Ken Chenault on Why Leaders Need Empathy and a ‘High Level of Self-Awareness’ During Challenging Times

Despite the pandemic, social unrest, and geo-political tumult of the past four years, more than half of CEOs expect 2024 to be a more challenging year for leadership, given the uncertainties of an election year and rapid technological advances in AI and other areas.

The way executives handle the expected — and unexpected — challenges of this year will easily determine their reputation as a leader, and no one knows this more than Ken Chenault, Chairman and Managing Director of the VC firm General Catalyst. During his 17-year tenure as CEO of American Express, Chenault, who sits on Chief’s Board of Directors, led his company through two turbulent events, including the September 11 attacks and the 2008 financial crisis. That's just one reason why he was selected to be a judge for Chief’s The New Era of Leadership Awards, which celebrates executive women and organizations who are redefining what it means to lead in 2024.

Chenault has a deep understanding of what it takes to be a good executive, during good times and bad, which is why we decided to take a look at some of the best leadership advice he’s shared with Chief over the years. Here are some of our favorites:

1. Demonstrate the right priorities.

“The first priority is your people,” he said in a 2020 conversation with Chief. “You've got to focus on their safety, health, and wellbeing — and the same for your customers and clients. Your organization, people, and customers need to know that you really understand and empathize with them. You have to continually communicate with transparency and provide context.”

2. Show a “high level of self-awareness.”

“Admit that you don’t have the full answer, but define what some small wins are — things you can control that you’re going to focus on,” he said in a 2021 conversation with Chief’s CEO Carolyn Childers. Doing this, he says, will help “to develop markers and give people reasons to increase their confidence” in you, as trust in leadership is a huge factor when navigating major challenges.

3. Communicate what you know — and what you don’t.

“In this uncertain environment where facts are constantly changing, you need to prepare people for a series of pivots, and give them context for why you're making those pivots,” he says. “You have to prepare your organization to be adaptable because the decisions that you're making now — some of those will change. The circumstances will change. So you have to explain your rationale and context for every pivot.”

Then and only then, he says, will you be able to move your business forward so that both you and your team come out stronger, regardless of the obstacles you’ve faced.

Click here to nominate a leader or company for Chief’s The New Era of Leadership Awards, which celebrates executive women and organizations who are redefining what it means to lead in 2024. The deadline to apply is Sunday, March 31. (Chief Membership not required).