What are the MOST valuable conversations you’ve ever had?

Hi. I’m getting comfortable with the idea that sometimes a conversation is “work,” even if there’s not a deliverable like a spreadsheet, trello board, landing page, ad, video, or product. I know, big revelation… well it is to me.

I’d love it if you replied with an example of one or two of the most meaningful conversations you’ve had in your business life that you paid for or would’ve paid for and had significant impact. Thanks!

One of mine: my COO coach. Every conversation with her is pretty magical. Two in particular condensed to this:

  • Her: imagine you’re on a highway or something… what kind of car would you be? Work with me here.
  • Me: A freaking F-14.
  • Her: Perfect! Okay Mr. F-14. Why have you been parked at the Kalamazoo airport?
  • Me: Because nobody wants F-14 services right now :'(
  • Her: Does your current company’s mission need car leadership or fighter jet leadership?
  • Me: it’ll be a good business on car leadership and it’ll be amazing on fighter jet leadership.
  • Her: Okay then. Tell your “car” CEO to let you lead, or get yourself out of there. Either way, take to the skies. Stop driving down the highway causing accidents, tryna park, taking up too many lanes, and trying to convince cars to come fly with you.

Life changer for me.


More Posts

Make Startup Bets *Quickly*

Imagine you’re at a roulette table with 100 chips. You’ve heard of this happening before but never imagined it would happen to you… the dealer

Focus on outcomes

Another post for “emergent tech professionals” on this list. Executives often express inputs as their desire. Inputs like “make an app,” or “do this,” and

Scroll to Top