How Might We is not built from the neatest parts of my CV.
It comes from the whole lot: the things that worked, the things that did not, the decisions I would make again and the ones I would approach very differently now.
I have had successes I am genuinely proud of. I have also failed hard, worked with tight budgets and over-egged targets, and seen brilliant people make difficult situations better.
Sometimes the outcome was within our control. Sometimes market change, timing or luck shaped it instead. That has made me less interested in performing certainty and more interested in finding the question that earns a useful answer.
That is where the name comes from: experience without the pretence that experience supplies every answer.
A default mindset
For me, How Might We is not a workshop technique. It is closer to a default setting.
When there is an obstacle in the way, my instinct is to look for a route: how might we get around it, work through it, remove it, learn from it or decide it is pointing us somewhere better? That does not mean forcing a positive spin onto every problem. It means refusing to treat the first obstacle or the first answer as the end of the conversation.
That is one reason books such as Ryan Holiday's The Obstacle Is the Way resonate with me. The idea is not that every setback is secretly wonderful. It is that how we meet the obstacle changes what happens next.
That instinct was present long before it became the name of a business. Naming How Might We simply made the mindset visible.
What growth has taught me
When growth falters, it is rarely because the people in charge do not care. They are usually working extremely hard, often too hard to step back and see the whole picture.
The problem is more likely to be a missing destination, competing priorities or too many plates spinning at once. Sales, marketing, customer, delivery and leadership may all be busy, but not properly connected. Failures happen, yet the learning does not travel. People spend all their time working in the business and none working on it.
Or everybody is simply too close. Too far inside the jar to read the label.
I have been that close myself. It is easy to mistake effort for progress when you are living inside the pressure. The question creates a little distance: enough to see the situation honestly and choose a practical way forward.
How
How asks for a route, not just an aspiration.
Businesses are usually good at stating ambition. We want to grow. We want to become more customer-led. We want sales and marketing to work together. We want to move faster.
The harder question is how. How will we choose? How will teams work differently? How will customers notice? How does this become more than another conversation or a strategy sitting in a folder?
How keeps ambition grounded. It asks us to turn intent into something people can actually do.
Might
Might creates possibility without pretending certainty.
I have seen confident plans work brilliantly. I have also seen confident plans fall apart. Experience does not make uncertainty disappear; if anything, it makes you more respectful of it.
Might gives us room to examine the first answer. The diagnosis could be wrong; the thing we want to do may not be the thing the business needs.
That openness is not indecision. It is a commercial discipline. False certainty is expensive, especially when it sends capable people working hard in the wrong direction.
We
The ‘we’ recognises that no one person sees the whole picture.
The founder sees one thing. Sales hears another. Marketing works from a different set of signals. Delivery knows where the promises become painful. Finance sees the commercial reality. Customers experience the combined result, not the organisation chart.
I have learned most from working alongside other people (clients, colleagues, leaders and teams) rather than arriving as the person with the answer. The ‘we’ does not mean consensus or another workshop where the sticky notes have a more successful career than the ideas. It means involving the people whose experience can change the quality of the decision.
A question that includes me
The name also keeps me accountable.
How Might We cannot just be something I ask of a client. I have to turn it on myself. Am I listening properly? Have I jumped to the familiar answer? Am I avoiding an uncomfortable possibility? Am I making the complexity useful, or merely making it sound impressive?
We can also become somewhere to hide. Shared responsibility can easily become nobody taking responsibility. Sometimes the more useful question is How Might I? What am I protecting, avoiding or failing to ask?
The work should be collaborative, but it still needs ownership, including mine.
Not blind optimism
How Might We can sound relentlessly upbeat, as if every obstacle should end with a bigger idea and an enthusiastic yes.
That is not what it means to me. Sometimes the answer is no. Sometimes it is not yet. Sometimes the useful move is to simplify, stop or change direction.
A good growth conversation should be safe enough for honesty and challenging enough to find clarity.
"I don't know yet" can be a stronger starting point than a confident answer nobody really believes.
The question behind the business
How gives us a route.
Might opens possibility.
‘We’ brings in the people.
Together, they describe how I approach obstacles and change: understand the reality, stay open to a better possibility and work out how to move.
How Might We is not a claim that I know everything. It is almost the opposite.
It is the mindset that all my experience (success, failure and everything less tidy in between) has led me to trust.