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Five Ice Breakers to Initiate a Mentoring Conversation with a Veteran

More and more, civilians are working closely with, and mentoring, military veterans. Whether the relationship is formal or informal, focuses on professional goals or personal issues, and the goals are measured and tracked or loose and abstract, mentoring relationships between professionals and veterans is growing.

When a civilian with no military background begins a mentoring relationship with a military veteran, some of the questions and challenges can include:

  • What can I, as a civilian, offer of value to a veteran?
  • What are their expectations about the mentoring process?
  • How will we know if my mentoring advice is helpful?
  • How to I start the conversation with a veteran?

Initiating the conversation is often the hardest step. Civilians don’t want to say the wrong thing, offend or upset the veteran, and we might recognize that mentoring is more familiar and maybe even more comfortable for the military service member, since the military culture supports buddy-to-buddy mentoring, sponsoring, and other forms of career support.

Before You Start If you’ve signed up to mentor a veteran through your work, community organizations, veteran service organization or an online platform, it’s important to get clear on:

  • Your biases: What do you believe to be true about the military? Are your beliefs based in fact or what you’ve seen on TV or heard from friends who weren’t in the military?
  • Your offer: What skills, talents, insight or connections are you able to share? Do you have unique knowledge into your company, industry or work which a veteran transitioning to the civilian sector could learn from? Has your career path been non-traditional and you can share lessons learned? Are you an entrepreneur who knows what it takes to be successful?
  • Your motivation: Why do you want to mentor a veteran? If you feel this is your patriotic responsibility and is a way you can thank a veteran for serving, great. If you seek to leverage your knowledge and help another individual, great. If you seek to sell your product, service or company to the mentees you will be serving, stop now. Mentoring is best performed when it comes from generosity and gratitude, and not a self-serving agenda.

Ice Breakers to Get You Started Those first few questions you ask your mentee to initiate the conversation set the tone and tempo of the relationship. If you ask questions which are too pointed or hard-hitting, you might cause your mentee to resist your input and not open up to you. If you are too soft and reluctant, the veteran might perceive your style as too indirect and not valuable. Finding a good set of opening questions and a pace that is respectful, attentive, yet also compassionate, is key.

Veterati, a web-based mentoring platform offering the opportunity for civilians to mentor military veterans at no cost, offers a list of ice breakers questions, including:

  • Have you had a mentor before, and if so what worked/didn’t work?
  • Why did you decide to join the military?
  • Why did you decide to exit (the military)?
  • What are the questions that keep you up at night?
  • Do you have current perceived weaknesses that you would like to work on?

These questions are designed to start a dialog, to open the conversation, and to show some understanding of the military reintegration process and challenges. When you ask one of these questions, then remain quiet and let your mentee respond. Give them time to answer.

Whichever way you initiate the conversation with a veteran mentee, mentoring someone from a military background is not only beneficial to the veteran. As a civilian who has mentored many veterans – in formal programs (I am a Veterati mentor) and informal – I can attest to the numerous emotional, professional and career benefits I have received by helping someone who served our great Nation.

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