Process, by Design.

Illustration by Isabela Humphrey

Recently a former manager and mentor Maria Giudice asked if given a blank slate what I might choose to do with my life. I honestly hadn’t really thought about this before, and my mind was first filled with thinking of my many obligations. The exercise of removing those blockers, even for a moment, allowed me to answer her — I’d study Spanish Literature. I would leave a Masters program being able to read and dissect Don Quixote and so many others in Spanish. Why? This was harder to answer.

Digging into my ancestry I find myself being more connected to Adjuntas, a small town in the mountains of Puerto Rico where both my great grandmother and grandmother came from. The region, known for many things in the early 19th century, was mostly a haven for Taino, Cimarrones (escaped African Slaves), Anusim (Jews forced to convert), and other Sephardi Jews fleeing persecution and forced conversion. So much of my life has been tied up in my identity of being both Puerto Rican and Jewish. My bloodline, not necessarily unique, is a mixed bag of conflict, as has been my life experience. Losing my mother at a young age naturally set me adrift. She was a woman who was the dominant figure holding our family together and the main tie to my identity. Without my mother’s guidance, I was left to piece together my own self-image. Through the fog of following what’s expected, my life’s slightly unconventional path brought me to a place that had seemed to be a fit for all misfits — Design.

Twenty years into my career I think about my responsibility as a Latina leading in this industry. It has bubbled much more to the surface most recently as the talk du jour is so focused on “belonging.” Having professionally almost always been an “only” in the room has left me deeply skeptical about what that actually means in our day to day environments.

Growing up in NYC, I was never different; in fact, thanks to Welcome Back Kotter, I had Juan Epstein as a comforting point of reference. This helped me normalize, and feel prideful in being different. I learned how to be an “only” after moving out of the safety of New York City to North Carolina for college. Being continually asked, “what are you?” forces you to question the same, at first defensive until eventually existential. As much discomfort and resentment I felt, instead of running back to New York, I stayed. Was it because I wanted to conquer my fear of being an “only”, or understand it better by total immersion? Regardless of why, it gave me one of the most valuable experiences of my life — perspective outside of my narrow view and safe community.

As the first woman in my family to graduate college, I tried to pave the way for myself in what was at the time a totally nascent industry. Persistence was the norm as my daily experience was discouragement. Time and time again I was called “mousey” or “meek” because I was quiet and thoughtful. Often dismissed but never lacking for drive and ambition. Many people not considered to be the traditional type for [fill in the blank] are continually underestimated and overlooked in how they can contribute, manifest change and influence culture.

Malcolm Gladwell has spoken in-depth about a “mirrortocracy”, and in my professional experience, this has become increasingly apparent. In universities, at conferences, and inside companies, we build our networks from a foundation of people who are like us. The main problem is there aren’t enough people who look like me to mirror, which perpetuates the reality that every room still looks the same, no matter how much we talk about diversity and inclusion as an exercise. As much as we talk the talk of nurturing and mentoring “onlies,” only when there are more of us, will that actually take root. That growth will be evidenced in diversity of thought, being, and experiences.

To feel left out is a deeply human problem, which is why its consequences carry such heft and why its causes are so hard to root out of even the healthiest workplaces. — The Value of Belonging at Work, HBR

I am not identity politics driven as I believe it distracts from the greater good of one’s purpose. However, I feel strongly that there is significant social impact Design and Design Operations can have in the way we hire and think about the makeup of our organizations. In many ways, Design Operations as a discipline is an exercise in Culture Design. Now that we have arrived, how are we actualizing change? A willingness to question our new and evolved environments will expose the cracks in the foundation, the gaps in our understanding of difference. Bringing self-awareness to our internal experience that values and prioritizes learning, compassion, and a propensity towards meaningful engagement can drive the change organizations often desperately need.

In thinking back to Adjuntas, a thriving community built as a refuge for such divergent groups of people experiencing some of the harshest realities of life, I wonder — what were the rules of engagement? How can we learn from those experiences and practice them in our daily rituals, bringing a reason for being to our professional communities? How do I show up as a leader allowing for collective and individual value systems to thrive?

