The New Yorker just published an interview with tennis legend Billie Jean King, where she discusses establishing women’s tennis as a global money-making sport.

The whole interview is a mini-masterclass on leadership. From the recognition of the importance of relationships, to the specificity of her vision (equal pay), to the relentless politicking she did behind the scenes to get everyone on board, this interview contains more wisdom about leadership than most books. 

What spurred this post was this passage, which I’ve… slightly altered:

I feel like most of the designers do not understand the business side of things. Designers say, What should I do? What should I learn about? I go, Learn the other side of the story—learn the business side. Most designers just want more money. And I’m, like, Just understand their side, so when you sit down to speak, and have dialogue, you actually have some understanding and empathy for them. And, if you can show that, I think they’ll start to think about you in a different way as well. It’s just about relationships—everything.

(Okay. She didn’t say “designers.” She said, “athletes.” But, literally, that’s all I changed.)

This quote reveals just how universal this is. For anyone to succeed in business, they need to learn the business side. And when a non-businessperson invests some time and energy in doing that, the businessfolks will pay attention.  

…that Adaptive Path launched. The website (from

Worth repeating the language on that homepage, as, 20 years later, it’s still an animating principle for me:

We believe that design is a strategic business issue, and that effective user-centered design improves profitability. We view success not only as launching an effective design, but also developing stronger organizations that can make wise decisions about design long after we’ve gone. That’s why we make sharing our knowledge and experience part of everything we do.

Through consulting, publishing, and speaking engagements, we develop high-quality user experiences, and educate people and organizations to do the same.

Adaptive Path accounts for both the highest highs and lowest lows of my professional career (I’m guessing this is true for any company founder). I’m deeply appreciative for the partnership of my co-founders who enabled me to be part of something I could have never done on my own. I’m grateful for the community that embraced us, and, more importantly, for the deep human connections I made with so many people in that community, who I consider close friends to this day (even if we haven’t talked for a while!).

A brief sidebar

As my announcement on demonstrates (you’ll need to scroll down), we enjoyed the “countdown” aspect of the date. We were also taking a dig at marchFIRST , a reference doubtless lost on anyone today. 


(What follows is a muddle of thoughts spurred by dialog across blogs, mailing lists, and Twitter. I don’t quite have the time to shape it into something that makes tight sense, but I hope it’s useful anyway, as a part of that larger conversation.)

In the most recent episode of Finding Our Way, Jesse had this to say about the dream of UX:

If I think about the original dream of UX, the dream was that these practices would enable product strategy, product definition, product decisions to be made with experiential outcomes as the primary criteria for whether or not something shipped. And the idea implicit in that, being that value would naturally flow from optimizing for experiential outcomes, that has not really happened. The designers have been sort of sent back to their desks to make more screens… The promise hasn’t been realized.

And there are a lot of the UX old school folks like ourselves who feel like something has been lost along the way, okay, and are getting pretty discouraged about what it’s going to take to recapture that or to fulfill that promise. But my question is, Was that promise one worth investing in, in the first place? Like was the dream of UX, really just a dream?

Since we recorded this, I’ve seen a couple demonstrations of “UX old school folks” discontent: Mark Hurst’s “Why I’m Losing Faith in UX,” or Cornelius Rachieru’s recent tweet: 

Thing is, they might as well just be saying, “Make UX Great Again.” Those were not glory days, as a whole, for matters of user experience. It was exciting for us practicing it, being on the vanguard of a new discipline, granted authority and influence long before we knew how to wield it (I ran a design team when I was 28). Oh, and we were younger, more naïve, had more hair.

But in no objective sense were things better for UX. Most companies didn’t know it existed. Most who did, drastically underinvested in it. Those who were willing to invest in it were savvy enough to listen to thought leaders, but that was a paltry percentage of the real work to be done.

UX in 2021

What’s happened by 2021 is that UX is not interesting in and of itself anymore. UX is a given. As Joe Lamantia said in a mailing list I’m on, “it’s furniture.” And the challenges and frustrations people are expressing are largely due to this maturation.

We’re moving from “the dream of UX” to “the reality of UX.”

