Advice
November 15, 2022

Top 4 Questions You Should Be Asking Your Mentor

Top 4 Questions You Should Be Asking Your Mentor

Mentor sessions take a lot of time and effort to set up and run but can become a total bust if you don’t put in the proper work ahead of time. ADPList Mentor Jasmine Rosen, Sr. User Experience Designer at Autodesk, explains how one can avoid generic mentor sessions and get the most out of their time together by using these 4 question types:

1. Experience Sharing

One of the best ways to learn from others is to hear their success (and not-so-success) stories. Asking experience sharing questions are especially great at the beginning of your mentorship period because they help facilitate that initial relationship building. When people share stories, it requires vulnerability and as a result creates that safe space that is so critical to a good mentorship experience.

Here are the basic ones:

  • When/how did you decide to get into this field?
  • What does your day to day look like?
  • What is the most challenging part about your job?
  • What qualities make a good [role]?

To go deeper, consider the overlap between topics relevant to you and the special experiences your mentor has. This way you can leverage that specific lens your mentor has to get a truly unique perspective. Here’s some examples:

1. How does your [experience/background/identity/beliefs] affect your perceived ability to [desired outcome]?

  • How does gender affect your ability to gain alignment? Any practices you follow?
  • How does being a bootcamp grad affect your perceived ability to get hired?

2. How important is the ability to [skill] related to [desired outcome]?

  • How important is managing an intern to becoming a manager?
  • How important is volunteering for team events to gain respect from peers?

3. What’s your most proud moment relating to acquiring [desired outcome]? How did you prepare?

4. Can you tell me about a time when you gave up on a pursuit? How did you know it was time?

5. Can you tell me about a time you recovered from a massive blunder? How did you do it?

6. Can you tell me of a time you were impressed/appalled by another colleague? What did they do to make themselves stand out?

7. Thinking back on your journey. How does your current reality match your expectations five years ago? What did you wish you knew before taking on role [X]?

2. Resource sharing

If you’re trying to develop a specific skill and need frameworks, tools, and resources to accelerate your learning, ask these questions. These are also great questions for “flash” or non-recurring mentorship sessions.

  • In your opinion, what are the criteria of success for achieving [desired outcome]?
  • Do you have any successful frameworks or templates you’ve used (or seen used) to get [desired outcome]?
  • Can you introduce me to anyone that may be a good resource to achieve [desired outcome]?

From my experience mentees often ask for resources without a specific target. Doing some self-reflection (or feedback surveying) to identify key area(s) of growth, and sharing them with your mentor, can help you get more tailored resources and have more focused meetings. To help you, here’s a list of some skills you may want to strengthen:

  • Adaptability (organizational change)
  • Advocating for the customer
  • Advocating for yourself
  • Balance work and personal life
  • Building and maintaining collaborative relationships
  • Communicating efficiently and effectively
  • Collaborating with others
  • Dealing with bullying/micro-aggressions/unfair treatment
  • Determining when to pursue vs pivot
  • Driving decision making
  • Displaying a global perspective
  • Enhancing domain knowledge or business perspective
  • Establishing/improving new processes
  • Gaining alignment & buy-in
  • Gaining visibility
  • Giving and receiving feedback
  • Identifying the right problem to solve
  • Identifying strengths and weaknesses
  • Navigating workplace politics
  • Negotiating compensation
  • Managing people/building talent
  • Managing expectations
  • Managing relationships (manager, stakeholders, and peers)
  • Managing stress/time
  • Planning & executing
  • Preparing for a performance review/interview/presentation
  • Prioritize career growth
  • Set healthy boundaries
  • Staying on task/time management
  • Staying inspired
  • Resolving conflict
  • Returning to work after a break
  • Risk analysis
  • Taking risks & innovating
  • Thinking analytically

3. Perception sharing

One of the best gifts a mentor can provide is an honest lens of how you are perceived by others. Hopefully they’ve seen how you prepare, problem solve, and receive advice and can accurately “hold up a mirror” to help you see how your actions are impacting how others see you.

Stuck getting the same basic advice? Generally people feel more comfortable providing constructive criticism on a specific topic if they know the asker is seeking it. Be specific in your ask for what area you’d like feedback on, and that should help you get the feedback you’re looking for. Here are other ways you can elicit more specific feedback:

  • Do I have a clear personal brand? If you could pick 3 words to describe me, what would they be?
  • Based on our interactions, how do you think I am viewed by X (ie. leadership, peers, clients, etc.)
  • What do you think is my greatest strength?
  • Do I appear to have any blind spots when interviewing? What would be some reservations you’d have before referring me for a role?
  • What do people say about me when I’m not in the room?

Also, remember that feedback is a gift and you can do the same for your mentor. You can always ask them if they would like feedback on how they may grow as a mentor, and I’m sure they’d be open to it.

4. Problem solving

Having a mentor to help you solve a specific issue you’re currently experiencing is such a gift. There is nothing like getting advice, applying it, and receiving real-time feedback to help you achieve a desired outcome over time. This is also incredibly rewarding for mentors because they can see the direct impact of their advice and gain feedback on their mentoring abilities as well. It truly is a beneficial experience for both parties and collaboratively overcoming problems together is the best way to take your relationship to the next level.

  • Last week I tried [action]. Does doing this make me come off as [attribute]?
  • Am I viewed as [negative attribute] when I [action]?
  • Last week I tried [X] and I wasn’t as successful as I hoped. Can we walk through my approach and can you provide insight on how I might tackle it differently next time?
  • When I [situation], I said this. Did my communication style support the message I intended to deliver?
  • I have to make a decision on [X]. Can you help me weigh the pros and cons or brainstorm alternate opportunities?
  • Next week I’m tasked to [X]. Can we role play the scenario and have you provide feedback?

We hope these questions help make your mentor sessions as valuable and productive as possible. Need more advice or design related tips? Head to our search bar and type 'Design', then look for your favorite mentor for a 1:1 session.

About The Author:

Jasmine Rosen is an ADPList Mentor and a Product Designer who started her career back in 2017 when she left teaching to join a UX program. Since then she has learned a lot about career switching, getting hired, making an impact, gaining visibility, and advocating for yourself. Connect with Jasmine on LinkedIn, Twitter, and Medium for more expert tips.