Design maturity FTW

It’s a pretty simple maxim — wherever I go, I try to leave things better than I found them.

I use time-tested methods of strategy and design. I typically apply it to how I set up and run teams, develop partnerships, and see impact.

Whoa! obvious Problems

When I was asked to take on a team of nearly 20 designers and managers at DocuSign after a tsunami of executive and leadership departures, I started out like I usually do: listening, watching, and talking to people.

I saw

• a set of overwhelmed managers, lead designers who felt pretty stifled, and mid-level designers craving mentorship

• three separate teams of designers who almost never spoke working on “editions” of the same SaaS enterprise product

• a sub-par user experience that designers felt they were having no impact on

• a leadership team that believed design was there to execute on a vision, but the vision couldn’t be developed because of…

• dangling product strategy questions about whether or not we’d integrate with the company’s flagship product, which stalled vision and design work

I started by mapping out the process and all of the red flags I saw in it.(See below)

The Diagnosis

We had

• a product that wasn’t so much a product, more a disparate, disjointed, kinda-sorta “workflow” thing

• a process that was simply not friendly to design or designers

• product managers incentivized to ship but not focus on quality

• engineers working on an aging tech stack — minimal changes only, please and thank you

• a high percentage of churning customers who would declare on departure that “this isn’t a DocuSign product”

I drew out a huge whiteboard on Miro with the process, my goals for improvement, and a big space in between for ideas on how to get there. I filled it, then deleted half the post-its right before I talked to my team to see how they responded and what they thought. (See Below)

In the changes I decided to make first, I prioritized the team’s health and the improvements I thought would have a high impact on people feeling more motivated or better about their work, because, well, that’s where you always have to start.

Changes I made

I only had six months here — we re-organized again — but because I thought this was going to be my team for while, I got moving.

Here’s what I was able to do in the time I had:

I moved designers from a product-centric model to a core jobs to be done model so that everyone would learn about similar functionality across editions without breaking the flow of work.

I asked lead designers to be responsible for a job to be done category, supporting product quality overall by leading critique and mentoring designers, with a focus on de-duplicating and bringing better continuity to the work being done between editions, which gave them a differentiated role from senior designers.

I also asked leads to use what they learned about inconsistency in conversations with engineering leaders to start bringing the idea of streamlining the user experience and product, which helped them start seeing better impact.

Managers were moved away from managing design work to managing relationships with product so that we could mature the conversations, which helped us get more involved in up-front planning — when we could propose research and testing.

I started escalating the product strategy issues to senior leadership in product experience and in forums where I had a chance to ask questions about it, which helped surface the need for clear decision making at the executive level.

The changes started to take hold and we started moving forward in more productive ways. Had I stayed in that role, I would have kept going with my plan, evolving it as I saw impact and need.

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Best. Workshop. Ever.

After running an effective priority- and roadmap-combining workshop for two DocuSign teams in Europe earlier in the year, word got around, and I was asked to do another workshop for our PLG team.

At first it sounded pretty rote and normal: a workshop about same-paginess and priority setting, with roadmap items emerging, but then... I learned there would be over 100 people, it would be in person, and the goals were highly ambitious for a DocuSign get-together.

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What I did

After learning that, I thought, I’m gonna need a bigger boat. So I got to work:

• Designing eight hours of in-person ideation workshops spanning 2 days for about 170 employees across all major functions — marketing, design, content, engineering, growth, and their leadership

• Recruiting and prepping nine facilitators and a photographer from my team and other teams to facilitate 30-person breakouts

• Supporting the selection and organization of a venue that would hold all of these people, work for the activities I designed, and purchase all the supplies (have you ever bought 200 Sharpies at once? It’s a comical amount of Sharpies.)

How’d It Go?

The space was extremely beige. The people started out ambivalent, not knowing what to expect. Pretty soon, though, we were shoulder deep in (compostable) Post-its, making new connections, and building partnerships that wouldn’t have otherwise existed.

