Archives

My first job at Expedia, joining a small crack team who all seemed wildly smarter than me* my manager was Tim Besse**. Once I was stuck on a particularly thorny problem over a bit of UX, and he stopped by to help. We brainstormed, we drew all over the whiteboards in my office***, we argued, we revised and we came up with something that solved the tangled issues to everyone’s satisfaction.

Relived, I went to write the whole thing up. Tim, standing back from the whiteboard, shook his head and frowned.

“No,” he said. “This isn’t good enough. We can do better.”

I felt anger, frustration — we’d finally come up with a way out and he wanted to discard it? We both had a long list of other things we needed to figure out. Checking this off and moving on was a huge relief and a victory for everyone.

I looked at him in dismay while he stared at the diagrams. I took a couple deep breaths and let go of the frustration.

“Okay,” I said. “Where do we start?”

We began again. I remember it as taking twice as long before, in wavy boxes with my chicken-scratch handwriting everywhere, we’d found something wildly better in every way.

We looked at each other and smiled. I felt a sense of rightness and satisfaction I hadn’t touched in the previous one.

I’ve carried that with me since: that when you’ve arrived at something that’s good enough, push on it a little. As much as I pride myself on being pragmatic above all else, push on good enough. Does it rattle a little? Is there a little give? Do you feel like there’s a hidden switch that’ll rotate the whole thing?

Take the time. See if you can turn good enough into something amazing. Challenge others to do better.

And believe that when someone says “we can do better” they believe it, and that you can.

Thanks, Tim.

— DMZ

  • In the words of Isaac Jaffe:
    “If you’re dumb, surround yourself with smart people. If you’re smart, surround yourself with smart people who disagree with you.”

** Tim went on to co-found Glassdoor

*** shared. As a Microsoft spin-off, we were all about private & shared offices. It was great! Then they abandoned it and I’ve never since enjoyed such productive work spaces.