Break into the hidden job market through heartfelt conversations

Medium - Requires some preparation Recommended

Alex had scoured hundreds of online postings and sent countless résumés—nothing stuck. Then he tried design-thinking’s secret weapon: genuine curiosity. He reached out to three people whose work in renewable energy sparked his imagination. “I’m fascinated by how you grew the microgrid project,” he wrote, “and would love to hear your story over coffee.” To his surprise, two agreed. He spent thirty minutes asking, “What led you here?” and listened hard, jotting down every pivot. As the conversation wound down, he asked, “What steps would I take to explore joining this work?” Their faces lit up: “Funny you ask. We’ve been thinking of an intern to test community surveys.” Alex got the offer on his first try, landing an internship that soon morphed into a full-time role. Harvard Business Review research backs this up: informational interviews—at their best, genuine prototype conversations—give job seekers access to unadvertised positions and insider advice. And the hidden job market, which is where 80 percent of roles reside, suddenly opens up.

Pick three professionals whose work you admire. Send each a sincere note asking for thirty minutes to hear their story—not for a job. During the meeting, ask open questions, then close by inquiring how best to explore joining that world. Watch the hidden doors swing wide. Give it a try this week.

What You'll Achieve

You’ll expand your connections, uncover unlisted roles, and impress insiders with genuine curiosity. Expect job offers and mentorship opportunities that never appear online.

Request genuine life-story coffee chats

1

Identify three role models

List people doing work that intrigues you, whether classmates, local entrepreneurs, or authors. Aim for those you can meet casually rather than cold-emailing CEOs.

2

Send sincere meeting requests

Draft a brief message: mention your genuine interest in their story rather than asking for a job. Offer to buy coffee and prepare two thoughtful questions about their path.

3

Close with the next-step question

At the end of each chat, ask, “What steps would I take to explore working here?” This invites them to help you navigate hidden openings and often sparks unexpected offers.

Reflection Questions

  • Who in your network lights you up just thinking about their work?
  • How can you phrase a request that shows genuine interest, not desperation?
  • What would you do if someone offered you a hidden-market role today?

Personalization Tips

  • • Tech: Meet a UX designer whose portfolio you admire; ask about their prototyping process.
  • • Health: Chat with a nurse-manager at your local ER; ask for one day of shadowing.
  • • Non-profit: Over coffee, ask a refugee support volunteer how you might lend skills in ESL tutoring.
Designing Your Life: How to Build a Well-Lived, Joyful Life
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Designing Your Life: How to Build a Well-Lived, Joyful Life

Bill Burnett, Dave Evans 2016
Insight 8 of 8

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