Introduction

An informational interview is an informal conversation where you learn about a career field, company, or role from someone currently in that position—it's not a job interview, but a strategic reconnaissance mission that often leads to opportunities.

If you're transitioning from military service, the civilian job market probably feels like operating without a clear chain of command or standard operating procedures. You've been told to "network," but cold-calling strangers for career advice feels uncomfortable, possibly even inappropriate. The thought of reaching out to someone you don't know and asking for their time might seem presumptuous or even like you're begging for help.

Here's the truth: informational interviews are not only acceptable in the civilian world—they're expected and respected. In fact, they're one of the most powerful tools you have for breaking into civilian careers, and veterans who use them consistently land jobs faster than those who rely solely on online applications.

Think of it this way: in the military, you wouldn't execute a mission without intelligence gathering. You'd study the terrain, understand the local culture, identify key players, and gather actionable intel before committing resources. That's exactly what informational interviews do for your job search—they're your reconnaissance before you commit to a career path or submit applications into the black hole of online job boards.

The civilian hiring process is fundamentally different from military assignments. There's no centralized personnel system matching qualified candidates to open positions. Instead, an estimated 70-85% of jobs are filled through networking and referrals rather than posted job applications. Informational interviews are your entry point into this hidden job market.

In this guide, you'll learn exactly what informational interviews are, why they're more effective than traditional job applications for veterans, how to identify and reach out to the right people, what questions to ask, and how to turn these conversations into job opportunities. You'll also get word-for-word templates that translate your military directness into civilian professional communication—because the way you'd brief a commanding officer isn't quite the same as how you'd approach a potential mentor in the civilian sector.

By the end of this article, you'll have a complete operational plan for conducting informational interviews, from initial contact through follow-up, including how to handle the awkward moments and what to do when these conversations start opening doors to actual job opportunities.

What Exactly Is an Informational Interview? (And Why Does It Matter for Veterans?)

The Civilian Intelligence Gathering Mission

Think of an informational interview as a reconnaissance mission for your civilian career transition. Just as you wouldn't plan a military operation without first gathering intelligence on the terrain, local conditions, and key players, you shouldn't pursue a civilian career path without understanding what you're getting into.

An informational interview is a 20-30 minute conversation where you ask questions and gather information from someone who's already doing the job or working in the industry you're considering. You're not asking for a job. You're not submitting a resume. You're conducting research to answer questions like: What does this job actually involve day-to-day? What skills matter most? How do people break into this field? What's the culture really like?

This is your chance to gather actionable intelligence before you commit resources—before you tailor your resume, before you apply, before you invest months pursuing the wrong opportunity. You're identifying whether this career path aligns with your skills and interests, learning the unwritten rules of engagement, and mapping out the terrain of an unfamiliar industry.

The best part? Unlike a job interview where you're being evaluated, you're in control of an informational interview. You set it up. You ask the questions. You decide whether to pursue this path further based on what you learn.

How Informational Interviews Differ from Job Interviews

Many transitioning veterans confuse informational interviews with job interviews, which can lead to awkward situations and missed opportunities. Here are the critical differences:

Who initiates it: You request an informational interview. An employer requests a job interview.

Who asks the questions: In an informational interview, you ask 90% of the questions. In a job interview, they ask most of the questions.

The goal: Informational interviews are about learning and relationship-building. Job interviews are about evaluation and hiring decisions.

Time commitment: Informational interviews typically last 20-30 minutes. Job interviews often run 45-60 minutes or longer.

Formality level: Informational interviews are conversational and relaxed. Job interviews are more structured and formal.

Outcome: An informational interview ends with insights, advice, and hopefully referrals to other people. A job interview ends with next steps in the hiring process or a rejection.

Your mindset: In an informational interview, you're the one evaluating whether this career path is right for you. In a job interview, you're being evaluated for a specific position.

Understanding this distinction is crucial. When you approach someone for an informational interview, you're not putting them in the awkward position of considering you for a job they may not have. You're simply asking them to share their expertise and experience—which most professionals are happy to do.

Why Veterans Have a Hidden Advantage in Informational Interviews

Here's something most career advisors won't tell you: veterans often perform better in informational interviews than traditional civilian job seekers. Why? Because the skills that made you effective in the military translate directly to successful informational interviews.

You understand mission planning and preparation. Civilians often show up to informational interviews unprepared, asking generic questions they could have answered with a Google search. Veterans naturally approach these conversations with the same preparation they'd bring to any mission—researching the person, the company, and the industry beforehand.

You show genuine respect for expertise. The military teaches you to respect the knowledge and experience of those who've been in the field longer. This translates into informational interviews where you're genuinely curious and humble, rather than arrogant or entitled.

You're comfortable with structured conversations. While civilians might ramble or lose focus, veterans typically keep conversations on track, respect time limits, and have clear objectives—all of which professionals appreciate.

You have a compelling story. Your military service immediately differentiates you and gives you credibility. Most civilians are genuinely interested in your background and want to help veterans succeed in their transitions.

