Getting Out of Your Own Shorts  

When you’re running a startup, you’re dealing with constant pressure to get things done as quickly as possible. Speed, we’re repeatedly told is the key to winning in the stupidly intense startup world. Do more faster. GTD. Kicking ass and taking names. While I would never argue the value of speed, as the NHTSA loves to remind us, speed also kills. This is alarmingly clear with technical founders playing CEO for the first time. Digging into code to fix stuff that no one else can is very often a familiar happy place in an otherwise chaotic environment.

But when you’re running the show, you HAVE to take a higher view. Getting lost in the details and not taking a long view can lead to disaster. If you don’t take a few moments, on a regular basis, to get your head out of your own shorts and look at things at a higher level, you might just end up as a painful statistic.

I’ve spoken at length to many startups about how picking your head up and understanding how you’re viewed externally is a key to effective marketing and positioning, but this concept goes way beyond that as I was reminded the other day.

My team and I were working on a financial report for the upcoming PivotDesk Board meeting. The monthly financial model had been reviewed over and over again by several of my other executives, and my part-time CFO, in addition to myself. We were all heads down cranking on numbers and reports so we had everything ready for the Board meeting. Checking off lists. Getting shit done. Everyone looked at the numbers.

It wasn’t until late in the evening, when I was sitting quietly putting together the overall report for the Board, looking at the longer term trajectory of the business and how we might evolve moving forward, that I saw the mistake. One wrong formula. One wrong number. And the projections were off by a factor of almost 40%. There is no doubt in my mind that the Board, not being caught up in the details that we struggle to juggle on a daily basis, would have seen this almost instantly. Aside from making all of us look bad, this one mistake would have led to the entire Board discussion being focused on numbers and projections and our ability to manage them moving forward, as opposed to what I wanted to talk about which was how to leverage the insight and value my Board members have to help move Pivotdesk forward. Missing that opportunity would have been a huge value loss for our business.

Everyone on our senior team saw the numbers I was almost ready to send out. As obvious as it was, everyone of us missed the mistake. If you ever want to know what a bunch of highly capable and skilled, yet incredibly embarrassed executives look like, just ask me. The only excuse we had as a team was that we were all too deep in the weeds to see the bigger picture.

Luckily, we caught this one. But it was an incredible reminder that if it’s your job to steer the ship, you have to get out of your own shorts and spend some time simply looking out of the window every now and then. Besides, it might just be an incredible view.


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