Fearless Creative Leadership

How much power do you give the past? Vincent Bragg and Joe Nickson are two of the co-founders of ConCreates. They started the company in federal prison where, as you’ll hear, you can learn a lot about business and even more about life. There are so many aspects to the story of ConCreates that it’s difficult to know which ones to highlight. The resilience of human beings. The power of imagination. The capacity to look beyond the easy, obvious presentation of who someone is to see the person beyond that. And the possibilities that appear when we become clear about the impact we want to make. All of these truths have one thing in common. A willingness to see ourselves not through the mists of our past - the stories we have told ourselves about our history, our circumstances, our limitations. But through a lens that is focused on our future. Who we want to be, the difference we want to make, the impact we want to leave behind. It is said that the greatest lesson of history is that we do not learn the lessons of history. Unless we do. And then everything is possible.

Edited highlights of our full conversation. How much power do you give the past? Vincent Bragg and Joe Nickson are two of the co-founders of ConCreates. They started the company in federal prison where, as you’ll hear, you can learn a lot about business and even more about life. There are so many aspects to the story of ConCreates that it’s difficult to know which ones to highlight. The resilience of human beings. The power of imagination. The capacity to look beyond the easy, obvious presentation of who someone is to see the person beyond that. And the possibilities that appear when we become clear about the impact we want to make. All of these truths have one thing in common. A willingness to see ourselves not through the mists of our past - the stories we have told ourselves about our history, our circumstances, our limitations. But through a lens that is focused on our future. Who we want to be, the difference we want to make, the impact we want to leave behind. It is said that the greatest lesson of history is that we do not learn the lessons of history. Unless we do. And then everything is possible.

If you don’t know what you don’t know, how certain should you be about what you do know? Parts of this conversation with Kerry Sulkowicz, the leadership confidant and psychiatrist, were featured in last week’s Look Ahead at 2022 episode. If you haven’t heard that yet - I spoke to nine different leaders about how society has changed as a result of the last two years, and what that means for leadership. The episode was featured in Fast Company and the link is in the show notes and on the Fearless website. Kerry works with leaders across the world and is also President-elect of the American Psychoanalytic Association. He knows a thing or two about the psychology of leadership. The human condition is attracted to certainty. To be fed and safe and healthy. To belong. To matter. It’s hard to get away from these instincts and the impulses that come with them. Which makes us more inclined to look for evidence that fits our desired view of the world and to overlook questions and possibilities and gaps in our knowledge that might contradict that view. Which, in turn, makes what we do know more risky and what we don't know more valuable. In most organizations, leaders sit or are placed on a pedestal. There is a structural hierarchy that directly affects the flow of information. When we allow ourselves to believe that the structure itself provides us with all the information that we need, we run the risk of never knowing what we don't know. If your goal is to be someone who leads empathetically and impactfully, a question to add to your leadership portfolio is the one that Howard Schultz reportedly asked himself and his leadership team at Starbucks every week. What do I not know that would make this decision wrong? And then follow it up with this one. Why am I afraid to find out?

This episode is featured in Fast Company. As we look to 2022 and beyond, how will the best leaders lead? As we wrap the wildest year that we’ve ever heard of, I thought it would be helpful to put some context around what just happened and where we go from here. Over the last couple of weeks I’ve been asking some of my previous guests for their take on four questions.  How have we changed? What does that mean for leadership? What does the future of the workplace look like? And, as a consequence of all that, how do leaders need to adapt and evolve to meet and lead the future?