Perhaps most importantly, civilians actively want to help veterans. Multiple studies show that professionals are more likely to respond positively to informational interview requests from transitioning service members. There's a genuine goodwill factor working in your favor—you just need to leverage it properly.

The key is approaching these conversations with confidence in your value while remaining genuinely curious about their experience. You're not begging for help; you're conducting professional research while building mutually beneficial relationships.

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How Do I Find the Right People for Informational Interviews?

Starting with Your Existing Network (Even If You Think You Don't Have One)

If you're thinking "I don't know anyone in the civilian world," you're wrong. You just haven't mapped your network yet.

Start with fellow veterans who've already transitioned. They've walked the path you're on and typically remember how confusing it was. Check your unit's Facebook group, reach out to people who separated before you, or ask your command about alumni networks. Veterans who've successfully transitioned are often the most willing to help because they understand exactly what you're going through.

Next, consider military spouse networks. If you're married or know military spouses, they often have civilian careers and professional connections. They're also familiar with military culture and can bridge the gap in your conversations.

Don't overlook TAP/TAPS connections. Those classes you sat through? The instructors, guest speakers, and even other attendees are all potential contacts. Follow up with anyone who made an impression or worked in an industry you're considering.

Friends and family count too, even if they're not in your target industry. Your college roommate's sister might work in cybersecurity. Your neighbor's husband might be in logistics. Your cousin might know someone in project management. These "friends of friends" connections—what LinkedIn calls second-degree connections—are often more willing to talk to you because of the mutual connection.

The key is to stop thinking in terms of "important" connections. You're not looking for CEOs and hiring managers at this stage. You're looking for people doing the actual job you want to understand—mid-level professionals who remember what it's like to be new and are close enough to the day-to-day work to give you real insights.

Using LinkedIn to Identify Target Contacts (Step-by-Step)

LinkedIn is your primary reconnaissance tool for finding informational interview contacts. Here's how to use it systematically:

Step 1: Optimize your own profile first. Before you start reaching out, make sure your LinkedIn profile clearly indicates you're transitioning military. Add "Transitioning [Service Member]" to your headline. This immediately signals your situation and often generates goodwill.

Step 2: Use the search function strategically. Type in the job title you're interested in (e.g., "project manager," "data analyst," "supply chain coordinator"). LinkedIn will show you people with those titles, prioritizing those in your network or geographic area.

Step 3: Apply filters to narrow your search. Use the "All Filters" option to specify location (where you want to work), current company (if you're targeting specific employers), and industry. You can also filter by connection level—start with 2nd-degree connections since you have a mutual contact.

Step 4: Look for fellow veterans in civilian roles. Search for your target job title plus keywords like "veteran," "former military," or "USMC/Army/Navy/Air Force" in the search bar. Veterans who've successfully transitioned are goldmines of information and typically very responsive to informational interview requests.

Step 5: Join veteran-focused LinkedIn groups. Search for groups like "Veterans in [Your Industry]" or "[Service Branch] Veterans Network." These groups are specifically designed for networking and most members expect to be contacted for advice.

Pro tip: When you find someone interesting, check their profile for commonalities beyond military service—same hometown, same college, shared interests, mutual connections. These give you additional conversation starters and make your outreach more personal.

Leveraging Veteran-Specific Resources and Organizations

Don't reinvent the wheel. Numerous organizations exist specifically to connect transitioning veterans with civilian professionals:

American Corporate Partners (ACP) pairs veterans with mentors from major corporations for year-long mentorship programs. These aren't just informational interviews—they're ongoing relationships with professionals committed to helping veterans.

VetsinTech connects veterans interested in technology careers with tech professionals and companies. Similar organizations exist for other industries: FourBlock for business careers, The Honor Foundation for special operations veterans, and Veterati for one-on-one mentoring.

Company veteran employee resource groups (ERGs) are internal networks of veteran employees at major companies. Many of these groups have external-facing programs specifically to help transitioning veterans. Check company websites for veteran initiatives or search LinkedIn for "[Company Name] Veterans Network."

Military fellowship programs like Wounded Warrior Project's Warriors to Work or Service to School (for veterans pursuing graduate education) provide built-in networks of professionals willing to do informational interviews.

The advantage of these programs is that everyone involved has already opted in to helping veterans. You're not cold-calling strangers; you're connecting with people who've specifically volunteered their time to support military transitions.

The "Warm Introduction" Strategy That Actually Works

The single most effective way to get informational interviews is through warm introductions—when someone you know introduces you to someone they know.

Why does this work so well? Because it comes with built-in credibility. When your former squad leader emails his college friend saying "Hey, I have a sharp veteran on my team who's transitioning and interested in learning about marketing—would you be willing to chat with him for 20 minutes?", that's infinitely more powerful than you reaching out cold.

Here's how to ask for warm introductions without being awkward:

Identify the connector: Look at your LinkedIn connections and see who's connected to people in your target industry or company. Your mutual connection doesn't need to be close friends with your target—even a professional acquaintance works.

