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Leading With Heart

What Makes Great Leaders? Ask the People Who Work for Them

June 21, 2022
Five core characteristics shine through.

The following is an excerpt from the new book Leading with Heart: 5 Conversations That Unlock Creativity, Purpose, and Results by John Baird and Edward Sullivan (Harper Business: 2022).

There is no arguing that we are in the middle of a leadership crisis. And not just in politics but in the business world as well. We know this first and foremost because people aren’t excited about their work. According to Gallup, two in three Americans are not “involved in and enthusiastic about their work and workplace,” and 50% are actively looking for a new job. When we investigate why so many people are looking for a new job, the problem is clear: too many people work for leaders who are disempowering, lacking curiosity and simply unwilling or unable to establish real emotional connections with their teams.

Employees want to feel seen and appreciated for who they are and for the unique things they can contribute. Yet far too many leaders treat their teams as little more than cogs in a machine.

As coaches who have been working on the front lines of business and politics for decades, we decided it was time to figure out exactly why some leaders are able to make that heart connection, and why others can’t.

Our journey began, like many journeys do, with a question: What separates truly transformational leaders from the rest?

Every year literally thousands of books, articles, and blogs are published espousing the proven technique for everything from leading companies and parenting children to swinging a golf club and roasting chicken. We’ve been led to believe by legions of self-proclaimed experts that there’s a right and wrong way to do nearly everything. Yet, as author and former Harvard professor Phil Rosenzweig put it, “for all the secrets and formulas, for all the self-proclaimed thought leadership, success in business is as elusive as ever . . . probably more elusive than ever.”

With so much advice out there, why is great leadership so scarce? 

Driven by that question, we decided to pressure-test some of those leadership how-to guides and listicles of simple leadership hacks. We looked deeply into the volumes of notes and data we’ve collected over our combined 40 years working with many of the world’s top leaders in business and politics to look for trends. If there were commonalities in behavior and habits among our most successful clients, we would surely find them. 

But after poring over the data, we observed that the leaders with the best bottom-line business and organizational outcomes (i.e., in terms of growth, exits, retention, and employee satisfaction) were all over the map in what we think of as normal leadership behaviors or habits. Take a dozen great leaders, and you’ll find they lead in a wide variety of ways.

  • Some are extroverted inspirational speakers, and others are introverts who are more comfortable communicating via long memos or in private conversations.
  • Some set crystal-clear visions for the future and chart a bold path forward, while others make general observations about a problem area or customer profile and let their teams figure out the innovative solutions.
  • Some have fixed morning routines, waking up at 5 a.m. to meditate, jump on their Pelotons or do sun salutations. Others roll out of bed when they feel like it and show up at the office over-caffeinated and frazzled.

Everywhere we looked in the data for common traits or behaviors among our clients—the traditional dos and don’ts of leadership and executive presence—we encountered more variance than anything else. 

What were we not seeing?

Redoubling our efforts, we delved even more deeply into our coaching archives—more files, more paper—but this time we asked a different question: What do the teams of great leaders— that is, the people closest to them, the people inspired by them every day—have to say about these leaders?

The answer, we realized, was right in front of us the whole time:

  • “He’s incredibly self-aware and isn’t afraid to take a hard look at himself.”
  • “She saw a potential in me I didn’t see in myself.”
  • “He always knows exactly what I need to hear to get motivated again.”
  • “She helped me overcome my self-doubt and begin to believe in myself.”
  • “He’s able to ask me questions and give me feedback in a way that helps me grow as a person and a professional.”

It didn’t matter whether these leaders were compelling public speakers, took a different employee to lunch every day, or placed their desk in the middle of the office to show how accessible they were. It wasn’t in their tactics, habits and hacks.

Instead, our data showed us that great leaders have five core characteristics that help them connect at an authentic human level with their people:

1. They are aware of their people’s needs. They get curious about what they and their teams need to feel creative and resourceful. Getting our needs met is the foundation of all higher-order thinking and working. When you aren’t taking care of yourself or don’t feel safe, you can’t show up with your A game. You’re not going to ask the hard questions or make the risky suggestions.

2. They confront their people’s fears. They directly address the fears that are holding people back. Fear keeps us from taking risks and compels us to do hurtful things and make bad decisions. If your team members don’t feel safe saying something when they smell smoke, you will always be putting out fires.

3. They understand their own desires and what drives their people. They get very honest about what their core desires and drivers are, as well as those of their team. What’s more, they make sure to keep those desires in check, lest they or their team be derailed by them.

4. They leverage their gifts. They search deeply inside themselves and their teams for unrealized gifts. World-class skill and talent are often wasted because it goes undiscovered. Leading with heart requires giving up the idea of what you are good at to unearth what you might be great at.

5. They connect with purpose. Finally, they connect with their own core sense of purpose, and help their teams connect with theirs. The greatest work is done by teams who believe they are serving some greater good. The easiest mistake to make is to assume all your team cares about is money or prestige.

Armed with this unique array of abilities, the great leaders we’ve worked with make people feel seen, inspire creative thinking, unlock purpose, and ultimately drive bottom-line business results. There was the tech CEO with the incredible penchant for seeing talents and gifts in her people that they weren’t aware of in themselves, often placing people in new positions and unlocking a new and powerful potential. Or the dating app CEO who, seeing that his top-down approach was killing morale and creativity, began pushing all product and design questions down into his team, giving them much-needed agency and authority. Or the social network founder who realized that his fear of failure was preventing him and his team from taking risks, making bold hires, and learning from customer feedback. There were literally hundreds of examples.

What we learned is that much more than following formulas or playbooks, the greatest leaders of our time are simply the most relentlessly curious, caring and insightful about themselves and their people. They have the courage and inquisitiveness to engage in conversations that are often considered taboo in the workplace. Conversations about what we really need to feel safe and creative, what we’re afraid of, what we most deeply desire, what we’re best at, and what our highest purpose is. Conversations that enable them to transform themselves, their teams and their organizations.

That is what we mean by leading with heart.

John Baird has been an executive coach in Silicon Valley for over 25 years. He built his career coaching in the C-Suite at companies ranging from Apple and Nike to start-ups like DoorDash and MasterClass. He earned a PhD in Organizational Leadership from Purdue University. He is currently founder and chairman of the executive coaching consultancy Velocity.

Edward Sullivan has been coaching and advising start-up founders, Fortune 10 executives and heads of state for over 15 years. His clients include executives from Google, Salesforce, Slack and dozens of other fast-growth companies. He holds an MBA from Wharton and an MPA from the Harvard Kennedy School. Edward is CEO and president of Velocity.

Leading with Heart: 5 Conversations That Unlock Creativity, Purpose, and Results is copyright © 2022 by John Baird & Edward Sullivan. This excerpt is reprinted by permission of Harper Business, an imprint of HarperCollins Publishers.

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