Five Challenges of Design Leadership
This is Part 2 of, “So You’ve Got a Seat at the Table. Now What?” Feel free to read this post independently, or check out Part 1 for the back story.
Challenge #1: Vision
The first challenge once you get to the table is vision — as in what is your vision for design in your organization? Your vision will be predicated on a number of things, not least of which is your philosophy of design and design leadership, but it will also depend on the type of organization you are integrating design into.
To understand the organization you have to know what already exists. You need deep knowledge of what makes the organization tick — the systems, dynamics, and processes currently in place so you can start to determine where and how design can partner and lead.
Unless you are a design founder you will be encountering values, processes, and an organizational identity that was formed with little to no design DNA. In Part 1 I briefly touched up on the distinction of design-from-the-beginning versus almost-the-beginning, and this is why it’s important to understand the difference. When design is present from day one as a partner in the organization it lays a foundation that is built upon as the days, months, and years pass. Retrofitting a foundation (or splicing DNA to follow the original metaphor) is no easy task and requires a different level of patience, effort, and diligence. This is why, for designers joining organizations with the express purpose of changing organizational DNA, it is so important to first understand the business, technology, and culture as it exists so you can make smart decisions concerning where to begin inserting and building out a design practice.
In the beginning you’ll be doing a lot of listening. As designers our research skills are quite handy and provide the requisite tools for sensemaking. David VanEsselstyn of MakerBot gave a great talk at MX Conf last year about his first 90 days at the company — he’s also a believer in the importance of spending time up front listening — in which he warns us to remember:
Design leaders are not just hired to listen and consult, we are hired to lead.
This is vitally important to keep in mind. If you aren’t leading then someone else at your organization is defining what design is. Or even worse, isn’t.
As you listen, start formulate ideas about what design should be at your organization both externally and internally. This will require some serious introspection and a long, hard, and honest look at the company, culture, clients, and products you are working with. You may find that after doing all this listening and analysis, the role you imagined for design doesn’t or can’t exist. And let’s be clear here — this process isn’t something that happens just once— it’s something you should be doing every quarter or two because your organization will grow and change. In parallel, be diligent and maintain an awareness of how design is growing and changing with the organization. Sometimes the two grow together, and sometimes they don’t.
If they don’t — if you find the role you envisioned for design just doesn’t exist — you may end up leaving (that’s okay too!), but if you stick around and you’ve been listening and thinking about what you want design to be, your north star will begin to emerge. As I began to understand SimpleReach’s identity as a technology company, the role that data played, and the types of users we had, my north star emerged as ‘data for humans’.
WWHED (What Would Harley Earl Do)?
Harley Earl’s north star was deceptively simple: oblong. Like, seriously. I’m not kidding. Earl thought cars should be lower and rounder because it pleased his sense of aesthetic proportion. He stated:
My primary purpose for twenty-eight years has been to lengthen and lower the American automobile, at times in reality and always at least in appearance. Why? Because my sense of proportion tells me that oblongs are more attractive than squares.
To be clear, this drove the engineers totally crazy, but Earl fundamentally changed the auto industry by never, ever deviating from his north star, and that, IMO, is pretty badass.
Challenge #2: Buy-in
Vision was about understanding the company. Buy-in is about getting the company to understand design.
One of the best ways to get buy-in is to show. This piece of writerly advice is as applicable to design as it is to writing because showing is interactive, participatory, and communicative, which helps people to learn, process, and understand new things.
The opposite of showing is telling. Avoid this at all costs! Do not assign people homework or send lists of articles, books, and videos (unless solicited, natch) with the expectation that people will spend non-work hours devouring the content and internalizing design. This isn’t going to happen. This never happens.
Your company is looking to you to show them what design does and how it does it. You already have a deep understanding of the company because of research you did when establishing a vision, so use this as a foundation to communicate the value of design as it relates to the company.
But there’s a caveat. You can’t use design language! At all. Design language is often exclusionary and can be difficult to grok (hell, just look at all the things we’re still fighting about defining). By using normal language you are meeting people where they are which demonstrates that you care, that you are willing to put in the effort, that you want to be partners, and most importantly that you can be trusted.
This was actually one of the bigger mistakes that I made several years ago. I was so focused on making a space for design and protecting design that I lost sight of both the bigger picture and empathy for my colleagues. Instead of doing “Yes, and…” I was doing “Yes, but…” and that was a bad place to be. Instead of sharing, teaching, showing, and explaining, I drew lines and shut people out. Unsurprisingly, this had a very negative impact on my effectiveness as a designer. I was on a path of exclusiveness, in inclusiveness.
The issue has since been remedied, but please, please learn from my mistake and be careful not to guard design. Instead, focus on sharing it.