In exploring these questions, I have begun the process of being more professionally intentional, striving to learn and pay it forward. Working towards addressing our most pressing organizational blind spots in how we can design our cultures inside to be more reflective of the realities, and idealities, outside.

Setting the Table for Dynamic Change

Often times in design (and especially at design industry gatherings), we collectively suffer from storytelling that doesn’t tell the entire story. I generally leave conferences feeling a bit behind the ball, as the stories told are often success stories that leave me questioning my own methods and experiences. But if you catch someone afterward, they will usually give it to you straight. So, I have often wondered, how do we share that authentic story? The ones about failures and learnings. Falling down and getting back up — because we’re gonna fall down a lot. Especially as the trailblazers in this nascent discipline (in a relatively nascent field), we are going at it alone, which makes that failure feels so much more acute.

As a person coming from design consulting, I definitely thought I could basically apply everything I knew to how things should work on the inside. At my first job in tech, my boss often referred to my style as the Marvel character Domino because I continually jumped in and out of burning buildings, putting out trash fires. Coming up with solutions to fix symptoms, generally being super lucky in my approach — until I wasn’t. He wanted me to be a little more like Captain Marvel, more thoughtful and intentional, certainly less reactive.

So, where does Design Operations fit into this very structured model of how change management as a discipline has evolved because most of us haven’t gone to school for this and are generally winging it. I have often found myself wondering if I should get an MBA, as an affirmation, or a tangible way of proving I know what I am doing. Design Operations in the last three years has evolved from the question of relevance to building a case for its existence, to actual tactics with many people doing ops both at large and small scales. Basically, we’ve become the hottest gig around. But what does that actually mean when so many of us are figuring this out as we go along?

Illustration by Isabela Humphrey

The nature of design is inherently to change an organization. At some level, things are changing at every organization. Design Leadership and change are inextricably tied. How do we lead through change when most organizations, and people, are unwilling to change but know they have to?

Many books have been written about Change Management — this is not new. During the most significant shifts in history, corporations have had to respond to changing technology and competition. In the early 2000s, when so much was changing, Change Management methodologies pressed the hot button of the “burning platform” to push the urgency behind the risk of staying the same. During this period, change management moved into how we generally think of it today as a management consultancy thing steeped in organizational systems theory. But what does that mean? What does the future hold for those of us who aren’t steeped in academics but are steeped in both the art and science of our industry?

Let’s talk about the art in that science. That soft layer to what has traditionally been a very scientific field and how we, as design operations leaders, are those specific types of change agents.

Hiring for design ops conversations usually goes like this:

Hiring Manager: We need someone to do DesignOps, which to us means… (lists one million things which all basically boil down to fix our entire infrastructure and in turn, customer experience.)

Me: Great! Just a few questions… Does this have buy-in from the top and cross-functional stakeholders? Who are the organizational partners?

Hiring Manager: [crickets]

These people seem to understand that a design operations lead will be focusing on the people within design as well as the processes by which they develop, grow, and produce. Still, they underestimate what it means to actually scale design throughout and organization. Change requires more than a single vision or a few projects. It takes careful orchestration throughout the organization to become a part of the working fabric of day-to-day operations.

It is a process, by design.

“ ‘This is a giant hairball.’

What a disgusting term!

Wait a minute! There’s a time when there is no hairball. So where do hairballs come from?”

Orbiting the Giant Hairball — Gordon Mackenzie

This quote is particularly relevant because so many of us (I would bet) come into each new situation with our 30/60/90 day plan and spend a majority of the first 6–12 months just trying to unravel the hairball.

Suffice to say, Design Ops is not just about design, and if we aren’t considering the system, then we are destined to fail. How do we begin to unravel the hairball? How do we think beyond our immediate context, learning to anticipate how change might be received or the ripple effects it could have. Striking the right balance is a delicate dance. I have often said, “I am not a designer,” and some excellent (and supportive) colleagues pointed out to me that process design is also design. How we think about applying the foundational principles of Design Thinking to our work as a system, as a journey, will allow us to open the aperture and approach our work with a broader understanding.

