The Paradox of Dynamic 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.

Puerto Rico Se Levanta

Credit: Dennis M. Rivera Pichardo for The New York Times

Originally published August 8, 2018

When I read about the island of Puerto Rico, a US Territory lost in 11 years of a recession, there is a plethora of data about corruption, poverty, lack of medical access, tremendous brain drain, and how tourism and tax shelters are the only things the island has left. But if you visit, and listen to the people you would hear a different story. One of passion, depth and wealth of culture, the desire to stay on their Isla – to rise up. Listen to the people who maintain their optimism under some of the direst of circumstances and continue to try and rebuild even in the consistent face of adversity, both manmade and natural.

The data would tell us many things that are grounded in truths –  after Hurricane Maria the loss of the economic and technical infrastructure (dependent on a reliable electrical grid) has driven hundreds of thousands of people off of the island. However, if we listened we would hear about the committed; the accelerators trying to bring Puerto Ricans back to the island, the start-ups, the innovation around agritourism pivoting into a regrow mission, and people like the independent chef selling her annual coquito or pastelles to people in New York that is the prize of the holiday season.

So the question becomes, how do we really hear these stories, how do we take the data and dig deeper? How do we qualify the quantitative so we can better understand how rebuilding a community can be supported by access to online tools that can support them and their business so that even when an entire infrastructure gets knocked out, there is still global access to the goods and services of which these business owners livelihoods depend on. What is the responsibility on those of us with access to the infrastructure, and the means (if even modest) that we take for granted? If we are curious and listen to the stories we can start to solve for better design of our products so that they provide access to those not only on the other side of the digital divide but support them in times of crisis. Often times organizations question the validity of qualitative research, not enough numbers, too small of a segment splice, but what I have consistently discovered is that one of the most meaningful differences between quant and qual research at its core is the difference between what people say, and what people do. The ability of the qualitative approach to building up our own muscles around cognitive empathy so that we can better understand these customers underlying motivations and as an organization, design products that truly serve their needs. To be able to prove that need through our work in a way that is most impactful at the end of the day is what will resonate with the communities that will continue to be marginalized if those who have the ability to buoy them, instead allow them to be left behind.