The 7 Habits Of Highly Effective Transformation Leaders

Taking a business on its digital transformation journey requires great leaders. We spoke with nine executives and thought leaders about what makes good leaders great, the habits that inform success, and specific skills they must hone to realize this transformation.

The 7 Habits Of Highly Effective Transformation Leaders

by Kristin Burnham

Posted on 02-21-2018

Ten years ago, businesses were racing to understand and capitalize on concepts such as data mining, search technology, and virtual collaboration.

Today, digital transformation—which describes how digital technology is fundamentally changing the ways businesses operate and deliver value to customers—rules the roost and is disrupting companies everywhere, from their operating models to their infrastructures.

But that’s only part of the equation. “Digital transformation is actually a human transformation,” said Brian Solis, principal analyst at consulting and research company Altimeter. “We’ve learned that people have mistakenly overemphasized the role of technology in change. What this comes down to is leadership.”

With that in mind, we spoke with nine executives and thought leaders about what makes good leaders great, the habits that inform success, and specific skills they must hone to realize this transformation.

1. Be Empathetic

Truly great digital transformation leaders understand how human dynamics—fear, politics, ego, sabotage, and safety—play into people’s feelings about change. They don’t assume their teams see the world their way. Rather, they see how others might perceive things, then “bridges between how they see it and what you’re trying to do,” Solis said.

“It’s not about getting people to follow you. It’s empowering people to lead their own initiatives and collaborate with you and others,” he told “It’s about unification of a bigger movement of getting people to bring about change because they want to—not because they have to.”

Amid all that change, when products and processes are shifting, leaders are tasked with ensuring that they weave humanity into every touch point, said Leesa Wytock, senior director of experience at brand strategy and design firm Siegel+Gale. That’s difficult to do without empathy.

“Empathy is what allows you to get the best work out of your team, it’s what makes you a good partner to work with, and it’s what makes your digital transformations successful,” she told “A lot of user experience work deals with behavioral science and empathy. You need to put yourself in the user’s shoes to get a product or process right.”

2. Step Outside Your Box

According to Jeffrey Brandt, CIO at national law firm Jackson Kelly, seeking out connections, experiences, and information outside of your particular industry can help light on what other businesses are doing in their digital transformations.

“It’s important to look at other industries and what’s impacting and challenging them, how they’re solving problems or implementing different techniques and workflows, and how all that may be applicable to what I’m doing,” he said. “Sometimes you discover an approach to something that you never would have thought about.”

Kathy Schneider, CMO at IT infrastructure company Sungard Availability Services, finds outside connections and opportunities at roundtable events.

“The dialogue and discussions are always immensely useful, and there’s a great amount of peer learning,” she said. “Talking with executives from other companies gives you perspective about what’s working for them and what isn’t, and how you might apply that where you are.”

Equally important is finding these experiences and opportunities for your team, Wytock added. Siegel+Gale, for example, brings culture hackers or thought leaders into the office for Ted-Talk-style discussions.

“Bringing in outside influences helps shake people out of their day-to-day and inspires them,” she said. “It’s been great for everyone and has even resulted in new product ideas.”

3. Hone Your Communication Skills

Communicating effectively—that is, knowing what to articulate, how, and in what context—is key to leading effectively, said Dominic Siano, digital marketing and transformation consultant at business and technology services company Cognizant. This means consciously reducing digital and technical jargon when you’re presenting to business stakeholders or with customers.

“In all of your communications, you want your audience—whoever it may be—to feel like they’re on your level and that they can participate in that conversation,” he said. “Learning to convey complicated messages simply takes time and practice but pays dividends. Other leaders and employees will find you more approachable, easier to talk to, and fully understood, which is key in leading a digital transformation.”

Another tip: Watch the room when others present or pitch ideas, Sungard Availability Services’ Schneider said. Look for techniques that are well-received, and note which ones fall flat.

