Just do the Demo

Back in 1999 I was at the bottom of the hierarchy of a 2000-person company, presenting to the CFO. After two slides she said, "OK, what's your recommended solution?"

I said, "I haven't finished laying out the problem!"

She said, "That's fine, what are your recommendations?"

I was young and stupid and insisted on showing her how significant the problem was before going on to the recommendations section. I had thought out the problem so well, and I felt upper management had to understand the arguments I was making.

In retrospect, I can imagine that she had some trust in the tech people working there, and believed when she was told there was a problem. But I had run into so many mid-level people who didn't understand that there even was a problem, that I felt I had to sell the CFO something she was already sold on.

I think this is part of that mystical quality, 'experience': realizing when the reality of someone you're talking to is different from the realities of the last 99 people you talked to, and adjusting the message accordingly.

I can imagine that, in terms of evaluating pitches, VCs and angels inhabit very different realities than one's friends & colleagues.

Learn to listen.

It's not just to listen to the exact words, but also to the message behind them. Learn to find the message, and if you're not sure what the message is, ask questions to elucidate.

In the case given the message is something like "I see your point, I trust you, move along, I don't need convincing."

If you think the do still need convincing, ask. They're being blunt with you, you be straight with them.

For neuro-typicals this is fairly easy. For most tech people it's a skill waiting to be learned.

Learn it - it's valuable. Trust me, and move on.

  After making Michael Arrington "no hand shake" jokes...

Does anyone would like to fill me in?