This episode is being published on Christmas Eve, which is my favorite day of the year.  Growing up, the anticipation of everything that was to come filled me with wonder and possibility. The month long build up of advent calendars being opened, trees being bought and houses being decorated, cards arriving, then food, then grandparents. The chill in the air, and the hope for snow that stays with me to this day. As I got older, and started to see Christmas through a different lens, I discovered A Christmas Carol by Charles Dickens. One of the most memorable experiences of my life took place on Christmas Eve 1994 when Chris and I saw Patrick Stewart’s one man performance of the story onstage in New York. I’ve never found a video recording of it anywhere. But if you’re willing to step back in time, you can buy the CD on Amazon. It will take you to Dickensian London from its first moment. Set amongst the despair and darkness of a struggling city, A Christmas Carol is the story of a powerful man led astray by greed. He creates a world that has no compassion or concern for others.  Sounds familiar.  Michael Wolff is a former editor of Adweek but is famous for his work as a columnist for New York Magazine, Vanity Fair, British GQ, The Guardian, and The Hollywood Reporter. He is best known as the author of several books on some of the leading figures of our time. Fire and Fury: Inside the Trump White House topped the New York Times best seller list for ten weeks in 2018. His most recent book, Too Famous, is a collection of stories and essays that he has written over the years about some of the world’s most powerful and controversial leaders - from Rupert Murdoch, to Harvey Weinstein. From Boris Johnson to Michael Bloomberg. These are people that he has come to know intimately and the effect of whom he has seen up close.  After listening to our conversation, you might believe that Michael is not a fan of leaders or, in fact, of leadership. In fact, I think it would be easy to come away from this episode feeling that some of the spirit of the early chapters of A Christmas Carol had seeped in, like frost through the keyhole.   But like A Christmas Carol, I think this episode is ultimately one of hope.  Next year is going to be chaos on steroids. The Great Resignation, work from home, vaccination passports, rapid tests, two plus years of physical disconnection, a fundamental change in the structure of society, a de-emphasis on work and a yearning for in-person experiences, the accelerating acceleration in the use of technology. In the middle of all that, we need some people to step up and provide a way forward. We will need leaders. Brave, bold, empathetic, caring leaders who will have to do this without case studies or classes or books or mentors who have experience, for the simple reason that none exist and no one has any. Given all of that, traditional leadership can no longer be the reference for how you meet this moment. So how do you lead with so little knowledge of what we’re facing and amidst so much uncertainty? The framework I think, lies in an answer that Michael gave in response to my question about how he is raising his children during the pandemic. If we have learned anything from 2020 and 2021, it is that we cannot know what 2022 will bring. The story we tell future generations about how we met this moment will depend on how we approach what comes next. With frustration and old rules. Or with grace, originality and some humor. Happy Holidays and Merry Christmas to you all.

Edited highlights of our full conversation. This episode is being published on Christmas Eve, which is my favorite day of the year.  Growing up, the anticipation of everything that was to come filled me with wonder and possibility. The month long build up of advent calendars being opened, trees being bought and houses being decorated, cards arriving, then food, then grandparents. The chill in the air, and the hope for snow that stays with me to this day. As I got older, and started to see Christmas through a different lens, I discovered A Christmas Carol by Charles Dickens. One of the most memorable experiences of my life took place on Christmas Eve 1994 when Chris and I saw Patrick Stewart’s one man performance of the story onstage in New York. I’ve never found a video recording of it anywhere. But if you’re willing to step back in time, you can buy the CD on Amazon. It will take you to Dickensian London from its first moment. Set amongst the despair and darkness of a struggling city, A Christmas Carol is the story of a powerful man led astray by greed. He creates a world that has no compassion or concern for others.  Sounds familiar.  Michael Wolff is a former editor of Adweek but is famous for his work as a columnist for New York Magazine, Vanity Fair, British GQ, The Guardian, and The Hollywood Reporter. He is best known as the author of several books on some of the leading figures of our time. Fire and Fury: Inside the Trump White House topped the New York Times best seller list for ten weeks in 2018. His most recent book, Too Famous, is a collection of stories and essays that he has written over the years about some of the world’s most powerful and controversial leaders - from Rupert Murdoch, to Harvey Weinstein. From Boris Johnson to Michael Bloomberg. These are people that he has come to know intimately and the effect of whom he has seen up close.  After listening to our conversation, you might believe that Michael is not a fan of leaders or, in fact, of leadership. In fact, I think it would be easy to come away from this episode feeling that some of the spirit of the early chapters of A Christmas Carol had seeped in, like frost through the keyhole.   But like A Christmas Carol, I think this episode is ultimately one of hope.  Next year is going to be chaos on steroids. The Great Resignation, work from home, vaccination passports, rapid tests, two plus years of physical disconnection, a fundamental change in the structure of society, a de-emphasis on work and a yearning for in-person experiences, the accelerating acceleration in the use of technology. In the middle of all that, we need some people to step up and provide a way forward. We will need leaders. Brave, bold, empathetic, caring leaders who will have to do this without case studies or classes or books or mentors who have experience, for the simple reason that none exist and no one has any. Given all of that, traditional leadership can no longer be the reference for how you meet this moment. So how do you lead with so little knowledge of what we’re facing and amidst so much uncertainty? The framework I think, lies in an answer that Michael gave in response to my question about how he is raising his children during the pandemic. If we have learned anything from 2020 and 2021, it is that we cannot know what 2022 will bring. The story we tell future generations about how we met this moment will depend on how we approach what comes next. With frustration and old rules. Or with grace, originality and some humor. Happy Holidays and Merry Christmas to you all.

