Fearless Creative Leadership

Stephanie Mehta is the Editor-in-Chief of Fast Company. They study, explore, analyze and report on innovation like no other media brand. Stephanie has been a writer almost since birth. Like the rest of us, she’s learned how to lead through trial and error and experience and asking and listening. Leadership used to be a two dimensional, top down, hierarchical practice. I say. You do. Today, it is a three dimensional role, powered by a leader's ability to use influence and in which they are the visionary, guide, architect, storyteller, as well as the supporter of multiple constituencies. Today, the leader is expected to have a point of view or to be clear - and credible - about why they don’t. The best way and, in fact, the only way, for leaders to navigate this complexity, is to establish a set of principles that guide them in moments of crisis and consternation. If you take the time to define your principles now - when things are quiet and the microphone isn’t being pushed in your face - you will dramatically increase the chances that what you come up with when the heat is on, will be clear, consistent and compelling. Three words by which to measure anyone’s leadership. And which increase the chances that whatever you say, you can live with the consequences of having said it.

Edited highlights of our full conversation. Stephanie Mehta is the Editor-in-Chief of Fast Company. They study, explore, analyze and report on innovation like no other media brand. Stephanie has been a writer almost since birth. Like the rest of us, she’s learned how to lead through trial and error and experience and asking and listening. Leadership used to be a two dimensional, top down, hierarchical practice. I say. You do. Today, it is a three dimensional role, powered by a leader's ability to use influence and in which they are the visionary, guide, architect, storyteller, as well as the supporter of multiple constituencies. Today, the leader is expected to have a point of view or to be clear - and credible - about why they don’t. The best way and, in fact, the only way, for leaders to navigate this complexity, is to establish a set of principles that guide them in moments of crisis and consternation. If you take the time to define your principles now - when things are quiet and the microphone isn’t being pushed in your face - you will dramatically increase the chances that what you come up with when the heat is on, will be clear, consistent and compelling. Three words by which to measure anyone’s leadership. And which increase the chances that whatever you say, you can live with the consequences of having said it.

Faith Popcorn is a futurist. To many of us she is the original and still the best. She told Kodak about digital imagery, Ford about electric cars and Coke about bottled water before any of them existed. In the 1980s she told P&G that everything would be home delivered. In every case they either laughed or threw her out of the room. That’s the price of forecasting change. The ability to see the future is, by definition an uncertain science. No matter how often you are right, you will be wrong far more often. And yet it is the what-ifs that we get remembered for. The what-ifs that change lives. Life is short. And unpredictable. And we have much less control over it than we think. Leadership is an opportunity to make a difference while we’re here.   Developing your appetite for the unlikely and redefining your view of the impossible make you an infinitely better leader of any business that depends on creative thinking and innovation. What do you think will definitely not happen over the next five years? And are you sure?

Edited highlights of our full conversation. Faith Popcorn is a futurist. To many of us she is the original and still the best. She told Kodak about digital imagery, Ford about electric cars and Coke about bottled water before any of them existed. In the 1980s she told P&G that everything would be home delivered. In every case they either laughed or threw her out of the room. That’s the price of forecasting change. The ability to see the future is, by definition an uncertain science. No matter how often you are right, you will be wrong far more often. And yet it is the what-ifs that we get remembered for. The what-ifs that change lives. Life is short. And unpredictable. And we have much less control over it than we think. Leadership is an opportunity to make a difference while we’re here.   Developing your appetite for the unlikely and redefining your view of the impossible make you an infinitely better leader of any business that depends on creative thinking and innovation. What do you think will definitely not happen over the next five years? And are you sure?

Jenny Just is the Co-Founder of PEAK6 Investments. She’s been described as the most successful business woman you’ve never heard of. A recent study by the World Health Organization reveals that working more than 55 hours a week causes a significant increase in premature death. If that’s true, it’s just one more reason why leaders should make decisions faster. And why they need to create an environment in which it’s easier for others to make decisions faster too. What’s the reason that decisions often take too long to get made? Risk. Risk of failure for sure. But also, and no less importantly, the risk of being wrong. The human fear that is often hidden behind a carefully designed wall of over-analyzed data and needlessly complex strategies. What’s worse than being wrong? Allowing risk to prevent you from discovering that you might be right.

Edited highlights of our full conversation. Jenny Just is the Co-Founder of PEAK6 Investments. She’s been described as the most successful business woman you’ve never heard of. A recent study by the World Health Organization reveals that working more than 55 hours a week causes a significant increase in premature death. If that’s true, it’s just one more reason why leaders should make decisions faster. And why they need to create an environment in which it’s easier for others to make decisions faster too. What’s the reason that decisions often take too long to get made? Risk. Risk of failure for sure. But also, and no less importantly, the risk of being wrong. The human fear that is often hidden behind a carefully designed wall of over-analyzed data and needlessly complex strategies. What’s worse than being wrong? Allowing risk to prevent you from discovering that you might be right.

Charlie Cole is the CEO of FTD. As you’re about to hear, Charlie is a high energy leader. Relentlessly positive, endlessly optimistic. He took over a bankrupt company in the early days of a pandemic. He put together an executive team that only now, a year later can he spend any time with in person. Charlie discovered something brand new about himself in the middle of all of that. That he has a breaking point. Every leader does. And thinking of yourself as a servant will shorten the time it takes for you to discover yours. Are you in service? Yes. To the change you want to create in the world, and to providing the business with what it needs to reach that goal. But you are not a servant. You have agency and free will. Oh, and you have one other thing. Access to the levers of power. When a servant pulls the levers of power, it’s called a revolution. When a leader pulls them, it’s called a decision.

Edited highlights of our full conversation. Charlie Cole is the CEO of FTD. As you’re about to hear, Charlie is a high energy leader. Relentlessly positive, endlessly optimistic. He took over a bankrupt company in the early days of a pandemic. He put together an executive team that only now, a year later can he spend any time with in person. Charlie discovered something brand new about himself in the middle of all of that. That he has a breaking point. Every leader does. And thinking of yourself as a servant will shorten the time it takes for you to discover yours. Are you in service? Yes. To the change you want to create in the world, and to providing the business with what it needs to reach that goal. But you are not a servant. You have agency and free will. Oh, and you have one other thing. Access to the levers of power. When a servant pulls the levers of power, it’s called a revolution. When a leader pulls them, it’s called a decision.

Dave Gilboa is the Co-Founder and Co-CEO of Warby Parker.  Warby Parker is a twenty first century business. A case study in what purpose driven, values based, agile, innovative and disruptive looks like. At the beginning of 2010, the company didn’t exist. Mid-way through 2020, it was valued at $3 billion dollars. They have given away more than 8 million pairs of eyeglasses, offering the gift of sight and changing the lives of people around the world. Books have been written about the strategic steps they have taken to grow this business. But I wanted to understand the personal journey that led to him starting this company and how he, his co-founder Neil Blumenthal and their senior leadership team are adapting to the challenges of our new world. What guides them today? 

Edited highlights of our full conversation. Dave Gilboa is the Co-Founder and Co-CEO of Warby Parker.  Warby Parker is a twenty first century business. A case study in what purpose driven, values based, agile, innovative and disruptive looks like. At the beginning of 2010, the company didn’t exist. Mid-way through 2020, it was valued at $3 billion dollars. They have given away more than 8 million pairs of eyeglasses, offering the gift of sight and changing the lives of people around the world. Books have been written about the strategic steps they have taken to grow this business. But I wanted to understand the personal journey that led to him starting this company and how he, his co-founder Neil Blumenthal and their senior leadership team are adapting to the challenges of our new world. What guides them today?