Design as an executive function is new, so Heads of Design are typically lonelier than their peer leadership positions. Your boss may have never had a truly senior Design leader report to them, and doesn’t really understand all that a Design team can deliver. You’re only Design leader on executive team, whereas there are multiple Product Management and Engineering leads.

This means that there’s no one to turn to internally as you try to figure out how to best lead your Design organization.

This is where I come in. I support executive Heads of Design in a mode I call “Thought Partnership.” I work with design leaders to accelerate thinking through their trickiest challenges, leveraging my experience (20+ years leading design teams; 5 years as a management consultant across all kinds of design organizations) to identify paths forward, enabling Heads of Design to make important, impactful decisions with confidence. Recent work with design leaders addressed such matters as:

  • Scaling from 30 to 100 team members
  • What their job actually is, where they should focus (and what they need to delegate)
  • Building career architectures and leveling frameworks
  • Improving recruiting and hiring practices
  • Establishing Design Operations
  • Elevating Design’s impact in the company
  • Evolving product development practices to better incorporate design throughout the process
  • Articulate a strategic vision to align product efforts

I’ve done this work ad hoc, in response to design leaders reaching out to see if I could support them. It has been some of my favorite work, capitalizing on my distinct vantage point to help leaders go from uncertain to confident, and see real impact in short time frames. 

As such, I’m now setting aside more time for this kind of work, and, well, telling the world that this is a service I’m happy to offer. 

It’s a small investment of time: the work is typically structured as one or two 1-hour sessions a month. In each session the Design Leader shares with me their topmost challenge, and we work together to figure out the best way forward. 

If this is something you’d like to take part in, please reach out through email, and we can then set up follow-up discussions.

On a recent episode of Finding Our Way, Jesse and I spoke with Tim Kieschnick. I worked with Tim for about a year, and learned a ton from our collaboration. He’s an interesting cat—he worked at Kaiser Permanente for 30 years (until retirement), and in that time helped establish their web presence, UX as a practice, service design, and HCD/Design Thinking/Design Sprints. He’s a reflective practitioner, and through his experience developed two frameworks which I have in turn used in my thought partnership practice with design leaders. I was eager for him to share his wisdom on our podcast.

The 3Ps of the Leadership Ceiling

A little over a year ago, at my urging (so I could refer to it without feeling like I was plagiarizing), Tim posted an introduction to The Leadership Ceiling. (some of what I write here will repeat what’s over there, but in my words.) At heart, it’s a simple construct: Leaders create a conceptual ceiling above which their organization cannot rise. Tim identifies three ceilings:

Purpose

Why does this organization exist? How is that purpose articulated? Are we driving toward output, or outcomes? How does our purpose inspire, connecting people with their higher, better selves?

People

Who is in this organization? What is the caliber of contributor? And, are we creating a truly people-centered organization that enables those folks to deliver at their best? 

Process

How is the work getting done? Does our process bog us down, or lift us up? How are we coordinating across functions? Are people spread too thin, across too many initiatives, or are they able to maintain focus and commitment? Are teams empowered to practice a process that is ‘fit for purpose,’ or is there an imposed standard way of doing things that cannot be deviated from?

(This is reminiscent of what Daniel Pink identified in Drive, in terms of what it takes to motivate people: provide them Autonomy (process), Mastery (people), and Purpose.)

In my experience, I don’t see three ceilings, rather one ceiling that is a product of how these three factors intersect. In my work with design leaders, looking at the intersection has proven helpful, because it illuminates why there’s cognitive dissonance between the message they’re getting from their leadership, and why the work doesn’t meet their expectations. 

The diagram to the right shows my take on this aspect, which is that the Leadership Ceiling is set by which ever factor is lowest. 

For instance, I’ve supported a number of banks and insurance services firms. And nearly all of them have high-minded aspirations for their business, with mission statements about empowering people’s financial wellbeing, or improving the health of all Americans. And these firms will also have committed to providing a much more conscientious work environment that encourages bringing your whole self, and stresses values of psychological safety and vulnerability.

