The first strategy I created as CTO of Storio was months in the making, pulling people away from their day jobs, despite some genuine benefits in bringing two recently merged cultures closer together, ultimately failed to return on this investment.

Before we kicked off a strategy refresh I first spent time reflecting on why. I want to share those lessons here because I think they apply well beyond my own experience and because they have fundamentally shaped how I approach strategy now.

The context

Around six months into the role I kicked off my first strategy process. Storio had recently been through a merger and every function was tasked with creating a vision for their future state. I also had two completely separate engineering organisations, each accountable for their own systems. Bringing them together under a shared direction felt like the right first move.

It was. The process itself wasn't the problem. The way I approached it was.

No company strategy to anchor to

At the time the company's long term strategy was still being developed. That meant I was building a technology strategy in isolation, without a clear end state to work towards.

Strategy should be reductive. It should make decisions easier by giving people a lens to evaluate options against. Without a guiding company view that lens doesn't exist and technology becomes a function optimising for its own goals rather than enabling the business.

The lesson: don't build a functional strategy ahead of the company strategy it needs to serve. If the business direction isn't clear yet, focus on foundations and how to enable future decision making.

Not enough time understanding the current state

We moved too quickly into defining the future without making sure everyone was on the same page about today. And by everyone I don't just mean the technology function. I mean the executive team and the other functions that depend on technology every day.

This gap didn't show itself immediately. It surfaced when we started implementing and realised that the wider organisation wasn't aligned with the need for change or the reasoning behind it.

The lesson: invest in current state alignment before you define the future. Make sure the people who will need to support and fund the change understand and agree on the problems you are solving.

A twenty-page document nobody used

Without clear outcomes defined up front we ended up producing a twenty-page strategy document. The debates that went into it were genuinely valuable but the artefact itself was too detailed for anyone outside the process to engage with. It required too much time investment to read, let alone act on.

The specificity also worked against us. We had come from a highly autonomous culture with a diverse technology stack. Being prescriptive about solutions meant every recommendation carried a huge cost of change across different teams and contexts.

The lesson: define how the strategy will be used in practice before you start creating it. If the goal is organisational alignment then the format needs to be accessible, concise and flexible enough to accommodate different starting points.

Too insular to drive real change

This was a technology strategy built by the technology function. The problem is that technology at Storio is an enabler for almost everything the business does. Delivering on our strategy required changes across multiple functions, not just our own.

Because it was created in isolation it lacked the cross-functional buy-in needed to drive those wider changes. The size, format and complexity of the document compounded this by making it hard to socialise beyond our own teams.

The lesson: if your function is an enabler then your strategy cannot live inside your function alone. The people who need to change their behaviour to make it real need to be part of creating it.

What this taught me

Looking back, these challenges share a common thread. Each one was a symptom of building in a silo. Siloed from company strategy, from shared understanding of the current state, from how the output would be used, and from the people who needed to act on it.

We still delivered on our wider organisational ambitions in spite of the strategy rather than because of it. That is not a position I wanted to be in again.

These learnings have fundamentally shaped how I think about creating strategy and what I believe makes one successful.