Here Are Some Questions to Ask Your Military Transition Mentor

(Staff Sgt. Jared Rand/U.S. Air National Guard photo)

Mentorship should be a big part of your transition from a military to civilian career. With a mentor, you'll get insight, information, resources and connections to key influencers, insights and opportunities. Your mentor will support, encourage you and hold you accountable to the goals you both agree are in your best interest.

While mentors come through both formal programs and informal relationships, there are certain questions to ask your mentor to ensure you extract the most value from the relationship.

Their Career

Your mentor is likely eager to share their own career experience and path. Whether they are also prior military or not, asking about how they got where they are today will reveal challenges and opportunities you can know in advance of your own civilian venture.

  • How did you get into your current career? What steps did you take?
  • Did you always want to do this work?
  • How did your previous training qualify or prepare you to do the work you do now?
  • What are the most positive aspects of your current work?
  • Which parts of your current job do you dislike? Why?

Your Career

If you're working with a mentor prior to separation, they can guide your thinking process and opportunity assessment. This can be very helpful for your first post-military job. If you've been in the civilian sector for some time, your mentor can serve to guide your day-to-day challenges and questions, provide resources and advice about growth opportunities and networks, and ensure you're managing your work-life balance.

  • After explaining your career goals, ask: Is my thinking and logic for my career path sound and realistic?
  • Are there blind spots I might be encountering as I exit the military?
  • Given your understanding of where I am and where I want to be, do you believe I need more education or more civilian work experience before I can pursue my ideal work?
  • Are there gaps you see in my skill set that I should address before venturing into my civilian career?

Industry and Company

Your mentor might be an expert in an industry or have spent their career in a particular field or with a company you're interested in. Ask them about the industry and the company they work for to get insights.

  • Where do you see the industry going in the next five or 10 years?
  • What threats exist in the industry today?
  • What do they believe are the keys to success in your industry or company?
  • What attracted you to the company (current employer)?
  • What keeps you committed to your current employer?
  • What makes someone successful at the company? Why do people leave?


Professional relationships will likely not have the common focus and mission of the relationships you formed in the military. Hopefully you will get to know people who will support, encourage and help you, but they still will be different. Your mentor can provide guidance here.

  • If your network is mostly military personnel, ask: As I'm just starting to build my professional network outside of the military, are there individuals you think I should meet and get to know?
  • Which groups, forums or communities (online or in person) should I become a member of and get active on?
  • Are there people in my career path I should avoid?
  • How can I tell if a networking relationship is healthy or toxic to my career?


While the focus of a mentoring relationship is likely to serve you, the mentee, your mentor would benefit from asking them one important question:

  • How can I help or support you?

Your list of questions will likely change a bit, depending on the nature of the mentoring relationship. If it's a one-time phone call, you might run through this list in order. If you enter into a six-month mentoring agreement, these questions will likely arise over time, in the context of many other questions and ideas that arise.

Mentoring is most successful when the mentee is focused ("What do I need?") and the mentor is equipped to meet those needs.

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