Every Company Needs An Asshole

Last Monday night, we had a board call and Hunter (Walk....Our 3rd board member) said to us, "If you need me to be the asshole, I will. Here's the plan I want to see and the questions I want to see answered by the next time we talk."

The next day, Alex and I had one of the best product discussions we've had since we first started building. We agreed upon a clear set of priorities and next steps. It touched off a week of great product planning and iteration. Having a bit of pressure from a demanding outsider asking tough questions--the right questions--really kicked us into gear. With the distraction of fundraising, we hadn't reengaged on our product thinking and the roadmap clearly needed a bit of repaving.

It's not surprising, either--because it's often the role I play when startups come to me seeking product feedback. With a singular focus on user value and a disregard for maintaining the pleasentries of day to day coworker repore, I can play the asshole role for a company clearly needing focus and product direction. It's just a matter of being direct, being constructively critical, and leaving nothing as too sacred to question.

It's difficult for the person driving the product vision to be its most demanding critic, so having a dedicated outsider can be more than good housekeeping. It can be a mission critical discipline.