Building a new (high impact) Design Team
The photo here is yes, of me, but also a small piece of what my team created in a “build a world” workshop I ran for the place they wanted to work. With me at the … helm? as the mothership.
The most important trait you can have as a leader is the ability to sense possibilities.
Everything else is follow through.
This is the story about how seeing possibilities moved a small group of super senior (but deflated) designers from obscurity and self-doubt to designing the future vision of a consumer technology service.
(If you’re tired of looking at portfolios and only want to see results with a handful of slides to look at, they are at the end.)
The Backdrop
Since my arrival at Docusign I worked on “satellite” teams — that is, not for the core eSign product. That team was already staffed up in San Francisco, and I had experience with integrations.
Those satellite teams were the result of acquisitions.
My first role was on a team that was a real estate brokerage transaction startup, located in a Chicago area office. They were acquired five years before my arrival.
Soon after my arrival two other companies were acquired, one a contract lifecycle software company out of Chicago, and the other, a startup out of Texas with a secure online notarization product.
Somewhere in there two other international acquisitions happened, one for identity verification and another for verified and digital signatures (more secure than basic eSign). Both of them are part of the future in legal signatures.
The idea all along was to acquire companies that already built things we could avoid building ourselves with a goal to integrate them into this larger “thing” Docusign was going to become. (Sound familiar yet?)
Org chart as navigation, the whole internet’s underpants problem*
* wearing your underwear over your pants
Same plan, so many versions
Our senior leadership struggled to communicate the vision. Named, renamed, presented, re-presented. Trying to inspire people who were perfectly comfortable in their silos is hard work.
The Product Experience team created “vignettes” — short videos and prototypes of possible futures — to try to jumpstart the work.
Our core eSign team resisted. Dug in, really. Docusign’s identity was to have the simplest path to signing, full stop.
Their pushback succeeded for at least three years. Effort after effort dissolved and disappeared. But the satellite teams were still there, still asking the questions. Still pushing.
After almost three years of “wait, but why?”
For those first two and a half years, I tried a LOT of things to try to advance this plot. More about that work is here.
In doing that work I built a reputation for
being trustworthy about what I said I would do
pushing on the status quo of the products and supporting designers in doing so
creating a safe space for people to share so that we could figure out a good way forward
inspiring teams, partners and designers to work together
helping teams and people see success they could build on
seeing opportunities when most people threw up their hands and walked away from yet another failed vision attempt.
It isn’t easy. I had days, weeks, even months where I thought, “what’s the point?” just like everyone else.
The most honest answer about developing the skill to sense possibilities is simple experience — trying things that sometimes worked out and sometimes did not.
Over time I developed a personal rule set for how to know when I was seeing a thing I should pursue and when I was having a terrible idea. It more or less goes like this:
Ask some questions
If I do this, how do I think it will unfold? What do I need to do or put in place to increase my chances of success?
What’s a realistic first step, when traced to my overall goal? What other things do I think I’ll need to do? What’s happened when I did this before?
When do I call it, if it’s not working ?
What’s the opposite approach? Would it work better? Or some combo of things?
Who do I need to persuade/convince/win over? What do I need them to do? How is that best done with that person/team?
Follow some rules
Do not map The One Path to success. Map out a first step and calculate possible futures that will get me to the ultimate goal.
Give it room to breathe. My ultimate goal is never an OKR or a metric or a dollar amount. That’s in the mix when relevant, but my intended outcome needs to be flexible enough to evolve. When I let go of “control,” 90% of the time the outcome is better than I imagined.
The only failure is not learning. Absolute failure is pretty rare. And today’s failure usually propels me toward a better direction.
Enter: the Integrated Experience team
That reputation and those skills are why our leadership asked me to start this service design function, within the product experience practice.
Our information architecture team led by Sam Voelkel (far left) joined us. My research partner in crime for the past two years, Deanne Stock (far right) , rounded out the team by recruiting researchers for what we called “strategic research” (as in, not product research). Below, we are at Monk’s Pub, a famous old dive in Chicago with a million beers and shockingly good pub food, when our new team was formed.
The energy and enthusiasm were high.