Personally, and perhaps idealistically, I’m still bullish on the promise and potential for the humanistic practices that UX represents. I work with companies, stupid boring old companies in industries like enterprise software, and banking, and insurance services, who see the potential for good design to advance their business in a human-centered way. I’m still hopeful that more people “doing UX” will continue to nudge human experience towards the center of business concerns.

I’m not naïve. I read, and largely agree with, Ruined by Design. I see design exploited to serve unsavory business practices. I witness product development organizations that view design as a production job, feeding assets to development like shoveling coal into a train engine. 

Things aren’t great. But then, they never were. 

But I see the massive investment companies are making in building in-house design teams, and more and more design leaders in the C-Suite, and I think things are getting better.

Yes, we’re going through a phase where design was largely seen as a contributor to production, as, to non-designers, that was the evident value of the practice. But I am also seeing more and more companies hiring “super senior IC” designers, as they recognize they’ve lost the positive influence that design can have on strategy, on holistic and coherent experiences.

What Design and UX need is engaged leadership

I guess what I’d say is, don’t confuse a moment in time for some new normal. Things continue to evolve. And instead of whingeing about how things were better in the old days, it’s on Design and UX leadership to do the hard work of figuring out how to advance our humanistic values. This means shifting our attention away from the ‘fun stuff’—tinkering with process, creating inspiring visions—and engaging with the difficult and messy stuff of people and organizations: communication, relationships, and education. It also means accepting what Noah Fang just tweeted in a discussion:

UX And Design also need new voices

As we move on from The Dream, I find that I’m way less interested in the solipsistic whining of successful middle-aged pale males, and instead disheartened by how we’re engaging the next generation of designers. A couple years ago, Jesse shared a tweet thread from a young designer at Instagram:

And more recently, a college student aired her self-flagellation of seeking purpose in UX Design:


i really thought designing buttons for apps was the answer to why i was alive…i cant

♬ original sound – sue ellen

And there’s clearly a disconnect about how we’re framing the work, and then how the work is actually being done. 

It’s also worth noting that, in those Bygone Days of UX Yore, industry leadership and public commentary almost wholly excluded voices of color. As we’re seeing in so many aspects of our modern life, we need to focus attention on our BIPOC peers, who are doing the work of charting a path toward a more truly inclusive future. Lisa Angela opened many eyes with Undoing the Toxic Dogmatism of Digital Design. David Dylan Thomas’s Design for Cognitive Bias shows us the traps we unknowingly step in. And Vivianne Castillo broke open my mind in her time on our podcast, and through her work with Humanity Centered, where she advocates for embracing truly human-centered practices (including self-care and trauma management) in our work.

As the UX profession matures, it’s time to wake up, and begin the real work of making those dreams a reality. But just because we’re moving away from the ‘dream,’ doesn’t mean we’re giving up hope. I’m quite hopeful of our collective ability to steadily move things in a healthier direction. 



Finding Our Way, the podcast Jesse and I conduct, is going on hiatus until about autumn. In our most recent episode, we reflect on the conversations we’ve had, and I thought I’d pull some key ideas from that, and dig into them here.

Perhaps the key tenet that emerged from the conversations in Finding Our Way is that “Leadership is relationship.” Even more important than having a vision is knowing how to relate to all kinds of people, getting them excited about possibilities, getting them to believe in their own capabilities, encouraging them to break down barriers between one another to achieve good things, and providing guidance for smart decision-making towards the desirable outcome.


Healthy relationships are built upon the craft of communication. Yes, it’s a craft, and one that you can develop and hone. The craft of communication encompasses

Spoken communication

Are you clear? Direct? Are you able to tailor your communication to the person(s) you’re talking to? Do you speak with confidence?

Written communication

Given the myriad places we now write, it’s crucial that you know how to shape what you write to suit the medium, the context (email vs chat vs document), the audience, and your message. 


Leaders often have to conduct ‘one-to-many’ communication, whether in a conference room with peers, reporting out to executives, or presenting at an all-hands. How presentations are shaped drive impact, so exploit narrative and storytelling techniques, build your argument, and provide a clear rationale.   