But these large legacy organizations are bogged down in process, for reasons including bureaucracy, poor organization design, unwillingness to truly empower teams, people spread too thin across too many workstreams, etc. 

And so, the Leadership Ceiling is established by that lowest factor. And the design leaders I work with, who may have been sold on a company’s vision and culture, then struggle when they realize that for all that high-and-mighty talk, their ability to deliver is severely hamstrung by a lack of attention to process. 

The ABC’s of The Leadership Ceiling

Once you understand the height of a Leadership Ceiling, then you have to figure out your relationship to it. Tim uses an ABC mnemonic to think through what you can do:

 

Diagram of the ABC of The Leadership Ceiling from Tim’s website.

You can try to work Above the ceiling

This approach is pretty common for designers, particularly new to an organization, who see their job as to ‘fix’ whatever came before, or to realize a bold new innovative vision. And they may see their leader’s Ceiling, and perhaps engaged in some effort where they bumped their head on the ceiling, and then see their job as the innovative iconoclast to work above the ceiling, to show to the rest of the org just how great it can be. 

This never works. You might get some time to play in that rarefied air, but inevitably the leader’s Ceiling does its thing, often in the form of the Leader being frustrated that the designer isn’t doing what was expected of them, instead pursuing some quixotic endeavor that was bound to go nowhere.

So, most of us end up working Below the ceiling

We realize that we are constrained by the leader’s ceiling, and focus our efforts there. The dream is to have a leader with a high ceiling across all 3Ps, providing all kinds of headroom to innovate and grow. But most of us find ourselves below a ceiling lower than our liking, and so we have to make a choice:

We can Bail. We may believe that we’ll never reach our potential, or that work will be endlessly frustrating, and given our limited time on this planet, we want to focus our energies elsewhere. (This has been what I do. This model has helped me realize that I have little tolerance for working under a low, or even medium-height, ceiling.)

We can Bide our time. We make the best of the situation in front of us, delivering excellence within the leader’s constraints. Biding may sound defeatist, but it shouldn’t be perceived as settling. It can be a smart and pragmatic strategy of getting things ready for when the time comes and either our leader raises the ceiling, or is replaced by someone with a higher ceiling. In the podcast, we talked to Tim about telehealth, which Kaiser Permanente had been pursuing for 25 years. And if you were passionate about telehealth, you were likely frustrated, because it never caught on the way you felt it should—the organization wouldn’t invest in it and the membership didn’t seem to appreciate the convenience. 
And then 2020 happens, the world goes on lockdown, and that causes the Ceiling to be raised on telehealth. And all those folks who had been biding their time, waiting for the moment, are now center-stage.

Some bold souls may seek to Change the ceiling

As Tim puts it, this “is not for the faint of heart.” But if you are frustrated by the height of the ceiling, and you’re not content working Below it, and you’re committed to the organizational cause and so you won’t just Bail, you can try to change the ceiling. This requires diagnosing just what is depressing the ceiling, developing an argument and a plan for raising the ceiling, and then doing the hard work of education and evangelism to persuade leaders to change the ceiling. This is particularly tricky, because those leaders, over their career, have received a lot of confirming feedback about the rightness of their decisions, and now someone within their org is going to tell them that they’ve got it wrong? So, it requires delicate, incisive, and persistent communication to figure out what stories resonate with the leader and encourage them to evolve their view. 

I’m so grateful Tim spoke with us, and driving broader awareness of this framework. I’ve found it quite useful in my work helping design leaders succeed, and I’d love to hear (or read) how it works for you. 

From a VP of Design I work with:

“I had to have an intense conversation with someone on my team, who is struggling with the shift from Design Manager to Design Director. The Product Lead this Director works with has started reaching out to me again. When I dug into it with her, I found that she’s still doing the thing that Product Managers love, getting into the nitty-gritty details. But the Product Lead is still waiting for a vision statement, a hypothesis around where the experience could be going. She went too deep too fast, and hadn’t gotten alignment on strategic direction.”

When working with executive design leaders across organizations, I often hear something along these lines. Their Managers and Directors don’t know how to best spend their time, and where to focus their attention. Interestingly, I hear something similar from C-level people about design executives—they’re too focused on their team, and not the organization as a whole.

