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Cold email to get informational interviews - a 9-item checklist

Matthew Du Pont

Matthew works 3 days a week for Poll Everywhere in software sales, and started a job search coaching business 11 months ago. He's been doing 1:1 coaching for a year and am now starting to create infoproducts. Previously, he raised VC funding for a mechanical part sourcing business, worked in a few product roles including at OkCupid, and was a consultant at BCG.

Matthew will send you a free copy of his ebook

What is an informational interview? The stated goal is just learning, but it's actually about learning, user feedback, sales, and connections.

This method isn't conclusive - it's only been used by 9 people with a 15-40% success rate. It's worth taking a look.

1. Similarities

Point out similarities between you and your cold email target. Not "We’re both entrepreneurs.", but "We both worked in product management before starting self-funded companies."

2. Right person

"You’ve sold to IT managers in your last few jobs, and I’m trying to learn what they care about most.", not "I'd like to learn more about sales."

3. Right company

Good: I’ve spoken with Person X and Person Y about ExampleCo, and they both raved about how willing the company is to invest in employee’s growth.

Bad: ExampleCo has a great culture.

4. Right conversation

Come in with specific questions, not open ended.

Good: I think the most important next steps for my business are X, Y, Z. I’d like to see if you agree, and talk about some strategy for X because you’ve used that tactic extensively in the past.

Bad: I want to learn more about your experience.

5. Offer to help (optional)

Good: It looks like your design team does a lot of user testing. Would it help if I was a tester in your next UX experiment?

Bad: I’d be happy to help if I can.

Bad: I'd love to help however I can.

Example cold email to Patrick McKenzie that nails the first five tacts of cold emailing. What's the one thing you should never do in a presentation? Put a huge amount of text on the slide and read it verbatim.

The next four are logistical.

6. Offer times, and 7. Offer a venue

Make sure you've got:

  • the timezone
  • times during the workday, in the evening, and on the weekend
  • send it far in the future. People don't know if they're busy in 2 weeks, so it's easier to accept
  • give the perception that you're busy. "I can do any time Monday, Tuesday, Wednesday, or Thursday. Please please please call me." is bad

Good: I can jump into a 15 minute phone conversation (all times PST) Thursday between 3PM and 7PM, Saturday between 2PM and 8PM, or Monday between 8AM and 11AM.

Calls or video conferences are less commitment and easier to say yes to. More commitment drinks or dinner is harder to say yes to but can create a stronger bond.

8. Send at the right time and 9. Follow up at least once

Don't get lost in the Monday pile of giant email. Tuesdays are good.

Try using Less Annoying CRM and error rendering link to keep track of


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