The new era of design leadership💡

Summary

Dive Club 🤿 - Episode Summary: "The New Era of Design Leadership 💡"

Host: Ridd
Episode Release Date: May 6, 2025
Podcast Series: Dive Club 🤿 - Where designers never stop learning 💪

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Introduction to a New Paradigm in Design Leadership

In this insightful episode, host Ridd delves into the evolving landscape of design leadership, highlighting the emergence of a new archetype of design leaders who seamlessly blend managerial prowess with hands-on craft expertise. Drawing from conversations with industry luminaries like Alex Schleifer, Mig Reyes, Derek Briggs, Teo Connor, and Diego Zaks, the episode paints a comprehensive picture of what modern design leadership entails.

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Fluid Leadership: Balancing High-Level Vision with Ground-Level Execution

The Falcon Analogy

Ridd opens the discussion with a compelling analogy from Alex Schleifer, former Chief Design Officer at Airbnb:

"You need to become kind of like a Falcon. You need to operate at that altitude, but you need to be ready to get down to the ground when something happens."
(00:17)

This metaphor underscores the necessity for design leaders to maintain a strategic overview while remaining agile and responsive to immediate challenges.

Mig Reyes on Dual Mastery

Echoing Alex's sentiments, Mig Reyes of Duolingo and Instagram adds:

"I've got to know the names of our components... but all the way to, here's where we're headed as a product in, you know, in the next several years."
(00:53)

Mig emphasizes the importance of leaders being deeply versed in both the minutiae and the broader trajectory of product development.

Derek Briggs: Leading by Example

Derek Briggs from Clerk shares his approach to leadership:

"I'm not going to let this job just be managing people and tasks... influencing the other designers and engineers on the team."
(01:15)

Derek highlights the value of active participation and hands-on contribution, ensuring that leaders remain integral to the creative process.

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Airbnb's Vision for Design Leadership

Teo Connor, Airbnb's VP of Design, elaborates on the qualities sought in modern design leaders:

"Leaders need to be able to know what they're talking about and to kind of uphold that craft... being trusted and respected design leaders."
(01:48)

Teo discusses a strategic shift away from traditional design management towards leaders who are also proficient designers, fostering credibility and high standards within their teams.

Alex's Chef Metaphor

Reiterating the hands-on leadership model, Alex Schleifer compares a leader's role to that of a chef:

"That person's still in the kitchen... if somebody cuts their finger, she can take over the sauce station."
(02:42)

This analogy reinforces the idea that leaders should remain actively involved in the creative environment, ready to assist and lead by example when needed.

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Revamping Design Management at Duolingo

Mig Reyes discusses his mission to transform design management from bureaucratic roles to influential positions within Duolingo:

"Design management... not enough leading design, leading product. Product design management. Let's get good at product."
(03:29)

Mig underscores the importance of design leaders being adept in product strategy and craftsmanship, ensuring that they can contribute meaningfully to both executive decision-making and day-to-day design excellence.

Leadership Credibility through IC Experience

Mig further emphasizes that effective design leaders must have a strong background as individual contributors (ICs):

"To be a great manager... you earn credibility from the business and the ICs from having once been an excellent IC."
(05:19)

This perspective highlights the necessity for leaders to understand the intricacies of design work deeply, fostering respect and trust within their teams.

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Diego Zaks: Collaborative and Constructive Leadership

Diego Zaks, VP of Design at Ramp, illustrates effective leadership through collaborative mentorship:

"Making my version... here’s a third version that's way better than anything I would have done by myself."
(06:16)

Diego explains his approach to guiding designers by deconstructing decisions and encouraging the creation of superior solutions, embodying the role of a coach who facilitates growth and innovation.

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The Integral Role of Coaching and Mentorship

Mig Reyes further elaborates on the expectations from design leaders:

"I really expect our design leaders to be excellent coaches, mentors and teachers... I feel safe to learn from you."
(06:58)

This assertion reinforces the dual responsibility of leaders to uphold high standards and create a supportive environment conducive to learning and development.