Make it easy for them: Don't just say "Do you know anyone in finance?" That requires them to think through their entire network. Instead, be specific: "I noticed you're connected to Sarah Johnson at Deloitte. I'm exploring consulting careers and would love to learn about her experience. Would you be comfortable introducing us?"

Provide a forwardable blurb: Write a short paragraph they can copy and paste when making the introduction. Something like: "I'm a transitioning Army logistics officer exploring supply chain careers in the private sector. I'm not looking for a job—just hoping to learn about your experience and get advice on how someone with my background can add value in this field. Would you be open to a 20-minute phone call?"

Follow up with gratitude: Thank your connector immediately, whether or not the introduction leads to a conversation. If it does lead to an informational interview, update your connector on how it went. This encourages them to make more introductions for you in the future.

The warm introduction strategy has a 60-80% success rate compared to 30-40% for cold outreach. It's worth the extra effort to find mutual connections before reaching out directly.

What Should I Say When Reaching Out? (Word-for-Word Templates)

The hardest part of informational interviews isn't the conversation itself—it's sending that first message. You're probably overthinking it, worried about sounding too formal or too casual, too pushy or too passive. Here's the reality: a simple, respectful message that clearly states your purpose works better than anything clever or elaborate.

The Cold Outreach Message Formula for Veterans

Effective outreach messages follow a simple formula: credibility builder + specific reason + small ask + flexibility + gratitude. Keep it under 150 words. Here are three templates you can adapt:

Template 1: Veteran-to-Veteran Connection

Subject: Fellow Veteran Seeking Career Advice

Hi [Name],

I'm a transitioning [Service Branch] [rank/role in civilian terms] currently exploring careers in [industry/field]. I came across your profile and noticed you successfully transitioned from military service to [their role] at [company].

I'm not looking for a job—just trying to learn from people who've walked this path before me. Would you be open to a brief 20-minute phone call to share your experience and advice? I'm particularly interested in understanding [one specific thing about their role or company].

I'm flexible on timing and happy to work around your schedule. Thank you for considering this, and thank you for your service.

Respectfully,
[Your Name]
[Your LinkedIn Profile URL]

Template 2: Cold Outreach to Civilian Professional

Subject: Transitioning Veteran Seeking Industry Insights

Hi [Name],

I'm a transitioning military [role in civilian terms] researching careers in [specific field]. I found your profile while learning about [their company/role], and your background in [specific aspect of their experience] really stood out.

I'm hoping to learn from professionals currently in the field before making my transition. Would you be willing to spend 20-30 minutes on a phone call sharing your perspective on [specific topic]? I'm not asking for a job—just career guidance from someone with real experience.

I'm happy to work around your availability. I understand you're busy, so I genuinely appreciate you even considering this.

Best regards,
[Your Name]
Transitioning [Service Branch] Veteran
[LinkedIn Profile URL]

Template 3: LinkedIn Connection Request with Message

Hi [Name] – I'm a transitioning [Service Branch] veteran exploring [industry] careers. Your experience at [company] caught my attention. I'd appreciate the chance to connect and potentially learn from your insights. Not looking for a job, just career guidance from someone who knows the field. Thanks for considering!

Why these work: Each template establishes who you are immediately, explains specifically why you chose them (not a mass message), makes a small and time-bound ask, emphasizes you're NOT asking for a job, shows flexibility, and expresses genuine gratitude.

Critical dos and don'ts:

• DO personalize each message with specific details from their profile

• DON'T send the same generic message to 50 people

• DO mention your military background upfront—it's an asset, not something to hide

• DON'T use military jargon or acronyms they won't understand

• DO keep it under 150 words—brevity shows respect for their time

• DON'T apologize excessively or sound desperate

What to Do When Someone Doesn't Respond

Set realistic expectations: A 30-40% response rate is normal for cold outreach, even with great messages. If you send 10 messages, expect 3-4 responses. This isn't personal—people are busy, messages get buried, or they might not feel qualified to help.

The follow-up timeline: Wait 7-10 days before sending a single follow-up. Your follow-up should be brief and add value, not just repeat your ask:

Hi [Name], I wanted to follow up on my message from last week about informational interviews. I understand you're busy—no worries if the timing isn't right. I recently read [article/news about their company or industry] and it reinforced my interest in this field. If you have 20 minutes in the coming weeks, I'd still greatly appreciate your insights. Thanks again for considering.

Send only one follow-up. If they don't respond after that, move on. Persistence crosses into pestering after two attempts.

Reframe rejection as redirection: Every non-response simply means that person wasn't your connection. The right conversations will happen with the people who respond. Focus your energy there.

