The Most Sensible Proposal in the Room Might Be the Wrong One
Maggie Holbrook has brought you the safest idea you will hear all day. That is exactly why she is worth thinking about carefully.
She is 52, Director of Finance Operations at Banyan Coffee Co. in Singapore. Twenty-eight years in finance across consumer goods and retail, four of them at Banyan. She is precise, unflappable, and slightly allergic to hype. While everyone else in the building is talking about AI as if it will levitate the company, Maggie has walked into your office with a proposal to use it for something genuinely boring: automating accounts payable and customs document processing.
No moonshot. No transformation narrative. Just a well-understood problem, a mature category of solution, a clear cost case. Invoices and customs paperwork are a known quantity. Vendors exist. The return is calculable. If you were grading proposals on how likely they are to work, Maggie's would score near the top.
So here is the interesting question, and it is the one this whole scenario is built to sharpen: is the sensible proposal the right one to back? And if it is, are you backing it for the right reasons, in the right way - or are you about to over-engineer something that should be simple, because a careful person brought it to you carefully?
The scenario
This is Cynefin in the Coffee Lab, free throughout July on RolePlays.ai. You are Head of Strategy at Banyan Coffee Co. The CEO, Lin Wei Chen, needs two or three AI initiatives that will move the bottom line. The private equity board wants them named in ninety days, with at least one live and measurable within a year. It is on you to decide which bets to make.
Five leaders come to you, each with a proposal. Your job in each conversation is not to say yes or no. It is to work out what kind of problem the proposal actually is, to surface how the person is planning to roll it out, to coach that approach so it fits the problem, and to read whether the organization is actually ready for it.
The backbone is the Cynefin framework - David Snowden's model for sorting problems by the kind of thinking they require. Some problems are simple: known cause, known solution, apply best practice. Some are complicated: knowable, but you need expertise to work them out. Some are complex: you cannot analyze your way to the answer, you have to probe, sense, and adapt. Getting the category wrong is one of the most expensive mistakes a strategist can make - and the most common one is treating a complex problem as if it were merely complicated.
We wrote about this scenario when it first ran, and led that piece with a different leader - the operations VP who wants to roll predictive maintenance across all 203 stores by Q3. This time I want to stay with Maggie, because the quiet, sensible proposal tests something the flashy one does not.
Why the safe bet is a real test
It is easy to be the strategist who slows down the reckless proposal. Someone charges in wanting to deploy unproven AI across the whole estate by the end of the quarter, and your job is obvious: apply the brakes, ask the hard questions, make them earn it.
Maggie is the opposite problem, and it is subtler. Her proposal probably sits in the simple-to-complicated range of Cynefin. AP automation is close to a solved problem; the customs piece has more wrinkles but is still knowable. The correct response to a problem like that is proportionate: do not wrap a straightforward, well-understood automation in a twelve-month transformation program with a steering committee and a change-management workstream. That would be treating a simple problem as though it were complex - the mirror image of the more famous mistake, and just as wasteful.
But Maggie is careful, and careful people are persuasive in a particular way. She will present her sensible proposal sensibly, and the temptation is to reward the carefulness by matching it - to add rigor, add process, add oversight, because she is clearly a serious person and serious problems deserve serious machinery. That instinct feels responsible. It can quietly turn a two-month win into a year-long project that delivers the same result later and costs more to get there.
There is also a readiness question hiding underneath the finance question, and it is the kind of thing that only surfaces if you ask about the people rather than the process. Maggie's proposal will change what her team does day to day. Whether she has thought that through - whether the organization around this tidy technical project is actually ready for it - is not on the slide. It is in the conversation, if you go looking.
What the right move is, I am not going to spell out. Working out how to back a good idea without gold-plating it, and how to surface what Maggie has not put on the page, is precisely what the scenario asks of you.
The others
Maggie is one of five. There is a VP of Operations who wants predictive maintenance on every espresso machine in the chain, fast. An SVP of Retail Operations with an IoT brew-consistency idea. A Director of Green Coffee and Sourcing proposing AI-driven demand forecasting on a genuinely complex, weather-and-geopolitics-shaped problem. And a newly arrived VP of Marketing, hired from a fintech startup, with an AI-driven customer experience proposal and eighteen months of pattern-matching from a very different kind of company.
Each one sits in a different place on the Cynefin map. Each one is pitched by a person with their own history, their own confidence, their own blind spot. The scenario is not a quiz about which quadrant each belongs in. It is about whether you can have the conversation that gets the classification right and coaches the person toward an approach that fits.
Who this is for
Anyone who has to tell the difference between a real opportunity and a confident pitch. Strategy leaders, transformation leads, executives sitting on the other side of the table from people who want budget and belief. The scenario happens to be about AI initiatives, but the muscle it builds - classify the problem correctly, then match your response to the problem rather than to the person's polish or panic - is the core discipline of strategy itself.
Try it in July
Cynefin in the Coffee Lab is free throughout July on RolePlays.ai. About twenty-five minutes. Five leaders, five proposals.
Start with Maggie, if you like. She has brought you the most sensible idea in the building.
Now decide what to do with it.