I finally cracked the code on informational interviews

I used to freeze up asking people for coffee chats about their careers. Then I started offering to buy them a $5 sandwich from their favorite deli near their office, and suddenly 4 out of 5 people said yes. Has anyone else found a small gesture like that that works way better than just asking for advice?

2 comments

2 Comments

patkelly1d ago

Oh man, food is such a weirdly powerful thing in the workplace... I've noticed how much people light up when you bring them a coffee or even just remember what they like to eat. It taps into that whole thing where small acts of thoughtfulness break down those invisible walls we all put up. There's something about sharing a meal, even a $5 sandwich, that makes a conversation feel less like a transaction and more like a real human moment.

veramartin1d ago

Respectfully disagree here. Offering food feels a little too transactional to me, like you're bribing them instead of genuinely connecting over their expertise. Most people say yes to informational interviews because they like talking about their own career journey, not because of a sandwich. I'd rather just send a short, honest email saying exactly what I admire about their path and ask for 15 minutes, zero pressure or gifts involved. The sincerity alone usually works just fine.