Pattern matching as a skill

“Experience” is often thought of as a countdown clock where we just need to grind out the years in order to get that next promotion or job. But part of “experience” is pattern matching¹ , and there are ways to speed it up.

Artists and musicians² study the masters and the world around them in order to grow their technical skill: the choices they made or didn’t make, the tools they used, the way light hits a tree. We can do the same.

1. In your everyday life, try to notice when you come across something — a product³ , a marketing campaign, a post — that sticks out as really good or really bad. Try to figure out what about it makes it really good or bad. What did they do that you should remember to do or not do?

2. Debrief with your peers and other leaders within your company. Do a (virtual) coffee 1:1 and ask them — how did it go? What worked? What didn’t? What was the conversion rate when you tried an onboarding quiz? When you added Apple Pay as a payment method, what impact did it have?

3. Study other companies that have tried to solve the same problem you are solving. What did they do⁴ ? Do you like it? What would you do differently?

4. Join a peer mentorship group or Slack community. Be a sponge and ask tons of questions. Has anyone done this before? How did it go?

5. When it comes to your own work, ask “why” five times. Why did this work or not work? And why is that? And why is that? Beneath the surface level answers — the UX we tried didn’t work, we didn’t do enough testing — are deeper patterns for us to notice and register for next time, about culture, process, communication, tooling.

In some ways, what I’m encouraging for all of us is increasing our mindfulness skills. Notice what’s happening underneath what’s happening. We are all so busy, so tired, so stressed that it’s easy to just blow right past something and move on. But there’s actually so much we can learn if we slow things down and get curious.

The Workshop

This is a newsletter-only section where I share a half-baked idea in hopes that y’all who are smarter than me can work it out with me.

What the hell happened to Amazon’s UX in the last 15 years? For all their reputation for A/B testing everything, I hate their discovery experience.

Background: I worked at Amazon from 2006-2008, first as a software engineer on the Community team (user-generated content features like customer reviews; I worked on two now-gone features, Listmania and So You’d Like To Guides) and then as PM for Personalized Recommendations.

In those days, we spent a lot of time thinking about merchandising — how to best choose and display products so that they would convert the best.

But when I look at the Amazon homepage now, it’s awful. And, as if it is a competition for worst UI ever, the Amazon Prime Video app is a joke.

Amazon’s always been good at spear fishing: I know what I want, just let me buy it. But when it comes to buying something I didn’t know I want, it’s almost like they just gave up.

I feel like there is a lesson to be learned in here, not just about what changes when companies grow from 10k employees (Amazon’s size when I was there) to whatever they are now (a couple million, I think? If you include non-corporate workers) but also about org structures, unintended consequences of strategic decisions, and culture. What do you think are the underlying reasons?

1  Aside from all the times when what’s really doing the talking is their unconscious bias. Pattern matching’s pernicious side is “looks like me”, “reminds me of me” — resulting in fewer opportunities for women and minorities. I’m more talking about “I’ve seen that before”, applied to strategic or tactical decisions.

2  Jazz improvisation students are taught to learn, note for note, the improvised solos of masters like Miles Davis or John Coltrane. Not only is there the work of painstakingly training your ear to transcribe what you hear onto a sheet of paper, but then you can go back and ask “why?”. “Why does this solo make me feel things that others don’t? Why did ‘this’ instead of ‘that’ work so well? Oh, I see what he did there, that’s genius.”

3  A few months ago, I became probably the last person you know to switch from Apple Music to Spotify. So far, I hate the UX. I’m an album guy. I like to take in an artist one album at a time, to really immerse myself in their body of work. It’s doable on Spotify, of course, but the UX makes me feel like I’m swimming against the current, as I dodge all of the playlists, podcasts, and singles being recommended.

4  I am not a fan of being overly reactive to the competition. First, we don’t know that what they did worked for them. We certainly don’t know if it would work for us — it could be they had different motivations, different constraints, different strategies. But we can intensely study what our competitors do to see what ideas it inspires within us.