Be Prepared.  Be Very Prepared.

Be Prepared. Be Very Prepared.

The room on Sansome

There were a dozen of us in a single room on Sansome Street in San Francisco.  Outside was San Francisco in 1999.  The tail end of the first dotcom boom.  Levi’s Plaza up the street.  A bit farther to the Fog City Diner.  When you really needed a break, the steps up to Coit Tower.

Inside:  No cubicles, just two conference room tables, six folding bridge chairs around each.  Each of us had a laptop and headphones.  I was a business development guy but I sat next to Curt, who was a programmer.  On the other side was our VP of marketing.  We ordered snacks from Webvan (look it up) and drank coffee.  Lots of coffee.

I was employee number seven at SquareTrade.  Even so, when the company needed someone to run product development, it turned to me. The digital world had no boundaries.  SquareTrade was far from an overnight success; instead it took thirteen years and several business models before private equity finally gave them their dough.

Nate, the new guy

But back to then. In 2000, with a bit more angel funding, we move to First Street.  More space.  A couple of offices.  Upgrade to cubicles.  More employees.  And a bit more structure.

There was this new guy, I think his name was Nate, who came in to run project management.  I needed something done that required company resources. We sat down over lunch to get to know each other, and for me to tell him about my project.  I figured, buy this guy lunch, make nicey-nice and then have him do my bidding.


What happened was this: Nate said had a process. He had a way of doing things.  That’s why he was hired. “I’d like you to sell me on your project,” he said.

“Excuse me?” I stammered.

“Sell me on it,” Nate answered.  “Tell me why it is important.  How will the company benefit from it specifically? And why should I allocate design and engineering resources to your project instead of someone else’s? “

WTF? “Sell” my project? Process? I don’t need a process little man? Didn’t he know that I was EMPLOYEE NUMBER 7!!??  Didn’t he know I ran product development AND I was the biz dev dude?   Didn’t he know I paid my dues in the crowded, smelly room on Sansome?   I was a big shot.  Listen “Nate” I want what I want and I want it now!  Screw your process, I thought.

But what I actually said was: “Um.  Well…”  And not much else.

Be prepared

It was one of the first times in my career that I did not get by on charm, force of personality and persuasion. Nate had a way of doing things which required me to bring my “A” game.  I brought nothing.

Whence my business maxim, “Bring a Gun to a Knife Fight.

Be prepared. Actually be over prepared. For example, when you come to a meeting to discuss creative ideas and strategies, show up with more than your “gut” reactions, and personal opinions. Those inputs are valuable, but what do you say when someone asks “Why data did you use to make that choice?” Or “What was your process?”

Or, “Sell me on your project.”

At a knife fight, sometimes the guy with a knife wins. But only sometimes. Instead bring a “gun.”

What’s the gun? In addition to your “gut” feelings, bring the data and research that supports your position. Then you can more easily respond to challenges. With Forrester reports. With case studies. With quotations and articles in the press. With eMarketer or Ad Relevance data. With data from JAMA, or the Federal Reserve, or whatever it is you need to support your case. The research is the “gun.”  At a knife fight, the guy with the gun always wins.