Below are four types of questions to ask your mentor, along with 10 related examples for each type. Implement these at your next meeting to keep things interesting–and valuable–for you and your mentor.
To break the ice, have your mentor tell a story from his or her own career. Hey, everybody likes to talk about themselves! For example, you could inquire: “How did you get to where you are today?” or “How did you land your current role?” But you could also ask more specific questions that address your career objectives and concerns. Some questions to consider:
• Was there a time you messed up and felt like you’d 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?
• Think back to five years ago. Did you envision your career as it is today?
• 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?
• 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?
• How did you develop the skill of speaking so engagingly in front of groups?
Now that the conversation is flowing, get more granular in your requests and bring a specific situation to your mentor–one that you’d like help navigating. For example:
• I tried to delegate a task last week and it did not go well. Can we work through what to do differently next time?
• Who are the people I need to align with in this organization to achieve success?
• My boss said I need to be more strategic. What does that mean?
• 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?
• When trying to gain buy-in to implement a new program, what tactics have worked for you?
• 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 weigh in 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 a stretch assignment could help my career trajectory. What are the pros and cons?
One of the greatest gifts you can give yourself is the gift of self-awareness, meaning the ability to see yourself as others view you. 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.
After starting with the obvious question: “How do you think others perceive me?” become more specific, so 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:
• How am I viewed? In other words, what’s my personal brand in our organization?
• Where do you see my strengths?
• What do you see as some of my blind spots and how can I improve?
• How I am viewed by leadership?
• What do people say about me when I’m not in the room?
• 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?
• Am I viewed as high-maintenance when I send my boss weekly status updates?
• How could I have communicated my idea more clearly?
• When I presented at the last meeting, how did I do? Did my communication style support the message I intended to deliver?
Is there a skill you’re currently working to enhance, such as project management, long-term strategic planning, delegating, or public speaking? Use questions like these 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 raise 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-energizing 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?
With these four types of questions and their accompanying examples, you’ll never sit through another mentoring conversation wondering if the other person is finding the discussion useful. And you can give this list to those whom you mentor, encouraging them to use it to maximize the value of the time you spend together.
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