Leadership Coaching – Get moving in your career

What to Ask a Mentor

When I was considering a career shift from railways to sports facilities, it was obvious that I should talk with people in that other industry.

However, I didn’t have a clear idea of what I wanted to do, and I doubted why anyone would give me their time yet alone their advice.

I asked for a chat

I wasn’t sure what I was doing, but I reached out to the director of facilities in the athletics department at my alma mater. He agreed that I could come by his office.

He may not remember that our brief chat even happened, but decades later I still do.

I remember how I felt, more than what he said

While I don’t recall much of what was actually said, I do remember how I felt.  I felt encouraged to keep exploring and asking questions.  I felt validated to be researching a wide range of career possibilities.  I felt more confident to follow my instincts.

He didn’t give me a job, or tell me what jobs I should apply for.  He simply shared his own experience, which is what a mentor does.

He unknowingly started a chain of events

As our chat ended, he picked up an industry magazine that was on his desk. He gave it to me, to take away and read. 

In hindsight, that’s how I discovered a conference, that I eventually attended, where I scouted prospective employers, and truly made the career shift happen.

Mentors have intriguing and helpful stories

I encourage you to consider mentors as people who have a role that intrigues you. 

You can listen to the mentor tell you about the path they took to reach that place.  It is up to you to choose if you want to follow the exact same path (if it even still exists), forge a different path, or just take some of their more practical advice. 

A mentor may knowingly or unknowingly offer you a key to unlock your opportunities, that you may not realize until later, but you’ll only get it if you’re willing to have the conversations.


So here are four things to help you talk with someone in a role that intrigues you:

1. How did you get through periods of feeling stuck on your career path?

  • This prompts a deeper story about their journey beyond what’s on their LinkedIn profile.
  • The reply can reinforce that it’s not just you who has rough patches to navigate.

2. What part of the bigger picture am I not yet seeing?

  • Having them share how they see the world, can give you a glimpse into new perspectives and expand your thinking.
  • This encourages you to keep going beyond the technical, and looking for connections and collaborations.

3. What do you read and/or listen to for industry knowledge and trends?

  • Some specific recommendations can help you pick up more terminology, and you can notice what further catches your interest.

4. Who do you suggest I talk to next?

  • No single individual can provide all the support and advice you need.  Keep networking by getting a fascinating person to introduce you to another fascinating person.

As a bonus, these questions can work with your current senior executives as well.

[Big shout out and thank you to everyone who has served as a mentor in just one conversation or in hundreds.  Your impact has likely rippled further than you can imagine!]

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Ann Drummie

Ann Drummie is a certified leadership coach, workshop facilitator, and speaker. She helps professionals get moving in their career. She is the author of "Wallet on the Rental Car Roof: A Guide for Young Professionals Growing Their Leadership Skills." She's also an avid traveller and curler.

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