Informational Interviews for Transitioning Military
James got 4 interviews in one week. Two became offers.
James, Air Force veteran — security and intelligence career
Informational Interviews for Transitioning Military
As you prepare to transition from the military, you have a unique opportunity to choose your next career. Even if you enjoy your occupation in the military AND it translates well into the civilian world, it's important to examine the available options in advance, so that you can chart the course ahead.
Choices
The military provides many supports than those that are available to the average person who's considering a career change. These programs vary widely, including everything from government programs like the GI Bill, SkillBridge, free certification, and mentoring programs. Together, these offerings allow unique opportunities to explore, study, and prepare for a new post-military career, but the only way to know whether a particular career, organization, or industry is a good fit for you is to talk with people who are in those roles.
What are Informational Interviews?
Simply put, an informational interview is a conversation with an experienced person who is working in your field of interest. Generally, these conversations are brief (15-60 minutes), using a script of several prepared questions specifically developed to quickly learn as much as possible about the role, the industry, and the incumbent's organization.
Plan to have more of these conversations than you might imagine, with 30 being a good target. Depending on your situation and how many options you eliminate in the process, you may need to do many more!
How Do You Find Interviewees?
To start, focus on finding veterans who have transitioned into fields you're considering. They will have the most relevant advice having previously completed the transition journey to those careers.
Additional candidates for informational interviews can be found through your network of personal and professional contacts of people you already know. Those direct contacts may introduce or refer you to still more professionals from their own networks. By researching companies online and through networking on LinkedIn and elsewhere, you'll begin to identify more potential candidates to interview.
Requesting Informational Interviews
When requesting an Informational Interview, clarify that your purpose is to learn more about their field, industry, and organization, so that you can make an informed decision about career choices and adequately prepare for your military career transition journey.
Suggestions for your interview request:
- Communicate your proposed time frame for the interview (e.g. next two weeks)
- Ask about their availability to schedule the conversation
- Request a time frame for the conversation (15, 30, 60 minutes)
- Suggest the meeting place (virtual platform, phone, or a mutually convenient location)
- Thank them for considering your request
If the person does not respond within a few weeks, it's probably safe to assume they don't have time, unless they were directly referred to you by someone you know. In that case, a follow-up call may be appropriate.
The Interview
Once you've arranged the meeting, doing your research on the interviewee, their industry, and organization in advance will allow you to get the most out of the conversation, while presenting yourself as an informed interviewer.
As with any other professional meeting, be punctual, respecting the other person's time; be prepared to take notes, and come armed with your carefully selected list of questions. Start the conversation by briefly introducing yourself, but keep the overall focus on them. You are there to gather information and learn. Do not ask for a job!
Based upon your preparation, tailor questions which may center around topics such as:
- What attracted them to this field
- How their military experience prepared them for this career
- What their typical day is like
- What their greatest challenges are
- What they love about their work, organization, and industry
- Recommendations for entry into the field (certifications, training, education, internships)
Near the close of the discussion, ask if there's anyone else they recommend you speak with. This critical step builds your network and maintains your pipeline of potential candidates to interview. Wrap up the conversation by thanking them for their time and generosity.
After the Interview
Your interview may yield action items. Be sure to follow-up on any suggested activities, such as reviewing a website, reading an article or book, or contacting someone else. Follow-up with a thank you email and again later with the results of any recommended tasking, as needed.
Benefits
After doing multiple informational interviews, you will quickly develop a sense of which careers, industries, and organizations are a good fit for you. Depending on the rapport that's created during the conversation, a few of your interviewees may become mentors who may eventually recommend you for job openings within their organizations.
Employers take employee referrals seriously, often paying generous referral bonuses for successful placements because hiring is faster, costs less, and retention is higher.
As an added bonus from your efforts, you'll be building your professional network and leveraging your growing understanding of your chosen field and industry, making you an outstanding candidate when you are ready to interview for positions. Best of all, you'll have much more certainty that the career choice you make will be the right one for you and your family!
Email Templates for Requesting Informational Interviews
Reaching out to strangers is uncomfortable for most people. Having a template makes it easier. Here are two approaches that work well for transitioning military.
