Fearless Creative Leadership

How do you know when something's impossible? This is the full conversation with the futurist Faith Popcorn that we recorded a few weeks ago, some of which we included in our first episode of the year - 'How Will The Best Leaders Lead In 2022.' Faith is the founder of The BrainReserve and she and her team are hired to tell companies and industries what the future looks like. Most people like the illusion of the status quo. The here and now is safe and warm, and predicting a future filled with disruption upsets companies and their leaders who are counting on more of the same to get them to next year. The world has never worked like that, actually. And as we approach the 24th month of the new society that we are building, I'm consistently struck by how many people still trying to use the past as the reference point for the future. The cost of entry to becoming a leader is imagination. The weekly fee for membership in the club of great leaders is the capacity and willingness to keep seeking out the seemingly impossible and then finding a way to make it part of the expected. And if you think I'm asking too much, consider this, courtesy of Faith's Twitter feed last week. Over the last 200 years, the average lifespan of our species has tripled. What makes any of us sure that won't happen again?

In the movie of your life, which part do you want to play? During award-winning costume designer Ellen Mirojnick's career, she's worked with directing greats, from Steven Soderbergh, to Ridley and Tony Scott, to Oliver Stone. She's the reason the name Gordon Gekko immediately conjures an image in our mind, and why Bridgerton swept millions of viewers off their feet. Ellen turns costumes into characters. How she does that is worth thinking about for every leader. Over the last few months on this podcast, we've been talking a lot about empathetic, sensitive leadership. About building trust and displaying vulnerability. Not any of which are words to attach to Gordon Gekko. Gordon Gekko was greedy, immoral, self-obsessed. Labels that fit some of today's leaders but are probably not descriptions that you aspire to, if you're listening to this podcast. Which brings up the all important question. How do you want to be described? Each of us play multiple roles in our lives. In every relationship, we have to decide which parts of ourselves we bring center stage and which we move into the wings. Which personality traits, which characteristics, which areas of expertise should be prominent, and which should take a back seat in that moment. In our private lives, there's - usually - more forgiveness and more latitude. But in our leadership roles, when we are confused or inconsistent about how we show up, we run the risk of being misunderstood or, worse, misrepresented. And the consequence of that inconsistency is an erosion of trust and confidence from everyone around you. The best leaders are clear about the attributes they want to be known for, and then turn them into a character that shows up, consistently, every day. Strategic, empathetic, ambitious, risk-taking, disruptive, loyal, creative, sensitive, rule-breaking. The choices are yours. And as long as they are true to who you really are, you'll have the foundations of a leadership character that can draw people with you on the journey, and will have people remember the impact that you made long after the final credits have rolled.

Edited highlights of our full conversation. In the movie of your life, which part do you want to play? During award-winning costume designer Ellen Mirojnick's career, she's worked with directing greats, from Steven Soderbergh, to Ridley and Tony Scott, to Oliver Stone. She's the reason the name Gordon Gekko immediately conjures an image in our mind, and why Bridgerton swept millions of viewers off their feet. Ellen turns costumes into characters. How she does that is worth thinking about for every leader. Over the last few months on this podcast, we've been talking a lot about empathetic, sensitive leadership. About building trust and displaying vulnerability. Not any of which are words to attach to Gordon Gekko. Gordon Gekko was greedy, immoral, self-obsessed. Labels that fit some of today's leaders but are probably not descriptions that you aspire to, if you're listening to this podcast. Which brings up the all important question. How do you want to be described? Each of us play multiple roles in our lives. In every relationship, we have to decide which parts of ourselves we bring center stage and which we move into the wings. Which personality traits, which characteristics, which areas of expertise should be prominent, and which should take a back seat in that moment. In our private lives, there's - usually - more forgiveness and more latitude. But in our leadership roles, when we are confused or inconsistent about how we show up, we run the risk of being misunderstood or, worse, misrepresented. And the consequence of that inconsistency is an erosion of trust and confidence from everyone around you. The best leaders are clear about the attributes they want to be known for, and then turn them into a character that shows up, consistently, every day. Strategic, empathetic, ambitious, risk-taking, disruptive, loyal, creative, sensitive, rule-breaking. The choices are yours. And as long as they are true to who you really are, you'll have the foundations of a leadership character that can draw people with you on the journey, and will have people remember the impact that you made long after the final credits have rolled.

Who do you really want to join you on the ride? Nils Leonard is one of the co-founders of Uncommon London. They describe themselves as a creative studio building brands that people in the real world actually wish existed. Nils has been on the show before. He was one of my early guests on the podcast and that conversation came in the early days of Uncommon and he was very open about his ambitions and his expectations for himself and his company. Four years on and it's hard to see the gaps between what he said back then and how he talks about the company today. In my experience - both as a company founder and as a coach - there is one aspect of leadership that brings many to their emotional knees. Firing someone. When to acknowledge that the fit between the person and the organization doesn't work. On a human level, we all want to belong and the fear - conscious or instinctive - that we might one day be on the receiving end of this conversation, makes many leaders do everything they can to avoid that moment. The one in which we say out loud, to someone's face, we don't want you. Even now, as you're listening, if you hit pause and say out loud, we don't want you, there will be a feeling in your stomach that you hope goes away fast. But there are three other parts of this that don't get enough weight in the emotional wrestling match. First are the hopes, needs and expectations of all the people that work for you who are contributing so much that they will never be part of a conversation like this. Whose talent and efforts and commitment to you and to the business are subsidizing the person who doesn't fit. Second are the needs of the organization as a whole, which has no agency and no ability to help itself, and which is as reliant on your protection and care as an infant. And third is the person who is receiving this news. Who knows, in almost every instance in my experience, that this job isn't a fit, that these people are not their tribe and that they are, to use Nils' description, a passenger on someone's else's ride. "Death twitches my ear. Live, he says I'm coming." They say that life is a journey. And so is building a business. Who gets to go on that ride is perhaps the most important decision that a leader takes.

Edited highlights of our full conversation. Who do you really want to join you on the ride? Nils Leonard is one of the co-founders of Uncommon London. They describe themselves as a creative studio building brands that people in the real world actually wish existed. Nils has been on the show before. He was one of my early guests on the podcast and that conversation came in the early days of Uncommon and he was very open about his ambitions and his expectations for himself and his company. Four years on and it's hard to see the gaps between what he said back then and how he talks about the company today. In my experience - both as a company founder and as a coach - there is one aspect of leadership that brings many to their emotional knees. Firing someone. When to acknowledge that the fit between the person and the organization doesn't work. On a human level, we all want to belong and the fear - conscious or instinctive - that we might one day be on the receiving end of this conversation, makes many leaders do everything they can to avoid that moment. The one in which we say out loud, to someone's face, we don't want you. Even now, as you're listening, if you hit pause and say out loud, we don't want you, there will be a feeling in your stomach that you hope goes away fast. But there are three other parts of this that don't get enough weight in the emotional wrestling match. First are the hopes, needs and expectations of all the people that work for you who are contributing so much that they will never be part of a conversation like this. Whose talent and efforts and commitment to you and to the business are subsidizing the person who doesn't fit. Second are the needs of the organization as a whole, which has no agency and no ability to help itself, and which is as reliant on your protection and care as an infant. And third is the person who is receiving this news. Who knows, in almost every instance in my experience, that this job isn't a fit, that these people are not their tribe and that they are, to use Nils' description, a passenger on someone's else's ride. "Death twitches my ear. Live, he says I'm coming." They say that life is a journey. And so is building a business. Who gets to go on that ride is perhaps the most important decision that a leader takes.

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.