Life lesson from a park bench

We all have pivotal moments in our career that stick with us, and form the story line of who we are. I’m a mash-up of many such stories.

Early in my career while working for a software start-up in Seattle, we had an opportunity to make a sale to a client that would put our tiny business on the map. The risk was…we didn’t yet have the product features they wanted to buy, and they were far larger than any prior customer so my area, software implementation, would be a real challenge.

Our CEO convened a meeting of all of his direct reports to get input and weigh the pros and cons of the opportunity. We all gathered around the table and each person took their turn discussing how their department might handle the challenge, then making a go/no-go recommendation about the deal. Everyone was aware of the challenges, but were in favor…everyone except me.

Yep – I was the one to rain on the parade. Logical and rational points about why it was too great a risk, but still the only no vote.

The CEO dismissed the meeting by thanking everyone for the input and promising to get back to us in a few days about his decision; but he asked me to stay.

I remember it like it was yesterday, He said “Matt, I am going to do something for you that my boss did for me when I was at about the same stage in my career.”

Okay, Gulp, I don’t know what it is, but I can feel it coming.

He invited me over to window of his corner office. It looked down into a city park that was usually occupied by homeless people having a nap and an occasional purveyor of recreational pharmaceuticals.

“Do you see that guy down there? The one sleeping on the bench?”

“Yes, I see him.”

“I could hire him to come up here and tell me what I can’t do. I hired you to tell me what we can do. I am not mad or anything, just take a day or two to think the opportunity over, and if you are still sure we can’t do it, let me know what we can do that will get us close.”

Huge life lesson: Challenges at work are about figuring out how to get it done with what you have, or at least get close.

Thanks for that one Tom.

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