Q: What is your biggest, most visible design regret?

Given that I believe the following…

Design is a set of decisions about a product. It’s not an interface or an aesthetic, it’s not a brand or a color. Design is the actual decisions. — Rebecca Cox

Key foundational decisions are: What founders will I align myself with? What market opportunity are we going after? What will be the initial set of features that we ship?

My biggest, most visible regret: designing failed or failing companies

I regret that earlier in my career I proceeded less thoughtfully about the business challenges and market opportunities I would pursue. Additionally, I didn’t fully appreciate or comprehend how significant the founders’ influence would be on the values, culture, product, and strategy. That underestimation led me to not vet the founding team thoroughly. And lastly, I often joined startups after the initial feature set was determined and failed to challenge those assumptions — assumptions based off of anecdotal evidence or intuition, rather than data and user feedback.

Without rigorously vetting the founders, the market opportunity, and the initial feature set, I can see now why some previous ventures were always destined to fail. Design could never have been really successful because 80% of the most foundational design decisions were already made and made poorly.

On the flip side, I understand now that given the right market opportunity, right founders, and right initial feature set, we’re 80% of our way to excellent product design. The remaining decisions are mostly details, which are a lot easier to execute and then refine.