Leaders sometimes forget that communication is two-way, particularly when practiced with the intent to build relationship. Being an active listener goes a long way to establishing bonds. 


Perhaps inferred within the prior components, but I felt it worth calling out, even if only as a reminder to myself. How do you ‘show up’ when communicating? Do you appear engaged? Are you distracted? Do you hold people’s gaze, or look away? Do you show confidence, and ‘hold the room’? Be mindful of, and intentional with, your physicality when communicating.

Information architecture

It may seem peculiar to say that a UX/content practice like information architecture is part of the craft of leadership. The logic is:

if relationship is built on communication,

that communication is very much about information (particularly in the kind of distributed, often asynchronous, reality we have found ourselves in),

and in order for that communication/information to have impact,

it must be structured and presented in a way that makes it understandable and accessible.

Such intentionality about the shape of communication suggests an architectural frame. 

When we discussed it on the podcast, Jesse extended this need for IA thinking:

[L]eaders are, of necessity, orchestrators of systems, and systems instantiate knowledge as information architecture within them. So, the IA that gets embedded and coded, baked into your systems, becomes the way that the organization understands the world. And so, it is on the leader to imbue, infuse, enrich that IA with as complex and nuanced and understanding as they possibly can.

For leaders, who seek influence and impact beyond themselves, communication is the means of wielding that influence. As such, every communication must be conducted with intent and consideration. It’s exhausting, but it’s just part of the deal. 

Many design leaders who have inherited a team have a story of being told, by their new boss, something to the effect of, “Yeah, so, you should know, there are a couple of people on your team who are underperforming, and you’ll probably need to manage them out.”

This sets immediate alarm bells, not about the designers, but about an organization that couldn’t handle its own mess. Thing is, nearly every time I’ve been in that situation, I’ve found that the reason the designers were underperforming had little to do with the designers’ themselves, and everything to do with the context in which that designer was operating (little guidance given around the problem being addressed, unreasonable expectations for executing within a certain time frame, constraints due to technical debt, etc.). 

Oh, and, typically, the designer had never been told directly that they were seen as underperformers. Ruinous Empathy (™ Kim Scott, Radical Candor) had lead their colleagues to provide anodyne feedback, while they talked behind their back, and to their boss, about how so-and-so “just doesn’t seem to be working out.”

So when I helped that designer improve their context, their performance improved as well.

I’m thinking about this as I read Patrick Lencioni’s The Advantage, which I’m finding to be an excellent read on team building and leadership. It contains ideas from his other books, notably The Five Dysfunctions of a Team, and one of those Dysfunctions is not holding people accountable. I highlighted this passage:

Some [leaders] will tell me that since they aren’t afraid to fire people, they must not have an accountability problem. Of course, this is misguided. Firing someone is not necessarily a sign of accountability, but is often the last act of cowardice for a leader who doesn’t know how or isn’t willing to hold people accountable. 

Holding colleagues accountable (whether peers or people in your organization) is one of the hardest thing for leaders to do, because it requires one-on-one, typically face-to-face communication, and where you will tell someone how they are not measuring up. But, done well, it’s the best thing you can do for that colleague, as it is through constructive feedback that they grow. Not being forthright with someone about their performance, or hiding behind performance review and PIP processes, is not being kind; it’s being selfish. 

Over the past couple of years, I have become obsessed with the dynamics of work teams, reading such seminal texts as TeamingThe Wisdom of TeamsThe Five Dysfunctions of a TeamTeam of Teams. It is from works such as these that we learn the importance of psychological safety, trust and accountability, and the distinct and evolving role of leaders. 

And while each advocates for small, cross-functional teams as the heart of how work gets done, I’ve yet to find someone address what I consider to be among the biggest barriers to collaboration within these teams—the distinct cultural values of each function

The function/discipline I can speak most for is design (including UX research and content design). I have conducted numerous sessions with design teams to identify the values they hold most dear, and inevitably among them are compassionate concerns such as: (all are drawn from actual team charters I facilitated):

  • Empathy (more on that in a moment) 
  • Humility
  • Caring
  • Inclusivity
  • Supportiveness
  • Approachability

Though I have not conducted similar exercises for other functional teams, having worked with product managers, engineers, marketers, sales people, etc., I do not believe these values would rank. I’m not saying other function are heartless—I’m just saying that design teams wear their hearts on their sleeves. 

