The Leap to Leader

When Penny Herscher stepped into her first chief executive role, at the tech firm Simplex Solutions, she felt sure she was prepared. After all, she had held marketing, business development, and general manager positions at her previous company, Synopsys, and she was comfortable taking on difficult challenges. Even so, her confidence quickly evaporated. “I had no clue how to be a CEO,” she says. “I kept finding myself in situations where I didn’t feel I had the experience and the tool set to know what to do, and I kept waiting for permission to make decisions.” Then one of the company’s directors took her aside. “You’re looking to the board for permission,” he told her. “We’ll give you advice, but you have to make your own decisions.” With that nudge she found her footing and went on to lead her company to a successful IPO.

As Herscher’s story illustrates, succeeding as a top leader has little to do with your title and everything to do with your mindset. As a journalist, I conducted in-depth interviews with more than 500 CEOs and other executives for “Corner Office,” a feature I created at the New York Times, and over the past six years I’ve interviewed hundreds more for my leadership series on LinkedIn. I’ve also coached hundreds of high potentials: people whose organizations are betting on them to eventually take the reins. From all those conversations clear lessons have emerged about what it takes to make a successful transition to a senior leadership position. I wrote the book The Leap to Leader, from which this article is adapted, to share what I’ve learned.

In this article I’ll explore the mental shifts needed to become a leader and to handle the challenges you’ll encounter in your new role. The process involves identifying and communicating your core values and learning how to approach tough decisions. It requires setting the bar for your team’s performance and learning to compartmentalize so that you can find the right pace for yourself. And it requires expanding your self-awareness and paying attention to the stories you tell yourself about your experiences—your successes and failures, your bad times and good ones—when you contemplate the arc of your career and life.

Being a leader means playing for the team’s success rather than your own and navigating the many balancing acts that make the job so challenging. The following guidelines can help ensure that you’re ready.

Be Clear About What You Stand For

Early in your career you may have been taught to hone an elevator pitch so that you could make the most of chance encounters with superiors or prospective employers. You were probably advised to have tightly scripted answers to questions such as “What are you working on?” and “What do you want to do?” As you move into a top position, you’ll need a pitch that tackles the questions “Who are you as a leader?” and “What do you care most about?” You want to be predictable in the best sense of the word: someone whose values are unwavering and clear. That way, “people won’t have the burden of always thinking, I wonder what he or she would do,” says Sue Desmond-Hellmann, a former CEO of the Bill & Melinda Gates Foundation.

When I work with up-and-coming leaders, I ask several questions to help them develop what I call their personal leadership brand.

• What three values are most important to you as a leader and a colleague?

• How have you lived them in your career?

• Why are they important for driving success?

• How would you describe your leadership philosophy and approach to a recruit?

• How would a team member describe them?

Take time to really think through your answers. Go beyond the bedrock notions that virtually all leaders subscribe to—such as the importance of DEI and the need for a relentless customer focus—and be as specific as you can. You want to create a narrative that feels unique to you, that takes others’ perspectives into account, and that you can bring to life with personal stories.

Pam Fields, a former CEO of the hat company Stetson, has a crystal-clear leadership brand. “Everybody who works for me knows that they matter and that I have their back,” she told me. “I will always put myself in the line of fire for them.” Paula Long, formerly the CEO of the data management firm DataGravity, tells her teams, “We are all subcontractors to one another,” underscoring the importance of mutual accountability and respect for others’ time.

However you define your leadership brand, be consistent: Show up in the same way in every interaction. Your team will be looking for signs that you’re a steady presence—someone who won’t abandon your values for personal gain or when under duress.

Hone Your Decision-Making

As you move up, the problems you encounter will become harder and more complicated, and you’ll be more accountable for your decisions. You’ll have to make more gut calls, because tougher problems often provide less data to draw on. You’ll be placing bets, and you need to become comfortable with not knowing whether they’ll pay off. There are plenty of decision-making frameworks out there, but here are the guidelines I’ve found most useful.

Get all the input you can from your team. This means creating an environment in which debate is encouraged and people don’t worry about stepping on others’ toes. Kathleen Finch, the chairman and chief content officer of Warner Bros. Discovery’s U.S. Networks Group, holds “pile on” meetings. “I bring about 25 people into a room and go over all the projects coming up in the next six months, and everyone piles on with ideas,” she says. “The rule is that you must forget your job title. I don’t want only the marketing person talking about marketing.” Always push to understand the “why” behind someone’s opinion and give everyone else permission to do the same.

