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Interview with Charlene Li, Part 1: Acts of Courageous Leadership

David Mizne
David Mizne

In this two-part series, we sit down with Altimeter Group founder and Senior Fellow Charlene Li ahead of the release of her new book, The Disruption Mindset: Why Some Organizations Transform While Others Fail. Recognized as one of the 100 most creative people in business by Fast Company and as a top 50 leadership innovator by Inc., Charlene is an expert on digital transformation and disruptive growth strategies.

“My happy place is on a ledge overlooking a quarry. When I’m about to go over the ledge is the scariest part. You’re hanging, your palms are sweating, you get this weak feeling in your stomach and legs. I feel alive,” says business leadership expert, Charlene Li.

It makes perfect sense for someone as open to risk as Charlene to speak knowledgeably about stepping outside one’s comfort zone. After all, she’s been doing it throughout her career. While at Forrester Research, Charlene excelled as an analyst, but found that her role insulated her from exploring newer disruptive technologies emerging at the time.  

“Disruption doesn’t know any boundaries by department, industry, or title. It impacts everybody across the organization.”

With that mindset, she left the security offered by a place like Forrester at the start of the recession in 2008 to start her own firm, Altimeter Group. Charlene’s company quickly made a splash in the space through its holistic, yet pragmatic approach to understanding the intersection of technology and talent. Her gamble paid off in 2015 when Prophet acquired Altimeter.

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“‘Life begins at the end of your comfort zone.’ I have it on my mug. I push my team to go out of their comfort zone because that’s how you grow. Not stressing yourself, but stretching.”

This leads to what Charlene calls “aha moments.” In other words, when struggling with a challenge, stepping outside familiar territory is often what leads to big ideas. For this to work, you not only need to be open to such moments, you also need to seek them out. It requires curiosity. It reflects boldness. 

And it begins at the top.

Courageous Leaders Are Leapers

For Charlene, jumping off cliffs into the unknown is as apt an analogy for leadership as it gets. Like she says, “leadership is a courageous act.” 

To fully understand what this means, she first indicates what it doesn’t:

• Managers, not leaders, manage the status quo. Courageous leaders create change. It could be big or it could be small, but it’s always about change.

• The attitude that “we may not be thriving, but at least we’re not failing” is, in fact, a failure in itself. There’s no room for complacency at the leadership level.

• Paralysis by analysis practically has the same effect as no analysis at all. Finding the perfect solution and removing all risk before moving forward is inherently impossible.

“These aren’t courageous acts. You don’t need a leader for that.”

At some point, leaders will face situations that force them to act outside their comfort zones to do what’s best for the business. They’ll be required to say “we’re going from here to there,” even though they may not know exactly where “there” is or how they’ll find it. 

According to Charlene, “Courage comes when you don’t know what the outcome is going to be. That takes a lot of guts.” Over the years, she’s observed many leaders who lack this mettle and run away from the cliff. Some even refrain from walking to the edge and looking over. The fear of personal failure or of steering the organization down the wrong path is too great.  

At the other end of the spectrum are those who don’t wait for their fear to go away but rather confront it head-on. “That’s when you’re putting on the mantle of leadership,” says Charlene. They also realize that just because they overcome their fear once doesn’t mean they’ll never be nervous about big leaps again. And that’s a good thing for business leaders. It shows they care about their company and, just as importantly, about their people. 

Adobe’s Aha Moment

Courageous leaders take risks. They have an ambitious vision of where their companies could go and they inspire those around them to follow. 

Charlene points to Adobe as one of the best examples of such disruptive thinking in action. When Shantanu Narayen became CEO of the San Jose software company in 2007, he did nothing short of upending the entire organization by dropping one-time licenses and packaging in favor of recurring, cloud-based subscriptions. Not only did he implement this at a time when no one was even asking for it, he did it in the midst of a global financial crisis.  

Predictably, this caused a painful transition for the organization, a substantial hit to its bottom line, and considerable unease on Wall Street. But, over the long haul, not only did Narayen’s courage to see his vision through end up saving the company money, it actually sent its stock soaring. It also paved the way for Adobe to enter the Fortune 500 for the first time.

Oh, and it reimagined the entire software market.

Courage and Company Culture

Strong, courageous leaders like Narayen have gotten to where they are, not by remaining in their comfort zones, but by accepting that feeling uncomfortable is part of the job description. Rather than give in to their fear and shy away from the unknown, they see it as an opportunity to be embraced. 

The good thing about courage is that it’s a learned trait. By definition, it flies in the face of a natural instinct that can only be overcome through strength of will. That means that courage does not have to be—nor should it be—confined to the corner office. If the rest of the team is tentative or complacent, that prevents valuable aha moments and stunts both corporate and personal growth

To become an organizational trait, courage must therefore be embedded in the company ethos. This comes from a healthy culture of sharing where decisions are transparent and discussions are ongoing. Only in this setting can people learn from, believe in, and ultimately follow their courageous leader’s example (then of course celebrate the wins that come as a result). 

However, Charlene is quick to point out that how this happens today is a major departure from how it occurred for previous generations. “Before, one of my only opportunities to share with people was when I stood in front of them, maybe once a quarter. So, everything had to be just right to get across the right points.” 

In the digital era, leadership has to know how to listen to and engage with employees in very different ways. Once-a-year performance reviews are falling out of favor thanks to more effective software like weekly check-ins and 1-on-1s.  In essence, the relationship is more fluid and ongoing today, and new media makes it possible, if not necessary, to follow many conversations at the same time. 

The workplace, like society at large, is evolving quickly and dramatically. Even today’s courageous leaders are facing unprecedented cultural challenges that can be more than a little uncomfortable at times. But, as Charlene argues, discomfort is fertile ground for growth. That makes a strong strategy for effectively engaging employees more important than ever. Only with that can leaders create a culture of courage, inspire the search for aha moments, and, like our friends at Adobe, disrupt their very industry.

In Part 2, Charlene discusses how this type of culture translates to an employee-centric strategy that meets the needs of today’s workforce. We then examine the positive domino effect this creates for a company’s brand and business.

David Mizne 15Five

David Mizne is Communications Manager at 15Five, continuous performance management software that includes weekly check-ins, objectives (OKR) tracking, peer recognition, 1-on-1s, and 360 reviews. David’s articles have also appeared on The Next Web & The Economist. Follow him @davidmizne.