Sometimes we get so good at what we do, we understand our industry so well, that we get blinders on. Black swans become difficult to imagine, and that can set us up for big surprises. That’s because we are limited by our own imaginations, and sometimes we fail to let our imaginations run wild.
This is an area where AI can help.
Today, I’ve got three simple and effective prompts that will help you imagine those black swans so you can prepare for them with your team.
Step 1: Start wide
Prompt:
Generate possible scenarios for the [sector category] in [jurisdiction] over the next decade, considering potential technological advancements, regulatory changes, demographic considerations, and economic factors.
I’ve taken to running these types of prompts into both ChatGPT and Perplexity. Here’s how each of them responded to my prompt about the real estate sector in Canada:
ChatGPT provided five detailed scenarios, each with a breakdown of the considerations I asked for. Here’s the full response I got. You’ll see that it provided four scenarios, each with a breakdown of the topical considerations I asked for. Here’s a snapshot of one of those scenarios:
Perplexity skipped straight to providing scenarios for each of my factors. You can see the response here. As the snapshot below shows, I got a useful answer, baked in current thinking on these issues:
But both of these feel too safe. You don’t need to be a real estate expert to conceive of these scenarios. If you find you’re getting predictable results, my next prompt will sort you out.
Step 2: Get imaginative
Prompt:
These scenarios are predictable. I need your help imagining black swan scenarios. Can you generate scenarios that might seem unimaginable on first blush?
Now we’re getting somewhere! ChatGPT came up with a much more interesting set of scenarios:
Nationwide property confiscation for climate refugees
Global cyberattack shuts down real estate market
Post-pandemic “work anywhere” boom leads to urban ghost towns
Alienation of foreign investors leads to global boycott of Canadian real estate
Quantum computing renders financial systems obsolete, crashing the real estate market
These are much better—even if they seem a bit ludicrous at first, they’ve got my brain thinking about related scenarios that may be closer to reality. This is exactly what I need. Think about all the potential scenario planning you could do with the fourth scenario, for example:
Perplexity also provided me with compelling scenarios:
Quantum Computing breakthroughs
AI-driven constriction
Nationalization of housing
Radical environmental regulations
Global financial crisis
Hyperinflation
Mass urban exodus
Cultural shift against ownership.
While many of these hue to the more realistic side, they are much more expansive than the original scenarios we got from Perplexity. Interestingly, there are some overlapping themes between ChatGPT and Perplexity. Here’s a snapshot:
Step 3: Get political
In our line of work, we need to game out a variety of political scenarios. This is where it gets really interesting. You can layer on hypothetical changes to give these scenarios different texture.
Prompt:
I would like you to revise these black swan scenarios to factor a political change, with [politician] becoming [prime minister/president/governor etc.] with a [style of] mandate.
When I asked ChatGPT and Perplexity to imagine a scenario in which Canada’s Conservative leader, Pierre Poilievre becomes the prime minister with a populist mandate, I got these types of edits to the scenarios:
From there you could go deep on each of the scenarios to build them out with further details or additional factors/considerations for your specific use case.
Et voilà! Let me know how these prompts work for you, or how you took them to the next level.








