The Most Important Overlooked Design Skill

After interviewing hundreds of designers, I’m surprised at how few recognize its importance.

As a design manager, I’ve interviewed hundreds of candidates for visual, product, UX, UI, and interaction design positions. Of all of the candidates, there is one skill that is always present in successful ones — and that’s the ability to critically conduct a retrospective on your work post-shipping.

It sounds straightforward, but roughly 70%+ of the candidates I’ve interviewed have never mentioned it. They either have no inclination to do it, aren’t aware of it, or simply implement it incorrectly. It’s the one skill I wish I cultivated sooner in my own career, instead, I ran around bumping my head on various walls until it hurt enough to stop.

Here’s a typical design interview conversation about the process:

Me: “Tell me about your design process”

Candidate: “I research the problem, brainstorm solutions, validate them with customers, and then create the visual artifacts and work with the development team to implement them.”

Me: “What would you have done differently to improve on the solution?”

At this point, the designer fumbles for words. Good answers mention user feedback and quantitative KPIs.

The great answers however show a thoughtful, critical analysis of the original problems, the measurement of success, and how the decisions made either impacted or did not impact the results.

Why does this skill matter so much?

What correlation does great retrospective have with great results?

We’re all learning. There is no perfect designer, there is no perfect design work. Because of that fact, the ones who accelerate their abilities the quickest are the ones who will, given the same amount of time, become the most skilled designers.

“Pain + Reflection = Progress”

— Ray Dalio, Author of “Principles”

If that’s true, how do we accelerate our abilities the quickest? I would share Ray Dalio’s opinion here in that the best way to grow is to set audacious goals, take note of all the problems and failures along the way, then glean principles from them to use for the next iteration of the cycle. It helped him become one of the most successful hedge fund managers of all time, so he must be doing something right.

Here’s some simplified great examples I’ve heard of this in design:

“After shipping, we increased conversion by 12%. I think it was largely because I didn’t take the support staff’s word for what the customer problem was. I made a decision to go straight to the customer herself to understand it, turns out it was different from what people thought it was.”

“We had a ton of positive feedback after we built feature X. I was happy with the quality of the design, but felt I could have gotten there faster. I wasted a lot of time going back and forth with product management because of unclear requirements. I now have a list of questions I always get the PM to answer before I move forward with solution brainstorming.”

“I was pretty personally happy with the results. The business certainly was. I did think though that if we spent a bit more time and created 3 variations of the solution instead of only 1, we would have arrived at an even better solution, or at least one that was less costly from an engineering perspective. The time saved wasn’t worth it in this case.”

Every outcome comes by way of two variables. The first is the quality of the decisions you make, and the second is luck. We can’t control the latter, so if we want to accelerate our growth, critical retrospective of the former is necessary.

You’ll notice every one of the answers above show a careful analysis of what the designer believed were the pivotal decisions they made that led to the result. Sometimes, the result is a bad one! The solution failed to reach targets, resonate with customers, etc. At that point our job is to figure out if it was caused by decisions we made or luck.

Be careful though, our natural inclination when we succeed is to attribute it to our decisions, and when we fail we like to attribute luck. Just think of how many times you’ve heard “that car hit me! just bad luck” or “I scored because I played better” and you’ll realize just how easy it is to mix the two. The smartest designers sift through and know whether an outcome was because of luck or decision making.

Cultivating a retrospective mindset

So if I’ve convinced you that a great retrospection is the most overlooked design skill, how can you start to cultivate it? Luckily, this is quite simple.

Start with the last project you worked on, and retrace every decision you made starting from when you first got the brief.

  1. Why did you make this decision? What forces caused you to make or not make it?
  2. How did the decision impact the overall result of the project? Do you know how it did or didn’t?

That’s it! All you have to do is go through this mental exercise after completing every project from now on. You’ll find yourself dissecting whether you should have used this color or this color, and whether or not it had an effect. Sometimes the measurement isn’t always quantifiable, but you can also look back over multiple projects and spot trends to come to a conclusion if you need to.

Most of us agree that a critical retrospective of each project is imperative, but few of us will do it. I often get lazy and complete projects without a second thought. But if we want to all improve at our craft, it’s time to put in the extra effort post-project — otherwise we’ll be repeating the same mistakes again and again.

I know, you already subscribe to way too many newsletters. But! I spend all my days thinking about how to get better at systematically making things people want, and I can’t do it alone. Want in? Join me for regular insights (and occasional ramblings) and hopefully we can make it happen.

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