I enjoy working in the messy creation and evolution phases of a product and, more importantly, the organization behind the product. Helping out with anything loosely related to design. Tools and tactics, people and processes. All of it is interesting and exciting.
Been doing this since 2002 — 20 years!
Here are a few highlights.
We worked with several fortune 500 companies, a handful of fortune 100, a few fortune 10, and a fortune 1 (Walmart at the time). I have first hand experience bootstrapping, selling, marketing, hiring, and all the other things that go along with building a small — but mighty — business from scratch.
That was a long time ago, but still profoundly influences my thinking.
For a few years I contracted exclusively for small software-as-a-service companies. Information architecture and interaction design, but many other “hats" were worn. I helped however they needed. If I was an accidental generalist before, it was now firmly in place.
Any kind of work loosely related to design. I've tried it.
I helped build the original design team, research team, and design system for HubSpot with the smartest people I've ever worked with. It was an insanely high-growth environment and I rarely had the time to think ahead or reflect on the past. There are likely as many bad lessons learned as good on that adventure, but I have first-had experience building large scale design teams, research teams, and design systems.
In between working at HubSpot and Iora Health I took five months to explore a potential startup. I was able to get to a point where it was used regularly by people I didn't guilt trip into trying. It was a big deal to me. I was proud I could build something real-ish (it was free) on my own.
As a Senior Design Manager at Iora Health I learned to back away as a contributor and put far more time and energy into exploring and clarifying a larger group's goals. To deliberately advocate to people without technology and design backgrounds.
At Iora Health I learned to investigate individual designer's aspirations and coach them towards their goals. Identifying space between personal and organizational expectations. Helping them to better concentrate on skills that are beneficial to them personally, while becoming more aware of what will help them succeed within the company.
Product management is a tough, but satisfying, job. It was an interim role at Iora Health that lasted six months. I facilitated an ambitious optical character recognition project that helped medical staff search, copy, and document details from tens of thousands of previously static PDFs. I also experimented with a team management structure (Now, Next, Later) that later evolved into the formal management structure of their four team (~20 people) web development group.
The goal shouldn’t be to have all design decisions be made by people with the word “designer” in their title. The goal is to make sure every design choice is made with rigor. With skin in the game.
Stop fighting for users. Stop fighting for the business. Start fighting for every single choice to be made as though the business and its users are inextricably linked.
Don’t talk about problems (or solutions). Instead, talk about progress. Only then can we be precise without dictating implementation details.
Working with abstract concepts doesn’t make us more strategic. It doesn’t mean we understand the big picture. It doesn’t mean we’re doing something more valuable.