When to fire your technology

Once you’ve added something to your tech stack, it can easily go on autopilot. Before long, another renewal notice arrives and another charming account rep wants to schedule a “quick check-in.” When this happens, you face a decision: should this technology stay, should it go, or should you consider switching to a different vendor?

According to the Spiceworks State of IT Report, 59% of business technologies are currently candidates for vendor changes. That’s more than half your stack potentially on the chopping block.

Most IT departments lack a systematic approach to handling this all-too-common challenge. We’re excellent at evaluating new technology purchases with formal processes, approval workflows, and ROI calculations. But when it comes to deciding whether to keep investing in solutions we’ve already approved, we rely on gut feeling, budget panic, or waiting until a vendor dispute makes the decision for us.

Over the long term, this decision paralysis creates an even more difficult IT management problem: technical debt. According to Gartner, about 40% of infrastructure systemsOpens a new window across asset classes have technical debt concerns. We’re maintaining systems not because they deliver value, but because we haven’t figured out how to get rid of them yet.

Creating a technology lifecycle framework before you need it

Waiting until your CFO demands budget cuts to start evaluating tools is like waiting until your car won’t start to think about oil changes. You need a proactive framework that continuously runs, so you’re not stuck reacting to crises.

A solid technology lifecycle framework has four components:

• Regular review cycles: Quarterly for critical systems, bi-annually for everything else.
• Clear evaluation criteria: Define these upfront so everyone agrees in advance.
• Documented decisions: Future you needs to remember why you kept that weird legacy system.
• Stakeholder communication plan: Surprise tool eliminations never go well.

Build this framework during calm periods (I know ”calm periods” is a relative term when you work in IT). Doing so protects you from vendor lock-in and falling prey to the sunk cost fallacy. You might be able to free up some budget and gain some flexibility in the process.

This approach also helps you head off tech debt in advance. Gartner estimates that by 2028, I&O leaders using structured methods for managing infrastructure technical debt will report 50% fewer obsolete systems than those who don’t.

Measuring what matters beyond basic usage stats

So how do you know if you should keep a particular technology? If nobody’s logged into a tool in six months, that’s a clear signal, but most elimination decisions are murkier than that and require looking at metrics that actually reveal value.

Track these metrics instead:

• Business outcomes: If you bought project management software to reduce missed deadlines, are deadlines being met?
• Integration complexity: How much babysitting does this tool require?
• Support ticket volume: High counts signal the tool isn’t working well.
• User satisfaction: Quick quarterly check-ins beat annual surveys nobody reads.
• Redundancy: Are three departments using three tools for the same task? Then you’ve got an optimization opportunity.
• Security overhead: Tools outside your SSO system could cost your business much more than license fees.

Hidden costs show up in staff time, security reviews, and the cognitive load of remembering which tool does what. Build simple dashboards that regularly surface this information, so you can base your elimination decisions on evidence instead of just politics (we’ll get to that).

Asking the hard questions about your technology

Now that you know what to measure, you need to figure out which strategic questions to ask about the tech in your environment. Not every evaluation requires the same rigorous analysis, but every tool should pass these basic tests.

Create standard evaluation questions:

• Does this technology solve a problem we still have?
• Could we accomplish the same outcome with other existing tools?
• What would break if we removed it tomorrow?
• Are we using it because it’s useful or because we paid for it?
• Does it create more work than it saves?

Once you’ve answered these questions, sort tools into three buckets:

• Consolidate: Same function as another tool
• Replace: Function needed but wrong tool
• Eliminate: Function no longer needed

Each bucket requires a different action plan. Consolidation means you’re keeping the functionality but moving it elsewhere—same outcome, better tool. Replacement means the function still matters but you’ve chosen the wrong solution. Elimination means the underlying need has changed and the function itself is no longer necessary.

Navigating the politics of technology elimination

Removing technology is always political. Someone chose it, their department uses it, and their budget paid for it. In this context, getting rid of a tool isn’t just a black-and-white decision based on cold, hard facts. It’s also a delicate dance. You’re not just eliminating software—you’re potentially telling people their judgment was wrong or their needs don’t matter.

Shadow IT creates extra complications. When departments buy their own tools outside IT oversight, they feel ownership over those tools. If marketing purchased their project management platform because IT’s approval process took too long and now you want to eliminate it for your enterprise solution, they’ll resist. And in this case, they’ll have a point.

So, focus on outcomes over cost-cutting when presenting elimination decisions to your coworkers. Instead of “we’re removing this to save money,” try “consolidating these tools will give everyone better support, stronger security, and reduce time spent tool-switching.” If you show them what they’re gaining instead of leading with why they can’t or shouldn’t have something, the conversation will go more smoothly.

If it looks like IT is just unilaterally making decisions without buy-in from the business, you’re probably going to get pushback. Talk to power users, department heads, and key stakeholders. Seek to understand their concerns and adjust your plan when they raise valid points. By announcement time, everybody should be on the same page.

Streamlining your tech stack without creating chaos

Moving fast is tempting, especially when you’re extremely busy, but you end up breaking things more often than not. A phased approach prevents the disasters that give IT a bad name. Nobody wants to be the person who accidentally nuked everyone’s projects because they jumped the gun.

Follow these steps:

• Communicate early: Announce eliminations at least 90 days before they happen.
• Handle data carefully: Provide your users with specific export instructions instead of giving them vague “save your data” directives.
• Offer real training: Don’t assume people will figure out how to adjust to technology change on their own.
• Build grace periods: Run old and new systems in parallel for a limited time. Yes, it costs money, but it prevents productivity crashes.
• Establish support: Designate team members for questions, create documentation, and hold office hours.

Once you’ve removed the tool, confirm that you achieved the intended result. Document your findings so you can begin creating a track record of successful eliminations, which establishes your credibility for future recommendations.

Taking the first step to technology simplicity

If all of this seems like too much to take on right now, that’s ok. You can start small and build from there.

Pick one underperforming tool this quarter and run it through a proper evaluation framework. As you go, document the lessons—stakeholder resistance you didn’t expect, data that changed minds, assumptions that turned out wrong. You’ll develop the muscle memory for elimination before tackling your entire stack, and those early lessons will save you time on bigger projects later.

Six months from now, when you’re managing fewer obsolete systems and earning kudos from the CFO, you’ll be glad you started.