And the point I want to make is less about compassion specifically, and more generally that every function has its own culture, values, intellectual foundation, and norms, and those fundamental characteristics lead to distinct ideals and differing behaviors. 

Related sidebar about empathy.

In literally every team charter exercise I facilitate, when we identify the values of the design team, “empathy” emerges as core.

Every time, I implore the team to reconsider, as “empathy” has become clichéd. And every time, the team, while acknowledging this, says that they need to keep the value, as no other function in their organization demonstrates the value, and so it is key to their identity in relationship to others.

Sidebar to the sidebar:
I think that’s kind of fucked.

And when we create cross-functional teams, we typically just throw people together from all these different backgrounds, and do nothing to help them find common ground. Given that, we should be surprised when teams perform well, instead of disappointed when they do not.

I’m realizing there are a number of different directions this line of thought could lead me:

  • How designers are marginalized because the compassionate values core to their identity are marginalized within businesses
  • Rituals for establishing teams that enable common ground that engenders trusting relationships
  • The schizophrenia/cognitive dissonance we ask of folks to be a good ‘team player,’ which requires some degree of sacrifice and compromise that isn’t every acknowledged

In later posts, I may pursue some of these threads. At this point, I simply want to shine a light on the very real and impactful influence of distinct cultures within teams, and how those must be acknowledged and addressed if we want cross-functional teams to thrive. 

When a design team is small, fewer than 10 people, design quality can be successfully managed informally—reviews, crits, swivel-the-monitor discussions. The Head of Design can reasonably keep tabs on all the work, and, through discussion, drive their team toward higher quality.

As design teams grow into design orgs, this oral culture approach frays. The Head of Design can’t see all the work. Quality is determined by design managers and team leads, who may have varying opinions as to what good looks like. The larger the team gets, the more chaotic this view of quality becomes. Additionally, a larger design org is part of an even larger product development org, which ends up exponentializing the voices commenting on design quality. 

With all this noise, the only way to handle design quality at scale is to establish clear frameworks, guidelines, patterns, and measures of success that can shift local discussions of design quality from personal preferences and toward organization-wide references. 

What surprises me is that pretty much every design organization I engage with, regardless of size, still maintains that folkloric approach to quality. This is dangerous, because, at the end of the day, all a design org has to show for itself is the quality of the work it produces. If there are no standards, if that quality is all over the map, that reflects poorly on the design function as a whole.

The trick is, how does one define design quality? Our colleagues in software engineering have it easier—there are industry-standard criteria (reliability, efficiency, security, maintainability) with clear metrics. These criteria all pretty much hew to “how well does the code function for the needs of the machine?” 

Design quality, though, is perceived in the messy context of people and business. When we say that a design is “good,” what do we mean? How do we distinguish that from “great”? How do we articulate a quality framework so that everyone on the team understands what is expected in terms of the sophistication of their work? (When I work with VPs of Design, I ask them, “How do we inform a 25-year-old junior designer in your most distant office what good looks like?”)

Over time, I’ve developed a an approach to establishing design quality within an organization. There are a slew of components:

Usability Heuristics

In 1997 I took Richard Anderson’s UC Extension class on “User-Centered Design and Usability Engineering.” (It is still the only formal training, outside of conference workshops, I’ve ever had in this field). Among the things he taught was “heuristic evaluation,” a method for assessing the usability of interfaces. 

24 years later—that tool is still useful. Jakob Nielsen developed an updated presentation of the heuristics late last year. This is as close to an ‘industry standard’ as we have for a quality assessment of interfaces akin to what software engineers have developed. They’re insufficient on their own, but they are a great place to start.

Brand Personality Characteristics

Usability heuristics are table stakes. Good design goes beyond that,  delivering experiences specific to the company and the context it  operates within. To avoid coming across as me-too, it’s important that design embody the personality of the company brand. This isn’t just for marketing design either—it is perhaps more important in product design, as that is where the promise of the brand is actually delivered.

