My answer to “How are you doing?” and hacking the startup CEO game

Wow, I haven’t posted in a while. TrueAccord is my main focus.

I once read a great piece – in PandoDaily, I think, but can’t find it – about how every startup CEO fears the “How are you doing?” question. How we all need to pretend all the time that everything’s going great. How we should continue to pitch, show the world how awesome we are, even when all is going badly.

I don’t like thinking that this is true since I learn my best lessons from other startup CEOs, as long as they’re willing to share. I learn from their stories about how awesome their company is, sure, but the best discussions revolve around difficulties and how we can overcome them. I also know that “all is going badly” is a typical, and temporary, entrepreneur mindset that can change in minutes. So even if people are defensive, I’m constantly looking for conversation starters that will get folks to tell me more, not less.

I found a good hack for overcoming this barrier and getting good conversations going. When I get asked the question, I say: “You know how startups are: one day you wake up and everything’s terrible, the next day everything’s great. Today’s great. Yesterday was pretty terrible.” I adapt the “terrible” and “great” based on stuff that I feel I can share – difficult time with a contract, a great hire, whatever makes sense.

If said in the right environment and with the right tone, I’ll get some nods approval. Someone might even say “Yeah, today is bad for me”. That’s my in to start a meaningful talk. That’s when I learn my best lessons. You should do that too.

Nobody’s doing great all the time. A little bit of vulnerability goes a long way in getting important exchanges going. Who knows, you might make a friend. Try it!


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