A new year feels like a reset.

Every conversation we start — whether it’s with engineers deep in the detail or people sitting in the core decision-making space — comes with a fresh set of possibilities. But only if we slow down enough to actually use them.

Most transformation work doesn’t fail because people disagree. It fails because everyone is answering a different question.

Engineering is thinking about feasibility and architecture.
Finance is thinking about cost and run-rate.
Leadership is thinking about risk, timing, and confidence.

All valid perspectives. But unless they’re aligned, the conversation just circles.

Transformation isn’t about moving tech

Transformation is often described as moving from one stack to another. In practice, that’s the least interesting part.

What really matters is whether the outcome fits the need, not just the want.

That only happens when we spend time asking the right questions — carefully, methodically, and sometimes more slowly than feels comfortable. I know the pressure well: timelines are tight, people want answers, and there’s always a sense that we should already be moving.

But skipping this part doesn’t save time.

It creates loose threads.

Those loose threads always come back later — usually when it’s more expensive, more political, and harder to fix. The cost isn’t just financial. It’s time, trust, and momentum.

Why I rely on structure (probably more than most)

One of the reasons I lean so heavily on workshops is simple: my brain loves structure.

Clear goals.
A defined space for discussion.
A way to stop ten parallel conversations happening at once.

The structure isn’t there to restrict thinking. It’s there to focus it.

In early sessions, I’m not interested in architecture or tooling. I’m interested in alignment:

  • What does success actually mean here?
  • Which risks matter now?
  • What genuinely moves the needle?
  • Where does ownership really sit?

Once everyone is answering the same questions, the conversation tightens naturally. Not because we rush it, but because we stop talking past each other.

What often looks like misalignment isn’t disagreement at all — it’s mismatched questions.

Listening (with mixed success)

There’s a reminder I try to keep in mind — with mixed success:

“We have two ears and one mouth so that we can listen twice as much as we speak.”
— Epictetus

It’s easy to feel the need to fill silence, to resolve every thread immediately, to demonstrate progress by talking.

But some of the most important signals only surface when you let a conversation breathe. When you listen long enough for people to say the thing they weren’t sure they were allowed to say.

That’s usually where the real work starts.