What many design leaders don’t understand is just how much their role changes, in particular, the relationships they need to have, as they advance in their career. 

Design Manager

A Design Manager is someone relatively new to formal leadership, and has people reporting into them, anywhere from 3 to 8 (any more than that, and the Manager will be overwhelmed). 

Diagram of how a manager spends their timeTheir primary orientation is downward. They’re focused on getting the most out of the team the manage, making sure they’re delivering on expectations in terms of addressing problems and upholding quality.

Their secondary orientation is sideways, working both with Design Manager peers to drive coherence across teams, and working with cross-functional peers (Product Management, Engineering), to coordinate and plan delivery efforts.

Design Director

When we promote a Design Manager to become Design Director, we often don’t communicate how this is a fundamentally different job than the one they had before. As the quote that started this post shows, many new Directors resort to the practices that helped them succeed as a Manager, but those will get in the way of their performance as a Director. 

Diagram of how a Design Director spends their timeA Design Director’s primary orientation is sideways, and not only that it’s mostly outside of Design. An effective Design Director should be spending more of their time and energy working with non-design peers and other stakeholders than with any other kind of colleague.

Their secondary orientation is downward, with a focus on managing their Managers. Their job isn’t to get into the nitty-gritty themselves, but to provide guidance and mentorship for their reports. Directors are also crucial for establishing the management culture and philosophy for their teams. But they shouldn’t need to spend anywhere near the time they used to in managing down, because, well, they have managers to handle that. 

Lastly, a Director will spend a small portion of their time managing up, to their VP and non-design leadership, keeping them apprised of what’s happening in their world, and learning overarching strategy and vision in order to make sure their organization is aligned with global goals. 

Design Executive (S/VP of Design)

When talking to CEOs, their primary concern about Design Executives is that they see themselves as a Design Leader first and an Organizational Leader second. CEOs expect Design Executives to see their cross-functional peers as their “first team.” with the design organization as their second.

How a VP spends their timeAnd in terms of time spent, it goes even farther than that. The Design Team should be where a Design Executive spends the least amount of time. Their primary orientation is sideways, toward their executive peers. This is about planning and strategy for the organization, identifying opportunities for the business and how their coordinated teams can realize them.

Their secondary orientation is up and out. It may seem counterintuitive that an executive would spend so much time engaging with a small number of even more senior executives, but that’s the reality. That’s your key audience. They’re the ones who are needed to support the plans of the Design Executive and their peers, to commit the resources necessary. “Out” may mean executive leaders outside your direct reporting chain, and in some environments it may mean key customers or partners. As a Design Executive, you now represent the company in a variety of contexts, both internally and externally.

A high-performing Design Executive should spend their least amount of time focused on matters within their Design Organization. It may take a while to get to this point—it requires a strong Design Leadership team, and effective operational practices around recruiting and hiring, staffing, performance management, quality standards, etc. But, really, a Design Executive shouldn’t need to spend much time orienting downward, because they should be able to rely on their org to get stuff done. 

 

 

This post builds on the Emerging Shape of Design Orgs.

As design organizations scale, I’ve worked with a number of design leaders who struggle with all that’s expected of them. Let’s look at the “HR Software” org I drew in the last post

No Time for Creative Leadership

The VP Design is a true design executive, and, as I wrote in The Makeup of a Design Executive, is expected to deliver on Executive, Creative, Managerial, and Operational leadership. The thing is, with a team this size, and particularly if it’s growing (as so many teams are), they simply don’t have the time to do it all (unless they work 60-, 70-, 80-hour weeks). And these VPs need to focus on what’s core to their role, which are the executive and managerial aspects, and so the creative leadership suffers.

Even the Design Director is spread thin—overseeing a team of 15-20 people, recruiting and hiring, encouraging professional development, building relationships with cross-functional peers. This takes up all your time, and, apart from weekly critique sessions, they don’t have capacity to provide creative and strategic leadership to their teams. 

Which Means No Time for Strategy

Design organizations are increasingly expected to contribute to product strategy, but these structures support little more than product delivery. If the team is asked to develop a vision for the future product experience 2-3 years out, how do they get it done? 

