Why “We’ve Always Done It This Way” Is Killing Your IT Strategy

Every IT department has a phrase that haunts it. It's muttered in meetings, scribbled into project notes, and occasionally weaponized to shut down new ideas. You know the one. “We’ve always done it this way.”

That little sentence has tanked more progress than any technical glitch ever could. It’s the perfect excuse to avoid rethinking a bad setup, skip a review of old systems, and keep duct-taping things until they eventually break at the worst possible moment. It’s comfortable. It feels safe. And it slowly drags your entire IT strategy into a swamp of outdated tools, reactive fixes, and missed opportunities.

No one wakes up and says, “Let’s make our business less efficient today.” But that’s exactly what happens when decisions are based on habit instead of usefulness. When no one stops to ask, “Is this still the best way to do this?” things stagnate. The systems stay the same. The problems pile up. And eventually, the IT team becomes a group of firefighters instead of strategic operators—always reacting, never leading.

You don’t need to overhaul everything. But you do need to be honest about what’s working, what isn’t, and what’s only still standing because nobody wanted to rock the boat. If “the way we’ve always done it” was designed for a team of 20 people five years ago, it’s probably not helping your team of 100 today.

Let’s talk about how that mindset creeps in, how it silently wrecks your IT foundation, and how to shake it off without sending your whole team into a panic.

The phrase usually shows up during budget season, system audits, or onboarding a new IT leader. Someone suggests switching tools, tightening access, or—heaven forbid—documenting processes. And someone else, with just enough confidence, says, “We’ve always done it this way.” Cue the nodding. Cue the silence. Cue the plan getting quietly scrapped.

This is how bad decisions stick around. The password-sharing setup from 2016? Still in place. That dusty server in the back closet that everyone’s scared to touch? Still humming along. That one login everyone shares because “it’s just easier”? Still completely unsecured. Nobody meant for it to stay that way—it just never got questioned.

Sometimes, it’s not laziness—it’s fear. Fear that changing something will break something. Fear that revisiting old systems will uncover more mess than anyone wants to deal with. So everyone agrees, silently or not, to just keep things as they are. After all, if it’s technically working, it must be fine… right?

Wrong. Because “technically working” is often one spilled cup of coffee away from “why is everything offline?” When systems evolve without structure, you end up with overlapping tools, forgotten users, and a setup that no one fully understands—except maybe Bob, who retired last month and took all his notes with him.

This mindset also kills innovation. IT isn’t just there to fix broken printers. It should help teams move faster, do more, and stay secure while doing it. But if the team is stuck maintaining a spaghetti mess of old tools and patched-together solutions, there’s no room to build anything better. They’re too busy keeping the wheels on.

And let’s talk about documentation—or the lack of it. “We’ve always done it this way” becomes a nightmare when nobody knows why it was done that way in the first place. Was it a temporary workaround from three IT managers ago? A quick fix that accidentally became the permanent setup? If the answer lives in someone’s memory and not on paper, it’s already a liability.

Leadership plays a role here too. If decision-makers aren’t asking for reviews, updates, or post-mortems on what’s working, the IT team has no reason to challenge the status quo. So the cycle continues. Old tools stay in place. Old problems never get solved. And the IT strategy slowly morphs into a collection of “meh, it’s fine.”

The good news? This isn’t about tearing everything down. It’s about creating space to question, to review, and to rethink. It’s about asking, “If we were starting from scratch, would we still do it this way?” That one question can shine a spotlight on everything from bloated software stacks to gaping security holes.

Conclusion

If you’re hearing “we’ve always done it this way” more than you’d like to admit, take it as a warning. Not because your team is lazy or careless—but because things have probably gone too long without a real gut check.

The stuff that “technically works” is often the stuff quietly holding you back. Not in dramatic ways, but in slow, everyday friction that wears down your team and drains your resources. Sticking with the old way just because it’s familiar doesn’t make it smart—it just makes it familiar.

You don’t have to change everything all at once. Just start asking better questions. Look at what’s running on autopilot. Decide what actually serves your business today—not what worked five years ago for a totally different setup.

And maybe next time someone says, “We’ve always done it this way,” you’ll finally have a better answer.