A good way to share is by using co-design practices. Sketching sessions, design studio, the design sprint, participatory design practices — this all goes back to the interactive and cooperative nature of showing. Invite people from across the company to join your brainstorming and user testing testing sessions. Make your methodologies transparent and accessible.
Make everything visible. Cover the walls with printouts of screens, wires, and sketches. Externalize design in order to pique people’s curiosity. Invite people to participate, have conversations, ask questions, and leave feedback. And what kind of designers would we be if we didn’t have Post-it notes everywhere? So throw some of those up on the wall too ;).
Showing is awesome, but there’s one extra step you should take, which is to also promote design. Promote your team and their work at all hands meetings, in newsletters, create company design blogs, have lunch and learns, make posters, you name it. When promoting your work be sure to talk about the what and the why. By doing so you are giving design a stamp of authority because, going back to vision and leadership, you are the expert showing how design works and how it adds value.
WWHED?
Despite the resistance Earl faced in the beginning, he was able to get buy-in over the years as he demonstrated to the company how design worked. The image above shows the use of sketching, concept exploration, and modeling prototypes to externalize the things design was working on and bring them to life in a way that people understood. He made the design process approachable and tangible. Going back to the idea of showing and promoting your work, this is a pretty good way to do it.
Back in Part 1 we talked about the resistance Earl faced when joining GM. Interestingly, as the years passed, the design studio became the place that everyone at GM wanted to be. It was a place of collaboration and cross-pollination. People loved to visit the studio and see what the design team was working on.
Challenge #3: Alignment
Okay, you’ve got a north star and people are starting to understand design. Now your challenge is getting the company aligned around the role design is going to play in your organization — getting them excited about what it looks like once you combine vision and buy-in.
Part of alignment is simple repetition — banging the drum about things that are obvious to designers but aren’t as obvious to everyone else. You’ll have to keep saying things like, “design isn’t just making things pretty” or “design isn’t lipstick on a pig at the end of the process”. Part of my repetition game is that every time someone says “make it pretty”, I do a shot. I don’t really do a shot (anymore), but the ritual has become such an reflex response that it helps everyone remember there is a lot more to design than pretty.
You’ll also have to repeat things like, “design begins at the planning phase”, “design is part of R&D”, “you include design from the beginning so you can make better quality products”. Sometimes you’ll need to keep talking about how “design is problem solving”, “design may find a different way to solve problems than engineering or business”.
But I promise, the day you hear a non-designer repeating this to someone new at the company, your heart will smile.
Speaking of repeating, keep everything centered on the customer. Focusing on the customer, rather than design, aligns people around a common goal. Going back to Airbnb, when I visited in 2012 they were very much a design-led company, but an article in Wired last year grabbed my attention with the headline, “Why Airbnb’s New Head of Design Believes ‘Design-Led’ Companies Don’t Work.”
The article talks about how design-led initiatives can often feel exclusionary for people who aren’t designers, so the shift happening at Airbnb is to spread the user-centric viewpoint into every area and division of the company. It isn’t that design lost the seat at the table, but rather that a customer-centric viewpoint is a more effective way to communicate and collaborate. And, going back to the whole participatory side of things, this involves the entire company and the customers.
Alignment can also be established by starting with small, well-scoped projects to demonstrate that, among other things, design can execute and have measurable value. At SimpleReach I started with an overhaul of the sign-up flow. It wasn’t the sexiest project, but it was tangible. Once we launched the new sign-up form we got more sign-ups, people submitted better and more complete information, and people even tweeted about it.
These types of projects help you establish early success that builds trust and credibility for design and the role it plays in the organization. Get a few of these small projects under your belt and you’ll have a foundation to start taking on larger, more complex problems with the support of the company behind you.
WWHED?
When it comes to alignment, Earl was a master. Not only did he align people within GM, but he also aligned the American public. He created the Motorama show, a precursor to the auto shows as we know them today, where he would showcase upcoming GM models. He also debuted the concept car, another Earl invention, that put GM’s innovation on display and captured the hearts and minds of the entire nation. These concept cars also gave him an additional avenue for research, gauging customer responses to new style and engineering ideas.
Challenge #4: Culture
Culture is your longest, hardest, most difficult challenge. It’s not that you want to create a culture of design necessarily, but that you want design to be a part of the culture.
Culture is about codifying alignment. But change is hard and people are resistant, which is why it’s important to have established vision, buy-in, and alignment.
Part of shifting the culture means inserting design into the decision making process. Be it strategy or execution, design should be a partner when it comes to deciding how things work and what to build.
Jared Spool’s market maturity model is a helpful framework to categorize your organization’s approach to creating customer value. If your company is at stage 1, you’re going to take a very different approach than you would at stage 4 when it comes to how the company organizes around, and thinks about, design.
Being included in decision making could mean a change to how design works, where design belongs, possibly new ways of collaborating, or maybe even a re-org across the entire company. Re-orgs can be especially difficult because there aren’t tons of examples to reference of when it comes to design being at the table.