One way is to hire external consultancies. And that can serve as a good kickstart, but such relationships should be seen as bridges toward when the design org is able to conduct its own strategic practice. 

And as design orgs scale, and design leaders develop organizational authority, a common move is to create a Design Strategy group, a small team of senior designers to tackle wicked problems outside of the constraints of business as usual. It may look something like this (building on the depiction of the growing design org from the last post):

Scaled design organization with Strategy team tacked at the end(There’s an argument to be made that the Strategy Team could be a pillar of the Platform team. The point that follows wouldn’t really change.)

Separate Strategy Teams within Design Orgs suffer the same problem that any separated team has—getting traction. Now, looking at the diagram above, you could say the same about the Platform team, but in that case, the Applications teams all understand why integrating with Platform makes sense—the Application teams can focus on the higher order work specific to their business area, and move faster. 

Now take the perspective of an Application team. That Strategy Team gets to do fun vision stuff, play in a space with little accountability, and then what… tell us what to do? And if we try to work with the Strategy Team, we’re told that they’re looking at broader, end-to-end experiences, and don’t want to be confined to any particular business area.

And so the Strategy Team gets frustrated because while folks may get excited about their ideas, it’s not clear how they get purchase within product development.

Two Birds (Creative Leadership and Strategy) and One Stone: The Shadow Strategy Team 

So, scaling design orgs have a problem. The acknowledged leaders (executives and directors) don’t have the bandwidth to provide the strategic and creative leadership expected of them, and necessary for the optimal effectiveness of the team. Building a separate Strategy team addresses some of this, but is typically too removed from the actual work to make an impact.

A solution lurks within the Emerging Shape of Design Orgs, with the addition of Super Senior ICs . Design organizations are increasingly hiring Principal Designers and Design Architects, as shown in this diagram (click/tap to enlarge).

Scaled org with Super Senior ICs added

Design Architect. Reporting to the VP of Design, they have no managerial or operational responsibilities, and so are able to focus on creative and strategic leadership. I’ve written this job description a few times over the past couple years, and here is what the “Responsibilities include…” section looks like:

  • Provide creative and strategic leadership for design and throughout product development
  • Advocate for user-centered design best practices within product development
  • Partner with product and engineering leaders across the company
  • Spearhead the development of experience-led product vision across the entire product suite
  • Provide guidance and direction for key ‘horizontal’ activities such as Design System development
  • Create strategic design deliverables such as strategy decks, customer journeys, visions of future experiences and evangelize these cross-product “blueprints” across teams
  • Build and maintain a framework for establishing and assessing design quality
  • Connect design with business value
  • Work with design, research, program management, and product leaders on process for product development

Principal Designer. This role is similar to the Design Architect, just within a specific business area, reporting to a Design Director. The primary difference is that they are also involved with design delivery, playing a very active role in design direction and critique, and occasionally serving as a “big project Team Lead,” spearheading important and challenging new product development.

The Shadow Strategy Team. With a Design Architect and Principal Designers in place, you now have the constituents of your Shadow Strategy Team. Instead of a separate group of strategic designers, they are woven into the fabric of the producing design organization.

The trick is, how to get them working as a team? That’s primarily the responsibility of the Design Architect, with leadership support from the VP and Design Directors to protect some of their time for organization-wide efforts. At a minimum, this team meets weekly to share what’s happening in their worlds, and to ensure efforts are connected across the end-to-end experience. Occasionally, the Design Architect may engage Principal Designers on vision and strategy work, with the benefit being that these Principal Designers ensure that the vision is grounded in the reality of the business areas.

Recapturing some of the Dream of UX

A common frustration among digital designers is how their practice has been reduced to production. I think a reason for this is that our organizations lacked creative and strategic leadership—we assumed it was coming from the executives and directors, but they were too busy just keeping things going. So it just wasn’t happening.

By having roles within this explicit focus, these super-senior practitioners provide can recapture the untapped potential of thoughtful, intentional design. 

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.  

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.

Communication

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. 

Presentation

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.   

Listening

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. 

Presence

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. 

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.