Any reasonably mature company should have a robust brand identity. This is more than a logo, typeface, and set of colors. It’s also includes a set of personality characteristics specific to the brand, traits that are important to express to help strengthen that customer connection.

Take those characteristics, and turn them into a set of “personality heuristics,” and as you develop, or review, designs, ask yourself—are we presenting ourselves in a way consistent with the personality we seek to express? 

Experience Principles

Experience principles are a set of statements for how people will experience using your product. Whereas brand personality characteristics are very much inside-out (how the company wants to be perceived), good experience principles are outside-in, based in user research, and distilled insights from what qualities users seek in their experience. 

Back in Ye Olden Days of UX, experience principles were all the rage. At Adaptive Path, they were a key aspect of any strategy and design work we did. From what I can tell, like other aspects of classic UX design (RIP site maps), they’ve fallen out of favor. Which is too bad—this post by Julie Zhuo makes clear how helpful they can be.

Former Adaptive Pathers Chris Risdon and Patrick Quattlebaum shared their practice in crafting principles, and here’s a website cataloging dozens of published principles. (Favorites include: Tivo’s original design principles, Microsoft Windows 7 Design Principles, Opower’s Design Principles, Asana’s Design Principles.)

As with brand traits, turn these principles into a set of heuristics, and assess your designs for how well they deliver on those heuristics. 

Design Guidelines / Design Systems

Perhaps the best known way to maintain a certain level of acceptable quality at scale is to institute design guidelines, or, if you have the resources and the need, a fuller-fledged design system. These help ‘raise the floor,’ of your design, by making sure that, at least in the content and interface, there’s consistency across the entire user’s experience.  

While I support the development of design systems, I’m wary of how they’ve emerged as a panacea to solve all design problems. I take issue with this because I see design as a fundamentally human endeavor. For design to thrive, it must be rooted in a healthy and humanistic context.

Design systems are about automation and, frankly, are dehumanizing. This can be okay if there’s a strong design culture in place that can wield the systems with taste and judgment. But if there isn’t, then design systems simply support the mechanization of design, reducing design practice to asset creation to feed the engineering machine.

Inclusive design and accessibility practices

Regrettably, my commentary here will be thin, as this is an area I haven’t explored in much depth. But my neglect shouldn’t be your excuse! Because when we say “quality,” there’s an implication of “quality for whom?” When we discuss Measures of Success next, we situate design quality in a business context, and, well, if a significant portion of potential users cannot engage with your design because it is ignorant of inclusive principles or accessibility guidelines, that’s bad for business, which is bad design. 

Quality toolkits for inclusive design have been developed by the University of Cambridge and Microsoft

Measures of Success

Fundamentally, the only measure of design quality that matters is how it contributes to (or detracts from) whatever has been agreed upon as a measure of success. Unlike engineering, where there are industry-wide standards for success, success for design cannot be extricated from what success looks like for the broader organization. 

In my experience, the most salient measures of success for design are identical to those for product management. Key “product” metrics around acquisition, retention, satisfaction, engagement, task completion, etc., are what designers should primarily be delivering against, and are the most important markers of ‘quality.’  

That said, it’s surprising how often product development work starts where the product team doesn’t have a clear understanding of success. I encourage my designers, and now the design teams I consult with, to not engage on any work until there are clear, shared measures of success. Without an understanding of what success looks like, decision-making becomes arbitrary, and designers find themselves jerked around… which inevitably leads to lower-quality work, as stuff gets shipped half-baked, it’s hard to say “No” to less important projects, people are spread too thin, etc. etc.

For more on this, I appreciate this article: Empower Product Teams with Product Outcomes, not Business Outcomes. (And just remember, design ‘outcomes’ are the same as product ones.)

Explained Exemplars of Quality Work

The next step is to take the elements discussed so far—traits, principles, guidelines, and measures—and show how they are embodied and delivered in final product. Every team should have a gallery of exemplary work, with clear explanations as to why the work can be considered, well, “good.” You can think of it as case studies, or a design team’s collective portfolio, though in this case, process is less interesting than the final product.