Cold Outreach (No Mutual Connection)
Subject: Transitioning Veteran Interested in [Their Field]
"Hi [Name], I am a [rank/branch] transitioning out of the military in [timeframe] and exploring careers in [their field]. I came across your profile and noticed your experience at [company]. Would you have 15-20 minutes for a brief conversation about your career path? I am not looking for a job referral — just trying to make an informed decision about my next career. I would be happy to work around your schedule. Thank you for considering it."
Warm Outreach (Referred by Someone)
"Hi [Name], [mutual contact] suggested I reach out to you. I am currently transitioning from the [branch] and exploring opportunities in [field]. [Mutual contact] mentioned that your experience at [company] would be valuable perspective as I plan my next career move. Would you have 15-20 minutes to chat this week or next? I appreciate your time."
Keep it short. Busy professionals scan emails quickly. If your request takes more than 30 seconds to read, it is too long. Always offer to work around their schedule and specify a short time commitment.
Sample Questions by Career Field
Tailor your questions to the specific field you are exploring. Generic questions get generic answers. Here are targeted questions for fields that veterans commonly transition into.
Project Management
- How does project management in your company compare to managing military operations?
- Is PMP certification required for entry, or can I get hired and earn it on the job?
- What project management tools does your team use daily?
- What is the typical career progression from entry-level PM to senior PM?
Information Technology
- Which certifications carry the most weight for getting hired — CompTIA, AWS, or vendor-specific?
- How much of your day involves hands-on technical work versus meetings and documentation?
- Do employers in your space value military IT experience, or do they see it as a different world?
- What is the salary range for someone entering with military IT background but no civilian IT title?
Federal Government
- How long did the hiring process take from application to start date?
- How did you determine which GS level to apply for based on your military experience?
- Is there a meaningful difference between agencies in terms of culture and work-life balance?
- How did you handle the specialized experience requirements on your application?
Defense Contracting
- How important is an active clearance for getting hired versus having a lapsed clearance?
- What is the difference in day-to-day work between a government employee and a contractor doing similar work?
- How stable is contract work — do people frequently move between companies when contracts change?
- What salary premium does a TS/SCI clearance typically carry in your experience?
Virtual vs In-Person Informational Interviews
Most informational interviews happen over video call or phone now. This is actually an advantage for transitioning military — you can connect with professionals anywhere in the country without travel.
For video calls, dress business casual, find a quiet space with a clean background, and test your connection beforehand. Treat it with the same professionalism you would bring to a formal meeting. These people may become references or refer you to opportunities later.
In-person meetings, when possible, build stronger connections. Coffee shops near their office work well. Offer to buy their coffee. Keep to the agreed time limit unless they choose to extend the conversation.
Whether virtual or in-person, send a thank-you email within 24 hours. Reference something specific from the conversation so they know you were paying attention. This small step separates you from the majority of people who request informational interviews and never follow up.
Summary
Informational interviews are a useful mechanism for doing in-depth career exploration, building industry knowledge, and learning about organizations. For transitioning military, these conversations often provide valued insight into civilian careers that cannot be accessed elsewhere.
Practice yours: Build your elevator pitch with the free BMR Elevator Pitch Generator.
Frequently Asked Questions
QWhat is an informational interview?
QHow do I ask someone for an informational interview?
QWhat questions should veterans ask in informational interviews?
QHow many informational interviews should I do before my transition?
About the Author
Lynn Eskite-Tant is a Licensed Clinical Social Worker (LCSW-C) and certified career transition coach specializing in military career transitions. With a Master's degree in Social Work focused on military service members and families from University of Maryland Global Campus, she brings deep expertise in helping veterans navigate their job search. Lynn volunteers as a Career Readiness Coach with FourBlock and mentors through MilMentor, demonstrating her commitment to the veteran community. She holds additional certifications including Certified Clinical Trauma Specialist (CCTS-I), Job & Career Development Coach (JCDC/JCTC), and Veteran Ready Healthcare Provider. Her unique combination of clinical social work expertise and career coaching credentials allows her to address both the practical and emotional aspects of military-to-civilian transitions.
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