It’s easy to reference change management theories as that path feels somewhat chartered, like a perfect baking recipe. It doesn’t necessarily consider how much of it is relational. How much of it is about building an environment where change is ready to be received, which involves psychological safety, trust, empowerment, and community.

I have tried to boil down some of these change management academics into four snack-size principles.

Illustration by Isabela Humphrey

Do not come in hot.

This was one of my biggest mistakes, thinking I knew it all. Remember, this is a process that should lean on Human-Centered Design practices. Discovery, which is, in good part, listening to learn. Figure out the partners that want to work with you, and the ones that don’t (both matter) understand the “high risk of failure” at your specific organization to come up with the right strategies. Maria Giudice calls this a “coalition of the willing.”

Illustration by Isabela Humphrey

When you’re first trying to figure everything out, it is hard to see the forest for the trees. I have learned that identifying a small area with great potential for impact can lead to the traction that will have a ripple effect and give you the runway you need to unlock other areas ripe to follow.

Talent resource management, for example. This is one that flies under the radar as a latent need. Most product-driven organizations don’t really know who’s working on what and how that ladders up to the broader company goals and roadmap. At a design consultancy, this is absolutely critical. Because what projects people are working has a direct impact on the P&L. In my experience, I am not sure if it should be that different in house, just approached with a different lens.

Illustration by Isabela Humphrey

In advertising, the term “effective frequency” is used to describe the number of times a consumer must be exposed to a message before the marketer gets the desired response (7.) This model can be applied directly to messaging within an organization. Those steps can be around:

  • Interacting with the people it will impact
  • Targeting the message to those people

A strong communication strategy and plan is a big part of the success of how you bring people along with you. Rinse / wash / repeat

Illustration by Isabela Humphrey

Don’t celebrate too soon, it’s a game of inches. When one part is complete, there’s more to be done, and you’ll have to start all over again. But don’t despair — you’ll have all your shiny new learnings from all your shiny new failures to put in your toolbelt to take with you on your next change journey.


There is something to be said for the level of maturity of an organization before Design Ops is brought in. In the InVision model, DOps is usually brought in somewhere between level 2 and 3. That doesn’t necessarily have to do with the ability for the organization to adhere to the practice of what design operations actually means beyond the day to day tactics (remember the hiring manager conversation.) Be mindful of what level your organization might be in, and retrofit your plan to what that stage might have an appetite for.

So much of what we are seeing and will see is a common pattern of behaviors. The situations are different, but so much of the work is the same. This is why frameworks exist (and why those system theories books exist for that matter.) We are all building from scratch, but the tools are beginning to fall into place. When I was in consulting, we all felt we could build something from scratch because it made it feel more authentic. Losing time and expending a ton of energy and effort when we could have been leveraging each other’s best practices and focusing on the customization of those best practices. Now that we have so many people building systems, we can identify the patterns and leverage those patterns to build on them, as a community.

So how do we actually walk the walk, when there is so much talk? Recognizing at the end of the day, it is not about design, engineering, or product — it’s about the customer. To push ourselves to deliver on the best and most cohesive end to end experience, we need to do more than introduce new or modify existing products or services, we need to change how our companies work and perceive innovation.

This is our job.

So how do we set the environment for change to be received? Think about those you are trying to lead through it, how do we allow them to inform the process? I like to imagine all the players are sitting at the same table. Some of them hate each other, some of them love each other, some of them tolerate each other. The fact is they are all there for a common cause. As Design Ops leaders, we haven’t only invited them, we have set the table.

And there will be a lot of noise at this table, so much it will at times feel like chaos. Listen for the trends and keep your ears open for the signals, mine that noise for gold. Most importantly, listen with tactical empathy. It’s easy to forget how, during times of change for individuals, teams, organizations — the emotion and anxiety loom large. We are all human. Always try to dig into underlying motivations when working with others so you can listen to learn, to understand, before expecting change to be received.

My former colleague and dear friend Alexis Lloyd said this often, and it applies so well to what we are trying to do. To have both resilience and grit, you must be able to absorb it all and keep going.

As you chart your path, you will hear and read stories from some fantastic leaders about their incredible experiences and tactics. I challenge you to take them all in, rationalize their stories with your own, and leverage that as your frame of reference for when you inevitably fall down and get back up again.

