Rude Q&As

There's a scene from the movie Big, I always think back to: Tom Hanks' character is sitting in his first big important meeting about a new toy launch, and he stops everyone in their tracks by saying "I don't get it... what's fun about playing with a building?"

His question isn't meant to be antagonistic. It's honest, it's earnest, and (most importantly) it gets right to the point.

One of the challenges we run into in our adult corporate lives is leaning so heavily on politeness that we introduce ambiguity ("we" should get this done...), and we combat that ambiguity with frameworks (OKRs, KPIs, SMART goals, etc.)

But sometimes, we need a bit of Tom Hanks in the mix. That's the power of the Rude Q&A - a document that captures all the blunt, direct, and even rude questions. It's great for after the ideation, research, analysis, refinements and iterations. It challenges, stress-tests, detects contradictions, revalidates assumptions for the thinking you believe is complete. It asks questions in such an informal but direct way that you're forced to respond in kind. "Why are we doing this?" "Is this just busy-work?" "Is this actually better, or is it just performative?" "Have we actually spoken to our users... is this really going to make things better for them?"

To pull a line reference from another movie, the Rude Q&A captures the "things we think and do not say." And the power of putting one together is it lets everyone stay polite - it's the document being rude, not me. It's no longer a me vs you, it's us vs the document.

While it's great (and cathartic!) to come up with all the rude questions on your own, it also makes for a great AI use-case - especially if it can access your emails, messages, meeting notes, documents and presentations. It's incredibly powerful at spotting bad assumptions, logical flaws, and biases. It's also great at spotting ambiguous language and when there's waffling.

The questions it can generate are often the ones you don't want asked, the ones you're afraid to answer, and (best of all) the ones you haven't considered.

While playing with Copilot Studio, I built a personal agent that will thoroughly research an area, ask a bunch of questions under a number of different personas, and will even pretend to be people I work with. My favorite part is it can also rudely (but constructively) critique my responses as well.

As an example, I took everything I wrote above up until this point and and fed it to my rude agent and then asked for a rude question that I may not have considered. It hit me with: "When does this whole thing actually backfire—and don’t give me a vague “it depends”—when does your AI-generated “rude Q&A” make decisions worse, not better? Be specific."

This conversation led to a long back and forth and then net result is it convinced me to add a couple of sentences to the post above (I'll leave it as an exercise to see if you can figure out which 2 sentences.)

Rude Q&A + AI. Give it a shot.

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