When I got to college as a city kid moving to rural North Carolina, I didn’t have a car or know how to drive. Why would I? I had the subway as my reliable ride. While most teenagers of a certain age in America drive, In high school, I had one friend with a license — Nancy. Nancy would borrow whatever car she could, and we would drive around Manhattan with complete abandon. I still remember taking a sharp circular turn onto the West Side Highway, hanging onto the side of the car’s open window, and screaming with laughter until one of that particular borrowed car’s tires blew out.

And so I arrived at university with no car, no license, no actual plans, and loads of determination. I had my mind set on a cute little VW Fox, and to make my life that much easier, I wanted it to be a stick shift. I needed to drive that car. In short, I bought the car, my father pleading with the salesman to give me a driving lesson which he did (one), and I set out to get my license. First car, then license, naturally.

I failed my first driving test and was devastated, but some friends were kind enough to prep me for my next in a giant [automatic] Lincoln Continental very much like Nancy’s “borrowed” car. K-turns and all, I passed the test, went and grabbed my Fox, and sputtered off the lot with a newfound sense of freedom.

Don’t get me wrong, fear and anxiety certainly serve their purpose — but as I become more thoughtful and intentional about my choices, I continue to get more curious about what purpose exactly. It’s helpful to remind myself that so many things I have done in the past have scared me half to death. I was a reckless kid, but I wasn’t fearless. Fear drove me to push myself far beyond my expectations. Not without failings, of course, but knowing I could keep at it until I felt I had grown — when my feet could touch the ground again.

As I embark on this new journey of so many things that incite fear, pulling the stories of my past where I pushed myself way outside of my comfort zone brings me a level of solace, knowing that just on the other side of fear is generally something worthwhile. Michelle Obama calls this “Comfortably Afraid,” which some people naturally have and some grow into. The truth is, you can continually grow into it, and evolve. So, still now, in midlife, I am looking to expand beyond the boundaries I have set for myself.

Story originally published on my blog

Ali, 48

Four years. That is how long it took me to save miles, set aside money, plan, organize, coordinate, and research our first big blended family trip to Hawaii. I love to travel — tasting different food, and experiencing the scents and sounds of new places and cultures is something that has always brought me immense joy. The plan was to celebrate two of our kids’ high school graduations. I was looking forward to experiencing a Hawaiian adventure together. We have five children between us. Three are his, one is mine, and we have our six-year-old caboose. By now, we all know how this trip story goes. COVID, canceled, fini.

Fast forward to 2022. Feeling trepidation, I was ready to try again. Spain. It had to be Spain, with its incredible architecture, culture, food, and direct flight from NYC. I don’t think I need to overstress how complicated planning a trip abroad (or across town) for a family of seven with five kids between the ages of 6–22 is. The requirements are as follows in no particular order:*

1. Food “that slaps”
2. A Pool
3. Bars and Clubs
4. Clubs and Bars
5. The beach
6. The tiniest bikinis
7. Culture
8. Laundry
9. Cabs
10. Wifi
11. Dating apps
12. Toy stores
13. As little sleep as possible

*this list does not include adult requirements of peace and quiet

My research-obsessed brain managed to find us the perfect spot just outside of Barcelona. I found a charming beach town outside one of my favorite cities, a magical place with something for everyone in our family. At first blush, everything was perfect. Afternoon light poured into the house, allowing us both indoor and outdoor living, and the pool was set to the perfect temperature. The welcoming town of locals greeted us with smiles and sunkissed skin, and the smell of freshly baked bread and fresh squeezed orange juice filled the narrow streets as we all explored on our first day together.

However, in short, within the first five days, our youngest gets COVID, and I get COVID (mind you, we both had it six weeks earlier). Then, our oldest gets a wisdom tooth infection. Then again, the youngest had a urinary tract infection.

I had fantasized about the beach and sangria, but the universe had another plan. I really tried for it not to get me down. I couldn’t let it. I wouldn’t allow it. I threw on some eye makeup and a mask disguising a deep frown for a trip to Barcelona. I would make the best of it. But, the effort of the outing resulted in a stolen wallet. I was done. Convinced the universe actually hated me. Like really, really hated me.

Resilience. Recovery. That’s a bunch of bullshit. What is true is the world expects us to carry its weight while simultaneously expecting us to show the light. This trip was the three-year break I desperately needed but partly broke me because, the show must go on.

