The dark arts of digital transformation — and how to master them

Resistance to digital transformation comes in many forms. And sometimes it takes a wizard — or a CIO with a satchel of magic tricks — to overcome them.

You’ll need to persuade employees and middle management to leave their comfort zones and change how they operate. You may find yourself stuck in bureaucratic quagmires or be forced to battle a ‘not built here’ mindset. You’ll probably encounter cutthroat corporate politicians determined to defend their turf.

In short, you’ll likely have to overcome apathy, ignorance, lassitude, technophobia, and plain old orneriness — but without making (too many) enemies.

This kind of wizardry requires tactics not typically found in business management guides (though you might find a few in the Book of Spells or the Necronomicon). We’ve asked top tech leaders for the tricks they use to overcome opposition and get IT done.  

1. Entrance your opposing forces

People don’t rise to the top of large organizations without strong opinions and even stronger egos. But you don’t need to practice voodoo or cast a spell to get these people to listen to you.

Sometimes all you need is a chocolate egg with a toy inside.

As a five-foot-zero woman in a field dominated by men, Joanne Friedman has had to work harder than most to get people’s attention over the course of her career. Her magic trick: Hand out Kinder Surprises.

“Chocolate is my favorite management tool,” says Friedman, who is CEO and principal of smart manufacturing at Connektedminds, a Toronto-based IT advisory group. A manufacturing industry veteran, Friedman came up through the ranks at IBM, Bristol Meyers Squibb, pharma giant GlaxoSmithKline, and Celestica. “When I was a CIO in meetings where someone was unmotivated or in a bad mood, I’d just launch a Kinder Surprise at them. They’d eat the chocolate and start playing with the toy, and the entire atmosphere in the room would change.”

Friedman kept a case of the sweets in her office. When word got out, other executives would stop by in the afternoons looking for a treat. Before long she had cultivated relationships with other key stakeholders, learned their concerns, and discussed how IT could help them achieve their business objectives.

Months later, when Friedman asked for an extra $400K to overhaul the manufacturing firm’s PLM system — an unbudgeted expenditure the CFO strongly opposed — she had the support of other business leaders in the room. Friedman ended up getting $600K for the project.

“I’m five feet tall,” she says. “I can’t play golf for love or money. But I can walk into a board meeting with a basket full of chocolates and ask, ‘Who’s getting which toy?’ And they love it. The best trick a CIO can pull is to do the unexpected in a positive way.”

Sadly, Kinder Surprises are not sold in the US, due to FDA restrictions about child choking hazards. So if you’re a US-based CIO, you’ll have to come up with your own sweet talisman.

2. Form strategic alliances

If you’re hoping to prevail over the Trolls and Goblins, you’re going to need help from the Elves and the Dwarves. Making the right allies within your organization is essential to being an effective tech leader, says Dylan Etkin, CEO and co-founder of Sleuth, an engineering efficiency platform.

“If you’re in a leadership role in Engineering, you aren’t going to succeed unless you have a strong ally in Product,” says Etkin. “Developers sometimes have this idea that management isn’t necessary, or they have disdain for the nontechnical side of things. That’s a terrible idea that will get you absolutely nowhere.”

Etkin, an early employee at Atlassian who was the original architect of Jira, admits that he wasn’t always good at building alliances with his peers. He had to figure out how to get on the same page with people who often had very different ideas about how to proceed. That meant asking a lot of questions and listening to the answers.

“You need to make sure you’re at least somewhat aligned with these folks because they are going to drive the things you do,” he says. “And if they have initiatives you think don’t make any sense, you might have a close enough relationship that you can influence some of their decisions.”

For example, while running the Bitbucket team at Atlassian, Etkin managed to persuade the company founders to abandon their favored distributed version control system (Mercurial) in favor of Git, which represented 80% of the market.

“It became clear that if we wanted to be competitive with GitHub, we needed to support Git, despite management’s reservations about the amount of technical debt we’d incur,” he adds. “Getting their buy-in was key to making us competitive in that space.”

Other key corporate stakeholders to form alliances with are Legal and HR, Etkin adds.

“Those people are either going to save your ass one day or make your life miserable, so I always make sure to be very friendly with them.”

3. Come to the aid of your enemies

A key thing to remember is that the dark forces you’re attempting to subdue may not be the individuals opposing you, but the systems in which they themselves are trapped.

Organizations that have found success operating in a certain way may see little reason to shake things up. Even when the changes are necessary, such as in the case of increased competition from disruptive new entrants or the emergence of transformative technologies, the effort required to overcome internal inertia could exhaust all your magic powers.

