Click to learn more about author Leon Adato.

Being careful and steady can carry IT professionals through a number of rough spots, but eventually, even the best technology gets old and jammed up with digital duct tape—patches, workarounds, and inefficiencies. When is it time to take that legacy jalopy out for a final ride? This is likely one of the most difficult decisions you’ll have to make, considering that if you leave too early, you’re wasting money, but if you leave too late, you’re still wasting money.

Hard to believe, but IT pros are just like regular humans: we’re subject to hesitation, inertia, and cognitive biases. Here’s how to decide when’s the right time to pull the plug on your legacy tech.

Do You Have a Dollar Auction Mentality?

First, make sure you’re not living in a dollar auction scenario, or a situation wherein you’re bidding against someone not because you need to win, but because you can’t bear to lose. There are many concrete examples of this imaginary situation—but consider the lesson of the Concorde, that infamous, billion-dollar European albatross.

The Concorde was a supersonic, delta-wing plane that looked great when it rolled out on the runway for its first commercial flight in 1976. But it was also a money pit made up of broken promises and massive cost overruns. The backers of the plane didn’t want to admit their plane was an impractical money loser, though. They kept the Concorde in the air, throwing good money after bad, for 27 years.

If you find yourself at a point where you’re justifying not changing a system because that system cost you so much in the first place, then you’re riding the Concorde. To avoid the Concorde fallacy, consider the goals you had for the original implementation of that legacy technology. Ask yourself:

• Are the original goals for this technology still valid for the business?
• Is the current technology meeting those goals?

If the answer to either one of those questions is no, then it’s time to pull the plug.

Are You Doing Without?

The moment you say it’s OK to live without something fundamental, like security patches, support, or the ability to upgrade, you’re failing. The minute you find yourself saying, “No, no – we can limp along,” you’re on the Concorde. Consider these questions:

• Have you found others using some other (freeware, unapproved, or “shadow”) application or system on the side because what you have is insufficient?
• Are you redesigning your business or your workflows because your tool can no longer adapt to the way your business works?

If the answer to either question is yes, move on to a new tool.

Is Your Internal Cost Rising?

It’s highly likely your legacy tech has a higher internal cost because you’re supporting it internally with on-location expertise when you have an outage or some other problem that wouldn’t come up with a more up-to-date or appropriate system.

Ask yourself:

• Are you spending more on customizations?
• Are you spending more to produce workarounds?
• Are you spending more on kludges?

If the answer is yes to any of these questions, consider your next step.

There are other questions to ask, like, is your staff concerned about skillset atrophy? Are you losing credibility among your peers? Will you lose out on potential gains from the latest technologies?

But, before you answer, be sure you don’t just pull that plug without talking to stakeholders first.

Did You Just Call That Baby Ugly?

You need buy-in. Listen to concerns—there could be someone who needs that moldy tech. You also need to make sure you’re not asking to replace a tool someone in management spent $2.5 million on just four years ago. Effectively, you just told everyone that baby was ugly.

When people have built their careers on ugly babies, you need their buy-in. Remember, they can be potential allies because they can explain the reasoning behind the original purchase of that once-gorgeous baby. They can also explain why it’s now outmoded and help you lay the foundation for a new investment.

Also, when campaigning for something more up to date, remember that trends are on your side. Most of us are coming to the realization that that the old, “No one ever got fired for buying IBM” mentality is done—along with its more-damaging corollary, “My tech should last 40 years.”

Stick-in-the-mud thinking is fading, because we know if we don’t keep up, we’re dead. The exponential rate of change in the data center—along with the macro trend wherein none of us stay with our companies for the long term, anymore—means we buy for immediate results. We’re therefore more willing to look at an ugly baby and say, “Yeah, it’s time to cut bait.”

That said, upkeep and change is still an issue for many small and mid-sized companies. They’re necessarily budget conscious. Managers at such companies can see these upgrades as a potential drain. You need to help these people see the value side of your options—and it’s likely in your best interest to provide stakeholders with a proof of concept for your proposed solution.

This process is a two-way street, so make sure everyone with concerns has a chance to address them. That doesn’t mean you have to fix every little thing for everybody before you go forward, but you should give people a chance to state their concerns, if only to get buy-in.

In the end, this procedure is painful. It’s painful for everyone—for users, management, and your team. Nonetheless, we have to go through a similar process in various parts of our lives. I had a chance to ride the Concorde one time when they flew the Cleveland Orchestra (of which my Dad was a member) and a few lucky family members. I can honestly tell you that there was nothing like it. When they shut down that service in 2003, I lost a connection to my youth. So, believe me, I know the pain of cutting loose. But, unless we do this, we’re all stuck on the runway. More importantly, we’re not taking on new challenges.