How to Respond When Someone Says Yes

When someone agrees to an informational interview, respond within 24 hours with a confirmation that makes scheduling easy:

Thank you so much for being willing to speak with me! I really appreciate your time. I'm flexible on timing—here are a few options that work on my end, but I'm happy to adjust to whatever works best for you:

- Tuesday, [Date] at 10:00 AM or 2:00 PM [their time zone]
- Wednesday, [Date] at 1:00 PM [their time zone]
- Thursday, [Date] at 9:00 AM or 3:00 PM [their time zone]

Would a phone call work, or would you prefer video (Zoom/Teams)? I'm comfortable with whatever is easiest for you.

Thanks again—looking forward to learning from your experience.

Always reference their time zone if you're in different locations. Offer 3-4 specific time options rather than asking "when works for you?" (which puts the work back on them). Suggest the medium (phone is usually easiest), but defer to their preference.

Once they confirm, send a calendar invite immediately with the call details, your phone number, and a brief reminder of the topic. This shows professionalism and makes it easy for them to remember.

What Questions Should I Ask During an Informational Interview?

You've secured the conversation—now what? The questions you ask will determine whether this becomes a valuable learning experience or an awkward 20 minutes neither of you will remember. The good news: you don't need to be clever or impressive. You just need to be genuinely curious and strategic.

Think of your question strategy in three phases: opening questions that build rapport, middle questions that gather intelligence, and closing questions that open doors to opportunities.

The Opening Questions That Build Rapport

Start by getting them talking about themselves. People enjoy sharing their story, and it immediately takes pressure off you to perform. These questions also help you understand their perspective and adjust your later questions accordingly.

Begin with their journey: "How did you get into this field?" or "What attracted you to [company name]?" These open-ended questions let them share as much or as little as they want. Listen for transition points in their career—those often reveal what skills or experiences matter most.

For fellow veterans in civilian roles: "What surprised you most about transitioning to the civilian workplace?" This question accomplishes two things: it acknowledges your shared experience and uncovers insights you won't find in any job description.

For civilians: "What does a typical day or week look like for you?" This grounds the conversation in reality rather than abstractions. You'll learn whether this role involves mostly meetings, independent work, travel, or firefighting crises.

These opening questions typically take 5-7 minutes and create a conversational tone rather than an interrogation. You're building trust before diving into the tactical intelligence gathering.

Essential Career Intelligence Questions for Veterans

Now move into the questions that will actually inform your transition decisions. Organize your questions into categories, but don't ask them in a rigid checklist format. Let the conversation flow naturally.

Skills and qualifications questions:

• "What skills do you use most often in this role?"

• "Are there any skills or knowledge areas you wish you'd developed earlier in your career?"

• "How does someone with a military background typically break into this field?"

• "What certifications or credentials actually matter versus which ones just look good on paper?"

Culture and environment questions:

• "How would you describe the culture at [company]?"

• "What are the unwritten rules in this industry that someone from outside wouldn't know?"

• "How does decision-making work here compared to other places you've worked?"

• "What do people who struggle in this role usually have in common?"

Career progression questions:

• "What does career advancement look like in this field?"

• "Where do people in this role typically move to next?"

• "How long did it take you to feel competent and confident in this position?"

Military-to-civilian translation questions:

• "I led a team of [number] managing [function]—what would that translate to in this industry?"

• "How do employers in this field typically view military experience?"

• "Are there any military terms or approaches I should avoid in interviews?"

Hiring process questions:

• "What does the hiring process look like for roles like yours?"

• "When companies are hiring for this position, what are they really looking for beyond the job description?"

• "How important is [specific credential/experience] versus demonstrated ability to learn?"

You won't ask all of these—choose 8-10 questions most relevant to your situation and their expertise. Take notes (ask permission first: "Do you mind if I take notes?"). This shows you value their insights and helps you remember specific details for follow-up.

The Closing Questions That Open Doors

The last five minutes of your conversation are the most important for turning this interview into ongoing opportunities. These questions plant seeds and create natural next steps.

The referral multiplication question: "Who else would you recommend I speak with to learn more about this field?" This is the single most valuable question you can ask. Most people will offer 1-2 names. If they don't volunteer contact information, ask: "Would you be comfortable introducing us, or should I mention your name when I reach out?"

The insider opportunity question: "Are there any industry events, conferences, or professional groups you'd recommend for someone trying to break into this field?" This often leads to invitations or introductions to communities where opportunities emerge.

The advice question: "Knowing what you know now, what advice would you give someone with my background who's interested in this path?" This invites them to synthesize everything into actionable guidance. It also subtly positions you as someone seriously considering this direction.

The timing question (optional, use judgment): "I know I said this wasn't a job inquiry, and it isn't—but if someone with my background were looking for opportunities in this space, what would be the best approach?" This keeps your word about not asking for a job while opening the door if they know of opportunities.

End with genuine gratitude: "This has been incredibly helpful. I really appreciate you taking the time to share your experience with me." Confirm next steps if any were discussed, and let them get back to their day.

What If I'm Too Nervous or Feel Like I'm Wasting Their Time?

