Prepared to Improvise
Do the homework so thoroughly that you can afford to throw it away.
- Difficulty
- Advanced
- Time to result
- ~months to results
- Steps
- 5
- Confidence
- 80%
Fussman describes his method as a paradox he refuses to resolve: there was preparation and understanding, and there was also a preparation to improvise. He knew the journalistic form he was supposed to execute, then deliberately innovated away from it without knowing where it would land. The Gorbachev interview is the proof — the plan was destroyed at the door, and the preparation to improvise is what let him invent a better approach in the moment. He characterises his whole career as a hybrid of knowing what he was supposed to do and allowing something else to happen.
Origin
Fussman arrived at Esquire with the conventional training of a newspaper columnist and journalism school, but carried a decade of improvised conversations from trains and buses. Rather than choose between them, he brought the bus-seat style into rooms with presidents and CEOs. The resulting column, 'What I've Learned,' written entirely in the subject's own words, became the magazine's most popular feature for about 20 years.
Core principles
- 01Preparation and improvisation are not opposites; preparation is what funds improvisation.
- 02Know what you are supposed to do, then innovate away from it deliberately.
- 03Prepare for the moment where the plan collapses, because it will.
- 04You do not need to know where it is going — you need to be able to let it happen.
- 05The hybrid of mastery plus permission to deviate is where the original work lives.
How to run it
- 1
Master the conventional form
Learn what you are supposed to do — the standard interview, the standard pitch, the standard structure — well enough that executing it would be safe.
Watch out Skipping this step is not improvisation, it is just being unprepared.
- 2
Prepare the substance, not the sequence
Do the research so no fact can surprise you, but do not commit to an order of questions. Preparation buys you freedom, not a script.
Pro tip Understanding the subject deeply is what lets you recognise the interesting turn when it appears.
- 3
Rehearse the collapse
Explicitly imagine the moment the plan is destroyed — the 90 minutes becomes 10, the room is different, the subject is hostile. This is the preparation to improvise.
Pro tip Ask: if I lost 90% of my time right now, what is the single move that saves this?
Watch out If you have not pre-lived the collapse, you will default to executing your dead plan faster.
- 4
Do something drastic when the moment demands it
When conditions break, recognise it immediately and act. Fussman knew at the door he had to do something drastic and chose the heart question on the spot.
Watch out Hesitating burns the little time you have left.
- 5
Allow it to happen
Accept that you have no idea where it is going and let it go there anyway. Fussman: 'I just allowed it to happen.'
Pro tip Judge the moment by whether it is alive, not by whether it matches your plan.
Watch out Steering back toward your prepared structure mid-flow is the most common way people kill their own best material.
In the wild
Fussman took the improvised bus-seat interview style he learned over ten years of travel into Esquire's rooms with Nelson Mandela, Gorbachev, Richard Branson, Jeff Bezos and Muhammad Ali. Rather than asking the journalistic questions designed to get to the core — which subjects sense and resist — he treated it like sitting next to them on a bus and went in curious. The resulting column was written entirely in their own words and contained the nuggets of wisdom they volunteered.
→ It was unlike anything else in the market and became the magazine's most popular feature for roughly 20 years.
Common mistakes
Treating preparation and improvisation as a choice
It looks like a paradox, so people pick a side: the over-prepared recite a list, the under-prepared flounder. Fussman holds both — deep understanding plus a standing permission to abandon the plan.
Executing the dead plan faster when time gets cut
The instinct when 90 minutes becomes 10 is to compress the same questions. That produces a rushed version of the canned interview. The correct response is a different move entirely.
Is it for you?
Best for
Interviewers, speakers, founders in investor meetings, and anyone whose best outcomes depend on reading the room live.
Not ideal for
Compliance-driven or protocol-bound work where deviation from the script carries legal or safety risk.
From the transcript
“There was preparation and understanding, but there was also a preparation to improvise, which may seem like a paradox.”
“That's where it came from — this hybrid of knowing what I was supposed to do, then innovating in a way that I had no…”
“When I walked into the room I knew I had to do something drastic.”
From the episode
Cal Fussman: The Power of Questions, Transform Your Life and Business with Authentic Connections
Cal Fussman