Strategy Doesn't Fail for Lack of Commitment

I've spent my career working in and leading organisations; from 20-person startups to 600-person scale-ups. Every single one struggled with strategy. Not in the obvious ways you might think. These weren't companies filled with people who didn't care or didn't try. Quite the opposite.

The leadership teams I worked with invested serious time and money into getting strategy right. They brought in consultants, ran off-sites, created frameworks. Everyone was genuinely committed to making it work. The CEO cared. The exec team cared. The middle managers cared. And yet, somehow, it still fell short.

Over time I spotted some recurring patterns. The problem wasn't motivation or investment. It was something more fundamental.

The Three Walls We Always Hit

The first wall showed up during strategy creation. We'd start strong - vision, mission, maybe some objectives. Then we'd need to translate that into actual work. How detailed should we get? Too vague and nothing happens. Too detailed and we'd spend six months in planning purgatory, arguing about implementation specifics that would change anyway.

We'd inevitably choose one extreme or the other, and both sucked.

The second wall appeared when we tried to communicate the strategy. A 40-page deck looks comprehensive in the boardroom. But when your product manager is deciding between two features at 3pm on a Tuesday, they're not opening that deck. They're making their best guess about what "customer-centric innovation" actually means for their roadmap.

The strategy existed. People just couldn't use it when it mattered.

The third wall was measurement. We'd set these big strategic goals and then... life happened. Urgent customer issues. Unexpected competitor moves. That new market opportunity that just opened up. Three months later, someone would ask "how are we tracking against the strategy?" and we'd realise we had no idea. The day-to-day had swallowed everything.

This wasn't happening once. It was happening everywhere I worked. And when I talked to Khoi and Martin, my co-founders, they'd seen exactly the same patterns in their organisations. Different industries, different sizes, same fundamental problems.

Why Now? Why Technology?

You might ask: if this has always been hard, why try to solve it now?

Two things changed.

First, we realised the core issue wasn't that people needed better strategy frameworks. It wasn't that they needed more training or better consultants. They needed something that would do the grinding work they simply didn't have time for.

Good strategy work requires iteration. It requires translating high-level goals into operational reality, then back again. It requires keeping everything updated as circumstances change. It requires making information accessible when decisions need to be made, not just during quarterly reviews.

People wanted to do all of this. They just couldn't. There weren't enough hours in the day.

Second, generative AI finally became good enough to help. Not good enough to replace human judgment—we'll come back to that—but good enough to handle the mechanical work that was eating everyone's time.

AI can take a strategic goal and draft the detailed actions needed to achieve it. It can take a complex strategy and generate different views for different audiences. It can track progress against objectives and surface what's falling behind. It can answer "how does this decision relate to our strategy?" in real-time.

These aren't revolutionary capabilities. They're exactly what organisations have been trying to do manually for decades. But manually, they're too time-consuming to sustain. With AI, they become practical.

The Human in the Loop Isn't Optional

Here's what I'm not saying: AI will write your strategy for you.

Current AI systems have a useful property: they make skilled people more effective. If you understand the core of your strategy, if you know what good looks like, AI becomes an incredibly powerful tool. It amplifies your capabilities. It handles the grunt work so you can focus on judgment and direction.

But if you don't understand the central themes of your strategy, AI makes you dangerous. It'll generate something that sounds impressive but doesn't actually work. It'll miss critical context. It'll optimise for the wrong things.

We're not trying to eliminate the need for strategic thinking. We're trying to eliminate the tedious parts that prevent people from doing enough strategic thinking.

The human provides the judgment, the context, the knowledge of what matters. The AI provides the capacity to act on that judgment at scale.

So We Built Something

Ciclo Strategy is our answer to these problems. It's not a replacement for strategic expertise. It's a tool that lets organisations with 10-200 people actually execute on the strategic work they know they should be doing but currently can't.

We're building it for the mid-market organisations we've worked in; companies large enough to need real strategy, small enough that they can't afford dedicated strategy teams. Where the CEO and leadership team know what needs to happen but don't have the bandwidth to make it happen.

If you've ever finished a strategy session thinking "this is good, now how do we actually make it work day-to-day," we're building for you.

Because strategy shouldn't fail for lack of time. It should fail or succeed on its merits. And we can finally make that happen.