UX leader interview: Matthew Krajewski @ AWS

Felix Desroches
Superkind Co
Published in
5 min readJul 20, 2024

It’s such a pleasant surprise when I chat with someone who happens to share much of my worldview. Of course, in writing a book I want to be careful to not live in an echo chamber, but on this journey of trying to bring self-aware, intentional and authentic leadership to the design industry, it’s really nice to connect with a like-minded soul.

Matthew is one of those souls.

He’s spent his career at a variety of companies, from small startups to larger companies like Indeed and now AWS, and is that unique PM-designer unicorn that’s so hard to find. He’s also unabashedly himself when it comes to showing up at work, leading teams, and delivering good product — all with a deft human touch.

It was inspiring to hear how he’s refined his take on authentic leadership, starting with his very first job. Read on for my top takeaways from our conversation.

Show up authentically at work and the rest will follow

One of Matthew’s early career memories is of being pulled aside by a well-meaning colleague and told to “tone down” his tendency to speak up and give executives feedback on their plans (constructive, of course).

“Don’t stick your neck out, because if you can’t deliver you never know how it’ll affect your career.”

His colleague no doubt had good intentions, but it was at this stage that Matthew realized he vehemently disagreed. He recognized that his colleague was operating from a place of fear — and this just didn’t resonate at all. Matthew knew in his bones that showing up authentically, which to him meant speaking his mind and engaging with teammates (even executives), that this was how he wanted to work.

It’s about doing what you believe is right, as opposed to what others may think, or this mental model of ‘how it’ll affect your career.’ I appreciated him trying to protect me, but I totally disagreed.”

Put your team and their development first and you will always exceed your goals.

I loved hearing this from Matthew, and not only because it aligns with my Servant Leader take on managing teams. I loved it even more because of the depth of thinking and feeling I could see he’d put into crafting a team culture that allows for people to show up in whatever way they see fit.

We have a leadership crisis because there’s all this talk about development (of people) but we don’t invest in it.

One of the team rituals he’s created to walk the walk when it comes to development is called “The Weather Report”, where he encourages people to check in with one another in a unique way:

“What’s your internal weather today — is it sunny? Cloudy? Are there thunderstorms on the horizon? And what’s coming up: is it personal or professional (or both)?”

At first glance this can sound like an average check-in with a minor twist, but he’s received feedback that team members actually look forward to this meeting every week. Just think of the last time you looked forward to a meeting! It speaks to a craving for more authentic human connecting in the midst of our 9-to-5.

The key to great leadership, Matthew believes, is providing a safe container and air time for the “neck down”, emotional aspects of people’s inner worlds. Everyone shows up in different ways depending on their comfort and ability, but just knowing thatthe safe space is available is key (I wholeheartedly agree).

Tech is a very intellect, data driven field.

We are emotional beings, and I tend to put it first.

It strikes me that in a society that is capitalistic in nature, that disproportionately rewards results and productivity and a hard-driving ethos — that setting aside time for people to connect as humans in a work context is actually pretty subversive. And necessary.

And pretty fucking awesome.

As a designer, invest in learning how to critique well

Coming from a fine arts background, where criticism is par for the course, Matthew is comfortable with critique as a practice. He also understands that it doesn’t come out of the ether, it’s not something we’re born with: it’s a skill like any other, and requires safety and vulnerability to be done well. Both of which are often missing in today’s tech workplaces.

I have an internalized idea that it’s not about the art you produce but that you’re able to deliver critique effectively to those around you — that’s the real skill.

Critique is an art.

Something else this brings up for me is that even if we as designers are comfortable with critique, this doesn’t mean our colleagues are! Through education and training and exposure we get good at delivering useful, honest feedback to one another — but imagine being someone, like an engineer or PM, who’s not used to receiving or delivering feedback in a healthy way? It could land like a lead balloon.

It reminds me of the book Radical Candor, that so many companies I’ve worked at have tried to implement without understanding the social context necessary to have it flourish. Delivering feedback or critique without the adequate social underpinnings steeped in safety and vulnerability — well, that just makes you an inconsiderate asshole!

Critique is an art and needs work and effort exactly because it rests on a foundation of authenticity and compassion. Something so many teams and executives miss.

Advice for younger designers: don’t be afraid to be your own PR machine

Matthew acknowledges that one of the downsides of being a servant leader is that you can back burner the need to advocate for yourself.

And this can happen even when you’re successful. That despite successfully crafting a healthy team culture and delivering good product results, the organizational context might not reward the fuzzier, human-centric aspect of your work as a leader.

I’ve realized because there is a mix of people with different motivations and work styles and personalities [that might conflict with your own], you have to take seriously being your own PR machine for your work and your career.

One way Matthew is putting this into practice is by intentionally connecting with his network, and capturing his perspective on his work with a writing practice.

Investing in an intentional practice to deepen your leadership skills and advocate for yourself strikes me as solid advice for us all.

Like what you read and want to add your $0.02? Let me interview you as part of my upcoming book, Leading UX: a no B.S. handbook for leaders in design.

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Felix Desroches
Superkind Co

Head of Product Design @Panther, surfer & tattoo artist in LA