Let's address the elephant in the room: you're probably feeling like you're imposing on someone's valuable time to ask questions you think you should already know the answers to. This feeling is completely normal, and it's also completely wrong.

Here's what's actually happening when you request an informational interview.

Reframing the "Burden" Mindset

Most people genuinely enjoy doing informational interviews. This isn't just feel-good advice—there's real psychology and data behind it.

A LinkedIn survey found that 89% of professionals are willing to help job seekers through informational interviews, and among those who've done them, 78% reported finding the experience personally rewarding. When you ask someone for career advice, you're actually giving them several things they value:

You're making them feel valued as an expert. Think about how you felt when a junior service member asked for your guidance on something you knew well. It felt good to share what you'd learned, didn't it? Civilians feel the same way.

You're giving them an opportunity to pay it forward. Most successful professionals remember when someone helped them early in their career. Your request lets them be that person for you.

You're offering a potential future colleague or connection. They're not just helping a stranger—they're potentially investing in a future professional relationship. Many hiring managers specifically do informational interviews to identify talent before positions open.

Veterans have an additional advantage here: civilians often feel a genuine desire to support veterans transitioning to civilian life. It's not pity—it's respect for your service combined with an understanding that the transition is challenging. You're not asking for a handout; you're asking for intel. That's a reasonable request.

If you're still feeling hesitant, reframe it this way: you're not wasting their time; you're giving them 30 minutes to feel helpful, valued, and connected. That's actually a gift.

What If I Don't Know Enough to Ask Good Questions?

Here's a secret: your "basic" questions are exactly what you should be asking. You're not supposed to be an expert yet. That's literally the entire point of an informational interview.

The people who struggle most in informational interviews aren't the ones who don't know enough—they're the ones who pretend to know more than they do. Authenticity beats false expertise every time.

If you don't understand something they say, simply respond with: "I'm not familiar with that term—could you explain what that means in this context?" or "That's new to me. Can you tell me more about how that works?"

These phrases show curiosity, not ignorance. Professionals respect people who ask clarifying questions rather than nodding along pretending to understand.

Your fresh perspective is actually valuable. You'll ask questions that industry insiders never think to ask because they're too close to the subject. You might ask "Why do you do it that way?" and uncover insights they'd forgotten weren't obvious.

Handling Awkward Moments and Conversation Lulls

Even with preparation, awkward moments happen. Here's how to recover gracefully:

If you run out of questions early: "I know we scheduled 30 minutes, but you've been so thorough that I think you've answered everything I wanted to know. I don't want to take more of your time than necessary—is there anything else you think would be helpful for me to understand?"

If they're clearly not engaged: Some people are just having a bad day, or they're not great at these conversations. It's not about you. Wrap up professionally: "I really appreciate your time today. I know you're busy, so I'll let you get back to your day."

If they start interviewing you: This is usually a good sign—they're evaluating you as a potential hire. Answer honestly and professionally, then gently redirect: "I'm happy to share more about my background. Should we shift this into a more formal conversation about opportunities?"

If there's a silence: Don't panic. A few seconds of silence while they think is normal. If it extends beyond 5-10 seconds, you can say: "Let me ask this differently..." or move to your next question.

The most important thing to remember: one awkward informational interview won't ruin your career prospects. Learn from it, adjust your approach, and move on to the next conversation.

How Long Does It Take to See Results from Informational Interviews?

If you're like most transitioning veterans, you want to know: when will this actually pay off? You're used to clear timelines and measurable objectives. The civilian networking world doesn't work quite that way, but there are realistic benchmarks you can use to gauge progress and stay motivated.

The Typical Timeline from First Contact to Job Opportunity

Here's the honest answer: most veterans see tangible job opportunities emerge 3-6 months after starting consistent informational interviewing. That doesn't mean you'll wait six months for your first conversation—it means the compound effect of multiple conversations typically takes that long to generate concrete leads.

Think of it like building combat readiness. You don't run one training exercise and declare a unit mission-ready. You run multiple exercises, refine procedures, build relationships across teams, and gradually increase capability. Informational interviews work the same way.

A realistic rule of thumb: conducting 10 informational interviews might lead to 2-3 genuinely promising connections, and 1 potential opportunity worth pursuing. That one opportunity might be a job opening, a referral to a hiring manager, an invitation to apply before a position is posted, or an introduction to someone who becomes a key advocate.

Why is this actually faster than applying online? Because 80% of jobs are filled through networking before they're ever posted publicly. When you apply cold online, you're competing with hundreds of other applicants for the 20% of jobs that made it to job boards. When you network through informational interviews, you're accessing the 80% that most job seekers never see.

How Many Informational Interviews Should You Aim For?

During active transition (roughly 6-12 months before and after separation), aim for 2-3 informational interviews per week. That's 8-12 per month, or approximately 20-30 total before you should expect to see concrete opportunities emerging.

This cadence is sustainable while you're managing other transition tasks—resume building, skills training, job applications, and family responsibilities. It's frequent enough to build momentum without burning you out or overwhelming your network.

