Speed up software upgrades—with a slow build of momentum

A key to upgrading outdated software: Get the conversation going.
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· 4 min read

As a consultant who helps businesses with their software strategies, John Harrison sometimes sees a kind of “speed dating” happen between IT managers and department heads.

But instead of “Are you a pet person?” or “Where’s your hometown?” these sessions have less romantic icebreakers, like:

What do you like and dislike about your current systems?

An applications director (in charge of the implementation of enterprise software) and supply-chain manager (in charge of the smooth operation of sending and receiving), after all, may rarely find themselves in the same room to discuss concerns.

Maybe the supply-chain manager, for example, is struggling with inventory accuracy. With scheduled conversations, the applications team lead can hear about department head headaches, better understand business priorities, and consider updated solutions that support those objectives (like RFID that provides electronic tracking).

“It just engenders that idea that, ‘Hey, I’m here to help you realize your vision and objectives,’” said John Harrison, managing director at the advisory Protiviti.

Information technology professionals must not make a case for upgrades on their own, according to business consultants who spoke with IT Brew. IT leads must create momentum for new tools and software by understanding the day-to-day goals of executives.

“By itself, IT cannot make the case. More often than not, they need to have really strong alliances with the business stakeholders in order to really illustrate and articulate the advantages that going to a more modernized platform can have,” Brett Sparks, senior director analyst at the tech-research firm Gartner, told IT Brew.

Oldies but not-that-goodies. Many big organizations have decades-old technology setups. Even Chuck E. Cheese (as well as the Japanese government) still uses floppy disks.

While Charles Cheese’s reliance on the floppy disk hasn’t led to a hack of any animatronic entertainment, old software can lead to serious downtime and other unwanted consequences.

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In mid-January, a breakdown in 30-year-old software led to an FAA outage. Weeks earlier, a crash in a decades-old crew-scheduling program SkySolver sparked unprecedented Southwest Airlines cancellations.

A recent McKinsey report found that more than 20 percent of a company’s technical budget is diverted to resolving issues related to tech debt, or off-the-books upkeep of current systems.

We’ll talk, no big whoop. Despite their importance to business operations, objections to tech upgrades often have to do with competing priorities:

Now’s not the time…

It interferes with other projects…

We don’t have the people…

A little momentum-building goes a long way in addressing these questions, says Will Perry, principal and US cloud innovation and engineering leader at the professional-services firm PwC, who suggests earning confidence informally and then setting up a structured process.

“When I look at these IT leaders who have been fantastic at this, it really starts with developing really good interpersonal relationships with each of the members of the senior leadership team. Knowing the CFO, the CEO, the chief marketing officer, the business unit heads, having personal relationships with them, and doing tiny, little, small things to build trust over time,” Perry told IT Brew.

In June 2022, CIO and VP at Signature Healthcare Nick Szymanski told IT Brew a golden rule of his: Always have IT leadership at the table with the rest of the business leaders.

While sending technology priorities to the top of an airline CEO’s to-do list is no easy task, successful IT pros get the conversations going among senior leaders and don’t try to make the upgrade case alone.

“You don’t want to create the wave. You want to help others build the wave,” said Perry.—BH

Do you work in IT or have information about your IT department you want to share? Email [email protected]

Top insights for IT pros

From cybersecurity and big data to software development and gaming, IT Brew delivers the latest news and analysis of trends shaping the IT industry, like only The Brew can.