What's the question about your company's future that you keep coming back to?
Perhaps nobody can answer it yet. But that doesn't mean you can't think about it better.
The What If? Conversation is a private, two-hour, one-to-one conversation designed to challenge how you're thinking about an important question or uncertainty critical to your future.
No slides. No prescribed methodology. No recommendations.
Just a serious conversation intended to take your thinking somewhere it hasn't been before.
WHY MIGHT YOU NEED SUCH A CONVERSATION ?
Sometimes you don't need another answer. You need a better question.
Senior decision-makers rarely suffer from a shortage of information or advice.
What can be harder to find is the opportunity to step away from the immediate pressures of the business and examine the assumptions behind your own thinking. That's what the What If? Conversation is for.
You bring the expertise in your company and industry. I do enough preparation to understand the context and challenge your thinking intelligently.
Then, together, we explore perspectives, possibilities, and implications.
I question assumptions. I introduce unexpected angles. I test what seems obvious. I ask what else might become true. And when something interesting appears, we pursue it.
HOW DOES IT WORK ?
There are four simple elements to the What If? Conversation:
1. Brief
We’ll have a short call beforehand to identify the broad question or area you want to explore.
2. Prepare
I do enough homework to understand the context — not to become the expert in the conversation, but to ask better questions.
3. Probe
We meet in person for two hours. We probe your question from different angles, challenge what seems obvious, and follow the most interesting thinking wherever it leads.
4. Distill
A few days later, you receive a one-page summary distilling the questions, assumptions, possible reframings, and signposts worth retaining.
NB: The conversation is completely confidential. Happy to sign an NDA. With your agreement, I will record our discussion solely to help me prepare the follow-up accurately.
AFTERWARDS, WHAT MIGHT YOU sEE DIFFERENTLY ?
Perhaps we uncover an assumption you hadn't realized you were making.
Perhaps the question you arrived with turns out not to be the real question that needs to be addressed.
Perhaps a company strength looks different when viewed from another angle — or an apparent weakness.
Perhaps an unlikely possibility becomes plausible enough to deserve attention.
Perhaps we identify something worth watching because it could signal that your business landscape is beginning to change.
Or perhaps the conversation gives you greater confidence that your present thinking is indeed robust.
Please note: There is no guaranteed “Aha!” But I can guarantee that we'll challenge your thinking — several layers deep.
The objective isn't to solve your question in two hours. It's to discover whether there's a more useful way of thinking about it.
WHY ME ?
You certainly know your business better than I do. I don’t ever pretend to be as knowledgeable or experienced as you are. So what do I bring to the table?
In short: a new approach to your issue.
In my two decades of experience working with senior decision-makers and leadership teams, I’ve helped organizations operating in many different industries around the world explore uncertainties and consider alternative futures. Sometimes quite surprising ones.
In the What If? Conversation, my role isn't to arrive with superior knowledge of your industry. It's to understand enough about it to question your assumptions intelligently — and bring an outsider's freedom to ask questions that may not normally get asked.
“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
WHAT IF… ?
Curious where such a conversation might take you?
You don't need to arrive with a perfectly formulated question. An important issue, uncertainty, or possibility that keeps returning to your mind is enough to get started.
Tell me a little about what's on your mind, and we'll take it from there.