Woof.
Lest you think it was all unicorns and rainbows, our CEO left in June, several execs, our design VP and two key leaders left soon after — in the same week. As a result, maybe 1/3 of our designers quit by the time I started this team.
Then a withering round of layoffs, in keeping with the layoff contagion in tech, left a bunch of designers with no engineers to work with and no guidance as to what anyone should do about it. People were just… gone. Products with roadmaps simply languished.
The designers who left told me they felt the company was being mismanaged by the interim CEO and that the company was in trouble.
Yes, and… there had been endemic issues for a while. 7,500 people are not needed for a one-product eSignature company. If Docusign was going to be around beyond 2024, things had to change. Did I mention the stock price? Yeah, that tanked too.
A few weeks after starting this team, we hired a new VP for the practice that no one in product experience had interviewed. He said that he not only did not understand service design but that to him, it seemed like a luxury at a time when the company was in turmoil. (Design as a field was in retreat.)
My team, pulled from across the organization so that we had representation from as many products and teams as possible, was jaded — at best.
They all worked for years on features that didn’t ship, weren’t adopted, or weren’t marketed enough to succeed. They saw designers working on the same exact features on different teams and all the indicators above that things were not gong well at Docusign. But I managed to persuade them to join me because this was going to be different.
What I didn’t expect was resistance from product experience leaders.
A lot of “why service design”, coupled with “you’re taking the strategic work away,” then “we already have managers who do this” with a big helping of “everyone needs to just change their products to fit eSign.”
So… instead of being excited for the support and new perspective, their reaction was to insist that their people were doing this work already, even though that was demonstrably untrue. I decided some of this was due to not knowing what service design is here to do, but most of it was fear of change.
I could see the day where we worked together better, I could see what it would take, and I had a plan.
What I did
First, I talked to my team about what they thought we should tackle and what kind of work they wanted to do most. Then I looked at what the PX (product experience) team needed. I already knew the situation for Docusign in the overall market.
First, we needed to establish relationships and find footholds in relevant work. I came up with a plan with my fellow leaders, Sam and Deanne, on how to start pushing in several directions to get us there.
I sensed possibilities:
First: enable my team to have a deeper, initial impact by seed planting around how teams thought about their incentives, roadmaps and ultimately shipped products.
The immediate potential outcome was people working together more often and deeply to build a service.
The benefits would start to show up in research findings and eventually in win/loss reports
My team would have relevant, challenging work to do.
I shaped them into opportunities:
I pitched design leaders about how we could help with integration work that was kicking off in earnest. My team knew what needed to be accounted for; we could help unite patterns, flows, and navigation. Not all of that work was an unqualified success, but it got us into product design teams and on their radar in helpful ways. This work also helped us develop our engagement model and our templates. Any team that’s new and tiny compared to its partners and stakeholders needs templates.
I kicked off a “current state assessment” which ended up being an enormous catalog of the many ways we had duplicated our feature set. That catalog became a valuable reference for designers and a jumping off point for our continuity design function.
I got asked to do some workshops, so I piloted some formats we might be able to lather, rinse and repeat.
To broaden our network, knowledge and footprint everyone had to introduce themselves to teams far outside of the sphere we had existed within. Growth, sales, customer success, strategy, and design systems for starters.
We started to gain traction and get attention for our work.
Results
>> My team and I became go-to people for workshops, including one really big one.
>> We established a continuity function so that we could create meta-patterns from our design system, for things like document pagination or import flows. Those larger interaction patterns would ensure no one had to keep reinventing the same wheel.
>> We worked with our research partners to create customer co-designing workshops, which were originally for further out thinking but became a group we tested the future vision work with
>> We got asked by our VP to build out a vision for the future of Docusign for our CPO to share with our CEO so that the work would be funded.
That vision work was successful, and is currently being built out as Docusign’s Intelligent Agreement Management platform.
Sadly, even doing high-priority visionary work can’t protect people from the big ol’ corporate hatchet. Most of us in integrated experiences were laid off before we could see the vision come to life.
Below are some snippets of the vision work we did as it was presented to c-suite leadership.
