Questions to ask a Mentor

CIOL’s new mentoring platform is proving popular and a good number of members have signed up as mentees, looking for support and guidance from fellow members. If you are unsure of the types of things you could ask your mentor, or if your conversations with a mentor have become repetitive, here are a set of questions that could really help you keep things interesting and valuable for you and your mentor.

Find out more about becoming a mentor or a mentee by logging in to access the platform here.


Four types of questions to ask a mentor

Ice Breakers

To break the ice, use some questions to help you find out something about his or her own career. For example, you could ask: “How did you get to where you are today?” or “How did you land your current role?” 

You could also ask more specific questions around your own career objectives and concerns. Questions like:

  • Was there ever a role you applied for and landed, but weren't 100% qualified to do? How did you proceed?
  • What do you wish you had known before taking your first management role?
  • Was there a time you felt like you had made a mistake and felt like you had failed? How did you bounce back?
  • How did you learn to embrace risk-taking?
  • Tell me about a recent business setback. How did you recover?
  • Did you envision your career as it is today, five years ago?
  • Which leadership skills were the most difficult to develop?
  • Can you tell me about a time when you had a difficult boss? How did you handle the situation?
  • What’s the most important leadership lesson you’ve learned and how has it proven invaluable?


Situations

Once the conversation is flowing, you can bring up more specific questions around situations that you would like your mentor to help navigate. For example:

  • My performance feedback indicated that I need to be more strategic. Can you help me understand what that means and how I can do this.
  • When trying to gain buy-in to implement a new program, what tactics have worked for you?
  • I tried to delegate a task last week and it did not go well. Can we work through what could I do differently next time?
  • Who are the people I need to align with in my organisation to achieve success?
  • How can I let my boss know that I don’t need to be micromanaged?
  • How can I stay connected to key influencers who do not work in same office or geographical area?
  • My performance review is coming up. What type of preparation do you most appreciate seeing from your employees?
  • I have two very different career path options available to me. Can you help me work through the pros and cons of each to help me make a final decision?
  • I'm considering a career transition. What are some other areas of the business that might be a good fit for me?
  • I’ve heard that taking an international assignment could help my career. What are the pros and cons?

 

Self-awareness

Having the ability to see yourself as others view you is very valuable in both your career and personal life. That way, if you like how you’re perceived, you can embrace it and take steps to strengthen that positive perception. If you don’t like how you are currently perceived, you can take steps to shift that perception to a more positive one that supports, rather than undermines, your career and leadership goals.

The obvious question to start with is: “How do you think others perceive me?” By becoming more specific your mentor can assist by “holding up the mirror” and providing detailed feedback on how your actions and communication are impacting the way others see you. Ask questions such as:

  • Where do you see my strengths?
  • What do you see as some of my blind spots and how can I improve?
  • Could you offer feedback on ways to improve my executive presence?
  • Do I come across as strategic or tactical in my day-to-day communication?
  • How could I communicate my ideas more clearly?

 

Skill-building

If there is a skill you’re currently working to enhance, such as project management, long-term strategic planning, delegating, or public speaking you can use the following types of questions to ask your mentor for advice and resources to help you polish that skill:

  • How can I become a more assertive negotiator?
  • Can we role-play asking for a pay increase and a promotion?
  • How can I become better at managing people who do not report to me?
  • Do you have any quick tips for re-energising an overworked team?
  • Can you recommend a book or resource for dealing with difficult conversations?
  • What practices can you recommend for dealing with nervousness when speaking to groups?
  • I have been asked to facilitate a team-building activity at a staff retreat. What are some keys to success?
  • What’s a good methodology or tool for project management and tracking team commitments?
  • Do you have a template that you use for long-range visioning and strategic planning?
  • What new skills do I need to move ahead?