Iterating on Culture

Whenever I hear someone speaking about their company's iterative culture, they're usually talking about product development. Ship fast and break things, lean/agile development processes, learning-through-failing, etc. are all pretty great ways to ensure your product isn't stagnant and that you're also able to measure and understand the effects of small changes in service of larger ones. On top of that, having an iterative product development process usually points toward healthy attitudes with regard to risk-taking and experimentation.

And while we certainly shouldn't stop iterating on our products, I think it's important that we look inward apply the same attitudes and methodologies to our own company cultures. It's astounding to me how often organizations, who subscribe to fail-fast-and-iterate with their products, hold their own internal processes and history so preciously. It's hardly just large companies who do this. I've seen small startups hire more employees and struggle to adjust, not wanting to "grow up" or "be corporate". Hell, I've been one of the employees who was annoyed their company was changing.

We have to fill out a time-off form now? Corporate bullshit.

The back door to the office got locked so I have to go through the front door? Unbelievable.

This is not our attitude toward change in our products and it can't be our attitude toward how are companies' structures and behaviors. We have to challenge ourselves to look at our cultures as fluid, to accept that change is not only inevitable, but an opportunity to learn. During my first month at Etsy, the two other design leads and I wanted to institute a structured design critique every week. We spitballed a format that seemed reasonable and were all ready to go. I remember talking to Randy, our Creative Director, about the format before we even had our first meeting.

This may not be the best format, I said.

That's okay, Randy said. If it's not working we'll all know it and adjust.

We've changed the format of that critique four times since its initiation a year ago. As we hire more designers, our format will break and we'll have to change it yet again. And again. And again. Just like our products don't work optimally forever, neither do our internal decisions. And just like we are honest about and tackle problems in our product, we should be equally truthful and enthusiastic about the difficulties we face as a group of people trying to make things.

What are the problems you face as an organization? Did the latest reorganization accidentally make things harder rather than easier as intended? Is your weekly product meeting getting too unwieldy and unproductive as you grow? Accept that and come up with a new solution. And, simultaneously, try not to be so frustrated when your company makes a change. Understand that all changes, successful or not, are in service of solving a problem. Only by taking the time to understand the problems can you be active in crafting a solution that feels right and gets you a little bit further down the road.

An iterative culture iterates on itself.