“I’m creating job titles for DesignOps roles and need some other models for reference.”

Good question! As these are early days, there is still some ambiguity in general around what role to hire for, never mind what titles should be. We have been having this conversation in one way or another for years. In the past we spoke of project management, program management, producer, etc. and debated nomenclature vs. semantics. And in this nascent discipline, I think the roles (and ambiguity) are analogous. Here’s what I have seen as the most common (and simplest) way to title:

Head of Design Operations
The person in this role leads the operations practice partnering closely with design leadership as the first point of contact in planning/road mapping and vision-setting. This role provides program management leadership and operational support throughout a design organization and across partner teams by increasing communication and connection points, streamlining the design process, and driving design excellence.

Design Program Manager
Design Program Managers support various aspects of product teams, enabling teams to focus their time on designing, building, and shipping products. Improving team communication, collaboration, and removing roadblocks. This role utilizes a full range of organizational and interpersonal skills to keep teams on track, execute specific design initiatives intended to grow team culture, industry expertise, and team impact, working with cross-functional teams to establish better processes and practices in working together.

Design Producer
The Design Producer is an organized, strategic, positive team orchestrator who is responsible for executing the project objectives and deliverables. Producers own the day-to-day project schedule and manage project costs, timelines, and quality while remaining flexible and focused on delivering the best creative solutions. They can build relationships to make sound decisions, communicate clearly, and actively manage the working team, project stakeholders, and partners. They are accountable for end-to-end management of design projects, from brief to product launch.
Leveling is an added layer to titling. Skill matrices are complex beasts and often controversial. The most straightforward and most basic model was laid out in Org Design for Design Orgs. However, this is not a one size fits all model. The framework is an excellent place to start, but there are many ways to customize in consideration for your team and the teams you are trying to build and grow.

What you have laid out seem like roles that are trying to encompass a few things in one. I might suggest considering the standard titles, level application as it suits your organization, and adding in the specialty as needed. I know finance can be a whole different beast in and of itself. Don’t try to do too much at once. Ask yourself the question of whether or not this is translatable to the industry as a title/role as career equity in the market is a thing.

As part of my role as DesignOps community curator for Rosenfeld Media, I answer DesignOps focused questions on a regular basis from the community. You can find a whole list of them there and I will also be reposting here.

The Paradox of Change

When I came into tech, I had over 15 years of experience as a Design Consultant. With that I brought some pretty definitive notions that I could basically apply everything I had learned as a client partner to the work I would be doing on the inside. As a consultant, I remember always thinking, “Why is this so hard? Why does our work never see the light of day?” I would  always chalked it up to the fact that even though a client had hired a big guns design consultancy, they weren’t actually ready. 

What I didn’t acknowledge was that implementing change within an organization requires more than a single vision or a few workshops. It takes careful orchestration throughout the organization to become a part of the working fabric of day-to-day operations.

In the first few months at my first in-house job, I did a listening tour to begin to understand our designers and the design organization. At the same time, I began to build relationships across the company with a handful of other partners. My idealistic mind thought – if I could just bring them all together, magic will happen. It was only when I began to uncover a bit of resistance that I was forced to reckon with the fact that design and development generally did not collaborate.

This is not uncommon. I have spent a lot of time speaking with other DesignOps and Design leaders and have learned the partnership paradox lies between the desire to collaborate and the reality of the day-to-day. It is in this process that silos naturally form. Connecting all the dots and building bridges is not a small task but when it comes down to it, communication and connection on a human level are the most fundamental of ways in which you can set the conditions for change to be received. 

Taxonomy of Skeptical Partners

In my experience, having surveyed the landscape enough times, these are a few potential partner archetypes I have encountered:

Legacy Subject Matter Experts

These are the people who have been at the organization since its inception. They have built the product from the ground-up and developed a reputation based on their great work – being known and cherished for it.

Shadow Subject Matter Experts (SMEs)

When new hires (anyone from outside who didn’t grow up in the ecosystem and are now mandating change) are brought in at executive levels – the legacy SMEs convert to shadow SMEs. They still have a significant amount of respect and trust, as they should, but how do you find them? This takes time, trust, and willingness to be an active listener. 