Judy Jackson is the Global Head of Culture at WPP which makes her responsible for providing the vision and strategy for building a culture that embraces 100,000 people. There’s no one size fits all approach that satisfies that brief. It’s a role that requires a three dimensional view of human beings.  Leaders aren’t particularly fond of displaying their weaknesses and vulnerabilities. After all, it takes time, work and a lot of sacrifice to reach a position of power. Why would you give someone the ammunition to knock you off that perch? How very 2019 of me. Leaders are going to have to get used to showing up as fully formed human beings - flaws and all. Because the pandemic has made us all more conscious of who we want to spend time with. Who we trust and who gives us hope. It’s also forced us - or perhaps better said - allowed us to show each other who we really are. Not the bib and tuckered, booted and polished professionals who think strategically and execute unerringly. But the harried humans who wear blue fuzzy Birkenstocks, whose offices are squeezed into the corner of their bedrooms and whose families don’t always provide the cathedral-esque silence appropriate for the seriousness of the Zoom call we’re participating in. If, after all of that, you think Judy’s wrong and you’re going to go back to showing the people the work for you only the good of you, you’re going to miss out on a couple of important opportunities. The chance to unlock your full potential. And the chance to help others unlock theirs.

Edited highlights of our full conversation. Judy Jackson is the Global Head of Culture at WPP which makes her responsible for providing the vision and strategy for building a culture that embraces 100,000 people. There’s no one size fits all approach that satisfies that brief. It’s a role that requires a three dimensional view of human beings.  Leaders aren’t particularly fond of displaying their weaknesses and vulnerabilities. After all, it takes time, work and a lot of sacrifice to reach a position of power. Why would you give someone the ammunition to knock you off that perch? How very 2019 of me. Leaders are going to have to get used to showing up as fully formed human beings - flaws and all. Because the pandemic has made us all more conscious of who we want to spend time with. Who we trust and who gives us hope. It’s also forced us - or perhaps better said - allowed us to show each other who we really are. Not the bib and tuckered, booted and polished professionals who think strategically and execute unerringly. But the harried humans who wear blue fuzzy Birkenstocks, whose offices are squeezed into the corner of their bedrooms and whose families don’t always provide the cathedral-esque silence appropriate for the seriousness of the Zoom call we’re participating in. If, after all of that, you think Judy’s wrong and you’re going to go back to showing the people the work for you only the good of you, you’re going to miss out on a couple of important opportunities. The chance to unlock your full potential. And the chance to help others unlock theirs.