Now that we are home, most of my family can reflect back with fondness. For me, it’s not that simple. But, I can recall and appreciate my little one’s joy as she learned how to cannonball into the pool (an actual pool!) The incredible seaside morning drive and first swim in the Mediterranean with my two exquisite daughters. The hysterical stories over paella lunch the twenty-somethings told us after their several semi-successful European all-nighters. A mistaken dinner at “all you can eat sushi” and the general vibe of feeling eternally grateful we are fortunate enough to do these things with one another and come out a bit stronger as a perpetually complicated but wonderful family.

Originally published on Fortyfifty.co

Ali, Age 48

I just returned home after dropping my 19-year-old daughter off at college. My oldest daughter, the person who made me a mother and brought magic into my life.

I was 16 when I lost my mother. There is so much I missed out on experiencing with her. Becoming a mother after losing mine early on in life was a fundamental shift in my own experience. My daughter’s presence always felt magical to me. She is an artist with a profoundly tender soul, her depth as a human being made our connection powerful.

Her father and I separated when she was two and half years old. From that point on, she and I became a singular unit taking on the world together. We took many trips — Hawaii, Puerto Rico, Mexico, Portugal, Oregon, and California. She was my travel companion, my adventurer. The kind of kid that would go with the flow.

Because of the divorce and our split schedule, my time with her always felt precious. Time was a commodity, a valuable entity that I was very conscious of slipping away. She was connected to me, and I to her. She leaned into my nurture and love and, in turn, taught me grace. All her interests and passions we shared, from anime to animals.

She did not rebel in high school and always wanted to be close to me. When she turned 16, the age when I lost my mother, we reached a pivotal point in our relationship. Because I had no experience of what mothering looked like past 16, I questioned if I knew how to parent beyond that point in her life. She was always conscious of my experience. So much so that on Mother’s Day, the year she turned 16, she made me a beautiful diorama-type box that said, “We face the future together.” Her gift epitomizes our connection, our relationship, and the way in which we care for each other.

As parents, we try to prepare for what we know is inevitable. I knew she would go away to school, and throughout her senior year, I continually reminded us both. We talked about it over and over. My mantra was she would leave, and I would be fine.

She was going to school in Michigan and always envisioned this big, fun, traditional journey to college. I did not want to do the drive, but how could I say no. In hindsight, I am so grateful we took the adventure together as it turned out to be incredibly special. We were able to be fully present one-on-one, having left everyone else behind. I made a playlist for her; she made a playlist for college. I felt emotional; she felt excited.

We drove the first half from New York to Pittsburgh and listened to music the entire time. We sang in the car and let our voices and the songs guide us. The second half of the trip was different; I tried to be incredibly present and just enjoy the time. I did not want to lecture her about any topics parents like to warn their children about. We were simply together on a road trip, having fun.

We had conversations about my family, mom, college experiences, and when I left home to go to school. Our time was uninterrupted by all of life’s distractions, and the memory of this pure togetherness is something I now hold very close to my heart.

When we arrived, we had a few days to explore. Our first time in Ann Arbor, where she would move for four years, was both exciting and nerve-wracking for us both.

We went to restaurants and walked around, exploring this beautiful new place she would soon call home. One night at dinner, I drank a lot of Sake trying to calm my nerves and started talking to her about sex and relationships. She’s emotionally mature but incredibly naive and inexperienced. I knew she would soon be on her own, making complex social and emotional decisions. She was open to the conversation — I thought she’d be horrified. So, I took the time to remind her to own her power. I had this nagging feeling I needed to pack in as much advice as possible at that moment.

The next day was her move into the dorm. Once everything was in her room, I offered to stay and help her settle in, but she said no. She felt she needed to sort and settle alone.

So, I left, feeling sort of numb. But, since I am a doer, I needed to do something at that moment. I decided to drive to Target and get a thousand unnecessary things I knew she did not need, but I felt she might miss. Up and down the aisles, I cried bursts of tears, grabbing random items, letting myself lose it entirely.

That night we went out to dinner with her roommate, and I took her out to breakfast the following day. By that point, she and I were both ready; we knew it was time to say goodbye.

I sobbed at the airport and on the plane and then came home and felt gutted, empty. You simply cannot emotionally prepare for it; that deep hollow feeling of sadness you are left to sort through on your own.

I tracked her phone for a while, but I don’t do it very often anymore. She has been communicative, and I have heard and read to give them space during this time. She sends me videos showing me her artwork or her process or her amazing new ballroom dancing skills. She still loves to get that mama affirmation. It’s beautiful, and I love it.