Underutilized Designers

The underutilized designer generally lives in limbo in organizations with a ship it first mentality (or where marketing leads product.) It is in these instances that design lends the finishing touch. A pixel polisher who’s been kept busy doing production design, but hasn’t been thought of to assist in leading strategic UX design. These designers can feel stuck and skeptical that change (for them) is long term. 

Efficiency Engineers

Engineering as a function operates very differently from design in that their inherent value is in delivery. Likely the most skeptical. “Design slows us down” is a common refrain which is why at times this partnership can be the hardest nut to crack. Often design research is an afterthought which causes friction when trying to build a shared understanding of the problems that need to be solved for the customer.

There are plenty of people who will see what you’re doing and be curious, defensive, envious (if needed change happens in one part of an org and not another), and will take a back seat on the ride of “high likelihood for failure.” 

Things I thought I knew, and then some

Mental models are meant to be broken, if you aren’t ready to break them – other people will break them for you. Failing at big and small parts of leading change forces you to quickly realize how wrong you are, while also learning how to pivot and grow from those experiences. Without building bridges, the changes you want to put in place will have nowhere to go. Setting the groundwork for these bridges is the way to build strength and resilience during times of change. Here are some tips and tricks I’ve developed as a kit of parts for my toolbox:

Build an advisory council

Probably one of the most important first steps as this is key to learning, buy-in, and scale. The first item in this HBR article speaks directly to this: “Most successful transformations begin with small groups that are loosely connected but united by a shared purpose.”

Ideas are easy: Execution is everything – John Doerr

In most product-driven organizations – engineers ship. There is no patience for design as it is perceived to slows things down. Therefore strategy and execution happening at the same time are critical. Build your roadmap and knock out the lowest hanging (but most impactful) fruit first. It’s all about the quick wins to build trust and gain momentum. 

Signal to noise

There will always be a lot of noise, even without change happening. Try to listen to the noise to hear the signal, trends always become clear. 

Lead with tactical empathy

When we have gone through the journey, it’s easy to forget about the full experience, the entire emotional journey. How during times of change for individuals, teams, organizations – emotions tend to take over, and anxiety looms large. Always try to dig into the underlying motivations behind people’s reactions.

There are ways to walk around, under, and with the elephant. Org transformation is hard, culture transformation is harder. Invest in the time it takes to understand the specifics of the organization you are working with in order to set the conditions for dynamic change. A deeper understanding of the process will allow for the level of change engagement it takes to reach a shared outcome. 

The Dreamer, The Realist, The Critic

A few months ago at the Leading Design Conference, I heard Margaret Lee give a talk on being a Reluctant Leader. Many, many, things from her talk resonated deeply with me. Most salient was when she spoke about Walt Disney’s Creative Strategy to lead as a triumvirate that includes The Dreamer, The Realist, and The Critic. It resonated mostly because I was able to directly connect that to one of the best partnership models I have had in my professional career to date. Although less than a year, the working collaboration between John Maeda (the Dreamer), myself (The Realist), and Alexis Lloyd (The Critic) at Automattic Design was just that. Through our natural styles, all ideas, plans, and actions were hashed out, thought through, and ahead of being either too reactive or not proactive enough.

Leading in Design is challenging. Leading in Design through change is ironically that much more so, as the foundation of Design is traditionally steeped in process and iteration. But no matter how you cut it, change is hard. Being led by a visionary, The Dreamer pushes the boundaries towards ideas outside of your purview. Signing on as a Realist often means you need to believe in that vision in order to find a way to make it a reality. Getting buy-in from all levels of an organization on that vision is much harder when they don’t have a clear line of sight into that future. As a DesignOps lead, my baseline mode of operation is to translate the Dreamer’s vision into a plan that can be executed. When establishing a DesignOps practice, keeping your eyes set on the executable plan is necessary, as the daily triage is a big part of beginning to understand the pain points and develop a plan for stabilization. However, too much time spent in triage purely focused on execution is not strategic. It is this balance of execution and strategy that will keep your work (and team) grounded. Without a roadmap that connects back to the overarching vision for the Design organization, your team won’t be able to have a clear understanding of where you intend to take them.