As we’ve discussed, whereas engineering quality is standardized and largely context-free, design quality is very much rooted in the context in which it operates. Also, design decision-making is not solely the product of a rational process. As such, there will always be subjectivity in the creation and assessment of design. By sharing exemplars in this gallery fashion, you can meld the subjective with the objective, and teach the team the language by which matters of quality can be communicated.  

Oh, and if your team doesn’t have their own quality work to share (because they’re so new, or they just haven’t been able to deliver on the kind of work they feel proud of), then start your gallery with publicly available work.

Unfortunately, there aren’t many examples of “good design” galleries in the spirit of which I’m thinking. I’ve always dug Milton Glaser’s critique of Olympics logos, as it’s not just preferences, but rooted in robust design values.   

Mature and inclusive critique practices

Critique is not a ‘nice-to-have’ in the design process. AsErika Hall said on an episode of Finding Our Way :

“The practice of design is creation and criticism in dialogue with one another. And I think we’ve emphasized creation and completely lost the sense of criticism, even though that’s fundamental, that’s one half of that dialectic.”

Critique is how we get to quality. We place our work up or review, we get feedback from other minds, and the refinements based on that input make it better. 

A problem, often, with critique is that it can feel arbitrary and rooted in preferences. That’s why I’ve placed it last—critique should be rooted in all the elements shared before. 

Even with all these elements in place, it’s crucial to attend to the practice of critique to ensure that it operates in an inclusive fashion. Braden Kowitz has written on practices that lead to improved critiques

I reviewed a number of explanations of critique processes. Some that stood out:

Design Critiques at Figma . Super extensive, and quite apt in our everything-remote world.

How to Run a Design Critique . From our pal Scott Berkun. 

Defining quality is of existential importance for design organizations

Because design teams are judged by the quality of their output, it’s essential for these teams to thoughtfully establish just what quality means in their organization. Clarity around quality empowers design teams to:

  • push back on unreasonable requirements (or, if no requirements exist, insist on developing those before doing any work)
  • incorporate quality determinations into the broader product development process, to discourage shipping crap
  • protect team members’ time, focusing on prioritized efforts that are meaningful and likely have impact, and ignoring executive brain farts that everyone knows won’t go anywhere
  • staff projects and programs appropriately to drive to those quality outcomes
  • consistently deliver good work, which leads to ongoing benefits, not just with customers, but internally for morale, retention, and hiring

This post is already too long, and I feel like I’ve only scratched the surface. I’d love to hear about how you define quality for design, and what resources you’ve found valuable in that work.  

For many professionals, today is the end of the work year. It also the end of my first full year as an independent consultant, and I thought I’d reflect on experiences and realizations I had, if only to remind myself that time has, indeed, passed, and it’s not somehow still March.

This will be a grab-bag. Bear with the assortedness. Here’s a TOC:

  • As Design teams scale, they need to define themselves
  • Leadership roles need better definition
  • The Resurgence of the Super-Senior IC
  • Recruiting and hiring isn’t taken seriously enough
  • Finding Our Way podcast

As Design teams scale, they need to define themselves

5 times this past year, I helped Design teams draft their charter. Each of them had reached a scale that they could not be managed informally any more. Perhaps more importantly, though, they had each come to the realization that their work had been defined by others, by non-designers, and that they had been placed in a mode reactive to the needs of others. 

These teams sought greater control over their work, but weren’t sure how to establish that. They worked with me to develop a charter so that they had a firm grasp of their purpose, values, norms, output, and measures of success. By actively defining themselves, they’re better empowered in internal discussions about just what they work on. 

Leadership roles need better definition

Another type of engagement that became common was helping companies better define their design leadership roles. A few times that was the most senior role, and that lead to the thinking shared in The Makeup of a Design Executive. I also helped define the distinct leadership roles of the team. Core to all this was something that Janice Fraser clued me into decades ago as we were building Adaptive Path:

For every role, particularly leadership roles, you need to align:

  • Accountability (how the role’s success is measured)
  • Authority (what decisions this role gets to make)
  • Responsibility (the areas which this role oversees)

More often than not, pain that individuals in leadership face occurs when these areas are not aligned. Particularly, when people are held accountable for things over which they have no real authority. 