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Conclusion: Embracing the New Era

Ridd wraps up the episode by affirming the industry's shift towards valuing leaders who possess both managerial and craft expertise. This evolution signifies a move towards flatter organizations where leaders and individual contributors share a common language and commitment to design excellence.

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Upcoming Episode Teaser

Ridd hints at future discussions, mentioning an upcoming interview with Zach Leach, Head of Design at the AI startup Gamma, promising more insights into cutting-edge design leadership.

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Key Takeaways:

• Modern Design Leaders must balance strategic oversight with hands-on involvement.
• Credibility and Respect are earned through a solid background as individual contributors.
• Active Mentorship and Collaborative Coaching are essential for team growth and innovation.
• Flatter Organizations benefit from leaders who share the same language and commitment to design excellence.

Notable Quotes:

1. Alex Schleifer:
   "You need to become kind of like a Falcon... ready to get down to the ground when something happens." (00:17)

2. Mig Reyes:
   "Design management... not enough leading design, leading product." (03:29)

3. Teo Connor:
   "Leaders need to be able to know what they're talking about and to kind of uphold that craft." (01:48)

4. Diego Zaks:
   "Here's a third version that's way better than anything I would have done by myself." (06:16)

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Resources:

For more episodes, key takeaways, and bonus resources, visit Dive.club.

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This summary captures the essence of the episode, presenting the core discussions and insights on the evolving nature of design leadership. Whether you're a seasoned designer or an aspiring leader, the episode offers valuable perspectives on integrating craft and leadership to drive design excellence.

Transcript

[Host]

The more I study today's top design teams, the more clear that it becomes that we're entering the era of a new type of design leader. And that's what this episode is all about. So let's start by hearing one of my favorite analogies from Alex Schleifer, the longtime chief design officer at Airbnb.

[Alex Schleifer]

I had this kind of philosophy around management to many counterintuitive, which was that becoming a, you know, rising up in a leadership change. I was often told, well, you change altitude, so now you see things from higher right? To folks, that meant when you're at that altitude, that's where you operate. You only operate at that altitude. But my philosophy around leadership is you need to become kind of like a Falcon. You need to operate at that altitude, but you need to be ready to get down to the ground when something happens. Right?

[Host]

This idea of moving fluidly between altitudes was something that Mig Reyes from Duolingo and Instagram talked about as well.

[Mig Reyes]

I'm the head of the whole function for product experience. I've got to know the names of our components. I'm going to articulate the details of why something feels off by a few milliseconds, but all the way to, here's where we're headed as a product in, you know, in the next several years.

[Host]

Another one of my favorite examples of this archetype of design leader is Derek Briggs. So here's a clip from his time leading design at Clerk.

[Derek Briggs]

I'm not going to let this job just be managing people and tasks that I'm going to be pushing a bunch of code and doing a bunch of design because I'm so passionate about it and I care so much about the output and being a part of the output with the team and influencing the other designers and engineers on the team. It's a really special position to be in, to influence the direction from a leadership perspective and then all the way down to pushing code right with everybody else.

[Host]

These are the exact type of leaders that Airbnb is still prioritizing. Here's their current VP of Design, Teo Connor, to share a little bit about what they're looking for today.

[Teo Connor]

Bringing in talent that were especially the leaders, were really still able to be in the work, so still able to be designers. And the reason that's important is if you want your team to kind of be experts in design and you want them to be showing up as leaders, you need their leaders to be able to know what they're talking about and to kind of uphold that craft and to be able to say, like, you know, we could change that interaction or we could do this differently. You know, they're going to be upholding that high bar. So there's a shift away from design managers or leaders being just people managers, which sometimes happens in organizations, and really still being able to be in the craft and being, you know, trusted and respected design leaders.

[Host]

It reminds me of another one of Alex Schleifer's metaphors.

