Estimated Runtime: ~10 minutes
Tone: Encouraging, tactical — demystifying a process that intimidates most
people
If I could give you one superpower for your job search, it would be this: the
ability to have genuine conversations with people who are where you want to be.
People who can tell you what it's really like, what they wish they knew, who
else you should talk to, and — when the time is right — who can advocate for you
from the inside.
That superpower exists. It's called the informational interview. And most people
either don't do them, or do them badly. Today, I'm going to show you exactly how
to do them well.
The biggest barrier isn't conducting the interview — it's getting someone to say
yes. Let me show you what works.
First, your outreach message needs three things: it needs to be short, it needs
to be specific, and it needs to be flattering without being sycophantic.
Short means five sentences or fewer. Nobody reads long messages from strangers.
Specific means you tell them exactly why you're reaching out to THEM, not just
anyone. You read their article. You noticed they transitioned from your field to
your target field. You admire their career path. Something real.
And flattering means you express genuine respect for their work without being
over-the-top. "I've been following your writing on supply chain innovation and
your recent piece on automation really resonated" works. "You're amazing and I'd
love to pick your brain" doesn't.
Then, ask for fifteen minutes. Not thirty. Not an hour. Fifteen. The lower the
commitment, the higher the response rate. And specify that you're happy to do a
phone call, video chat, or even just exchange a few messages — whatever's
easiest for them.
Your response rate should be thirty percent or higher with good outreach. If
it's lower, your messages are too long, too vague, or too self-serving. Fix the
message, not the volume.
You've got the meeting. Now what? Start with gratitude. Thank them for their
time specifically. Then do a quick version of your thirty-second pitch — just
enough context for them to understand who you are and why you're interested in
their perspective.
Then shift into your questions. You should have eight to ten prepared, but you
won't get through all of them. Pick the five to seven most relevant ones, and be
ready to follow interesting threads when they emerge. The best informational
interviews feel like conversations, not interrogations.
Here are the questions that consistently generate the most valuable responses.
"What do you wish you knew before starting this role?" gives you insider
intelligence. "What's the biggest challenge your team is facing?" tells you
where you might provide value. "What skills separate good performers from great
ones in this area?" helps you position yourself. "How is this function
evolving?" shows industry awareness.
And then, the Golden Question — the one you must ask every single time: "Who
else should I be talking to?" This single question transforms one conversation
into two or three new ones. And when you reach out to those people, you now have
an introduction: "Sarah Chen suggested I reach out to you.
Watch the clock. If you asked for fifteen minutes, wrap up at fifteen minutes.
Respecting someone's time builds trust. If they want to keep talking, great —
but let that be their choice.
Within twenty-four hours, send a thank-you message. Not a generic "thanks for
your time." A specific one: "Thank you for the insight about the shift toward
automation in your department — I'm going to look into the certification you
mentioned.
Connect on LinkedIn if you haven't already. If they recommended a book, article,
or person, follow through and tell them you did. "I read that HBR article you
mentioned — particularly the section on distributed teams. Really changed how
I'm thinking about my next role.
This follow-up turns a single conversation into an ongoing relationship. And
relationships — not applications — are how most people find their best
opportunities.
The informational interview is your unfair advantage. Most job seekers apply
online and hope. Informational interviewers build relationships, gather
intelligence, and position themselves before the job is ever posted. Start with
three outreach messages this week. Next lesson, we'll build your personal Board
of Advisors — a small group of people who accelerate your career over the long
term.