Plan and Run Your First Informational Interview in 5 Steps

Foundation — Month 4

Job Search Fundamentals • Informational Interviews — Practical Exercise

Plan and Run Your First Informational Interview in 5 Steps

Job Search Fundamentals — Practical Exercise

The deep dive made the case for why informational interviews are one of the most powerful tools in a job search. But knowing why doesn’t make the first one feel any less uncomfortable to actually do. This exercise walks you through the whole thing — from choosing your person to sending the follow-up — so you have a clear plan before you reach out. Doing this once, with intention, shows you that the conversation is almost always better than the fear of asking for it.

The Exercise

1. Choose your person (5 minutes) — From your target employer list or your existing network, identify one specific person you’d genuinely like to learn from. They should work in a role, organization, or field you’re actively curious about. Pick someone whose path or perspective would actually be useful to you — not just the most impressive name you can think of. A second-degree connection (someone a step away through someone you know) is often easier to approach than a cold contact.
2. Write your outreach message (15 minutes) — Draft a short, genuine request. Keep it to three to four sentences: who you are, why you specifically want to talk to them (something specific from their profile or background), what you’re hoping to learn, and a clear, low-pressure ask for 20 minutes. Don’t describe your whole career history. Don’t say you’re “looking for opportunities.” Just ask for a conversation.
3. Prepare four to six real questions (15 minutes) — Before the call, write down your questions. Good ones go beyond what you could find on their LinkedIn page. Try: What does your average week actually look like? What do you wish you’d known before taking this path? What skills have mattered most that don’t usually show up in job descriptions? Is there anything about this field that surprised you once you were inside it?
4. Run the conversation (20 minutes) — Start by thanking them and reminding them of the purpose: you’re there to learn, not to ask for anything else. Then follow your questions, but stay flexible — let interesting threads lead you somewhere unexpected. Take brief notes. Aim for them to talk 70 percent of the time. In the last two minutes, ask if there’s anyone else they’d suggest you speak with.
5. Send your follow-up within 24 hours (10 minutes) — Write a short, specific thank-you. Mention one thing they said that was genuinely helpful or that you’re going to act on. If they offered an introduction, remind them gently and express enthusiasm. This step is what turns a one-time call into an ongoing relationship.

What to Do Next

After your first informational interview, write down three things you learned that you didn’t know before — and one thing you want to follow up on or look into further. Then identify your next person to reach out to. The goal over this month is to have two to three of these conversations across your target employer list. Each one builds on the last, and your questions will get better with every call.