I have been in a lot of conversations about AI recently. A lot. Most of them follow roughly the same arc. Someone mentions agents. Someone mentions headcount. Someone calculates efficiency savings. And then, usually within the first ten minutes, the word “jobs” appears, followed by a slightly uncomfortable silence.
So when Whynde Kuehn joined me on Whatever Next? Unplugged and the conversation went somewhere entirely different, I noticed. She talked about the world we could build. Not the efficiencies we could extract. The world.
That distinction matters more than it might seem.
Whynde is the founder of S2E Transformation, an author, and one of the sharpest strategic thinkers I have spoken with about what organisations are actually doing with AI versus what they could be doing. She is not a sceptic. She is not a cheerleader either. She is something rarer: a practitioner who is genuinely asking the harder question.
That question is this:
If we are going to use AI to transform how organisations work, what kind of organisations are we actually trying to build?
Not “which processes can we automate?” Not “what does the business case look like?” Not “how do we upskill the workforce for the new tools?” Those are real questions. They are just not the first question.
The first question is about intent. What are we building this for? And in most organisations, that question is being skipped.
Whynde described walking into room after room where seventy-five percent of the conversation is technical and twenty-five percent is human. She is trying to flip that ratio. Not because the technical conversation is wrong, but because it is happening without the strategic conversation that should be framing it.
Start at the strategy table. Ask what this means for your business model. Ask what kind of organisation you want to become. Then bring in the technology.
Simple sequence. Rare in practice.
After we finished recording, I found myself sitting with the conversation for longer than I usually do. Something in it was familiar. Not just as a conversation about AI. As a description of something I had been writing about.
I went back to the Reimagine lens, one of The Five Human Lenses of Transformation™ in Whatever Next?, and re-read it. Whynde had not been describing a theory. She had been living it. The world she was envisioning, the one she wants organisations to start building toward, maps directly onto the conditions I argue have to be in place for transformation to work at all.
Not as a checklist. Not as a methodology. As a set of questions that most organisations are either not asking yet, or asking in the wrong order.
So this post is my attempt to bring those two things together. Whynde’s vision of what becomes possible. The Reimagine lens as a way of seeing that could help organisations actually get there.
The Reimagine lens begins with a provocation. If we do not intentionally reimagine the future we want, we risk executing flawlessly on plans that no longer matter.
That is not a warning about laziness. It is a warning about the cost of skipping the intention question. You can build an excellent roadmap. You can govern it well, resource it properly, and deliver on time. And still end up somewhere nobody actually wanted to go.
Whynde is watching this happen in real time. Organisations are deploying AI with discipline and rigour. The agents are running. The dashboards are full. And the first question, that was never asked:-
What do we actually want to become?
Intention is not vision-statement writing. It is not a slide about purpose or values. It is the answer to a harder question: what are we saying yes to here, and what are we choosing not to be? That question belongs at the start of the AI conversation. Not after the pilots. Not when the resistance surfaces. At the very start.
Most organisations skip it because it feels philosophical. It is not. It is the most practical thing you can do. Without it, everything downstream is guesswork dressed up as strategy.
The second place where Whynde’s conversation and the Reimagine lens meet is on the question of who gets to be in the room.
She described the best organisations she has seen. The ones where customer personas are visible everywhere. Where the mission is spoken at the start of meetings, not filed away after the annual offsite. Where teams work end to end toward shared purpose rather than optimising their own corner of the process. Where a person in any role can point to how their work connects to what the organisation is trying to become.
That is not culture by accident. That is collective vision, made operational.
The Reimagine lens asks a pointed question here: who gets to be in the room when we imagine the future? Because the answer shapes everything that follows. If the future is imagined by the same people, using the same assumptions, in the same formats they always have, the result is not reimagination. It is incremental change with better branding.
Whynde is not asking organisations to run bigger workshops. She is asking them to widen the circle of whose experience, whose knowledge, and whose perspective shapes what comes next. That is a governance question as much as a culture question. It is about who has legitimate authority to define the future, not just who is available to attend a session.
And it matters enormously for AI. Because if the people closest to the work, the ones who know where the friction is, where the workarounds live, where the judgement calls happen every day, are not in that room, you are designing with incomplete intelligence. No matter how sophisticated the model.
Whynde used the word “leapfrog.”
She was describing organisations that have the opportunity, right now, to stop incrementally improving broken models and instead to design for what they actually want to be in ten years. AI makes that possible in ways it was not before. The constraint is not technical. It is cognitive. Most leadership teams cannot hold a ten-year horizon and a quarterly pressure simultaneously. One of them always wins.
