Leading Design at DockYard
How I came to be Director of Design
In 2021, I had the opportunity to apply for a Designer Manager position at the software consultancy DockYard. DockYard at the time had two product offerings: digital app development for clients, and engineering staff augmentation for large companies. The latter offering was stable and successful, while client work had been turbulent after initial success.
The Director of Design needed someone who could come into DockYard and hands-on manage the team throughout the delivery stage of projects. He, in turn, would focus higher on the offering, building awareness in DockYard’s design capabilities, and pitching to clients. I landed the management job, and immediately on accepting the offer, the Director gave his resignation. I was in fact pre-filling a power vacuum at a critical time where DockYard’s key client Johnson Controls (JCI) was not happy and the team was underperforming. They had already missed deadlines and deliverables, creating a perfect storm.
My first few weeks at the company were unusual. I did my best to meet the team, get what intelligence I could from the departing director, and ramp up on the design project at hand. I focused primarily on making sure that we didn’t lose JCI, and figuring out who on staff was ready and able to meet the challenges of the next months. I could wait to integrate better into the company as a whole, and the leadership was excellent at providing me the space needed to do so.
I needed to meet with JCI and build a relationship with them rapidly. We decided to pass the baton in Boston where the departing DoD and myself had two days holding strategy and continuity meetings with the leadership there. The meetings were a success to the point that JCI was no longer a flight risk, and we had a short time to recenter the project and come up with a workback schedule that allowed design to catch up. My decade prior in design agencies and then 5 years of consulting came in handy build rapport and smoothing tensions.
At that point DockYard was comfortable enough to promote me to Interim Director of Design. After a few months leading the team and helping to rebuild the pitch process, the interim was dropped.
Managing designers
Prior to DockYard, I had managed product and project managers, but my individual ability to move fast at startups had made hiring more designers the last priority. I had leadership experience without management experience.
Being a designer who is fascinated with processes and sociology, I treated the acquisition of management skills much like I would a new design project. I did research, empathized with my employees, and designed a rational and repeatable management system that was transparent to all. My personal motto of never surprising someone was generalized into a pro-active communication style that gave everyone a stable foundation and opportunities to grow. From there, I iterated and improved based on feedback and sensing what was and wasn’t working. Ultimately, these were the core tenants of my management style:
Every individual has different needs and styles, but the team has common goals and a single roadmap for improvement.
Assessment of skill should be consistent, transparent, and provide opportunities for the designer to choose their own improvement path.
Building a strong team means the internal team can be vulnerable with each other to strengthen collaboration.
Building a strong team also means being good citizens with our partner cross-functional team members and making their jobs easier.
Always approach challenges with truth delivered with kindness.
No secrets that don’t have to be secrets. A team working with full visibility is a confident team.
Support each other when working with external teams and clients. If there are issues, work on them in a smaller venue.
Self-determination theory provides the answer when faced with situations where I—as Director—want to correct course. Counsel rather than take over if you want employees to stay engaged. Let them fail gracefully if the situation allows it. I will take the blame if it doesn’t work out.
Existing staff
At the beginning of my time at DockYard, there were 3 designers left of a team that had had up to 16 in earlier iterations. A mid-level designer had started 2 weeks prior to me. A junior designer was in her first job in software. Lastly, my senior designer was struggling with both personal and professional challenges that were volatile. I needed to staff up in key areas to meet the needs of JCI while leveling up those who were here. The new designer was not flashy, but he was rock solid and willing to stay flexible rather than run for the hills. I got him set up as the “lead” on delivery of the first round of deliverables, with support from the other two. The aforementioned challenges the senior designer was facing prevented her from properly leading the project, but that was also compounding her performance issues.
Recruiting new staff
My first recruitment need was to find a lead designer in the Boston area to be able to connect with JCI in person. (It turned out that one of the main reasons they wanted to work with DockYard was they thought everyone was local, even though it was a highly distributed remote-first consultancy. Not sure how that happened!) This was a time where product designers were a hot commodity, and FAANG was starting to vacuum up all the talent. I had to be creative, and look in corners that weren’t typical. I created a job description that would signal that we were interested in people who didn’t fit the mold. Even still, finding someone in Boston was difficult until a designer who had been out of work for a year cold applied. His critical thinking skills and ability to adapt overcame his lack of experience in software, and I hired him. That hire is now leading design at DockYard, and has become a great manager himself.
Next, I needed two more ICs quickly to meet a demanding schedule. I turned to contract work knowing that it was another gamble. Contractors can be excellent, or they can create chaos in multiple ways. There is not enough time to vet completely, so I went with people who presented as organized, competent, and showed latent talent. One of my hires turned into a rock star who anchored the JCI project through multiple contract extensions. The other turned out to be a scammer who was over-employed. Luckily, this was not my first time seeing the behaviors that are apparent by these individuals. I cut ties within 2 weeks, and in the meantime the other contractor had made it unnecessary to hire someone else.
Assessing skills and competencies
From there, I finalized a competency matrix that allowed the designers to understand how they would reach promotions and how I was assessing their skills. I wanted this to be a conversation rather than a grading, so I devised a solution where I would use non-grade shorthands for whether they were consistently meeting each competency. I then met with each of the designers so they could hear my rationale. I also invited them to challenge any of my assessments and let me revise based on their feedback.
This transparent way of letting the designers know where they stood had an immediate settling effect on the staff. They knew where they stood, they knew I was attentive to their needs and abilities, and they had an indeterminate path forward to reach the next level. This also allowed me to introduce a new structure to the team that afforded paths that continued to build strength at the IC level if management wasn’t their interest. When I arrived, the paths were junior > mid > senior > manager > director. I created two branches: after senior you could move toward higher levels of strategy work, or you could follow a manager > associate director > director path.
I also coordinated with my Product Management counterpart to build a Strategy function that could be fed into from both of our staff. We hired an Associate Director of Strategy to help create continuity across an engagement’s lifecycle that previously required client relationship hand-offs in many cases.
Throughout my time at DockYard, I promoted people multiple times utilizing the competency matrix as a way to both sell the promotions to the wider company and mark the point where they had transcended to the next role in most cases. These were merit-based, but required individual coaching and access to opportunities to improve. I counseled and mentored each designer along the way, and worked with their individual learning styles.
Dealing with employee behavior and performance issues
The competency matrix also had another intended feature when it provided a transparent way to tell my senior designer that she wasn’t meeting the level of performance that we required for the role. Using truthfulness with kindness, this turned a tense situation into a clear path forward for her to meet and develop the skills required for the job. From that point onward, we had concrete discussions about whether she was moving in the right direction. Unfortunately, her personal challenges prevented her from being able to meet expectations, and after 6 months I managed her out via a humane choice between a formal performance improvement plan, a demotion, or ample time to find her next job. She chose the latter.
Interpersonal strife is the second hardest thing I faced while managing designers. Two of my designers were collaborating to provide user research findings to a client. As the presentation commenced, the more junior designer was presenting work in a way that wasn’t as specific as the senior designer wanted. The senior designer then started side-Slacking the presenter while she was presenting. The junior designer rightfully ignored this as it wasn’t our practice to interrupt in that way. The more senior designer become livid, and immediately after the call yelled at the junior designer for not correcting course immediately. The junior designer was shell-shocked.
I worked with our HR team to make sure that my course of action was sound, and then I quickly built a custom retrospective plan to find out all of the context surrounding the flare-up. I interviewed both designers and wrote down their answers live in the call so they could see my notes. I then got both designers together and moderated a conversation between them where each expressed how they felt. It was abundantly clear that the more senior designer had crossed a line or two with their behavior, but I made sure that they themselves understood the impact on the other party. I then had a follow-up meeting with the more senior designer where I unequivocally told them that they could not dress coworkers down, and that their need for control over the situation was against the team tenants. This was not a situation where the consequences were existential or irreparable. I made sure they knew that another outburst lead to immediate termination.
The way in which I ran the retrospective also healed the two designers’ relationship quickly. They understood exactly what had happened and were more empathetic to why each behaved differently in the situation. They continued to be able to work together afterward, and in some ways they were closer. I don’t want people to trauma bond, but in this case the outcome felt healthy and the apologies were sincere.
Budgets and people
The arc of DockYards executive leadership changed while I was leading the design team, with a former CEO and founder replacing the departing CEO. I was starting between a generation where they had had high success, lost one of their anchor clients by surprise, and was diversifying to get back to a healthy place. The CEO saw that the company was on the upswing and decided that was the right time to step down.
With any new CEO, there are changes that occur outside of the common ways of working. The design team was building on our strong success with JCI and had added multiple new clients of our full product development offering. Things were going well, except the business model did not properly accommodate junior staff. We were parachuting into complex existing software with expertise, not building from scratch. When the new CEO arrived, the luxury of using my junior designer as an internal designer while helping out on projects was no longer a reality. The speed at which that decision was made created a point in my management that I couldn’t maintain my tenant for no surprises. New boss, new rules: the junior designer had to be laid off.
The act of laying someone off is painful, and is much like a death of a loved one. The person suddenly disappears while the people left behind are no longer in their comfort zones. This one was exacerbated by the surprise at the new world order within DockYard. My former employee needed support finding her next thing, and my designers were looking over their shoulders wondering why we were laying people off when the business was thriving. Trust is everything in design, so it took time and an apology from me for selling them a reality that wasn’t true any more before people got (mostly) over it. I couldn’t throw the CEO under the bus, but I did need to rebuild the foundation of our contract with employees within DockYard.
Beyond personnel, I maintained the budget for my team. It wasn’t a large team so this was relatively straight-forward. Even so, I looked for ways to cut our capital expenses and proactively moved us off of usertesting.com based on our usage of the tool. We ultimately got an upgrade in our tooling at 1/20th of the cost. We also never used our full budget to the point that I had to remind my employees off the employee development benefits that they weren’t utilizing.
Getting work
When I joined, there was a plan in place to build a design studio inside DockYard as a separate function. Our work with JCI was the first experiment in that model, and it wasn’t great in multiple ways. First, DockYard was a company known for their use of a specific Elixir development stack, and all marketing was tuned for that. Design was a natural extension of that marketing, but it was not the focus. We were up to 8 designers, while engineering was up to 70. The other issue was that it was pulling us further away from our cross-functional teammates. Our ability to provide world-class product development required knitting ourselves into the workflow and building economies through ways of working. If the whole design team was focused on their own projects, that created friction in sales and cross-functional leadership.
After righting the ship within the design team. I ultimately put my main focus on new business and how we earned it. This was definitely not focusing on the presentation design — this was creating relationships that were built on us being a partner with high expertise in areas that our clients didn’t have on hand. I took the lead in building these relationships through a strategy of giving potential clients free counsel where they needed it most. If a client came in and had never been through an acquisition before, I’d help them understand how that generally worked at a software, design, and leadership level. If they wanted to vet an idea quickly, I provided them solutions to do so that were outside of DockYard’s production-ready focus so they didn’t waste money chasing bad bets. If they needed workshops to focus and come up with a plan for their product, we would set up tiny contracts to do so. The strategy was mostly free so that they were comfortable enough with us to move forward with us.
This immediately paid dividends where we went from a sales-led pitch to a partnership pitch. We quickly reached our development and design capacity with multiple multi-year engagements. We were the steady but flexible solution that overcame the fact that we were not the cheapest. This also allowed us to hire the aforementioned Associate Director of Strategy to provide a focused function for client relationships that was not production-oriented. Managing resourcing, teams, and existing clients was putting a huge burden on Product Management that made our ability to provide high-quality service to prospective partners difficult. Our strategy lead immediately fixed that problem, then started to work on improving our presence in the industry. We also collaborated on how to sell strategy as a paid offering in situations that warranted it.
Keeping clients happy is an art in of itself, and much of it is the leaders of the functions maintaining contact with key contacts throughout and having honest conversations about how the work is going. I enjoy the feedback loop for clients as an improvement vector, and spent as much time as possible connecting with clients and stay in that loop. One new area that adding a strategist afforded is how to end partnerships in healthy ways. We started thinking about how to prepare for the end while things were going smooth so that we avoided surprises and thrash. That was achieved with our relationship with Kamana. They had come to us for a general professionalization of their software offering after hacking a complex product to the point of profitability. As the partnership reached a year, we started counseling their leaders on what a natural and humane disengagement would be like. We started to build into their contract extensions more consultation and less code while we pealed team members off the project in managed ways. This ended up becoming a huge success for all parties where our resourcing was rational (enough) and the clients were happy that we were supporting them while not continuing to push people at dwindling needs. They went through their own ownership change in the middle of the engagement that made our investment in their success less apparent to their parent company, and we helped them hire leaders in the separate functions that would be replacing our expertise.
Die a Hero, or Live to Become a Villain
I was thriving as a people manager and client whisperer, but changes at the CEO level made the business side of DockYard much harder to navigate. There was a large push to move engineering staff off client work and onto internal Elixir tooling projects. The economics of the plan did not make sense, and pulling billable people off projects while DockYard promoted itself at Elixir conferences made our clients twitchy. As the company became more of a playground for the CEO, my values increasingly diverged from our direction. I voiced those disconnects, and rather than tempering the business strategy, that put the focus on me. Ultimately, the CEO of any company is responsible for business decisions, and the new CEO’s plans and management style were incompatible with mine. I was out.
I felt like the rapid success we had found was going wither after I left. I am sad to say that it transpired. After multiple pivots and exoduses, DockYard is a cautionary tale with a skeleton crew. My first hire is in charge of a design team of 1, and his magnetically affable demeanor keeps him employed. At least some clients got some top-notch work and my employees had good experiences while I was there.