Digital Transformation


How IT leaders can plan for the long term in a rapidly changing world

By Minda Zetlin

Fall 2019

“The only constant is change.” That quote, attributed to the Greek philosopher Heraclitus, seems like it was written for today’s technology professionals. Formerly mature industries are being disrupted by high-tech upstarts. Enterprise leaders understand digital transformation as a permanent condition rather than as a process with a beginning and an end. Technology leaders are faced with a constantly shifting landscape that requires them to react and adapt more quickly than ever. At the same time, CIOs and other IT leaders are expected to think more strategically than ever.

In CIO’s latest “State of the CIO” survey, 59% of the respondents said their organizations expected them to act as strategic advisors, proactively identifying business needs and opportunities and making recommendations to the business on how to address them. IT leaders are being relied on to predict and plan for the future just when the future is getting harder to predict. And they still have to make sure that systems and applications stay up and running, that maintenance takes place on schedule, and that security and compliance best practices are observed. “It’s not for the faint of heart,” says Jen Kurtz, CTO of Vertex, a tax software provider and Oracle partner. “But those are the requirements of a CIO- or CTO-level job these days.”

How can today’s IT professionals strategize for a rapidly changing future? Here’s what some experts advise:

Throw Away That Crystal Ball

The best way to plan for the future is to accept that it is unpredictable, says David Weinberger, coauthor of the bestseller The Cluetrain Manifesto (Basic Books, 2000) and author of the new book Everyday Chaos (Harvard Business Review Press, 2019). “The approach is to refrain as far as possible from anticipating what the future is going to be.” Instead, Weinberger advises, let internal users and external customers tell you what they need and be ready to constantly adapt to fill those needs. Or, better yet, allow them to customize your products and technologies to suit themselves.

Gaming companies in the 1980s did this by allowing gamers to modify their games, creating their own rules and graphics— two core elements of any video game. Years later Apple did it by creating the world’s first mobile application store. Rather than try to anticipate what iPhone owners would want their devices to do, Apple let customers and third-party developers figure it out in an open marketplace.

So how can IT leaders refrain from anticipating the future? Practically speaking, the only answer is to stay as flexible as you possibly can and avoid getting locked in to any one technology or business process. And that’s exactly what today’s successful CIOs say they are striving to do.

Eric Johnson, CIO of data integration company Talend, says his “worst scenario” would be for his IT team to buy a solution intended to address several specific business problems, deploy it, and then be faced with a related business challenge that the solution can’t handle. “If that happens, now you have to go find something else to bolt on that is likely more expensive and more complex.”

Being married to particular software or a particular platform can be a bad idea, agrees Thomas Phelps, CIO of document management company Laserfiche. He says it’s important to regularly assess whether the technology you offer serves current user needs. “If not, you have to be ready to quickly pivot and identify what you can put in place within a reasonable time frame, with the right change management, security, and controls.” He says he’s cautious about signing vendor contracts that last longer than one year or that have autorenewals, to avoid vendor lock-in. When it comes to a core system, such as CRM, which would take significant effort to migrate onto a new platform, he might consider a three-year contract, he says.

“It’s important to take into account who your business stakeholders are and how their needs will change over time,” he adds. He recommends considering your organization’s culture and whether the organization is risk-averse or embraces change, when evaluating technologies and services.

You can’t live in the world of technology; you have to live in the world of business. If you can’t immerse yourself in and understand the business, you can wind up with the wrong vision.”—Harry Moseley, CIO, Zoom

Opting for technologies that are interoperable and open to integration is another way to stay ready for whatever the future brings, Weinberger says. “When you have lots of information and stuff available ubiquitously and it’s not just ubiquitous but also interoperable, you’re not fighting against the epochal change we’re going through. You’re surfing on top of it.”

A Vision, Not a Plan

It’s clear that in today’s fast-moving world, “big bang” projects that take years to complete are a relic of the past. So how can IT leaders plan for the long term or prepare for a different future?

By focusing on a vision, such as empowering employees or customers, rather than having a specific plan, says Harry Moseley, CIO of videoconferencing service Zoom. “The way to avoid creating technological debt is to constantly review your vision and make sure the course you’re on is the right one. By doing that, you’re always identifying new creations and technologies that weren’t there when you began your journey.”

Another useful strategy is to break any large or long-term initiative into small pieces. “Lean has taught us that you still need to know where you’re going, but you have this ability to chunk things up, not only the app delivery team but IT leadership as well,” says Kurtz. That enables IT staff to make adjustments along the way, based on feedback from business leaders and users.

Of course, for this to work, you need a close relationship with those business leaders, something experts agree is essential if you want to prepare effectively for the future. “You can’t live in the world of technology; you have to live in the world of business,” Moseley says. “If you can’t immerse yourself in and understand the business, you can wind up with the wrong vision.”

Get Out of the Office

Spending more time interacting with business leaders and users in your organization will get you only so far. To prepare for an unknowable future, CIOs and IT leaders have to spend time out in the market talking to other business leaders, IT leaders, and analysts to find out about industry needs and what digital transformation means in different organizations. Phelps says it’s important to bring those insights back into your organization so you can improve your own technology.

It’s important for CIOs, CTOs, and other IT leaders not to get overly focused on executing their own strategies for their own companies, Kurtz adds. “Understanding industry trends and new technology requires an outside-in view.”

Get Good at Failure

Conducting a pilot program—trying out a new technology on a small group before rolling it out to the whole enterprise—is a long-standing practice in IT. But to be ready for the future, IT leaders need to take it a step further and try many different new technologies, some of which they know won’t succeed. In other words, in one of today’s most overused phrases, they need to fail fast.

“And fail cheap if you can do it,” Johnson says. IT leaders should create a team that’s accustomed to trying new things, taking risks, and being OK with it if a new concept or technology doesn’t pan out, he says. It’s important to set clear parameters on projects such as these—limits on both money and time spent—so you don’t wind up wasting too many resources on an initiative that doesn’t deserve it. Sometimes, he adds, once they’ve poured funds or effort into a project, IT professionals start feeling committed and don’t want to let go. “You really need to create an environment where the team feels comfortable knowing they can walk away from something and won’t be penalized for it,” he says.

Moseley says he dislikes the phrase “fail fast.” After all, no one ever starts a project or IT initiative with the objective of having it fail. “The notion that we should call it a failure is wrong,” he says. “My preference is to call it an experiment. In high school, I studied chemistry and we did lots of experiments. They didn’t always work, so we tried different approaches until it did.”

Whichever term you use, there are always more and newer technologies to try out. “When you look at the tech landscape today versus a year ago, versus two years ago, there’s exponential change and exponential growth, and I don’t see that changing anytime soon,” Moseley says. And that’s a good thing. “Whether you’re a CIO, a CTO, a chief digital officer, or a chief transformation officer, there’s never been a better time to be leading a technology organization,” he says. “Because the capabilities we have and will have are consistently growing. And it’s fun.”

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Illustration by Wes Rowell