This Might Be Crazy Test
Force unconventional options into strategy discussions before selecting a bold bet.
- Difficulty
- Easy
- Time to result
- ~days to results
- Steps
- 5
- Confidence
- 98%
The This Might Be Crazy Test is a meeting-level forcing function for differentiated strategy. During ideation, participants deliberately introduce multiple proposals with the phrase “this might be crazy,” signaling permission to challenge assumptions and move beyond standard practice. The team does not expect every idea to survive; most should be rejected after examining feasibility, ethics, economics, and strategic fit. The value lies in preventing premature conformity and finding the small subset of unusual ideas whose novelty is connected to a real advantage. Promising concepts are then reduced to bounded tests rather than launched recklessly. The framework separates productive boldness from indiscriminate risk-taking: generate extreme options freely, evaluate them rigorously, and scale only when evidence supports the underlying mechanism.
Origin
Extracted from Marketing Against The Grain, where the host described forcing himself to use a specific phrase repeatedly during strategy conversations.
Core principles
- 01Conventional discussions naturally converge on conventional tactics.
- 02Ideas that initially sound unreasonable can contain differentiated advantages.
- 03Most extreme ideas should be rejected quickly and cheaply.
- 04A small minority of unconventional ideas can produce outsized results.
How to run it
- 1
Create Permission for Extremes
Tell participants that the session must include ideas outside normal operating assumptions. Use the forcing phrase to make unconventional contributions socially acceptable.
Pro tip Set a minimum number of unconventional proposals before evaluating any of them.
Watch out Do not use the exercise to excuse unethical, deceptive, or dangerous conduct.
- 2
Generate Crazy Options
Propose actions that invert category conventions, reveal normally private information, use an unexpected format, or engage an unusual partner. Keep generation separate from judgment.
Pro tip Ask what a team with no inherited category assumptions might attempt.
Watch out Immediate criticism will push the group back toward safe consensus.
- 3
Inspect the Advantage
For each option, identify why its unusual nature might produce attention, trust, participation, or distribution. Reject ideas that are merely shocking without a useful mechanism.
Pro tip Look for an insight hidden inside an impractical proposal.
Watch out Novelty alone does not create business value.
- 4
Apply Boundaries
Evaluate legality, ethics, brand fit, reversibility, cost, and downside. Eliminate ideas with unacceptable risks.
Pro tip Convert a risky concept into a smaller reversible variant when possible.
Watch out Do not let enthusiasm suppress basic safeguards.
- 5
Test the Survivors
Turn the strongest ideas into controlled experiments with success and stop criteria. Scale only after observing real market response.
Pro tip Preserve the unusual element instead of sanding it away during execution.
Watch out A safe test that removes all differentiation cannot validate the original idea.
In the wild
Sharing venture-backed company revenue publicly sounded contrary to standard investor-update norms. Tyler Denk used the unusual transparency as part of Beehive's build-in-public strategy, creating accountability and attention.
→ A convention-breaking idea became a recognizable distribution advantage.
Ramp hired Kevin from The Office, a character culturally associated with accounting, to upload receipts. The unexpected connection made an otherwise routine product behavior memorable.
→ The stunt translated an unusual idea into category-specific attention.
Common mistakes
Being Weird Without a Mechanism
An idea that shocks people but does not strengthen attention, trust, identity, or conversion is noise rather than strategy.
Evaluating During Generation
Criticizing each proposal immediately prevents the group from reaching genuinely unconventional territory.
Betting the Company on an Untested Idea
Bold ideation should lead to bounded experiments, not reckless irreversible commitments.
Is it for you?
Best for
It is best for teams seeking memorable marketing or distribution plays in saturated categories.
Not ideal for
It is not ideal for safety-critical, regulated, deceptive, or irreversible decisions where novelty must remain subordinate to strict controls.
From the transcript
“One of the things that I force myself to do is if we're having a strategy conversation, I force myself to use the phrase, this…”
“And I would say about like 70, 80% of those things, like they get dismissed pretty quickly because they get chalked up to all Kipy's…”
“I want to make sure that I am doing something so different outside of the norm that everybody in that conversation might think I am…”
From the episode
Inside the Hidden Playbooks of Businesses That Actually Win