I struggled with this at SimpleReach — of the examples I found, none fit our particular organizational structure or philosophy. I think part of the issue was that certain things cannot be solved with org structures, and it takes some experience to know what those things are. I have a lot more clarity these days, but the complexity of the problem is so interesting that I’m currently in the process of applying to MBA programs so I can follow the white rabbit to wherever this leads.
Hiring, of course, is exceptionally important when it comes to culture. You should own this yourself rather than outsource it to a recruiter. This isn’t to say you can’t work with recruiters, but you need to be the lead. Even something as small as writing your own job descriptions can have an outsized impact. Designers can immediately tell if the job posting was written by a designer or a recruiter, and it makes a difference.
Early hires are key. Find people who share the same values and principles as you do — folks you trust — to strengthen your foundation and help shift the culture. Speaking of which, culture fit trumps skill. Of course, a certain level of skill needs to be present, but most skills can be trained up. Culture fit cannot.
Another problem bringing design into the culture of an organization is creating space for it, so be very wary of the execution phase. This is a problem we had at SimpleReach but I imagine it’s not that uncommon, and after thinking about it for a while, I’m not sure it’s avoidable (especially if you are in a start-up). Either way, it’s something to be aware of.
This problem happens when the company is small and things are moving quickly, which tends to get design stuck in the execution phase, essentially masquerading as engineering. Early on when we were heads down getting our v1 out the door I was the only designer, writing a large part of the the production code for the interface. We basically lived in our code editors and git. There was little time for anything else.
By the time we raised a round of funding and started building out a design team the damage had already been done. Because we were stuck in the execution phase there wasn’t enough room for design to do all the things design is good at. We had NO definition phase.
We’re currently in the process of re-designing the process to make sure we get design up front way before any build phase happens to ensure we are creating things that bring the most value to our customers. Peter Merholz’s double diamond model has been invaluable for communicating where and why this space needs to exist.
Like I said, this may not be avoidable, but you can be aware of when it’s happening and set expectations accordingly so that design can move away from pure execution as soon as is feasible.
WWHED?
We’ve already looked at a number of ways Earl had an impact on culture with design studios, Motorama shows, and concept cars. But he also impacted culture with his hiring practices. GM was the first company to employ women designers as full equals in the Art and Color section. He figured that in order to sell more cars to women, he should probably involve them in the design process.
Unfortunately, all Earl’s hard work was undone when his successor promptly demoted all women saying:
No women are going to stand next to any senior designers of mine.
Pardon my French, but fuck that.
Challenge #5: You
The final challenge, one that I realized maybe later than most, is you. Well… me. But you. You know what I mean.
The first thing to remember is to celebrate wins and learn from losses. This is especially important if you are the only designer because it’s entirely possible the rest of the company won’t realize when these milestones are happening. Be sure to celebrate your wins even if no one else knows there were any, and be vigilant about losses. Reflect, reassess, and adapt as you go.
Always be learning! I debated whether I should even include this as it seems like a no-brainer, but decided it’s important to emphasize because a lot of the learning you’ll be doing won’t be about design itself, but about the business of business. You’ll be learning about growing an organization, business models, tech stacks — the same stuff you spent the first 90 days learning about. It’s also worth emphasizing the reciprocity of this because you are asking the business to keep learning about design, so it’s vitally important that you keep learning about the business.
Be sure to find mentors and colleagues outside the organization to help you reflect and grow. People who are willing to also listen to you vent. Especially if you are the only designer because work can be lonely and frustrating without other design-minds around.
If your organization is amendable, get an executive coach. Coaches will help you grow in your executive and leadership functions, find your path, and be effective in the goals you want to achieve. I started working with an executive coach about 10 months ago and she has completely changed my life.
Something that Catherine Courage always points out is that this is a journey. Don’t forget this! Change will not happen overnight, nor is it something with a finish line. Like World of Warcraft, the journey never ends. Keeping this in mind will help you contextualize the day to day, the ups and downs, as you build design into the identity, culture, and processes of your organization.
Dealing with these 5 challenges — vision, buy-in, alignment, culture, and you — will help you in your journey at the table and in demonstrating the value of design.
Harley Earl joined GM in 1927. He was made Vice President in 1940 and by 1950 the Art and Color section had equal decision making power alongside finance and engineering. Concurrently, GM’s market share skyrocketed. But there was a 10 year period between when Earl got the title and when he got decision making power.
The table is just the beginning.
For further reading, I’ve compiled a list of resources that have helped me along the way. In the end, what this all comes down to, is being designers and using our designerly ways of knowing and doing to build the roles we want, and the organizations we want.
Super special thanks to Lis Hubert, Binh Tran, Ray De La Pena, Daniel Weinand, Ian Swinson, Brad Nunnally, and Russ Unger.
