TWO HOURS.
CHALLENGE YOUR THINKING.
SEE WHAT SURVIVES.
What uncertainty about the future of your business keeps coming back to you?
Something you feel sure will matter enormously — but you still can't quite make sense of it or see clearly where it might lead. Such an uncertainty could arise from almost anywhere:
A technology that could transform your industry. A geopolitical shift whose consequences are unclear. Unexpected customer behavior. A competitor making a move you can't quite fathom. A regulatory change whose implications could be profound.
To help you develop your company’s strategy — which would include responses to these kinds of changes — you probably already have excellent advisers. Good!
This is different.
The What If? Conversation is a confidential, one-to-one, two-hour conversation devoted entirely to dissecting one significant uncertainty about the future of your business.
This is not a workshop. I don’t kick off the session with a presentation. There’s no set methodology to apply. And no attempt to predict the future.
Instead, what we do together is much simpler: We put the uncertainty on the table and take it apart.
YOU'RE NOT SHORT OF ADVICE
CEOs usually have plenty of smart people around them — colleagues, board members, consultants, lawyers, bankers, analysts and industry experts of all kinds.
But access to expertise isn't necessarily the same as having somewhere to think out loud.
Some uncertainties benefit from being explored before they become a strategy paper, a board discussion, or a decision that needs defending.
A place where you can comfortably say:
“I don't know what to make of this.”
And then spend two uninterrupted hours tearing apart the assumptions behind your own thinking and exploring alternative ways the future might unfold.
That's the space The What If? Conversation is designed to create.
HOW DOES IT WORK?
There are four simple steps to the What If? Conversation:
1. Brief
We begin with a short conversation beforehand. You tell me about something you know matters, but you can't yet see it clearly. Together, we decide whether it's the right uncertainty to put on the table.
2. Prepare
I do my homework.
I familiarize myself with the issue, its context, and some of the different ways it could develop. The aim isn't to arrive with answers. It's to arrive well enough informed to challenge you intelligently.
3. Challenge
Then we meet in person for two hours.
We'll probe different angles. Introduce alternative possibilities. Question assumptions that may already be shaping your thinking — perhaps prematurely.
I'll ask “Why?” And perhaps “Why?” again.
I'll make you explain and defend what you think you know. Some of your arguments may emerge stronger. Others may not survive the scrutiny.
Think of it as a two-hour boot camp for your thinking.
4. Distill
Afterwards, I'll send you a short confidential distillation of the perspectives, questions, and observations from the conversation that seem worth retaining.
NB: The conversation is completely confidential. With your agreement, I’ll record our discussion solely so that I can revisit the thinking accurately when preparing this follow-up. The recording is not shared.
YOU MAY FIND THIS HARD WORK
I'm not there to agree with you.
At the same time, I’m not there to disagree with you just for sport.
One of my key roles in the conversation is to stop us from settling too quickly for the obvious explanation, the comfortable assumption, or an answer everybody else seems to have accepted.
We will pursue an idea wherever it leads. That means we might discover it goes nowhere. OK, let’s try a different angle. We may stumble across something neither of us expected. We may discover that the uncertainty itself needs to be reframed.
We might also validate your current thinking. That in itself is very valuable.
My only goal is that when we emerge from the conversation, your thinking on this uncertainty is sharper, clearer, and more defensible.
For you, this may mean two hours of hard work — and maybe a little discomfort along the way.
WHAT WILL YOU GET WHEN IT'S OVER?
Certainly not a 30-page report with “the answer.”
Instead, you might find yourself looking at the issue quite differently:
Something you've been worrying about may matter less. Something you've overlooked may matter much more. An assumption may no longer look so solid. A possibility you had previously dismissed may suddenly deserve attention after all.
Or you may discover that by reframing the issue you brought into the room, it comes into sharper focus — and how to manage it now looks like a different challenge.
Above all, I want you to leave with a clearer view of what's really at stake, and better prepared to notice indicators that weren't on your radar before: ones that could signal which way your environment may be changing.
Please note: There is no guaranteed “Aha! ”
This is important. The What If? Conversation isn't theater, and I cannot promise you that a revelation will conveniently arrive right at the 1:55 mark.
The value of the conversation lies in giving one consequential uncertainty the quality of attention it rarely gets: two uninterrupted hours of serious, independent examination.
WHY ME?
I've spent more than 20 years helping executives and organizations think about uncertainty and alternative futures.
Most of that work has involved scenario planning: challenging assumptions, exploring plausible alternatives, and helping decision-makers prepare for futures no one can confidently predict.
The What If? Conversation takes that same forward-looking instinct but strips away all the heavy machinery. No workshop. No slides. No team. No scenario matrix. Just you, me, and one important uncertainty worth examining properly.
In my foresight career, I've worked with organizations in more than 35 countries, written extensively about scenario thinking, and taught scenario planning at Master's level. Earlier in my career, I served on the Executive Board of the World Economic Forum in Geneva/Davos and before that earned my MBA from Harvard Business School.
But for these two hours, my biography isn't the important part.
The important part is that I come to your uncertainty with no stake in the answer. Just an inquisitive mind, a relentless approach (some would say annoyingly so) to questioning the way you’re already thinking, and a real desire to help you see more clearly what may lie ahead.
“He quickly learned about a totally new business and enthusiastically applied his approach to our objectives. Working with Woody, we have a better understanding of the risks and the possibilities now.”
- Christine Perey
Augmented reality expert, Switzerland
READY TO PUT YOUR UNCERTAINTY ON THE TABLE?
Curious where the conversation might take you?
If there's something important about the future of your business that you still can't quite get your arms around, let's put it on the table and see what happens when we attack it together.
THE WHAT IF? CONVERSATION
Two hours • One-to-one • Confidential
Includes advance briefing, preparation, and a short written distillation afterwards.
Bring me the uncertainty. Let's see what we find.
Interested? Tell me what's on your mind.