A Short Guide to My Thinking on Transformation

Every week someone new subscribes to Chiefly Product and asks me the same question... “Where should I start?”

It’s a fair question. After more than 220 articles, the archive has become large enough that browsing chronologically probably isn’t the best way to understand what I believe. Some essays explore Product. Others focus on AI, Private Equity, leadership, organisational design, or strategy. They often begin in different places and tackle different problems.

Yet the more I’ve written, the more I’ve realised that almost all of them are really attempts to answer the same question.

How do organisations make better decisions under conditions of uncertainty?

That question sits underneath almost everything I do professionally as well. Whether I’m supporting an investor evaluating an acquisition, helping a leadership team rethink its strategy, or working with an organisation adapting to AI, I’m rarely interested in the technology or the process in isolation. I’m interested in judgement. How leaders decide what matters. How organisations choose between competing priorities. Why some transformations compound while others quietly lose momentum.

If you’re new here, I thought it might be useful to pull together a handful of essays that best explain how I think about transformation. They don’t repeat one another, but together they form something close to a philosophy.

Technology dominates almost every conversation about transformation today. That’s understandable. AI, automation, large language models, agentic systems - they all promise extraordinary capability.

It’s tempting to believe that choosing the right technology is what separates successful transformations from unsuccessful ones. I don’t think that’s true.

Technology amplifies whatever already exists. It can accelerate good organisations and expose weak ones, but it rarely fixes poor judgement. Before selecting platforms, building roadmaps, or experimenting with new tools, leaders need to understand what is actually true about their business. Which problems genuinely matter? Where is value created? Which assumptions have gradually become accepted as fact?

Those questions have always mattered. AI simply makes them more important.

If this resonates, I’d suggest beginning with this article, where I explore why discernment has become one of the most valuable leadership skills of the next decade.

Transformation is often described as though it were a programme of work. I’ve increasingly come to think of it as a sequence of decisions.

Every meaningful transformation requires trade-offs. Yet many organisations spend enormous amounts of time trying to avoid making them. New initiatives are added without retiring old ones. Projects accumulate. Priorities multiply. Leaders reassure themselves that they can somehow accommodate one more request, one more feature, one more strategic objective.

Eventually complexity wins.

One of my favourite essays explores what I believe is the most dangerous sentence in any transformation: “We’ll just add one more thing.” It’s such an ordinary phrase that it rarely attracts attention. Yet I’ve seen it derail more strategies than almost any technical limitation.

The longer I spend working with ambitious organisations, the less I think strategy is the limiting factor. Most leadership teams already know, broadly speaking, what they should be doing.

The challenge is that they have committed themselves to more than they can realistically deliver. Strategies become crowded. Priorities overlap. Teams are stretched across too many initiatives. New work begins before existing work has landed. The organisation becomes incredibly busy while making surprisingly little progress.

I’ve gradually come to believe that one of the most important responsibilities of leadership isn’t deciding what to do next. It’s creating enough organisational capacity for today’s commitments to succeed before making tomorrow’s.

Whenever I write about focus, prioritisation, or saying no, that’s usually the underlying principle I’m trying to explore.

Much of my professional work sits between Commercial Due Diligence and Technical Due Diligence. That’s an unusual place to spend a career, but I’ve become convinced it’s one of the most interesting.

Commercial Due Diligence asks whether there’s an attractive market. Technical Due Diligence asks whether the technology is capable of delivering. Neither really answers the question I find myself asking most often… Will customers actually care enough for any of this to matter?

That’s the role Product Due Diligence plays. It connects commercial opportunity with technical execution. Without it, organisations risk building impressive capabilities that solve problems nobody particularly values.

Over the past few years I’ve written extensively about PDD and why I believe it deserves to be recognised as a discipline in its own right rather than being absorbed into either commercial or technical assessments.

If that’s an area you’re interested in, these two essays are probably the best place to begin.

People sometimes assume that writing about AI means writing about tools. I find the organisational questions far more interesting.

Those questions will remain relevant long after today’s tools have been replaced by tomorrow’s. That’s why much of my recent writing isn’t really about AI at all. It’s about how organisations adapt when technology changes the nature of work itself.

If you’d like to explore that theme further, this is a good place to continue.

Looking back over the archive, I can now see something that wasn’t obvious while I was writing individual articles. I’m not really writing about Product, or AI, or Private Equity, or even transformation… Those are simply the contexts in which I happen to work.

What I’m really writing about is organisational judgement. How leaders make better decisions. How organisations choose what matters. How businesses create the conditions for meaningful change rather than simply hoping change will happen by itself.

Everything else - Product, AI, due diligence, strategy, organisational design - is simply a different lens through which to explore those same ideas.

If you’ve only recently discovered Chiefly Product, I hope these essays provide a useful starting point. They won’t tell you everything I believe, but they should explain the questions I find myself returning to time and again.

And if you’ve been reading for a while already, perhaps they’re a useful reminder that, despite appearances, I’ve probably been writing about the same thing all along.