I’ve sat across from a lot of leaders—nonprofit operations directors trying to stretch limited grants, startup COOs scaling like their hair’s on fire, and SMB owners juggling twelve different roles. Different goals, different industries, different pressures—but I keep hearing the same question:

“What should we actually be planning for in our IT next year?”

It’s a fair question, and a hard one—especially with the way things keep changing. In the last few years, we’ve seen dramatic shifts in how people work, how threats evolve, and how technology either holds teams back or helps them fly.

So I want to offer a grounded take on what your IT roadmap might look like in 2025. Not as a list of fancy trends or buzzwords—but as a working document you can actually use to guide decisions, reduce stress, and future-proof your organization.

Let’s get into it.

Start With the Honest Conversation

Before you draw up a roadmap, have a real conversation with your leadership team. What’s working? What’s not? Where are people constantly putting out fires?

A roadmap isn’t just a tech document. It’s a health check for your entire organization. Are your systems supporting your goals—or quietly slowing you down?

When I work with new clients, I often start by asking:

• Where do you feel least confident about your IT setup?

• What’s the worst-case scenario that keeps you up at night?

• What would make your day-to-day life feel lighter?

The answers to these questions shape everything else. You’d be surprised how many teams are one system failure or data breach away from chaos—and don’t know it until it’s too late.

The Silent Cost of “Just Dealing With It”

Many organizations are operating with “invisible tech debt.” Systems that technically work, but require a ton of manual effort, workarounds, or luck to keep running.

Imagine working with a nonprofit that used to reboot their donor database server once a week because it kept freezing. It would become normal for them. But it would be quietly wasting hundreds of hours a year—and worse, they wouldn't trust the system during the fundraising season.

That’s why your 2025 roadmap should begin with identifying these friction points.

Not everything needs to be replaced right away. But naming what’s broken (or barely holding together) gives you power. It lets you prioritize upgrades before they become emergencies.

Stability First, Then Strategy

There’s a lot of talk in tech circles about innovation, AI, automation, and transformation. I love a good new tool as much as anyone. But most of our clients don’t need the latest thing—they need peace of mind.

And peace of mind starts with stability.

If your team doesn’t know whether the Wi-Fi will work during a presentation, if your backups haven’t been tested in six months, if you’re not sure who has access to what—then you’re not ready for the “strategic IT” phase yet.

Lock down the basics first:

• Do you have consistent, fast connectivity at all sites?

• Are your endpoints secure and up to date?

• Are backups running and restorable?

• Do people know who to call when something breaks?

Only when your foundation is stable does it make sense to talk about roadmaps for scale, automation, or analytics. Strategy without stability is just a wishlist.