Look in the “ugly mirror.” One of the biggest stumbling blocks for organizations is an unwillingness to be brutally honest about the difficulties they face. And it’s impossible to drive change if people aren’t aligned on why it’s needed. “You can have a group of supersmart people, but they can waste a lot of energy going down the wrong track,” says Yuchun Lee, the CEO of the sales software company Allego. Resist the temptation to be a cheerleader for the company. Keep initial discussions about challenges as fact-based as possible so that everyone can see that the status quo is not an option. Have the courage to do a harsh reality check on where your organization currently stands. “You have to look in the ‘ugly mirror,’” says Laurie Schultz, a former CEO of the software firm Galvanize. “And you’ll want to contrast that with the ‘beautiful mirror.’ The two in tandem can really lead to change.”

Beware the “logic box.” I’ve had a few experiences when I was utterly certain of the rightness of a decision, only to later slap my forehead and wonder what I’d been thinking. When I retraced my mental steps, I’d realize the problem: My framework for the decision was fundamentally flawed. I think of this as becoming trapped in a faulty “logic box.” Part of a leader’s role is to push people to avoid the logic box by examining the assumptions underlying their ideas. Are they absolutely clear about what problem they need to solve? Have they thought through all the possible consequences? For the economist and author Dambisa Moyo, one of the most important qualities in a leader is the ability to use several mental models to analyze options. “If an investment looks attractive from a financial perspective, it might look less attractive through a geopolitical or environmental lens,” she explains. Penny Herscher has another way to stay out of the logic box: Ask yourself, “What would have to be true for you to be wrong?”

Listen carefully—but take charge. One of the most consistent messages to leaders in recent years is that employees want to be heard. They want a voice—even a vote—in company policies. That means listening has become a crucial skill for leaders. (For more on how to develop it, see “Are You Really Listening?” HBR, March–April 2021.) “You have to meet people where they are,” says Clarke Murphy, a former CEO of the executive search firm Russell Reynolds. “People will follow leaders who are listening more than pronouncing.” But employees also expect leaders to be decisive, especially during a crisis. “I learned in the pandemic that people really value directional guidance—not micromanagement but directional guidance,” says Saundra Pelletier, the CEO of Evofem Biosciences. “Being prescriptive can help people get to the right outcome faster.”

Provide context. As important as it may be to act decisively, it’s equally important to explain your thinking. People will be more willing to act on a directive when they understand the rationale and how it fits the bigger picture. And your thought processes can serve as a compass for their decision-making. “Employees make thousands of micro-decisions every day,” says Gregory Bryant, an executive VP and the president of global business units at Analog Devices. “If you don’t give them context, it’s going to be a problem. You have to be clear about the vision and the strategy and connect them to what people are doing every day.”

Set the Bar for Your Team’s Performance

This is one of the trickiest balancing acts of leadership. Set expectations too high, and people may be demotivated. Set them too low, and you won’t achieve the necessary rate of change. People crave predictability, and it’s up to you to determine the pace and adjust as needed. Leading means continually fine-tuning expectations, says Andre Durand, the CEO of the tech firm Ping Identity. “It’s like a big sound-mixing board, and you’re constantly trying to keep the organization in balance. You don’t control the external environment, and things are always changing—which means you’re constantly changing your balance.” Setting unrealistically ambitious goals, he says, creates dissatisfaction and an emotional drag—and when a company is exceeding expectations, “there’s a different kind of buzz.” As a leader, “you hold the strings to the emotional well-being of the company.”

Master the Art of Compartmentalization

Just as it’s your job to set the pace for your team, you need to set the pace for yourself. That’s hard when you’re faced with tight deadlines, people problems, crises, and the pressure to do more with less. Time to think can become a rarity unless you compartmentalize to some extent. The following tactics will help.

Stay focused on what matters most. When problems pile up, it’s tempting to seek order in the chaos by listing every issue that needs attending to. “It’s not helpful to rank 12 things in terms of what’s most critical,” says Dave Goebel, a former Applebee’s CEO. “You need the discipline to prioritize and keep the list to fewer than five. That’s crucial to delivering on the most important elements of your strategy.”