The Resurgence of the Super-Senior IC

Over on the Org Design for Design Orgs blog, I wrote about the Emerging role in design orgs: The Super Senior Individual Contributor (Principal Designer, Design Architect).” Some took me to task for the word “emerging,” saying it had been around for decades. And while that’s true, it had really only gotten traction in savvier tech companies, particularly those that already had dual-track career ladders for engineers. If you look at the comments on the post on LinkedIn, you’ll see just how pioneering this role still feels.

As design orgs scale, I suspect we’ll be seeing much more of this kind of role. 

Recruiting and hiring isn’t taken seriously enough

For all the talk of “people are our most important asset,” most companies do not take the activities of recruiting and hiring seriously enough. They toss off job descriptions, have no clear career ladders or levels framework, loosely structure hiring interviews, and leave candidates hanging, or provide only the most cursory follow-up.

This past year, I had the fortune to really dig in and develop a thoughtful and thorough recruiting process for a big enterprise (who were needing to hire rapidly), and I surprised myself as I realized just what it takes to create a process that’s fair and equitable, that appropriately assesses competencies and skills, and that’s manageable for an internal team.

To build such a thing is quite onerous, as when you pull on the recruiting thread, the whole org design unravels. You need to understand levels, professional development, have a clear taxonomy of (technical, strategy, professional) skills and an understanding of what progression looks like, and a view of how the work gets done (embedded in scrum?, dual-track agile?).

You then need to structure a recruiting process that sources and vets candidates efficiently, effectively, and fairly, that doesn’t waste people’s time, and leads not just to hiring, but successful fit that lasts. 

This is all real work, and it is exceeeeeeedinly rare to find companies willing to put in the effort.    

Finding Our Way podcast

Recording the Finding Our Way podcast with Jesse has been perhaps the professional highlight of my year. He and I hadn’t worked together since I left Adaptive Path, and I missed our conversations. We are grateful for the overwhelming and positive response we heard from the community—we seemed to tap into some themes and concerns that were on many minds. 

A few episodes stand out for how they reshaped my thinking:

10: We Have Trust Issues

You cannot successfully lead for any length of time without a basis of trust. But deconstructing trust demonstrates just how slippery a concept it is. I think we do a good job poking at it from a variety of perspectives, and what we unpacked here became an undercurrent in later discussions.

18: How Agile and Scrum ruined product management, and other things ft Melissa Perri)

Our second season featured conversations with design, product, and research leaders, all of whom I learned from. This discussion with Melissa Perri helped us realize just what degree design leaders have been gaslit about product management practice.

20 —The business model is the new grid, and other mindbombs (ft Erika Hall)

Jesse and I have known Erika for about 20 years, and she’s always been a useful provocateur. This discussion possibly ranged the farthest, while retaining remarkably high signal. 

23—Make UX truly human-centered by addressing trauma, power, and other necessary and uncomfortable realities (ft Vivianne Castillo)

While many discussions helped me better articulate what I already felt, this conversation with Vivianne actually changed my perceptions, specifically around the practice of user research, and the responsibility we have to those who conduct the research and the participants. I’m still grateful for how Vivianne opened my eyes. 


Here’s to a new year!

While 2020 was an undeniable crapshow, I’m grateful that it proved to be fruitful for my work. I look forward to thought-provoking opportunities in the new year, and appreciate all of you who take the time to read what I write, and share your thoughts with me.

To 2021!

I’m reading The Manager’s Path, an excellent book on managing technical teams, that’s wholly relevant for people managing design. Towards the end, Camille Fournier addresses “The Big Leagues,” and what it should mean to be a Chief Technology Officer:

First and foremost, a CTO must care about and understand the business, and be able to shape business strategy through the lens of technology. He is an executive first, and a technologist second. 

It’s a light edit to make this work for Chief Design Officer:

First and foremost, a CDO must care about and understand the business, and be able to shape business strategy through the lens of design and user experience. She is an executive first, and a designer second.

Thing is, when I talk to CEOs, GMs, and others who are looking to hire a design executive, a common criticism I hear is that the people they talk to are designers first, second, and third. 