Two pieces most design organizations have buy-in on is first a leader (The Dreamer), and then someone to help operationalize (The Realist). What became clear to me through this working partnership was the fundamental need for The Critic. The Critic consistently asks, “what problem are we trying to solve and why?” as a way to help balance between dreams and tactics. In this piece, I wrote about the value of partnership as a yin-yang balance. How in these partnerships, we gain velocity towards a common goal. What I learned is that it’s not just the right balance of two or three people, but the balance of the kinds of roles those people play in partnering. The trust and respect they instill in one another to play that role, challenging assumptions, and the openness to being wrong. 

Our usual MO is to listen to fix or listen to win. In the former, we are being efficient — diagnosing a situation to quickly solve a problem. In the latter, we may be set in getting our way, convinced of our rationale and rectitude. In listening to learn, however, we remain open and curious, setting aside preconceived notions and assumptions to gain new perspectives. – Margaret Lee

Design often becomes a victim of its success, forgetting the fundamentals of what it means to practice Human-Centered Design. Those examples in practice are set from the top. From the shape the leadership team takes, to the form, to the day-to-day. We can (and should) continue to influence that, but also need to influence healthy behaviors in relationship patterns to remain human-centered in how we lead, change, and grow.

Five Phases of Centralized Partnership

Originally published May 9, 2019

The list of tech companies making big moves in the news goes on and on, Pinterest, Slack, Facebook, Airbnb etc. and while the focus is often on IPO’s and the end result, what runs in the background and central to their core is the partnership of design, dev, and engineering. As many organizations shift their focus towards customer centricity the need for actualization is generally where DesignOps comes into play. However, transitioning to a customer-centric model often reveals infrastructural people & process pains.

Over the past year, I have been leading Automatic Design through the transition towards a Centralized Partnership Model. The intention has been to build a cohesive design organization, improve accountability and growth for designers, reduce silos across product and engineering, and level up our collective understanding of product needs.

Managing through organizational changes is often unclear. In order to provide further clarity on the path forward, I built an outline for the “Five Phases of Centralized Partnership” as guidance on where we are and what our designers can expect as we move through these changes, together. These changes are a macro overview, our evolution has not been linear: like the product teams, we work in cycles, orbiting through our design thinking process of discovery, hypothesis, deliver and listen.

We are currently in phase 3

What we’ve left behind at each stage:

The Five Phases

The new gains/benefits incurred in improving our products and services at each stage:

We are currently in Phase 3, and if anything I have learned that working in a matrixed organization like Centralized Partnership, without clarity and accountability runs a high risk of failure. Transparency in thinking and process is critical to its success. As we work through each of these phases and focus areas we will continue to provide definition around the why as it relates to the tradeoffs, gains, and benefits incurred in improving our products, the environment for our people, and the overall experience for our customers.

Values in Progress

Last month I was fortunate enough to spend three days at the Within retreat (many thanks to Automattic for the generous sponsorship). I had never at any point in my life taken much time to reflect and take stock of where I am professionally, let alone personally. The pace of my life never really afforded me the luxury. Like many people my age in Tech, I ended up on my path not through deliberate intention but through the need to find a job post-college that paid the bills.

And so I have found myself in my forties, at my first job in Tech, operating at a high-level, and thinking about what it means to live and lead with integrity. Which makes me think about what a value system can mean not only to my life but to an organization. Reflecting back and looking forward, I am fortunate now to think intentionally about where I want to be, how I wish to behave, who I want to surround myself with, and how best to lead. My time at the retreat was the perfect time to engage in mapping out my core values are as a person and in turn, how I can leverage that system as a leader.

Like many things, a value system has a core foundation, but over time, it changes as you move and grow. I believe all of these systems have been in place for me my entire life, but by naming them now, it allows me to loosely frame them around a vision for living and leading with integrity. I do this knowing that I will continue to move and grow and change and that those around me will continue to inform this vision, test it, and evolve it.

