Point at any rule, routine or “must” and ask, with real curiosity: does it have to be this way?
Every problem comes wrapped in things nobody questions: rules, routines, must-haves and “we can't” statements that feel like facts. Challenge is the habit of pointing at one of them, on purpose, and asking: Why is it like this? Does it have to be? Could it be another way?
A challenge isn't a complaint or an attack. You aren't claiming the current way is wrong, only that it might not be the only way. Often the honest answer is “yes, it really does have to be like this”, and that's fine. But every so often a rule turns out to be an old habit, and a whole set of new options opens up.
Because each challenge takes a minute, you can use it anywhere: when you're first defining a problem, in a stuck meeting, or to test a plan before you commit to it.
Use it when a team keeps saying “we have to” or “we can't”, when you're defining a problem and want to know what's really fixed, or when every new idea looks like the last one.
Point at one part at a time. The left side is how it works today; the right side is the challenge.
Who made this rule, and does the reason behind it still hold?
Does it really need this, or have we just always had it?
Why is it done this way, and is this the only way?
Why does it stop here, and what lies on the other side of the line?
Do we really have to choose, or could we have both?
Why can't it be done, and what would have to be true for it to work?
Every working day runs on assumptions; we couldn't function without them. Challenge brings a few into the light so you can decide whether they still deserve your trust.
Most of what limits a solution is never written down. It's just “how things are”. Saying an assumption out loud is the first step to seeing it as a choice rather than a fact.
Many rules were sensible answers to problems that have since gone away. The rule survives because nobody remembers why it started. Asking “what was this for?” often shows that the original reason no longer applies.
Because a challenge doesn't claim the current way is wrong, nobody has to defend it. The conversation stays curious instead of political, even when you're questioning something a colleague designed.
Each assumption you drop removes a wall. Once “it has to happen at city hall” goes, a whole range of places, times and formats becomes possible, options that were invisible a minute earlier.
Write the current situation plainly: what happens, where, when, who's involved and what rules apply. You can't challenge what you haven't described.
Read your description and underline every rule, must-have, method, boundary, either-or and “impossible”. Listen for words like always, never, have to and can't. Those are your targets.
Point at a single target and ask: Why is it like this? Does it have to be? What else could it be? Write down the honest answer, even when it's “yes, it really must”.
Where a challenge cracks something open, stay there. List the alternatives that become possible once that assumption is gone. Don't judge them yet.
For the most promising openings, find out what kind of rule you're dealing with: a law, a contract, a policy or a habit. Pick one or two to test, and note who you need to ask.
A plain description of how things work now, a pen for underlining assumptions and 15–20 minutes. With AI, the prompt below plays the outside challenger for you.
Subject: a city's annual budget consultation. Goal: hear from more renters, young families and newer residents. Constraint: one formal public hearing is legally required.
“Input happens at the public hearing.” The legal requirement turned out to be one hearing, not that the hearing is the only way to give input.
“Residents need the full budget to comment.” Most care about a few lines. A one-page “your street, your taxes” summary could replace the 200-page document.
“Staff present, then take questions.” Why that order? Residents could set priorities first with a simple budget game, then hear the trade-offs.
“It happens at city hall on a weekday evening.” Why there? Try pop-up tables at the farmers market, school pickup and the main bus stop.
“Deep input from a few, or shallow input from many.” Why not both? A five-minute online poll for many, plus a workshop for those who want more.
“Young families won't come, whatever we do.” Who decided? Free childcare and a simple dinner at the workshop had never been tried.
Pop-up tables at three busy spots, a one-page summary, and a priorities game to open the workshop. The formal hearing stays, but it's no longer the only way in.
Inside a team, it's hard to question the rules everyone lives by. AI has no history with your rules and no reason to protect them, so it makes a useful outside challenger. What it can't know is which rules are real legal or safety requirements and which are just habit. That check is your job.
Have AI flag every hidden must, can't and always in your description.
Here's how our budget consultation works. List every assumption in it, from obvious to buried.
Ask why, then why again, until you reach the real reason for a rule.
Ask me 'why?' about our hearing-only habit, up to five times, one question at a time.
Find others who challenged the same assumption, and check what happened.
Which cities have gathered budget input outside formal meetings? Say how sure you are of each.
Once an assumption falls, map what becomes possible.
Suppose input doesn't have to happen at city hall. Give me 10 alternatives, from easy to bold.
Describe how things work now, pick a mode, then copy the prompt into Claude, ChatGPT, Gemini or Copilot. In coach mode the AI helps you find hidden assumptions, then challenges them one at a time and waits for your answers.
The “Open in” links put the prompt in the web address. If your challenge includes anything sensitive, copy and paste instead.
After the session, click one to copy it, then paste it into the same chat.