You need to identify where the real blockages are so you can direct your fire at the right target, notes Bryon Kroger, founder and CEO of Rise 8, a full-stack digital transformation firm.

“When you’re being blocked in your efforts to affect change, it can often feel like the enemy is a person or group of people,” he adds. “While that’s sometimes true, it’s important to first ask, ‘Am I being resisted by a person or by a culture?’”

Kroger, whose job title on LinkedIn is “bureaucracy hacker,” spent 10 years in the US Air Force. As co-founder of Kessel Run, the USAF’s agile software development lab, he knows a thing or two about how to deal with deeply hierarchical organizations.

When building Kessel Run, Kroger and his team often found themselves at odds with the USAF’s extensive governance risk and compliance processes. But instead of treating their auditors as the enemy, the Kessel Run team took time to understand their pain points. They then designed a new system that automated and streamlined the auditing processes, allowing the compliance team to get reports in real-time.

“Instead of producing one report a year, we were able to achieve continuous compliance, without having to throw out any of their risk management frameworks,” he says. “Instead of running security scans once a quarter, we ran them on every single commit, multiple times a day. By the end, we were able to do everything they needed without impeding our delivery speed whatsoever.”

The key to their success boiled down to a single magic word: Empathy.

“You need to practice empathy first,” Kroger says. “You need to ask, ‘How can I make your job easier, faster, and more efficient?’ And the truest form of empathy is to meet somebody where they’re at, with no expectation of change.”

4. Be fearless

Whenever you try to drive transformation, arrows will come flying at you from every direction. Orcs carrying torches and spears will beat down your castle door. Some will be competitors, but many will be people within your organization who have hidden agendas or are resistant to change.

“When I was a CIO, there were always at least 15 people who wanted to run me over with a truck,” says Gary Hoberman, now founder and CEO of Unqork, a codeless application development platform. “And if that number ever got below 15, I felt I was not doing my job.”

Prior to founding Unqork, Hoberman spent 25 years on Wall Street, much of them as a managing director in charge of technology for a Fortune 50 financial services firm. Creating enemies came with the territory.

“My role as CIO was to transform the entire organization,” he says. “I believed that my customers weren’t my business partners, they were the customers of the company. That means I was constantly going against the norm, fighting the antibodies that try to shut you down.”

In the mid-2000s, Hoberman developed an ecommerce platform that was widely deployed throughout the firm. The head of trading then asked him to develop software to onboard newly recruited traders more quickly. At that point in time it took two weeks to provision traders with computers and accounts, costing the firm millions in lost revenue. Within a month, Hoberman’s team had automated the entire process, allowing traders to get to work immediately.

“Once this was working, the corporate bureaucracy kicked in and I was told, ‘Great, we’ll roll this out month by month, building by building, over the next four years,’” Hoberman remembers. “I said, ‘Screw that, I’m making it available tomorrow. You guys figure out how to catch up to me.’”

He estimates the software saved the financial services firm about $300 million a year in productivity gains.

“As a technology leader you need to be fearless,” Hoberman says. “You need to be unafraid to say, ‘I’m going to support my team, drive change, and break things.’ That’s the secret.”

5. Make peace, not war

When you’re outgunned, it’s usually better to lay down your weapons and negotiate. And while office politics are often anathema to tech leaders, it almost always beats the alternative, notes Jonathan Feldman, CIO for Wake County, N. C.

“IT folks have traditionally been ‘anti-politics,’” Feldman says. “But I always remind my staff that the alternative to politics … is war. War is never beneficial to both sides and someone always gets hurt.”

Engaging in some level of politics can lead to a higher understanding and mutually beneficial cooperation, he adds.

Even when you know in your heart management is making the wrong decision, there are times you’ll need to “disagree but commit,” says Etkin. For example, shortly after his startup was acquired by Atlassian, Etkin was told they had to implement a single-sign-on system.

“We quickly saw it would take nearly a year to migrate and offer very little in terms of value for our customers,” he says. “We eventually did it, and it wasn’t worth the investment. But it was a bet the company made and we had to roll with it.”

You need to ask the right questions, listen, and try to understand management’s point of view, says Etkin. Then do your best to champion that POV to your team.

“You might not have the context to fully understand why they are making that decision,” he says. “In the end, you have to remember that you are a steward, not the king. Your job is to do the right thing for the realm without getting your head chopped off.”

Business IT Alignment, Digital Transformation, IT Leadership, IT Strategy