1/ Curiosity first

Listening is a highly undervalued superpower. Making an effort to really listen involves taking yourself out of the equation, not always easy but essential when thinking about how to mentor vs. direct. Caring personally means not only being able to be candid and direct but to make room for hearing the things you might not want to hear but need to.

2/ Lead with courage

Venturing places you have never been before takes courage. Running into the face of ambiguity has never frightened me because I have enough confidence in myself to know that when I get there, I can leverage everything I know to figure it out. However, essential to note that for most people, this is not a comfortable mode of operation. For that reason, act with consideration.

3/ Never apologize for ambition

Transformational work can often feel like being a bull in a china shop. However, being told something is “too ambitious” can be veiled and often times, gendered language. Make no apologies for setting the bar high and continuing to expect excellence from yourself and your peers.

4/ Grace in the face of adversity

Doing the hard work is just that, hard. Be honest (and kind) with yourself, share what makes sense to open up the lines of communication with others often experiencing similar issues, and approach difficulties with openness. There is so much to be learned from your community, and even more importantly, there is support.

5/ Ferocity tempered with kindness

My daughter likes to talk about what animal each person in her family is. She tells me I am a Tiger (and not a tiger mom) because of my ferocious love, loyalty, honesty, and grit. I was recently told that living with integrity means walking away from something important to you towards something you stand for. Make no exceptions for high expectations in all aspects of living and leading with integrity. But do so with loving-kindness. Leading with kindness is often the uncommon way, but as Fred Rogers said so eloquently:

There are three ways to ultimate success: The first way is to be kind. The second way is to be kind. The third way is to be kind.

Three Days in the Desert

Operationalizing Design to deliver at scale starts with designers and ends with how they work with each other and with the rest of an organization. Over the past year at Automattic Design, I have worked towards designing better processes, removing the blockers to allow for a closer designer culture, facilitating better cross-team and cross-functional collaboration, nurturing the designers’ career journey, and listening to what the collective needs to do their best work. When successful at scale, we’ve seen design thinking and design infused processes in almost all of the work we do to better service our customers. And this is what we saw during our first Design Collaboration Meetup in Arizona last week.

Matrix organizational structures, in which people report to two (or more) groups, can also help develop cultural brokers. Despite their inherent challenges (they can be infuriatingly hard to navigate without strong leadership and accountability), matrices get people used to operating at interfaces.

Just under 100 people from all across the company joined in to work together towards our three shared goals of:

1. Building practical skills and a strong cross-functional community.

Because we can only do our best work when we are solving our customer problems together. Design + engineering + product + happiness, together. FTW!

2. Developing new leaders through focused leadership training.

Supporting current and rising Design Directors to live and lead in our matrixed organizational structure by piloting leadership training that focuses on professional development and performance management. Because the future of the success of our design organization depends on seasoned and well-trained leaders.

3. Collaborating to make and deliver work together.

Spending time during each day to lean on and learn from one another. The more people are empowered, the more we can celebrate what cross-functional partnership can bring to our work IRL, the faster parts of the customer experience can improve.

The Personal Professional Mission: Building a Framework

Illustration by Isabela Humphrey

Throughout my career, I have managed and built many different kinds of design teams. I prided myself on being intentional about building teams knowing that implicit in the role of Design Operations is culture creation. Why do healthy teams matter? Because great teams = great work. At frog, we would kick off projects with what was called a “team leap,” which established team and individual purpose. This process had two key components: establishing the essential goal of the team, and identifying what everyone hopes to get out of the project. Framing each project as an opportunity for individual growth helps people feel motivated. Clarity of team purpose helps drive alignment and empowerment. As a team, we would hold each other accountable to these “playbooks” as well as stay mindful of everyone’s established personal and professional parameters.

Once I made the transition into tech and away from project-based work, I was inspired to focus on the whole Designer Experience. Going through the exercise of mapping the designer journey, I was able to uncover some of the most salient moments that matter in opportunities for personal growth and professional development.

Knowing the top three reasons people leave companies are centered around lack of career path and reason for being, I quickly built a framework for the Personal Professional Mission (PPM) that could orient designers at every stage in their career. Over time the overarching designer journey would be the foundation for one’s broader personal, professional journey. This approach can organically foster a sense of belonging, connection, and community. Additionally, putting in place a support system that sets a clear path for growth and development can increase discipline in practice. In short, fulfilled people = great work.