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All the activities we did over two days.

Sounds fun, but what were the outcomes?

Most importantly for where DocuSign was at as a company, I was able to

• Facilitate conversations that built unified momentum for relevant business change that will continue for at least two years

• Galvanize our product-led growth teams to action, exploring shared ideas for reaching ambitious goals that went into their OKRs

• Help PLG executives build a successful case for the CEO to include the ideas we developed in the product team’s roadmaps

• Make the Product Experience team look great at a moment when the products were under a lot of (warranted) experiential scrutiny

The most gratifying outcome was what people said to me afterward. I was approached by multiple people, including sponsoring execs, who told me that was the most effective, engaging gathering they’d ever attended for work.

I’d be happy to chat more about how I chose the activities I did, how I designed the interactions, and how I kept the energy up for two whole days in a beige ballroom. This piece would be much too long if I explained all that here!

Lastly, here’s an update from a PLG leader about a week after our workshop:

Accessible investing

There is almost no subject more thought about and less discussed than money.

One piece of the money space that seems to make people the most angry and frightened — often to the point of avoiding it altogether — is investing. But unless we are independently wealthy, all of us have to do it to keep pace with the rate of inflation — at least in the United States, if we ever want to stop working.

And yet, in our society, it’s not okay to admit you don’t understand financial instruments or the stock market or how 401(k)s work. Not learning or avoiding it leaves millions of people in a combined state of ignorance and unpreparedness.

What does this mean? This means that we’re about to confront a retirement crisis in the US. (Spoiler: It’s already happening.)

I was hired at Morningstar to help change that.

My metric for success was simple: raise the national average rate of saving for retirement by at least 1%.

I mean, what’s the point of tiny goals?

Investing speak ahead:
For people who want to know if I know what I’m talking about — Morningstar wanted to use Goals-Based Investing, where you set a time horizon, an amount of money you’ll need for drawdown over time, and you are delivered options for a model portfolio that matches your risk tolerance. Then you move your money in, add to the account over time, and voila! Pretty soon you are okay for retirement or other goals.

Morningstar was also behind the curve on what people called “robo” tools, a trend that didn’t exactly work out that well in the end for anyone.

(Let me warn you now: this story does not end happily, and that still occasionally brings a tear to my eye. In fact, when the product manager broke it to me we both cried because we were so committed to solving this problem.)

So, what did I do about it?

Defining lots of moving parts

My earliest collaborators were a lead researcher and a behavioral economist. We looked at models we could use and how to translate them into a combination of education and product, we thought about what kind of support a service like this might need from real people, we went into homes to talk to people, and then we talked to more people.

When it was time to add some pixels to the mix, we chose a few psychology theories and Morningstar methodologies to design an onboarding flow that was mobile first. We talked to more people, testing the heck out of it until we got to a Tinder-like flow for choosing financial goals and a conversational onboarding flow.

We also had to think about where people would be putting their money, which really meant what we were going to do with Morningstar IP and technology. We chose our goals-based model portfolio creation tool, talked to the team that owned it, and started integrating that into the product. That was pretty hard, from a design perspective, to do on a phone. We thought most people would probably move to a larger screen for that part but still designed for a small one.

We also had to figure out how transactions would run once people opened an account. We chose a custodian and set it up to run through Morningstar’s existing registered investment advisory (RIA). Custodians handle actual trades, deposits or withdrawals when people invest in a new portfolio or it needs to be rebalanced. We started integrating their tech with ours.

Just as it was all coming together, when we were ready to pull all of that together to execute on an MVP, the company pulled the plug.

For those of you interested in the evolving design-y aspects of this work, including what I created… well, honestly, I tried but because it’s a service, not a product, it just doesn’t lend itself to a sensible set of visual deliverables... there’s just way too much work for a blog post to do it justice.

I am more than happy to share it in a conversation.