A Team of Devil's Advocates

Fred Perrotta

At Tortuga, when we first discuss an issue, you might have a hard time telling where everyone stands. Surprisingly, this is a good thing.

We've built a team and nurtured a culture of taking the "other" side in a discussion. At Tortuga, we all play the devil's advocate.

Jeremy is our unofficial ombudsman, but I've noticed more of the team taking this approach, which makes for healthier, more productive conversations.

Taking the other side is not about arguing. Taking the other side helps us think through every aspect of a decision, even if we were all on the same page to start.

When everyone agrees initially, taking the other side is even more important. Having someone willing and able to argue against the team's instinct helps to avoid groupthink and to cover every angle of a decision.

Be careful not to let alignment be an excuse for intellectual laziness.

For example, our web team was discussing whether or not to include comments in the next version of Packsmith, our blog. I ranted about comments and trolls for a few minutes. Then Taylor stepped in to lay out the case for comments as a marketing and community-building tool. We talked it out and eventually decided to omit comments from the redesign. Only then did Taylor reveal that she was anti-comments all along. She took the other side to make sure that we considered the positives that we would be giving up, not just the obvious negatives (which I was complaining about).

I wrote this post to suggest devil's advocacy as a means of generating better conversations and increasing intellectual rigor around decision making. It's worked for us.

While this isn't relevant, I had to link to Hari Kondabalu's bit asking, "Why does the devil need an advocate?" NSFW.