Early on, I thought there was a paradox in mapping:
You can’t know what map to make until you’ve made a bunch of maps!
And so the advice became:
Just go do a bunch of practice. Maybe you’ll find something insightful then!
Well, I don’t like practice for practice’ sake. I am impatient. I’ll spare you the stories, but to sum it up my mentor eventually suggested that I take interest in questions, not just maps.

Turns out he was right. So now I tell people:
You can’t know what map to make until you’ve found the right question to ask!
(Okay that’s not quite true… you can still make exploratory maps without knowing what question to ask… but questions help… a lot.)
So then the advice became:
Go figure out what questions you have. Maybe you’ll make maps that give you insight then!
The next gap becomes obvious:
Well, what questions can I even ask?
And it turns out there are a lot of interesting questions.
- Do we understand the basics of our situation?
- Do we know who our users are? (If not, make a list.)
- Do we know what their user needs are? (If not, make a list.)
- Do we know what capabilities combine together to meet those user needs? (If not, make a list.)
- Do we know how those capabilities fit together, what depends on what else, etc.? (If not, turn that list into a value chain.)
- Do we know how far behind the market our capabilities are? (If not, turn that value chain into a Wardley Map.)
- Do we “see” how things are going?
- Do we have the right “core” for now? Does it need to change?
- Are we prepared for the likely ways the market is changing?
- Do we know what other organizations are up to?
- Do we know how to be prepared?”
- Where should we build, buy, outsource?
- Where should we agile, lean, six sigma?
- Where should we T&M, outcomes, fixed fee, unit / utility?
- Where are we too bloated and big to sustain?
- Where are we overcommitted to past paradigms or mistakes?
- What should we do?
- Where can we intervene?
- What moves are available to us?
- What could go wrong?
- What actually happened?
And these are just the generic questions.
There are dozens and dozens in Simon’s Climate, Doctrine, and Leadership tables. They’re written in short hand, but each one definitely has a question or two behind it, just waiting to be asked. Not to mention that each situation also has its own set of interesting and important questions to explore.
In all cases, the trick is noticing them, articulating them, and then making maps to explore them fully.
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