Why 2025 felt turbulent for digital leaders & how to avoid repeating it

Many of the leaders I met with this year were managing shifting priorities, changing budgets, and urgent requests tied to AI or modernization. Plans kept adjusting, and the expectations around digital work shifted with them. Now that we’re nearing year-end, teams are feeling stretched thin and unsure which initiatives are actually moving forward.

I don’t think teams ended up here because they made the wrong decisions, but rather because they were never given the space to make intentional ones.

What made this year so difficult for digital teams:

A few patterns showed up again and again:

• Competing requests from every direction
• AI conversations happening without clear outcomes
• Legacy systems slowing down daily decisions
• Projects starting before teams agreed on what success meant
• Budgets freezing for long stretches, then reopening quickly, and work being picked back up without revisiting whether it still deserved a yes

These challenges added up, creating a working environment where teams have remained in reaction mode far longer than they wanted.

Why firefighting becomes the default:

When outcomes are unclear or priorities keep moving, leaders often try to accommodate as much as possible. Work that paused during budget freezes tends to come back into the queue once funding returns, even if the context has changed.

Over time, teams end up carrying more than they can deliver, and work piles up without clear sequencing, sizing, or connection to a business result. In that environment, stalled initiatives accumulate quietly, and it becomes hard to tell which efforts are gaining traction and which ones are simply absorbing energy.

How to break the cycle in 2026:

As frustrating as they are, stalled projects reveal something useful. They highlight where alignment wasn’t strong enough, where capacity was unrealistic, or where the problem wasn’t defined in a way teams could act on. A turbulent year brings these gaps into view, which gives you a chance to reset before they carry forward.

A helpful reset starts by narrowing your focus and giving the most important work enough room to succeed. I call this digital discipline (and I outlined the full framework here if you want to dig in).

There’s one question I use often with leadership teams because it brings clarity quickly: “If we take this on, what will have to wait?”

This prompt helps teams understand the implications of each choice and commit to priorities in a way people can rally around.

A simple way to evaluate what deserves attention:

When leaders sort through the work ahead, these four lenses help conversations move from instinct to clarity:

• Impact: Will this create measurable business progress?
• Alignment: Does it support the direction we’ve already committed to?
• Capacity: Do we realistically have room to deliver?
• Momentum: Can this show meaningful results in the next 6–12 months?

These questions help you see which initiatives are ready to move forward and which ones should wait.

As you close out the year, one short conversation with your core team can bring needed clarity. Look at where progress actually happened, where work stalled, and where you might pause efforts so your top priorities have space in the first quarter.

If you’re looking at your 2026 priorities and want a sounding board, feel free to reply. I’m always glad to think through it with you.

Talk soon,

Josh