Raja Rajamannar is the Chief Marketing & Communications Officer for Mastercard and is also President of the company’s healthcare business. His list of accomplishments is long and significant. He was recognized as the Global Marketer of the Year by the World Federation of Advertisers, was named one of the Top 5 “World’s Most Influential CMOs” by Forbes, and one of the Top 10 “World’s Most Innovative CMOs” by Business Insider. He has been inducted into The CMO Club Hall of Fame. He has also been recognized as one of AdWeek’s most tech-savvy CMOs. So what matters to him today? How do you live your life well? That question is at the very heart of the upheaval of the employer - employee relationship. Whether we come to call it ‘The Great Resignation’ or ‘The Great Self-Reflection’ or anything else. For the first time in the history of our society, the people who do the bulk of the work are discovering they don’t have to do it on someone else’s terms. They can decide what a ‘life well lived’ looks like on their terms. They’re discovering that they have agency in their own lives. The pressure this puts on leaders is almost more than we can understand. It changes everything. And if you thought ‘it’s lonely at the top’ was true before, it’s going to become an even more meaningful cliché as we stumble into 2022. Leaders are going to have to adapt and evolve to these dramatic societal shifts. Leadership is going to have to change at its very heart and soul. But as you personally confront these challenges, my hope is that you will place at the center of your thinking that very same question. How do you live your life well? Empathy, vulnerability, care and compassion are going to have to be building blocks on which your leadership is built. I don’t see a way in which you can succeed from now on without those as the foundations from which you lead. But you can’t fake these qualities. They’re not sustainable unless they reflect the life that you want to lead. What do you want to do with your life? What do you want to spend your time on while you are alive? These are questions that scare us. Questions that can feel judgmental or too filled with consequence if we really confront them. But when we are willing to confront them, the answers unleash such reservoirs of possibility, that soon we cannot imagine why we lived for so long without the clarity and the confidence they provide. And they come with the added benefit that they will make you a world-class leader for as long as you choose to lead.

Edited highlights of our full conversation. Raja Rajamannar is the Chief Marketing & Communications Officer for Mastercard and is also President of the company’s healthcare business. His list of accomplishments is long and significant. He was recognized as the Global Marketer of the Year by the World Federation of Advertisers, was named one of the Top 5 “World’s Most Influential CMOs” by Forbes, and one of the Top 10 “World’s Most Innovative CMOs” by Business Insider. He has been inducted into The CMO Club Hall of Fame. He has also been recognized as one of AdWeek’s most tech-savvy CMOs. So what matters to him today? How do you live your life well? That question is at the very heart of the upheaval of the employer - employee relationship. Whether we come to call it ‘The Great Resignation’ or ‘The Great Self-Reflection’ or anything else. For the first time in the history of our society, the people who do the bulk of the work are discovering they don’t have to do it on someone else’s terms. They can decide what a ‘life well lived’ looks like on their terms. They’re discovering that they have agency in their own lives. The pressure this puts on leaders is almost more than we can understand. It changes everything. And if you thought ‘it’s lonely at the top’ was true before, it’s going to become an even more meaningful cliché as we stumble into 2022. Leaders are going to have to adapt and evolve to these dramatic societal shifts. Leadership is going to have to change at its very heart and soul. But as you personally confront these challenges, my hope is that you will place at the center of your thinking that very same question. How do you live your life well? Empathy, vulnerability, care and compassion are going to have to be building blocks on which your leadership is built. I don’t see a way in which you can succeed from now on without those as the foundations from which you lead. But you can’t fake these qualities. They’re not sustainable unless they reflect the life that you want to lead. What do you want to do with your life? What do you want to spend your time on while you are alive? These are questions that scare us. Questions that can feel judgmental or too filled with consequence if we really confront them. But when we are willing to confront them, the answers unleash such reservoirs of possibility, that soon we cannot imagine why we lived for so long without the clarity and the confidence they provide. And they come with the added benefit that they will make you a world-class leader for as long as you choose to lead.