ep. 84. The Importance of Anticipation

5 min read

Dec 18, 2025

“Weather here always comes from the West. If you look towards Sierra Teta, you can predict what the weather will be 20 minutes from now.”

I immediately whipped out my phone to jot down this quote from the co-owner of our lodge in Futaleufú (Chilean Patagonia) before snapping this photo:

The Weather Channel in Futaleufú, Chile.

Practically speaking, this local knowledge was helpful because (a) you often experience all four seasons within a day in Patagonia, and (b) traditional weather forecasts aren’t particularly helpful here. An oracle-mountain to inform your clothing choices before going out on your morning run is kind of perfect.

The quote’s significance didn’t stop there.

The local knowledge of Sierra Teta helps you anticipate the weather to make better choices. It just so happens that I’m also working on a chapter of my book, Designing Automated Futures, that deals with anticipation and automation: How can you better anticipate (and mitigate) unintended consequences of deploying automated systems? And how do you see around the corner when technology is evolving at unprecedented speed?

That brings us to today’s episode.

Incidentally, this is also the final episode of 2025. What better theme than anticipation to ring in 2026?

Two Flavors of Anticipation

In a product development context, I like to think about anticipation taking two forms: tactical and strategic.

Tactical anticipation asks: What could go wrong when you deploy this, and how do you mitigate it? Strategic anticipation asks: How might the landscape shift, and how do you position yourself?

Tactical anticipation addresses immediate risks. You identify what could go wrong when you launch your technology and what you can do to mitigate those problems now.

For example, what happens if your AI-assisted diagnostic tool provides incorrect information to the doctor who is using it? What can you do to mitigate those problems now?

Strategic anticipation explores potential futures more broadly. For example, you might examine how changes in regulation, user behavior, or competitive dynamics could reshape your industry, creating opportunities or threats that don’t exist today. From there, you can adjust your strategy to remain competitive regardless of which future materializes.

For example, how might shifting customer expectations around data privacy alter what products succeed in the future? How will you adjust your strategy accordingly so that you are resilient across different potential futures?

When to do What

Both types of anticipation are important, but they serve different roles at different stages of product development:

Tactical anticipation happens during execution. It occurs during system design and testing, ideally before deployment. The goal is to catch and fix problems before they reach customers.

Strategic anticipation happens as you form your strategy across time horizons. Do this before committing to major investments, when you still have flexibility to change direction. Revisit it regularly (the frequency depends on your industry’s pace of change) and when emerging signals suggest the landscape may be shifting. You need enough lead time to reposition your organization, not just react to changes already underway.

What are signals? They’re small, often local, innovations of people doing things that differ from how the mainstream believes the world functions. They might be new ideas, technologies, or habits. Recent examples include synthetic users for research or AI-driven usability testing (more here).

A Few of my Favorite Tools

While there are several tools you can use for both types of anticipation, here are some of my favorites. These should all ideally be run in a workshop setting with your team, rather than in isolation. You’ll need to synthesize outcomes into themes, share out insights and recommendations, and ensure you follow through so that they’re actioned upon.

Tactical Anticipation Tools

Pre-mortem: Imagine your product has failed. Work backward to identify what went wrong.
Tarot Cards of Tech: Ask questions like, “what happens when 100 million people use our product?” and “What’s the worst headline about our product you can imagine?”
Sidenote: I’ve used the Tarot Cards of Tech for years with graduate students in my Intro to UX Design class. They conduct an ethics impact assessment on the design direction their team has converged on, following a round of prototyping testing with participants. Shoutout to Sheryl Cababa for this awesome tool.

Again, these are best used before your product has launched, and while you still have some runway to make changes to mitigate the risks you identify.

Strategic Anticipation Tools

The Futures Wheel: Visually map ripple effects of a change (or signal!) by identifying potential primary and secondary consequences (you can keep going to tertiary consequences, if you want).
Futures Wheel Template (rest assured, it rarely looks this neat in practice)
Horizon Scanning: Systematically monitor signals, trends, and wild cards across multiple domains.
Tip: Track your signals using this foresight database template created by Sam Ladner.

These two tools come from the discipline of strategic foresight, which is devoted to exploring possible futures and preparing for them. Remember, apply these tools before committing to major investments, when you still have flexibility to change direction.

Why Anticipation Matters Now

Generative AI is evolving at an unprecedented rate. You can automate things that weren’t possible to automate even a year ago. Let me give you an example:

Last year, my Intro to UX Design class was still prototyping “the old fashioned way”, without generative AI’s ‘assistance’. Most students used Figma for the final project prototypes. Tools like Cursor or Figma Make weren’t even released.

This year, most students vibe coded prototypes for their final projects (after structured, hands-on practice and discussion of the pros and cons of this approach, of course).

The pace of generative AI development changes the stakes for both tactical and strategic anticipation:

Tactically: Generative AI systems behave differently than rule-based automation. Identical inputs can produce different outputs; edge cases are difficult to predict in advance. You need to anticipate how the system performs across contexts it wasn’t explicitly trained for, how users might manipulate it through carefully crafted prompts, and what happens when it’s deployed for purposes beyond your intended use cases.

Strategically: Technology developments that used to take years to develop now take months. What seemed unfathomable to automate 1-2 years ago is becoming standard practice, and in turn, changing ways of working. (See: My AI-enabled prototyping example). This makes it much more challenging to see around the corner, especially for longer time horizons.

No one can predict the future, but anticipation helps steer us towards a preferable one. Of course, that now leaves the question, “Who decides what’s preferable?” But that’s a question for another year.

If you liked this episode, you’ll love my book. Designing Automated Futures is coming in 2026 with Rosenfeld Media. 🔗 Sign up to be the first to know about new book releases, sales, and events.

🚀 Sendfull in the Wild

Recording of my November 21 talk, Still in the Loop: Leading with Human-Centered Design in the Age of AI, at the University of Toronto Faculty of Information.

Recap of the AI & Human-Centered Design Panel at the Rotman School of Management, written by event co-host, DesignMeets.