DX Land: The Game of Digital Transformation or Stagnation

When standard formats couldn't capture how unpredictable and human digital transformation really is, we designed a Chutes-and-Ladders-style game, and used AI-generated art to build a world around it.

The Concept

The game of Digital Transformation (DX) is hard to win. After experiencing multiple digital transformation projects, we wanted to know what makes them succeed and what makes them fail. How much is chance vs. skill?  

The Players

This was a cross-institutional collaboration between UC Santa Cruz and the California State University Chancellor's Office, to pool our collective experience in transforming digital experiences into a conference poster. We all created the conceptual framework. I lead the visual design direction and took ownership of the AI art generation process, which was new territory for all of us at the time.

Translating tacit knowledge into a game system

We started with a synthesis exercise — pooling years of cross-institutional DX experience and asking: what are the patterns? What reliably accelerates a transformation? What reliably kills it? What's genuinely within a team's control, and what isn't?

We structured the collective experience of the team into a Chutes and Ladders-style game, one that intuitively communicates the non-linear, chance-influenced nature of digital transformation. Each game element was mapped to real patterns we'd observed: accelerators that fast-track progress, traps that can set teams back, and the role of institutional context that no amount of best practice can fully control.

The chance element was intentional. One of the hardest things to communicate about DX is that luck matters — that the same team, the same strategy, and the same execution can produce wildly different outcomes depending on timing, politics, and circumstance. The dice roll embedded that truth into the game's structure without us having to say it.

Solving a real design constraint with an emerging tool

To execute our concept, we needed sci fi spooky artwork that would fit our “Stranger Things” theme. In the past, creating concept images could mean spending hours drawing or sourcing licensed assets. Neither fit our timeline or budget. Instead, we turned to DALL-E 2, then just months old, as our image generation tool. The result was imagery no stock library could have provided.

What I also found was a tool that rewarded patience and iteration in ways I hadn't expected. The prompts that worked weren't always the obvious ones. Specificity helped, but so did unexpected combinations. "Project graveyard IT servers monitors tombstones" took many attempts before it produced something that balanced eerie atmosphere with enough visual clarity to read at poster scale.

Outcomes

The poster generated genuine engagement at the conference. A format that could have been a dry matrix of best practices became a conversation piece. Participants engaged with the game format as a lens for reflecting on their own DX experiences, making the knowledge transfer more effective than a standard research presentation would have been.

It also gave me an early, grounded view of where AI tools in design actually add value and where they don't. The tool didn't make creative decisions for us. It expanded the space of what was possible given our constraints.

The Poster - high resolution file