How top IT leaders create first-mover advantage

CIO Hall of Famers Steve Randich and Neal Sample weigh in on what it takes to build and lead IT cultures that deliver transformative results.

In a business environment defined by volatility, uncertainty, complexity, and ambiguity (VUCA), the most successful CIOs are more than technology leaders; they’re “chief intentional officers.” These CIOs have the vision, steadiness, and laser-sharp focus to navigate both the promise and the risks of disruptive technologies, positioning their teams and their organizations to gain and sustain an edge.

At FutureIT in Chicago, I moderated a panel discussion with two such leaders, CIO Hall of Famers Steve Randich, executive vice president and CIO at FINRA, and Neal Sample, CIO at Walgreens Boots Alliance. We had an insightful conversation about how to approach the adoption of emerging technologies as well as what it takes — and when it makes sense — to gain first-mover advantage in this environment.

Timing is everything

With rapid, constant change one of the hallmarks of this VUCA reality, many business executives and board members feel compelled to seize on the next big thing that promises to disrupt the world. Yet Sample cautions CIOs to take a step back and make sure the supposed game-changer is something your business really needs to participate in.

Before jumping on a new technology, Sample suggests mapping the characteristics of the solution against the specific problems you need to solve. That way you can make an informed decision driven by business needs, not hype.

“The right timing comes from a first principles approach,” he says. “That means pushing back against a lot of pressure, sometimes against the board or the executives. Everyone’s going to come in and have an opinion, but sometimes the right thing to do is say, ‘That’s a great and interesting toy, but for us it’s just a toy, because it doesn’t solve our core problem.’”

Neal Sample, CIO, Walgreens Boots Alliance

Walgreens Boots Alliance

There are also times when it’s best to be what Sample calls a “fast follower” rather than a first mover. This again requires a CIO who can push back strategically against pressure, sometimes from their own team eager to build a capability, when a more prudent choice would be to wait until it becomes widely available in the market.

Building a business case

This business-problem orientation provides CIOs with not only a decision-making roadmap but also a strong case for their vision, which may initially be met with skepticism by other areas of the business.

For example, Randich recalls the process that led FINRA, a regulator in the financial services industry, to become a first mover with public cloud.

“We were drowning in scale,” he says. After looking at various vertically scalable solutions, including private cloud and hybrid, his team realized the right choice for FINRA’s needs was to go “all in” on public cloud.

Steve Randich, EVP and CIO, FINRA

FINRA

The experience not only confirmed they’d made the correct decision; it demonstrated the power of strong vendor partnerships. When a big data-consuming organization like FINRA put out the word it was seriously considering public cloud, all the big vendors came calling. Randich ultimately partnered with Amazon Web Services and worked directly with Amazon President and CEO Andy Jassy.

“We were on his weekly Monday morning status call, and they helped us succeed,” Randich says. “They helped us learn how to do this, and we eventually became experts at it.” Jassy clearly recognized this would be a mutually beneficial relationship, as evidenced by the fact that the engineering teams producing these emerging cloud computing services and products came into FINRA’s organization to help them with the initiative.

“They wanted us to be successful because we had all the things they wanted on their marketing brochures,” Randich says. “And it gave them the opportunity to learn, too.”

Randich points out that FINRA moved to the public cloud before anyone of its size or industry was considering it, even though his organization was dealing with a board of directors and senior management that were skeptical about security. “By about 2016 that became a non-issue because we very confidently could say we’re more secure in the public cloud than we could ever be privately,” he says.

As Randich’s team continues to analyze new risks and concerns, the benefits of the decision are clear and tangible. He notes that many of the new risks are insignificant compared to what they would have faced trying to host the level of data they have today in a private cloud or on-premises data center. In addition, they recently completed an analysis that showed the cost of a private data center would have been at least eight times higher, an emphatic reinforcement of the business case.

Core leadership traits that make the difference

Whether your strategy is to gain first-mover advantage or to succeed as a fast follower, new technology isn’t likely to achieve your goals if you can’t articulate the message in a way that resonates with the business. The ability to tell a story that gets the C-suite on board and connects with a non-technical audience is key.

“The first thing I coach my teams on is how to speak the language of your audience,” Sample says, “and it’s generally not the language of engineering. It’s the language of business. If you can’t do that, you will not be effective at garnering support for your initiatives.”

And the key is to craft a compelling story that puts technology into the business context. “We start with the end in mind: This is the problem that we’re going to solve, and this is why it’s relevant,” Sample says. “And then we communicate it in a language that is relevant to the business, not necessarily the language that we use when talking about those problems among ourselves.”

Considering the data consistently shows major digital transformations have a failure rate upwards of 90%, courage is another prerequisite for leading any big technology initiative. Randich, who says he developed a sixth sense for recognizing what projects are going to fail when he worked in management consulting at KPMG and IBM, emphasizes that it’s also important for CIOs to develop the courage muscle in their team members.

“I make sure the talent we bring in and promote follow that culture of courage,” he says. “We need people to be able to identify the characteristics of projects that are likely to fail early on, because without that, a high percentage of IT projects will fail and the manifestation of that is people lose their jobs. All roads lead to having a successful delivery, and it requires courage. It also requires the ability to basically say, ‘I’ve got risks. This project could fail.’”

With ambitious initiatives on deck and a tight talent market, the ability to cultivate strong teams has also become mission-critical for IT leaders today. Sample suggests experimenting with different approaches to win in this talent market.

“I’ve found that we’re able to make a difference when we’re behaving differently — whether that’s increasing the pipeline of underrepresented communities in tech, challenging partners in HR to think differently about hurdles in the process when it comes to formal education, or finding non-traditional ways to increase a talent pipeline,” he says.

Sample adds that he is also focused on the “team” in team-building: “Of course, I need experienced, competent people, but ultimately, I’m hiring with the goal of building a high-performing team versus a single individual.”

“Some of the less talked about aspects of a high-performing team are the human traits: trust, respect, genuine enjoyment of each other,” Sample says. “I’m looking at experience and skills, but I’m also thinking about how the person will function collaboratively with the team. Do I believe they’ll have the best interest of the team at heart? Can the team trust their competency?

Sample also says he focuses on “will over skill.”

“Qualities like curiosity and craftsmanship are sustainable, flexible skills that can evolve with whatever the new ‘toy’ in technology is,” he says. “If you’re approaching work with that bounty of curiosity and that willing mindset, the skills can adapt.”

Creating a culture that enables big moves

Another common characteristic of leaders who successfully spearhead transformation? They radiate a sense of calm in the storm.

“I got advice from a boss years ago that I needed to slow down because we were in a hurry,” Sample says. “I thought, that seems like the time to go faster, but my boss said, ‘No, we can’t afford to make a mistake.’ And that stuck with me. One of my favorite expressions of it comes from the Navy SEALs: ‘Slow is smooth and smooth is fast.’ When you don’t have time to rework, when you can’t afford to make the mistake, when you need to execute the first time, when you’re in that storm, that is the time to be the most calm.”

Randich, too, learned from previous career experiences the value of being calm in times of crisis, having seen the chaos that can erupt when emotions take over and people stop listening to one another. It’s up to the CIO, he says, to the lead the way by making an intentional effort to calm down, focus on the facts, and think rationally. After all, he says, “That’s the way you’re going to get yourself out of the situation.”

Steadiness and calm from the leader create the kind of culture where people are encouraged to take risks and work together to solve big problems and execute on bold agendas. That, ultimately, is what enables a technology organization to capitalize on innovative technologies. In fact, reflecting on his legacy as a CIO, Sample believes it’s not really about the technology; it’s about the people. His success, he says, has been in building the teams that operate the technology.

“What I have found is that the perfect plan with an unqualified team doesn’t matter. They won’t be able to operate it. They will invariably fail. On the other hand, you take a mediocre plan — it’s a little too conservative or a little too expensive — and you put an excellent team behind it, they will not only deliver; they will outperform,” he says. “The lesson is that, the technology of the day is going to change, but the excellent teams are what help you overachieve.”

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