Quality matters more than quantity. Five thoughtful, well-researched conversations with the right people will generate better results than fifteen rushed conversations where you're just checking boxes. Focus on people who are actually in roles or industries you're targeting, not just anyone willing to talk.

When to adjust your pace:

• Speed up (4-5 per week) if you're within 3 months of separation and need to accelerate your timeline

• Slow down (1-2 per week) if you're getting overwhelmed, not adequately preparing, or starting to sound robotic in conversations

• Pause temporarily if you're in active interview processes for specific jobs—focus your energy on those opportunities

Signs That Your Informational Interviews Are Working

You won't always see immediate job offers, but there are leading indicators that tell you you're on the right track. Watch for these signals:

People start introducing you to others without you asking. When someone says "You should really talk to my colleague Sarah—let me make an introduction," you've made a strong enough impression that they're actively advocating for you.

You receive invitations to company events, industry meetups, or professional groups. This means they see you as part of their professional community, not just a one-time conversation.

People remember you and follow up weeks later. If someone reaches out to say "I saw this job posting and thought of you" or "How's your search going?", you've stayed on their radar.

Your contacts ask for your resume before you offer it. This often signals they're thinking about specific opportunities where you might fit.

You hear about openings before they're posted publicly. Inside information about upcoming roles is one of the most valuable outcomes of informational interviews.

Your LinkedIn profile views and connection requests increase. This suggests people are researching you after conversations or being referred to you by mutual connections.

The transition timeline can feel frustratingly slow compared to military operations where execution follows planning quickly. But remember: you're not just looking for any job—you're building a professional network that will serve your entire civilian career. The relationships you're forming now will matter long after you land that first position.

What Do I Need to Prepare Before an Informational Interview?

Think of this as your pre-mission brief. You wouldn't walk into an operation without understanding the terrain, the objective, and your equipment. The same principle applies here. The good news? You don't need days of preparation—just focused effort on a few key areas that will help you show up confident and professional.

Research Requirements (The Pre-Mission Brief)

You need enough information to ask intelligent questions and show respect for the person's time, but you don't need to become an expert on their entire company history.

Here's your minimum research checklist (should take 15-20 minutes total):

Their LinkedIn profile: Read their career path, note where they've worked, look for shared connections or experiences (military service, similar roles, geographic locations). Identify 1-2 specific things about their background that genuinely interest you.

Company basics: Visit the company website. Understand what the company does, their main products or services, and roughly how large they are. You should be able to explain in one sentence what the company does.

Recent company news: Google "[Company name] news" and scan the first page of results. Look for recent announcements, awards, expansions, or challenges. This helps you ask timely, relevant questions.

Industry context: If you're completely new to the industry, spend 10 minutes reading a basic overview. Search "[Industry name] explained" or "what does a [job title] do." You're not trying to sound like an insider—just avoiding asking questions that a quick search would answer.

How much is too much? If you're spending more than 30 minutes researching for a single informational interview, you're overdoing it. Save the deep research for actual job interviews.

Create a simple one-page prep sheet: At the top, list the person's name, company, role, and where you found them. Below that, write 3-4 bullet points of background facts, then your 8-10 prepared questions. Bring this with you (or have it open on a second screen for virtual meetings).

Your 60-Second Introduction as a Transitioning Veteran

You'll almost certainly be asked "Tell me about yourself" or "What's your background?" This is not an invitation to recite your entire military career. You need a concise, jargon-free introduction that explains who you are and why you're talking to them.

The formula: Your role in civilian terms + one concrete accomplishment + what you're exploring + why you chose this person.

Example for combat arms transitioning to operations/logistics:

"I spent six years in the Army leading teams of 15-30 people in high-pressure environments where we had to coordinate complex logistics across multiple locations. In my last role, I managed a supply chain operation that moved $2M in equipment with 99% accuracy. Now I'm transitioning out and exploring operations management roles in manufacturing. I reached out to you because your background in lean manufacturing at [Company] is exactly the kind of work I'm trying to learn more about."

Example for intelligence analyst transitioning to data analytics:

"I was an intelligence analyst in the Air Force for eight years, where I analyzed large datasets to identify patterns and brief senior leadership on actionable insights. One of my projects reduced threat response time by 40% by building a new tracking system. I'm transitioning to civilian work and exploring data analyst roles in the healthcare sector. I wanted to talk with you because you made a similar transition from military intelligence to healthcare analytics, and I'd love to learn from your experience."

Example for technical/IT background transitioning to cybersecurity:

"I was a network administrator in the Navy for five years, managing secure communications systems for a team of 200 people. I also led our unit's cybersecurity training program. Now I'm looking at cybersecurity roles in financial services, and your path from military IT to becoming a security engineer at [Company] is really interesting to me. I'd love to hear how you made that transition."

Practice this introduction out loud until it feels natural. You should be able to deliver it in 45-60 seconds without sounding rehearsed.