“Communication, especially during a digital transformation, is so, so important,” she said. “It requires buy-in from executives and teams from across the organization, and knowing how to finesse your style and frame the argument for why you’re doing this and why it’s important is key to your success.”

4. Ask ‘Why?’

At the core of every transformation should be an “insatiable” curiosity—“whether it’s about a new technology, the results you’re seeing, or understanding what people are struggling with,” according to Chris Hall, VP and GM of customer experience at Adobe (’s parent company).

“As leaders, we’re presented with a lot of information about the ‘what’ when we really need to understand the ‘why?’” she said. “For example, being told we fell short of our goal is not enough. We need to understand why did we miss? Are other markets experiencing something similar? What are the factors that are impacting it? If the answer is, “That’s the way we’ve always done it,’ then … you need to challenge the norm.”

Transformation, she added, can be “big and messy,” accompanied by plenty of fatigue. “The faster you can arrive at a hypothesis and test for the ‘why,’ the more you can focus on the thing that really matters,” she said. “Curiosity and focus are two things that differentiate most leaders. These need to be pervasive. Anchoring around curiosity and focus will get you beyond the ‘what’ to understand the ‘why.’’’

5. Tune Out The Noise

A digital detox might seem like a counterintuitive move for digital transformation leaders, but doing so has helped Jeff Pundyk, chief strategy officer at Techonomy, find more time to focus on strategy, innovation, and big-picture thinking.

“I cut my social media to a bare minimum and removed Facebook, Instagram, and Twitter from my phone. For me, these are all very low-value, high-time applications that, over the past 12 months, have sucked up an enormous amount of time and energy,” he told

That’s not to say social media doesn’t have value; understanding these technologies is important for any successful digital leader, he said. It’s important, however, to acknowledge and act when they—and other time-sucks—become too consuming.

“You have to be disciplined,” he said. “Not only does it take up time when you’re using it, but it takes up headspace when you’re not. In the moments when you could be thinking big thoughts, you’re on social media. Those are missed opportunities.”

6. Develop Emotional Intelligence

While it may be a trendy buzz-phrase in business today, emotional intelligence—the ability to identify and manage your own emotions and the emotions of others—sets leaders apart, said Michael Heiser, IT director for the Wyndham Hotel Group.

The term was coined in 1990 in a research paper by two psychology professors, and later put in business context by Rutgers University psychologist Daniel Goleman: “The most effective leaders are all alike in one crucial way: They all have a high degree in what has come to be known as emotional intelligence. It’s not that IQ and technical skills are irrelevant. They do matter, but … they are the entry-level requirements for executive positions,” he wrote.

Heiser, who started his career as an engineer, said that honing his emotional intelligence has helped him develop and fortify his relationships with his engineers.

“They don’t respect leaders who can’t understand the technology that they’re dealing with,” he told “You need to know the right things and the wrong things to say in certain situations. You need that emotional intelligence to be a competent leader.”

Empathy, mentioned earlier, also plays a role. Digital leaders need to identify with others’ feelings—while also understanding their own—and use that information as a guide when making business decisions.

7. Think Like A Futurist

Because the future is anything but certain, digital transformation leaders need to stop ruminating about what may or may not happen as an absolute, said Jacob Morgan, author of “The Future of Work.”

“When it comes to digital transformation, business leaders need to remember to think in terms of different scenarios and time horizons instead of thinking in terms of one outcome during one time period,” he told

Focusing on the “transformation” piece of digital transformation and what businesses should do to prepare limits thinking, Morgan added. Instead, digital transformation leaders need to think about what they can do to build the future of work they want to see.

“This … allows digital transformation leaders to go from being passive participants to being active creators,” he said. “Everything we do is about choice. It’s a chess match where each move we make can lead down a different path.”

Keeping that in mind will ensure that business leaders are prepared for any uncertainty that comes their way, Morgan added. “We no longer work for factories,” he said. “We work for laboratories, and those who can run the most experiments the most often will win.”

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Topics: CMO by Adobe, Insights & Inspiration, Experience Cloud, Leadership, Future of Work,

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