Which, to me, is understandable. Design Leaders have had to expend so much effort fighting for their teams, their practices, their perspectives, that such a pose has become their default as organizational leaders. 

However, it’s holding them, and their teams, back. True design executives need to see their executive peers as their “first team,”  and their design organization as their second team. To be a design executive is to be an organizational leader. If you consider yourself simply the senior most design person, then you (and your team) will be constrained in its ability to make a broader organizational impact.

And I get it, this is hard. For so many design leaders, Design is core to their identity. But it’s time to recognize that for design to truly earn that ‘seat at the table,’ design executives must, perhaps counterintuitively, make design their secondary concern. 

A common oversight companies make when hiring a Design Executive is that they do so in a vacuum, and thus overload the role with responsibilities. They seek a Creative Leader with Executive Presence who can Scale an Organization, Build a Compelling Culture, drive Design-Lead Product Strategy, ensure High Quality, and Deliver Business Results. 

And it’s not that you can’t find an Executive who can do this. But they can’t do this all at once, and they will have distinct areas of strength and weakness. But companies hold out for a Design Jesus, talking to countless candidates, and only after 6 months, 9 months, even a year, come to grips with reality and figure out what they actually need in that role.

Companies should instead think about how to establish a Design Leadership Team, a small group of senior design leaders who collaborate to ensure the effective practice and delivery of design. Every time I develop a profile for a Design Executive, I do so in the context of building a Design Leadership team, making clear that each member of that team has distinct emphases that, when combined, should lead to a whole greater than the sum of the parts. 

In The Makeup of a Design Executive, I listed the four components of that leadership makeup: Executive, Creative, People, Operational. This can help us navigate the makeup of the leadership team, as we place different emphases on the different roles.

Design Leadership Team

SVP of Design, Chief Design Officer

Executive and Creative Leadership

  • Holds own with executives
  • Strategic partner with end-to-end vision 
  • Inspirational and enabling leadership—models the culture
  • Recruiting and retention strategies
  • Advocate/champion for design
  • Establish quality standards

Head of DesignOps

Operational Leadership

  • TeamOps (effective delivery of Design, program management)
  • PeopleOps (recruiting coordination, onboarding, review programs)
  • Resources, facilities, and services for Design
  • Design Education programs
  • Vendor management

Design Directors

Creative and People Leadership

The folks typically oversee a significant swath of the design org (~20 people), and could be organized by product, customer type, or stage in a customer journey. They oversee the design teams doing the work, collaborating cross-functionally, and delivering the user experience. 

  • Uphold quality standards through the work
  • Connects design effort with product and business strategy
  • Recruiting and hiring for their teams
  • People and performance management (for designers)
  • Process and practice, both internally and cross-functionally 

Heads of Functions (e.g., UX Research, Content Design)

Creative and People Leadership

Obviously, Design is typically the most prevalent practice within a team, and doesn’t warrant specialized leadership. Other practices, such as UX Research and Content Design, typically are not staffed at the same rate, and the roles are deployed differently. It’s important to have heads of these functions to ensure:

  • Establishing best process and practices, internally and cross-functionally
  • Developing quality bars for these practices
  • Recruiting and hiring within the practice
  • Appropriate staffing across project work
  • People and performance management (for their function)

Principal Designer, Design Architect
(Super-Senior Individual Contributor)

Creative Leadership

I recently wrote about this role at length, so won’t duplicate that here. What I will say is that as design organizations scale, the SVP of Design and the Design Directors, who are expected to contribute Creative leadership, find that the other responsibilities of their role (Executive Leadership, People Leadership) take time away from creative engagement. And while they may be able to provide Creative leadership in bursts, they cannot sustain it. If that is the case, it is time to bring on Super-Senior Individual Contributors who can focus solely on Creative leadership.

With the idea of a complementary Leadership Team in place, it becomes easier to think about how to hire for each role, as you no longer are considering them without context.

And you may find yourself rejiggering the Leadership types represented here. Say you recognize the need to bring on an SVP of Design to scale the organization and drive design advocacy throughout the company, and you already very strong Creative leadership at the Director level. In that case, an SVP with emphasis on Executive and Operational leadership may be more suited to this context.