Materials to Have Ready (But Not to Push)

Your resume: Yes, bring it (or have it ready to send digitally), but don't lead with it. This is not a job interview. Only share your resume if they specifically ask for it, or if the conversation naturally shifts toward opportunities and they say something like "Send me your resume."

Your LinkedIn profile must be updated first: Many people will look you up before or after your conversation. Your LinkedIn profile should be current, professional, and free of military jargon. If your LinkedIn still lists your MOS code without explanation, fix that before scheduling informational interviews. This is where tools like BestMilitaryResume.com become invaluable—having a professionally translated military resume and LinkedIn profile ready ensures you're always prepared when opportunities emerge from these conversations.

Note-taking approach: Bring a notepad and pen (or have a document open if virtual). Taking notes shows you value their insights and helps you remember key details for follow-up. Ask permission at the start: "Do you mind if I take a few notes?" No one will say no.

Thank you note template prepared: Don't wait until after the conversation to figure out what to say. Have a template ready that you can quickly personalize with specific references from your conversation. You want to send this within 24 hours while you're fresh in their mind.

The goal isn't to show up with a briefcase full of materials. The goal is to be prepared enough to have a genuine conversation without scrambling or appearing disorganized. When you've done your homework, you can relax and focus on building a real connection.

What Could Go Wrong? (And How to Handle It)

Even with perfect preparation, informational interviews don't always go according to plan. That's normal. The civilian professional world is less predictable than military operations, and you're dealing with individual personalities, not standardized procedures.

The good news? Most "problems" that come up are actually opportunities in disguise—or at least valuable learning experiences. Here's how to handle the most common scenarios that catch veterans off guard.

When the Conversation Turns Into a Job Interview

You're ten minutes into what you thought was an informational conversation when suddenly they ask: "So what are your salary expectations?" or "When could you start if we had an opening?"

Why this happens: It's usually a very good sign. They see potential and want to explore whether you might be a fit for their team. Sometimes they have an opening they haven't posted yet. Other times, they're impressed enough to create a role.

How to handle it gracefully: Don't panic or get flustered. Take a breath and say something like: "I really appreciate that. I came into this conversation hoping to learn from your experience, but I'm definitely interested in exploring opportunities. Would it make sense to continue this conversation now, or should we schedule a separate time to discuss potential roles?"

This acknowledges the shift while giving them the choice to continue or formalize things. Most will continue the conversation right then.

Be ready for screening questions: Even in informational interviews, keep your 60-second introduction polished and be prepared to discuss your background professionally. Have 2-3 concrete examples of accomplishments ready to share if asked.

Follow up differently: If the conversation turned into a job discussion, your thank-you note should acknowledge that shift: "Thank you for taking time to discuss both the industry landscape and potential opportunities at [Company]. I'm very interested in the [role/team] we discussed and would welcome next steps."

If They're Negative About Their Company or Career

Sometimes you'll ask "What do you enjoy most about working here?" and get a surprisingly honest (or bitter) response about dysfunction, poor leadership, or regret about their career choice.

This is actually valuable intelligence. In the military, you learned to read between the lines of official communications. Apply that skill here.

What to do with negative information: Listen carefully and ask thoughtful follow-up questions without turning it into a complaint session. Try: "That's helpful context. What would you do differently if you were starting this career path today?" or "Are those challenges specific to this company, or common across the industry?"

Don't gossip or pile on: Resist the urge to agree too enthusiastically with their complaints. Stay professional and curious. You don't know who they talk to, and the civilian professional world can be surprisingly small.

Decide whether to continue pursuing that path: One negative conversation doesn't mean you should abandon an entire career direction, but patterns matter. If three people in the same field express similar frustrations, that's data worth considering.

Thank them for their honesty: End with something like: "I really appreciate your candor. That kind of honest insight is exactly what I need to make informed decisions." People respect when you value straight talk.

Common Mistakes Veterans Make (And How to Avoid Them)

Being too formal or rigid: Informational interviews are professional but conversational. You don't need to sit at attention or use formal military bearing. Relax. Smile. Let it be a genuine conversation, not a briefing.

Using military jargon: If you say "I was the S-4 NCOIC" without translation, you've lost them. Always use civilian-friendly language. Practice describing your experience without acronyms or military-specific terms.

Making it a one-way interrogation: This isn't an interview board. Allow for natural conversation flow. If they want to share a story or go on a tangent, let them. Some of the best insights come from unplanned moments.

Not doing basic research: Asking "So what does your company do?" when that information is on the homepage wastes their time and signals you're not serious.

Asking for a job directly: Remember, this is intelligence gathering, not a job application. Don't end with "So are you hiring?" Instead: "Based on what you've shared, who else would you recommend I speak with?"

Not following up: Sending a thank-you note isn't optional—it's expected in civilian professional culture. No follow-up signals you didn't value their time.

Forgetting to ask for referrals: The question "Who else should I talk to?" is how one conversation becomes five. Don't leave without asking.