I try not to text her all the time, but then I find reasons to text her. Knowing she’s obsessed with clothes, I will text her a random question, “what do you think about these shoes?” knowing she will respond. And when she does, I know she’s alright, which is all I care about.

I’m always going to be her mother. And I’m always going to mother and nurture her and do all the things mothers should do. But now I can step back. The other day I checked her bank account and saw she had $3 left. In stepping back, I had to remind myself not to give her money. I already gave her money; she has a budget that she will need to figure out how to manage.

There is this process of trusting that I am trying to lean into now. I gave my daughter the skills to be an empowered woman, a doer who can solve her own problems. Now I must figure out how to not enable or force any kind of learned helplessness on her.

I will visit her in two weeks, and I’m so excited to see how she has settled into her new home. She can show me all her spaces and places, I can meet her friends. Suddenly, I am in a new role, taking the passenger seat on the road trip of her life. As it turns out, Michigan is not as far as I thought.

Originally published by FortyFifty.co

I have always prided myself on being adaptable in both my job and life. Being a New Yorker, knowing the nature of New York is to change is the environment in which I was shaped. Never constant, constantly changing. Over time though, I have learned that this nature is not always natural for others and is often uncomfortable. I’ve even written about steps that can be taken to alleviate some of these pains in navigating business, but in life, it’s less precise (and, of course, where do we even separate).

Recently, I’ve been wondering more and more about why some are more comfortable with the ambiguity that comes with change than others. Maybe it’s midlife or post-covid [dis]comfort. Regardless I’ve been searching for answers about what happens to individuals, communities, and the world during prolonged periods of uncertainty. What starts to take up space in the absence of knowing.

We saw many behaviors in response to the past two years. COVID highlighted how unclear and out of our control futures are. What it also highlighted was how connected our behaviors are. Reactions to this experience varied significantly across the world. In some instances, people focused on community and leaned into one another to bridge the gaps and find solace. In other cases, people battened down the hatches and looked out for themselves and like-minded close ties. What creates these responses? How is the soil cultivated in which one or the other takes root?

It’s hard not to fluctuate between both Player and Victim mentality in these times. It’s also hard to know which game you should play. Short-terms wins? Long-term gains? As designers, we are taught to ask, “what is the problem we are trying to solve, and for whom?” But if that problem feels outside of your control to solve, it’s might be natural to lean towards self-preservation. Should I be resilient? Should I see all these experiences as longer-term lessons? I cannot see the forest for the trees by focusing on myself, but maybe that’s necessary for recovery, to re-anchor ourselves.

Shaquille O’Neal and Kobe Bryant were teammates for eight years, three of which the L.A. Lakers won the NBA championship. They were compatible teammates but also had beef, mainly because they had different approaches to the game. This friction is well articulated in this conversation:

One time when Bryant wouldn’t pass the ball, O’Neal went to speak to him, and said: “Kobe, there’s no ‘I’ in team.” Kobe, Shaq said, replied, “I know. But there’s an ‘M-E’ in that motherfucker.”

I have been processing this as I experience my own uncertainties and figure out the best ways to proceed. Applying it to being in a space where you have no control, no answer, and no clear path forward. If you take the M-E mindset, is it ego, self-preservation, or narcissism? Does it matter? Is it wrong to look out for yourself? I know my generation was taught it was, even as I watched my parents do just that. Finding balance takes a beat.

The quote from Marcus Aurelius reads, “The mind adapts and converts to its own purposes the obstacle to our acting. The impediment to action advances action. What stands in the way becomes the way.”

What stands in the way becomes the way. Only time will tell.

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.

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.

But, you will have zero successes if you’re not trying at all.

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?

History of Change Management (as a thing)

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?

DesignOps as an Agent of Change

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.

Thinking in Systems

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.

Change Management Core Principles

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.

Start with a small group

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.”

Identify a foundational change.

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.

Roadshow it.

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:

• Sharing the idea
• 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

Surviving victory (aka it ain’t over till it’s over.)

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.

Organizational Maturity

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.

Designing for change that lasts.

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.

Leaning into Dynamic Change.

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.

“Move thoughtfully and fix things.”

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.

Setting the table for dynamic change was originally published in UX Collective on Medium, where people are continuing the conversation by highlighting and responding to this story.

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

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.

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.

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.

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.