The key to prioritizing is creating a strategy document. I learned a highly effective approach from Dinesh Paliwal, a former CEO of the electronics company Harman International. He suggests describing every business strategy on a single page containing concise answers to four questions: “What is your core message and goal?” “What are three actions needed to achieve that goal?” “What are three challenges?” and “How will you measure success within a specified time period?” Using this framework can sharpen your focus and keep you from listing evergreen and lofty priorities that would only weigh you down. As when defining your personal leadership brand, take the time to really dig into the exercise. Then concentrate on the specific actions needed to set your strategy in motion.

Don’t get pulled down into others’ problems. You need to maintain a certain altitude to think clearly and see the big picture. So be prepared to push back if people try to park their problems with you or ask for meetings simply to get face time or elevate their own importance. Keep any necessary meetings as short as possible so that they don’t overwhelm your schedule. “People want you to understand their problem and will try to bring you into it,” says Joanne Berger-Sweeney, the president of Trinity College. “But as the leader, you often have to stand outside someone’s individual problem to see holistically and make the best decisions for the organization as a whole.”

Delegate and ask for help. It’s tempting to shoulder everything yourself. After all, you probably got to where you are in part because of a strong sense of ownership and accountability. But taking on every challenge isn’t leadership—and people usually want to pitch in. “One of the most important demonstrations of leadership is to reach out and ask for help,” Pam Fields says. “It’s not about putting on your Superman cape and thinking you can fly around and protect everything yourself.”

One simple question—“What’s best for the organization?”—can help you maintain the necessary altitude to clarify your thinking.

Give yourself a break. It’s a good bet that you have high standards for yourself and want to get everything right. But there are limits to what any leader can accomplish. “When I hear first-time CEOs being hard on themselves, I say to them, ‘If you talked to your friends the way you talk to yourself, you’d have no friends—so stop talking to yourself like that,’” says Bob Brennan, a veteran leader who has headed organizations including the software firm Veracode and the information management company Iron Mountain. “Part of the learning curve is that the job shouldn’t involve self-flagellation.” And although a leader’s job includes helping others succeed, you’re not responsible for whether they ultimately do. If you have to let someone go, so be it. Your team will respect you more if you push out those who aren’t carrying their weight.

Always ask what’s best for the organization. When faced with hard decisions, particularly people problems, it’s natural to want to study them from many angles. But you can become paralyzed by worrying too much about potential fallout. One simple question—“What’s best for the organization?”—can help you maintain the necessary altitude to clarify your thinking. “When I look in the mirror, what’s important is the question ‘Is what we’re doing absolutely right in the midterm and the long term?’” says Christian Klein, the CEO of the software company SAP. “As long as I can say yes, I know that I’m doing the right thing for all stakeholders.”

Build Self-Awareness

Everything you say and do has an outsize impact. People are studying you closely and will project meaning onto every gesture and offhand comment. When Reuben Mark was the CEO of Colgate-Palmolive, he had his assistant keep track of which floors he visited so that no department would feel slighted. “The little things matter,” he says.

Keep your emotions in check. Self-awareness involves recognizing your feelings and operating within a fairly narrow band of emotions. You want people to focus on their work rather than expend energy trying to read your mood. It’s OK to occasionally confide that you’re struggling with something or having a bad day. But being authentic doesn’t mean sharing every feeling in real time. “You often have to be an actor,” says Barbara Khouri, who has led turnarounds at six companies, including Swatch. “It’s an art.”

Know your triggers. Self-awareness also means identifying your triggers: the moments of stress that can spark an overreaction. That may require some excavation of your early years. Everyone has some emotional scar tissue, and certain circumstances remind us of the experiences that caused it, sometimes leading to reactions we later regret. Facing your triggers honestly is the first step toward creating some emotional distance from them and controlling your reactions. Paul Block, a former chairman and president of Revlon International, always tries to understand the hidden motivations of the executives he mentors. “As they become aware of the issues that drive them, they become much more effective as managers, leaders, and human beings,” he says. “It makes them much more compassionate.” Corey Thomas, the CEO of the cybersecurity firm Rapid7, asks potential hires what their triggers are. “If an executive can’t answer, that’s a nonstarter,” he says. “If you’re not aware of your triggers, you probably lack maturity around them. If people are aware of their triggers, I ask how they manage them.”

