WEBVTT

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Estimated Runtime: ~10 minutes

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Tone: Encouraging, tactical — demystifying a process that intimidates most

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people

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If I could give you one superpower for your job search, it would be this: the

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ability to have genuine conversations with people who are where you want to be.

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People who can tell you what it's really like, what they wish they knew, who

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else you should talk to, and — when the time is right — who can advocate for you

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from the inside.

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That superpower exists. It's called the informational interview. And most people

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either don't do them, or do them badly. Today, I'm going to show you exactly how

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to do them well.

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The biggest barrier isn't conducting the interview — it's getting someone to say

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yes. Let me show you what works.

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First, your outreach message needs three things: it needs to be short, it needs

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to be specific, and it needs to be flattering without being sycophantic.

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Short means five sentences or fewer. Nobody reads long messages from strangers.

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Specific means you tell them exactly why you're reaching out to THEM, not just

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anyone. You read their article. You noticed they transitioned from your field to

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your target field. You admire their career path. Something real.

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And flattering means you express genuine respect for their work without being

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over-the-top. "I've been following your writing on supply chain innovation and

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your recent piece on automation really resonated" works. "You're amazing and I'd

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love to pick your brain" doesn't.

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Then, ask for fifteen minutes. Not thirty. Not an hour. Fifteen. The lower the

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commitment, the higher the response rate. And specify that you're happy to do a

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phone call, video chat, or even just exchange a few messages — whatever's

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easiest for them.

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Your response rate should be thirty percent or higher with good outreach. If

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it's lower, your messages are too long, too vague, or too self-serving. Fix the

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message, not the volume.

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You've got the meeting. Now what? Start with gratitude. Thank them for their

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time specifically. Then do a quick version of your thirty-second pitch — just

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enough context for them to understand who you are and why you're interested in

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their perspective.

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Then shift into your questions. You should have eight to ten prepared, but you

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won't get through all of them. Pick the five to seven most relevant ones, and be

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ready to follow interesting threads when they emerge. The best informational

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interviews feel like conversations, not interrogations.

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Here are the questions that consistently generate the most valuable responses.

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"What do you wish you knew before starting this role?" gives you insider

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intelligence. "What's the biggest challenge your team is facing?" tells you

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where you might provide value. "What skills separate good performers from great

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ones in this area?" helps you position yourself. "How is this function

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evolving?" shows industry awareness.

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And then, the Golden Question — the one you must ask every single time: "Who

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else should I be talking to?" This single question transforms one conversation

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into two or three new ones. And when you reach out to those people, you now have

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an introduction: "Sarah Chen suggested I reach out to you.

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Watch the clock. If you asked for fifteen minutes, wrap up at fifteen minutes.

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Respecting someone's time builds trust. If they want to keep talking, great —

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but let that be their choice.

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Within twenty-four hours, send a thank-you message. Not a generic "thanks for

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your time." A specific one: "Thank you for the insight about the shift toward

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automation in your department — I'm going to look into the certification you

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mentioned.

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Connect on LinkedIn if you haven't already. If they recommended a book, article,

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or person, follow through and tell them you did. "I read that HBR article you

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mentioned — particularly the section on distributed teams. Really changed how

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I'm thinking about my next role.

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This follow-up turns a single conversation into an ongoing relationship. And

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relationships — not applications — are how most people find their best

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opportunities.

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The informational interview is your unfair advantage. Most job seekers apply

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online and hope. Informational interviewers build relationships, gather

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intelligence, and position themselves before the job is ever posted. Start with

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three outreach messages this week. Next lesson, we'll build your personal Board

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of Advisors — a small group of people who accelerate your career over the long

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term.