Taking too much time: Respect the agreed-upon timeframe. If you scheduled 30 minutes, wrap up at 28 minutes unless they explicitly extend the conversation.

Waiting to talk instead of listening: Your goal is to learn, not to prove how much you know. Ask questions, then actually listen to the answers. Take notes. Follow up on what they say rather than just moving to your next prepared question.

Most of these mistakes come from nervousness or unfamiliarity with civilian professional norms. The more informational interviews you do, the more natural the process becomes. Give yourself permission to be imperfect, learn from each conversation, and adjust your approach as you go.

What Should I Expect During and After an Informational Interview?

Knowing what to expect removes a lot of the anxiety around informational interviews. Unlike military operations where there's a detailed OPORD, these conversations are more flexible—but they do follow a predictable pattern once you've done a few.

Here's the reality: most informational interviews feel surprisingly natural once they get going. The structure is loose enough to allow for genuine conversation but focused enough that you'll walk away with actionable intelligence.

The Typical Flow of a 30-Minute Informational Interview

First 5 minutes: Rapport building and context setting. You'll exchange pleasantries, maybe some small talk. They might ask how you found them or what prompted your interest. This is where you deliver your 60-second introduction and explain what you're hoping to learn. Don't rush this part—it sets the tone for everything that follows.

Next 20 minutes: Your questions and their insights. This is the core of the conversation. You ask your prepared questions, they share their experience and advice. Let the conversation flow naturally. If they go off on a tangent that's valuable, follow it. If they ask you questions, answer them briefly and redirect back to learning from them.

Last 5 minutes: Referrals and next steps. This is where you ask "Who else should I talk to?" and "Is there anything I should read or research based on our conversation?" Thank them for their time and ask if it's okay to follow up occasionally as your transition progresses.

Who controls the time? You do. They're doing you a favor, so it's your responsibility to keep things on track. Set a timer on your phone if you need to. At the 25-minute mark, start wrapping up even if the conversation is going well. Say something like: "I know we're coming up on our scheduled time. I have two more quick questions if that's okay."

Flexibility built in: Sometimes they'll extend the conversation themselves—"I've got time if you have more questions." That's great, but don't assume. Always respect the original timeframe unless they explicitly offer more.

The Critical 24-Hour Follow-Up Window

In the civilian professional world, thank-you notes aren't optional—they're expected. This isn't just courtesy; it's how you stay memorable and demonstrate professionalism.

Why the 24-hour window matters: Send your thank-you note within 24 hours while the conversation is still fresh in both your minds. Wait longer and you risk being forgotten among their daily responsibilities.

Email vs. LinkedIn message vs. handwritten note: For most situations, email is best—it's professional, timely, and easy for them to reference later. LinkedIn messages work too, especially if that's how you initially connected. Handwritten notes are impressive but slower, so only use them if you have their mailing address and the role isn't time-sensitive.

Template with personalization points:

Subject: Thank you for your time and insights

Hi [Name],

Thank you for taking time to speak with me this [morning/afternoon] about [specific topic you discussed]. Your insight about [specific detail they shared] was especially valuable and gave me a much clearer picture of [industry/role/company].

I'm going to follow up on your suggestion to [specific action item they recommended]. I'll also reach out to [referral name] as you suggested—thank you for offering to make that introduction.

I'll keep you updated on my progress, and please don't hesitate to reach out if there's ever anything I can do to help you.

Best regards,
[Your name]

What to include: Reference something specific from your conversation (this proves you were listening and makes the note personal), reiterate the value you gained, and mention any next steps discussed. Keep it to 4-5 sentences maximum.

How to Maintain the Relationship Long-Term

One conversation doesn't build a relationship—consistent, low-pressure touchpoints do. The goal is to stay on their radar without being annoying or seeming like you only reach out when you need something.

Update them on your progress: Every 60-90 days, send a brief update. "Hi [Name], wanted to let you know I took your advice about [X] and just accepted a role at [Company]. Thank you again for your guidance—it made a real difference."

Share relevant articles occasionally: If you come across an article or resource related to something you discussed, send it along with a quick note: "Saw this and thought of our conversation about [topic]. Hope you're doing well."

Congratulate them on promotions and achievements: LinkedIn will notify you when they change roles or share accomplishments. A quick "Congratulations on the new role!" message takes 30 seconds and keeps you connected.

The 90-day check-in: Three months after your initial conversation, reach out with a genuine update and ask one follow-up question if appropriate. Don't make it about you needing something—make it about staying connected.

Eventually offer value back: As you gain civilian experience, look for ways to help them. Maybe you can introduce them to someone, share insights from your new industry, or offer to speak to other transitioning veterans they're mentoring. The relationship should eventually become reciprocal.

The key is consistency without being intrusive. You're building a professional relationship, not stalking them. Quality touchpoints a few times a year are far better than radio silence or constant contact.

Find your match: Translate your MOS to civilian job titles or explore career paths by branch.

Practice yours: Build your elevator pitch with the free BMR Elevator Pitch Generator.