The Reimagine lens calls this Decade Thinking. Not as a planning exercise, but as a permission structure. When you give people genuine distance from the present, something shifts. The sunk-cost logic loosens. The inherited assumptions start to look optional rather than fixed. People stop asking “how do we improve what we have?” and start asking “what would we build if we were starting from what we actually know today?”
That is a different conversation. It produces different ideas. And it tends to surface the assumptions that were quietly limiting the first conversation, the ones nobody named because they felt like facts rather than choices.
The question I find most useful in this space: what are we doing now that our future selves will thank us for? It sounds simple. It is surprisingly hard to answer. Because it forces you to think about legacy, not just delivery.
This is where I think the conversation gets most interesting. And most uncomfortable.
Whynde made an observation that was really worth hearing. She said she sees it completely differently from most people in the room. Where others see AI as an automation play, she sees it as the prompt to redesign the business model. To ask what the technology makes strategically possible, not just what it makes operationally efficient.
The Reimagine lens frames this as what AI is actually revealing. Not just what it can do, but what it exposes about how we currently work. AI makes friction visible. It makes assumptions legible. It shows us, in ways that are hard to ignore, where our structures are built around the limitations of an older set of tools rather than the needs of the work.
If we respond to that by automating the existing structure faster, we miss the point. We accelerate the problem.
If we respond by asking what the structure was designed to achieve, and whether AI gives us better options for achieving it, we have a genuinely different conversation. One that connects technology to purpose rather than technology to efficiency.
This is not anti-efficiency. Efficiency matters. But it is a means, not an end. And organisations that treat AI primarily as an efficiency mechanism are making a choice about what they value. Often without realising they are making it.
The final piece of Whynde’s vision and the one that connects most directly to why the Reimagine lens exists in the first place is about structure.
She described an architecture-driven future. End-to-end accountability. Teams organised around capabilities rather than functions. Change management as the first thought, not the last. Organisations built for learning and adaptation rather than just execution.
She called capability thinking “the keystone.” I think she is right. Because capability is the connective tissue between strategy and experience. It is what allows intent to flow through structure and land in practice.
The Reimagine lens is clear on this: reimagination without structure evaporates. Ideas that are not given form return to the old logic. The vision Whynde is describing does not happen because organisations feel inspired. It happens because they make structural choices that reinforce the direction.
That means asking what form the future will take. What values it will be built around. What governance will protect those values when the quarterly pressure arrives, as it always does. What the operating model looks like when human judgement and AI insight are working together rather than in competition.
These are architecture questions. They are also human questions. They cannot be answered by the technology alone, however sophisticated it becomes.
Whynde closed our conversation with a question.
What if?
Not as a rhetorical gesture. As a genuine provocation.
What if we took this moment seriously?
What if we stopped optimising the past and started designing for what we actually want to be?
What if AI gave us the opportunity not just to work faster, but to work differently, with more humanity, more purpose, more coherent connection between what organisations say they value and how they actually operate?
That disconnect is the human gap: the distance between the plan and what people actually believe, experience and do.
The Reimagine lens in Whatever Next? is built around the same two words. Because I have spent enough time inside transformation programmes to know that the question “what if?” is far rarer than it should be. Most organisations do not suffer from a lack of capability. They suffer from a lack of permission to imagine something genuinely different.
The permission has to be created deliberately. Someone has to ask the question first. Someone has to hold open the space long enough for an honest answer to form.
Whynde is doing that in every room she walks into. The question is whether enough people will join her.
If you are leading a transformation, or sitting in a room where AI is being discussed as a technical and operational challenge, here is what the Reimagine lens suggests you do.
Ask the intention question before the solution question. What kind of organisation are we trying to become? Not what do we want AI to do. What do we want to be known for in ten years?
Widen the circle of who shapes the answer. The future imagined only by those with the most to gain from the current model will look a lot like the current model. Bring in the edges.
Use AI as a mirror before you use it as a tool. Look at what it reveals about how you currently work, where the assumptions are, where the friction is buried. That reflection is often worth more than the first wave of automation.
Give the future a structure, not just a story. Vision without operating model is aspiration. Find the keystone that Whynde is describing the capability architecture that connects intent to experience and build toward it deliberately.
And if you are the person in the room who is still asking “what if?” when everyone else has moved on to the roadmap: keep asking. That question is doing more work than it looks like.
Whatever next?
Listen to my full conversation with Whynde Kuehn on Whatever Next? Unplugged:
