People have been debating what makes a good leader for millennia. Ancient Egyptians were chiseling their ideas about leadership into hieroglyphs 4,000 years ago, explaining that good pharaohs were authoritative communicators, perceptive, and just. 

Some leadership traits like these transcend time and place—who wouldn’t want a boss that was clear, observant, and fair?—but technology is accelerating the pace of change beyond anything we’ve experienced before. Today, we’re at the cusp of an era of intense digital transformation, where the leadership traits that were valuable in the past aren’t going to be as useful. 

“Many companies found themselves forced into digital transformation by COVID, whether they liked it or not,” writes Dr. Gerald C. Kane, professor of information systems in the Carroll School of Management at Boston College. “However, it is unlikely that we will ‘go back’ to pre-pandemic ways of working once the danger of the pandemic has passed… the coming few years could be among the more exciting and disruptive periods of innovation that many of us will experience in our lifetimes.”

Dr. Kane shares his observations in a new research report that examines the characteristics of  effective digital leaders. The report, “The Digital Hero Mindset: The Traits People Need to Innovate in a Technology-Driven World,” was co-developed by the company I lead, AppDirect, and features a qualitative analysis of 35 interviews with leaders across a range of companies, including Patrick Pichette, Chairman of the Board at Twitter; Kathleen Taylor, Chair of Royal Bank of Canada; and Jim McKelvey, co-founder of Square. 

Protecting Curiosity from Organizations Designed to Kill It

In his research, Dr. Kane identified four traits that define individuals who are successful in leading digital transformation projects. Three of the characteristics—passion, vision, and tenacity—are probably not a surprise. But the fourth trait, curiosity, is often overlooked, or even worse, outright discouraged. 

According to Square’s McKelvey, “big organizations are designed to kill new ideas unless they actively try to counteract it.” He suggests—half jokingly, half not—that companies should give teams trying to drive digital innovation a “get out of jail free card” that would allow them to get around a company’s stifling rules.

Why is curiosity seen as such a potential problem? For the modern results-obsessed corporation—which, let’s face it, is the vast majority of today’s enterprises—encouraging employees to let their minds wander for hours on end with nothing to show for is a non-starter. As the report points out, that’s why today’s digital change agents need to learn to focus their curiosity. “[T]heir magic formula is a combination of radical self-inquiry and continuous learning. Either one by itself is fine. The magic is the connection of the two,” says Brad Feld, the Managing Director of venture capital firm Foundry Group.

Learning to Love Curiosity and Risk

In his analysis, Dr. Kane also describes how curiosity can spark a flywheel effect that leads to greater risk tolerance—a critical ingredient for innovation. “A disciplined curiosity increases risk tolerance by shifting emphasis from success or failure to the amount of learning that occurs. More learning increases the number of potential questions that the digital hero can explore,” he writes.

But if organizations embrace curiosity, do they run the risk of becoming too tolerant of failure? Laela Sturdy, General Partner at CapitalG, is skeptical. She says companies are “not going to become huge failure boats. It’s more of a shift, from being right 95-100 percent of the time to 70 percent. How does that feel? What you want to avoid are teams that are trying to be perfect, such that they don’t tolerate any mistakes.” 

For many companies, making the shift to a culture that encourages curiosity can feel like a titanic challenge. Short of “get out of jail free” cards, the best way to cultivate curiosity is to start small. Hélène Barnekow, CEO of Microsoft Sweden, explains how she asks her team to place two-hour “learning blocks” in their schedules. “People can use them to do online training… you can take on an unexpected meeting, you can go speak at a conference. You have to plan a scheduled time that reminds you of something new, learning, and being open-minded. The busier you get, the more important it is to look for that time, so you cannot forget it.”  

As technology accelerates everything around us, the ability to keep an open mind to unexpected opportunities might be the greatest benefit of all for companies that support curiosity-driven leaders. As Amy Chang, who sits on the boards of the Walt Disney Company and Procter & Gamble, says, “You need to keep an open mind and allow for serendipity to happen. If you’re too stuck on any one idea, a lot of times you’ll miss the signals that are coming towards you that, maybe, you shouldn’t be ignoring.”

Click here to read “The Digital Heroes Mindset” report in its entirety. 


  • Daniel Saks

    President & Co-Founder


    Daniel Saks is President and Co-Founder of AppDirect, as well as host of AppDirect's podcast, Decoding Digital. An expert in cloud technologies, he is an advocate for cloud-based delivery and frequently advises Fortune 500 executives on software distribution and cloud strategies. He holds degrees from McGill and Harvard universities