Glossary

I know, some of these words and phrases seem so… jargony.

So here are explanations of what we’re talking about.

Design Thinking, in plain language

If you’re dealing with messy, “wicked” problems — things like homelessness, downtown decline, or climate resilience — Design Thinking gives you a different way to tackle them.

It comes from the way designers work. It’s creative, practical, and very human. It’s not about making art or sticking Post-its on a wall. It’s about surfacing ideas you don’t normally hear and testing what might actually work in the real world.

Design Thinking is especially useful when:

  • You don’t already know the answer

  • You’re open to real change, not just small tweaks

  • Leaders are willing to hear what people really think

If you’re just looking to confirm a decision that’s already been made, this is the wrong tool. If you’re looking for innovation — it’s the right one.

Where this shows up

I often use Design Thinking with cities, nonprofits, and organizations that want to tap into the hive mind of:

  • Residents and community members

  • Local businesses and service providers

  • Staff, leaders, and partners

That might look like:

  • Defining a city’s essence in 2030

  • Understanding how people actually use recycling or transit

  • Exploring how a community might better support people marginalized by homelessness

Along the way, two big things happen:

  1. You get ideas and insights your in-house team wouldn’t have come up with alone.

  2. The people who took part know they were truly heard — and often become advocates for the solutions.

How I work with groups

Most of my sessions involve 20–80 people, working in small groups of about five.

I don’t arrive with one rigid method. I bring a toolkit and choose the right tools for the challenge, the culture, and the time we have. But most workshops draw on three types of tools.

1. The Welcome Mat

First, we help people relax and feel safe to participate.

This warm-up has nothing to do with the main topic. On purpose.

We might:

  • Do “Draw Toast” (everyone quickly sketches how to make toast), or

  • Ask each table to “make something about summer” using only the items on their table — working together, without speaking.

It’s playful and low-stakes. People start to laugh, collaborate, and realize they’re not being judged. The room loosens up, and only then do we move toward the real work.

2. Walk in Their Shoes

Next, we build empathy for people who aren’t in the room — or aren’t usually heard.

Inspired by Kareem Abdul-Jabbar’s line, “Make a friend out of someone who doesn't look like you…,” I ask participants to create a “friend” who lives a different reality: a newcomer, a teen aging out of care, a senior on a fixed income, a small business owner on a struggling street.

Groups give this person a name, a morning, a worry, a hope. Then we explore:
How do they move through this community? What gets in their way? What helps?

This is where the “aha” moments often start.

3. Stories from the Future

Finally, we pull everything together.

Groups are asked to imagine a few years from now and tell a short story about:

  • Their “friend”

  • Their future community

  • Or a promising solution

It might be a simple story, a “news headline from 2030,” or a rough storyboard.

We ask: What’s changed? What does a good day look like now? What had to happen to get there?

These stories reveal priorities and directions that usually don’t show up in standard surveys or reports.

I use other tools as well, depending on the group and the level of change they’re ready for. But they all serve the same purpose: helping people see differently, think together, and imagine a future they can genuinely commit to building.

What are wicked problems?

Wicked problems are tangled, complex issues. They involve complexity in culture, finance, politics, education, and various other societal norms and expectations that make creating an absolute or global solution impossible. There are multiple parameters for a wicked problem. Generally, they are ill-defined and the solutions are not true or false. They cannot be tested as one would in science. The solutions lie in trials, and “every trial counts” as part of the solution. The success of solutions are dependent on how well the question is defined, as in “How might we apply community-driven methods to reduce the social stigma of homelessness?”

Labelled “wicked problems” in 1973 by UC Berkeley design theory professors Horst Rittel and Melvin Webber, these kinds of challenges can often be more effectively addressed through multidisciplinary co-operation guided by people like designers and design strategists who, through their experience with divergent thinking and using abductive reasoning and collaborative sensemaking, can assist subject experts to see new ways of solving problems. 

What about the not-so-wicked problems?

Not every challenge is as noble as shifting a social stigma. But with climate change, pandemics, and other external forces pressing on communities and companies, many organizations are wrestling with what their future looks like and how they need to reposition to adapt.

In these cases, bringing the community together around the issues can empower people to become agents of change. Instead of simply answering survey questions, participants are given tools to create and tell stories — many stories. When leadership is genuinely visionary, those stories are heard, recognized, and folded into design solutions that feed back into the community and celebrate the people who contributed.

The goal, always, is to create opportunities for more resilient communities and, maybe, a better world.