“The single most important thing a boss can do is focus on guidance: giving it, receiving it, and encouraging it.” Kim Scott, Radical Candor

Using the traditional SWOT analysis as the basis, the approach to the PPM starts and ends with an environment of psychological safety. The process in co-creating this “mission” establishes a relationship between managers and individuals based on mutual respect, openness, trust, reflection, and self-awareness.

There are four steps to building a PPM. Step one in the framework is to brainstorm four areas:

  • Successes: Recognizing what’s worked well throughout your career, on your teams, and in project work.
  • Strengths: Past successes or underutilized skills.
  • Opportunities: Areas from which to learn, improve, and grow.
  • Passions: A critical piece of the personal part, and often most difficult to assess. Aligning one’s passions to their work opens up the ability to think holistically about your personal, professional trajectory.

The second step is to (collaboratively) identify themes, cluster commonalities, and rank the three areas that would be most impactful to you and your professional development.

Once you have identified those areas of focus asking the harder questions such as How do you use your successes to take advantage of opportunities? and What can you do about your opportunity areas to better align with your areas of passion? allows designers to think hard about things that are most important to them, the areas they want to focus on right now, and proactively plan for the path they want to take. Through this process, I worked with my team to set up individual OKR’s that mapped to 3, 6 and 12 months. While this document is living, establishing a baseline is critical. Referring back to that baseline over the year to track progress can give each person a sense of purpose, a mission, and actual measurement tools to get there.

The only thing one can truly own is their path. Jobs come and go; it’s what you bring to and take from each experience that stays with you. The PPM is not a performance management tool, but it is a professional development tool that can begin to build a clearer map towards the greater journey.

The Partnership Lens

A former colleague and friend called me recently and said: “I’ve started my own business, I am only a few months in and I could desperately use your guidance.” Coming from someone I admire, a classically trained industrial design leader, I was flattered. We had worked for years together when I was in consulting and had developed a great partnership across all of our client work. But for all the years I was in consulting he was only one of a handful of people who actually treated my role as equal to theirs. In Design, the designer reigns and operations have traditionally been seen as the necessary evil. Specifically, the operations role has often been seen only through the lens of the tools we commonly use – spreadsheets, Gantt charts, meeting scheduling, research coordinators, etc. (In fact, the icon that was used for my group at the time was a clipboard.) But in truth, this myopic view diminishes the real power of operations as the critical partner to the designer.

As Design exponentially becomes an integral part of many major company’s business focus, the field of Design Operations is taking mature shape. The kind of work I have been doing a majority of my career is being recognized as a vital and emerging discipline that enables organizations to not just bring design in-house, but to actualize design potential. At the heart of this actualization is the realization that the work of designers and the work of design operations are inextricably tied. As in any good partnership, it is driven by a Yin and Yang element, similar but different.

“How seemingly opposite or contrary forces may actually be complementary, interconnected, and interdependent in the natural world, and how they may give rise to each other as they interrelate to one another.”

There is so much opportunity in the field of DesignOps, and to avoid it getting relegated back to the work of spreadsheets (although yes, this is a real thing) and clipboards, we must begin to unpack it’s potential. Much of this starts and ends with partnerships.

There is design, and there is business value, and the talk du jour often conflates the two. When I sit with my friend as he tries to plan for how he is going to get past the reactive phase of building his business, we can both recognize that he is skilled in ways I will never be but overwhelmed by the prospect of planning and operationalizing his business to maximize its potential. There are hundreds of articles about the habits of the most successful people, none of them include finding the right partner/s and having the self-awareness to hire for your weaknesses.  Charles Eames understood that Ray was an equal partner in their creations, and he was always eager to acknowledge her integral role. “Anything I can do, Ray can do better,” he said.

There is already a plethora of great DesignOps material out there to help drive our discipline forward. As the field and everything around it evolves, we must not lose sight that the consistent core is founded in the relationship capital of great partnerships. It is in those partnerships that we gain velocity towards a shared goal.