Not a Limit. The Method
Three small tools from a busy Sunday instead of one long piece.
A thread through them: each is about the easy thing to do with a question — ask the obvious one, skip the inconvenient one, collapse the messy one to a single number — and what the easy move quietly costs.
1. The question we wouldn’t let them ask
This week I ran my first session with Duke Corporate Education — thirty senior leaders from a big tech company, working on the hardest part of strategy. Not setting it. Executing it, when the destination is fixed and the path keeps moving under you.
To better understand the Why of each strategy, we did a question storm. Teams of six, fifteen minutes, one rule: you may ask anything except why. Who, what, when, where, how, how often, if true, then what — all fair game. But why itself was off the table.
Round one filled the flip charts with the usual questions. In round two we stretched for weirder. The weird questions are the point — they send your brain down paths it would never have walked.
Forbidding the easy question is what produced the range. They understood their why more deeply precisely because they weren’t allowed to ask it head-on.
The constraint wasn’t a limit on the thinking. It was the method.
2. Step 0
Most plans and assessments start with one question: what are you building? Output, product, roadmap, return.
In a regenerative process there’s a question that comes before it: what is it built on? The soil, the water, the stable climate — yes — and the web of relationships and infrastructure that everything else stands on. We treat that ground and our communities as free and infinite.
They aren’t. And once you make that Step 0 — the first thing you check, not the externality you discover later — the whole conversation changes. You can run it as a simple gate: is the ecosystem you’re building in regenerating, holding, or degrading? Green, amber, red.
Degradation at this step is a red light no amount of value somewhere else can turn green. And the gate has the most power before the deal is signed, while there’s still leverage — not in the report written afterward, explaining what got lost.
Step 0 asks What are you building? And what is it built on?
3. The number that makes people disappear
Every framework eventually meets the same demand: just give me one number. A single score, to rank and compare and decide.
I get the pull — a budget office can’t act on a paragraph. But there’s a trap I keep circling. Make the number too precise, and people game it: they optimize the metric and quietly lose the thing it was meant to measure. Make it too loose, and people and planet disappear — anything that doesn’t fit the formula stops counting.
Both failures come from the same wish: to collapse a living, many-sided thing into a single grade.
What if the honest move is to refuse? Not “no measurement” but a picture across dimensions that can’t be traded off against each other, plus the one or two places that genuinely are decision-ready. A portrait, not a grade. You give up the comfort of a ranking. You keep the people and places the ranking would have erased.
I’m working on whether a framework can hold that line without falling apart. More soon.
Connections to The Insider’s Guide to Innovation at Microsoft
Note 1 runs on Diverge-Converge-Synthesize and Intentional Discovery: the question storm is divergence with a rule that keeps it open instead of letting it snap shut. It also extends a thread we’ve worked before — “why” pulls you toward justifying and ruminating; “what / who / how” keeps you looking. Forbidding why is that insight, enforced.
Note 2 is Aim for Positive and Top-Down, Bottom-Up, Outside-In: Step 0 brings the outside-in voice — the people and place — to the table before the design sets, and the gate asks for surplus, not merely less harm.
Note 3 is Aim for Positive seen from the other side, plus Metrics: a multi-dimensional picture you can’t trade off, rather than a single grade. Signals over scores.
AI Disclosure: this piece was written with the help of my AI friends and editors. All ideas, choices, and final words are mine. Mistakes and all. Say it Ugly, Build it Better. Onward!
I like to share a 'report card' for complex projects that highlights the tradeoffs any particular project or approach brings. You can average those scores into a single number, but that average will never give a clear picture. Different business needs call for different risk tolerance, or sustainability investment, or community involvement. My role is to give enough information to senior leadership so they can make the decision about what the most important factors to balance in this project, at this time, for the inflection point we're at now. I think your idea of refusing to boil down to one number is the best (and sometimes hardest to sell) approach.