Don’t talk about problems (or solutions). Instead, talk about progress. Only then can we be precise without dictating implementation details.
I enjoy working in the messier creation phase of a product and, maybe more importantly, the organization. Helping out with anything loosely related to design. Getting from nothing to something.
Been at it for close to 20 years. Here's a few highlights.
Cofounded a design and marketing agency
We worked with several fortune 500 companies, a handful of fortune 100, a few fortune 10, and even a fortune 1 (Walmart at the time). So 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.
Worked with many early-stage startups
For a few years I contracted exclusively for small software-as-a-service companies. Mostly interface design, but — as you can imagine — many "hats" were worn. I helped however they needed me to help. If I was an accidental generalist before, it was now firmly in place. Any work that's loosely related to design, I've probably tried doing it.
Built design and research teams for a high (hyper?) growth company
I helped build the original design and research team at HubSpot with some of 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 as good lessons learned on that adventure, but I have first-had experience building large design and research teams.
Created a software-as-a-service proof of concept
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. That may not seem like a big deal, but it was to me. I was proud I could build something real-ish (it was free) on my own.
Managed a functional team (design)
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. Also, to deliberately advocate to people without technology and design backgrounds.
Managed direct reports
At Iora Health I learned to investigate individual designer's aspriations and coach them towards their goals. Identifying the space between personal and organizational expectations. Helping them to better concentrate on skills that are beneficial to them personally, while also becoming more aware of what will help them succeed within the company.
Managed a web development team
A very tough, but extremely satisfying, job. It was an interim role at Iora Health that lasted six months. I experimented with a management structure (Now, Next, Later) that evolved into the formal management structure of their four team (~20 people) web development group.