[Alex Schleifer]

A leader for us should be a chef. That person's still in the kitchen. She's not chopping carrots, you know, doing prep or whatever, but she's in the kitchen and if somebody cuts their finger, she can take over the sauce station or whatever. Right? That's the type of people you want on board as much as possible. And turns out that if you hire people like that, you need less people. You can build flatter organizations. Everybody's talking the same language. Performance management is easier because everybody kind of understands the expectations for an individual contributor. And also individual contributors benefit from it because they're learning from people who know what they're talking about.

[Host]

That idea that Alex and Teo are talking about was a guiding principle for MIG when he was brought in to revamp design management at Duolingo.

[Mig Reyes]

I think design management in the industry has perhaps devolved into paper pushing, running performance reviews, you know, doing a lot of hand wavy organizational things and not enough leading design, leading product. So that was the change I wanted to bring to Duolingo. Product design management. Let's get good at product. Let's get good at talking about design. Because the way we're going to earn trust into being in more executive decision making rooms is no one will be able to talk about craft as good as us. You are hiring leaders for their pace, their bar, for excellence. I expect you to be able to evaluate your entire team's body of work. You should consider yourself the studio head of your team and be able to bravely flag where work is falling short.

[Host]

Real quick message and then we can jump back into it. So I'm working on a lot of video and playback features for the first time and honestly, I have no idea what I would do if it wasn't for mobbing. You can use natural language to search for anything that you're working on. They even have visual search so you can upload a screenshot of your designs and then see relevant UI for inspiration. But it's a total cheat code and I cannot imagine designing without it. So head to Dive Club Mobin to get started today. If you're working at a startup right now. Then I have some pretty good news for you because Framer just released an incredible offer that gives startups free access to their launch plan for a year. That's $900 to design and ship your site with Framer, which is a total no brainer. I mean I even took advantage of the deal myself, so definitely don't miss out on this offer. You can head to framer.com startups to learn more. Okay, now onto the episode. The reality is it's almost impossible to have leaders who are capable of operating as this keeper of the craft unless they have a rich background as an ic.

[Mig Reyes]

The thing that is true of every manager on our today, at one point in their career they were an excellent ic. I really think that to be a great manager it is a hard job, you have to love the people side, but you earn credibility from the business and the ICs from having once been an excellent IC in your career before now. That doesn't mean just because you're an incredible senior. I see you'll you'll automatically be a good manager. But the art of knowing actually what you're talking about being able to jump into Figma if it push came to shove to to jam with an ic, that's what I was looking for.

[Host]

I pretty much rejected the management track from the beginning. It just felt synonymous with a separation from the craft in my mind. But maybe that doesn't have to be the case. Also, listening to MIG talk about leaders jamming with ICs reminded me of Diego Zaks, the VP of design at Ramp, and how thoughtfully he collaborates with other designers on the team.

[Diego Zaks]

I've had to change from designing the solution and showing people like hey, here's what I wanted you to have done to making my version. Trying to deconstruct the decisions that were made to arrive at a different version and then share that framework for how I made my decisions and then sharing that with people and saying now go make your third version that's better. Like all the good stuff of what you did, some of the good stuff that I did, and here's a third version that's way better than anything I would have done by myself.

[Host]

This is what being an effective coach looks like and it only works if you're able to dive into the details and meaningfully contribute at the pixel level.

[Mig Reyes]

I really expect our design leaders to be excellent coaches, mentors and teachers. You have to be a support person. You have to be a peer that we can go to. Go you have high standards, but I feel safe to learn from you.

[Host]

At the same time, I'm not devaluing people skills. That can be a whole episode on its own. The point is that as an industry, we're valuing a different type of leader, one with taste in the skills necessary to uphold craft. So that's all for this episode. I'll be back after config when we get to hear from Zach Leach, who's the head of design at one of the hottest AI startups called Gamma. So I will see you on Friday.