Uncover your blind spots. You also need self-awareness to close any gaps between how you think you’re leading and how your team perceives you. Structured feedback mechanisms such as 360-degree reviews can help, as can honest confidants. But you also need to go after your blind spots yourself. Be relentless about asking for input: “What do you need me to do more of, less of, or differently to better help you?” Show appreciation when people respond and let them know how they informed your thinking or prompted a behavioral change.

Craft Your Personal Narrative

All of us, not just leaders, sometimes trip ourselves up through the stories we tell ourselves about our lives. People fall into several common traps in this regard. If you’re aware of them, you’ll be better equipped to mentor others—and you’ll become a better leader yourself.

Don’t let fear of failure stop you. People sometimes get stuck in the face of a tough decision. They might stay in an unsatisfying job because the thought of moving to something different is overwhelming. They might not seek a promotion, stand up to the boss, or express a controversial opinion. In such situations it’s important to ask, “What’s the worst that could happen?” For most people, the answer is that they could get fired. But that fear is often unfounded—and even if it’s realized, the change might lead to a better place.

Becoming comfortable with the idea of failure also involves reframing what it means. To be in a high-stakes position where failing is a real possibility suggests that you accomplished something significant to begin with. “There’s no genuine opportunity to be a hero without the opportunity to be a chump,” says Jake Wobbrock, a cofounder of the customer-engagement software firm AnswerDash. “If you embrace both possibilities, you may see the moment more for what it is and fear it less. That allows you to perform a little bit better.”

So be courageous and take the shot. Do your job as though you have nothing to lose. That’s what leaders do.

Choose the stories you tell yourself. Few remarks have stayed with me quite like five words from Leila Janah, who headed the antipoverty social enterprise Samasource and the skin care company LXMI until her death, in 2020. After describing a childhood marked by divorce, instability, and racial and class bias, she told me she had never let adversity hold her back. “Reality is just source material,” she said. “All your background, your bad experiences and your good ones, are just what you decide to make of them day-to-day.” That doesn’t mean reflexively adopting a glass-half-full outlook. It means being intentional about what to highlight as you craft the narrative of your life.

Leaders also have an important role to play in challenging others about their narratives. “I often say to people, ‘Help me understand that,’” Dave Goebel says. “It’s an indirect way of saying that there might be a different way to look at things.” Nudged in this way, people often recognize their flawed assumptions. If they don’t, you can take a more forceful approach and point out the glitches in their story.

Don’t be a victim. Another trap people fall into is the belief that they have no control over events. This is a particularly dangerous notion; it can lead them to feel sorry for themselves and shut down. I’ve concluded that entrepreneurs are wired a bit differently from most people—one way being that they tend not to dwell on bad news. “When you’re a victim, you’re not owning or fixing anything,” says Seth Besmertnik, the founder and CEO of Conductor, a search-engine optimization firm. In 2018 he sold the company to WeWork, only to scramble to repurchase it after that company’s IPO failed and investors started scrutinizing its business model. And then the pandemic struck. “When I knew things were about to fall apart, I immediately went to OK, what’s the opportunity here?” he told me. “We moved fast and didn’t waver and turned a terrible situation into an amazing outcome. But that happens only when you take ownership. If you see yourself as a victim, you’re going to be a victim.”

. . .

I asked Ruth Simmons, a former president of Prairie View A&M University, Smith College, and Brown University, what guidance she most commonly shares with students. “They should never assume they can predict which experiences will teach them the most about what they value or what their life should be,” she said. “You have to be open and alert at every turn to the possibility that you’re about to learn the most important lesson of your life.”

Leadership lessons are all around you. Take in as many as you can and make the time to reflect on what you discover. That’s an essential part of leadership. The intensity of the role—the variety of problems encountered, the need to spot patterns early and often, the sheer amount of work—requires the human equivalent of machine learning. Continually scanning for potential lessons is key to making the leap to leader and flourishing once you get there.

Editor’s note: Adam Bryant is the author of The Leap to Leader: How Ambitious Managers Make the Jump to Leadership (Harvard Business Review Press, 2023), from which this article is adapted.

Copyright 2023 Harvard Business School Publishing Corporation. Distributed by The New York Times Syndicate.

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