I keep noticing the same thing in different businesses.

Systems go in. A lot of work goes into them. People try hard to make them succeed.

And yet, I’m often left with the sense that some of the underlying problems are still there.

When I think about why that happens, I usually end up back at the same place — the solution gets chosen too early. Once a tool or platform is locked in, everything that follows is about making it work, not questioning whether it was the right thing in the first place.

I’ve seen this most clearly with infrastructure. People lean on what they know. I get it — familiarity feels safe, especially when you’re responsible for keeping things running. But I’ve also watched that familiarity quietly shape decisions, even when the business context is different from before.

With SaaS and applications, it plays out differently but lands in a similar spot. Decisions happen inside teams. They know their space well, but not always how it fits into the wider picture. The gaps don’t show up straight away. They appear later, when changing course is expensive.

None of this feels malicious or careless.

If anything, it feels like experience doing what experience does — narrowing your field of view.

That idea stuck with me after reading an interview with Ricardo Amper from Incode Technologies. He talked about valuing people who haven’t built up too many assumptions yet, because they start from first principles. It made me wonder how often “knowing too much” gets in the way of asking the right questions.

I’ve found that when I’m most useful, it’s early on — when things are still unclear, when the problem isn’t well defined, and when there’s a bit of discomfort in the room. That’s usually where the real work is, even though it doesn’t look like progress yet.

I still care a lot about technical depth. It matters.

But the longer I do this, the more I think good IT leadership is less about having the answers and more about staying curious for longer than is comfortable.

The best outcomes I’ve been part of didn’t come from clever tools. They came from slowing down early, resisting the urge to jump to solutions, and being honest about what we didn’t understand yet.

That’s the mindset I keep trying to hold onto — even when everything around me is pushing for quick decisions and familiar answers.

Image – Tasmania, Derby on a moutain bike trip. The early morning fog burning off.