Fearless Creative Leadership

Edited highlights of our full conversation. How are you creating your company's culture? Melissa Waters is the Chief Marketing Officer at Upwork. They describe themselves as the world's work marketplace. For any business, if your success depends on unlocking creative thinking and innovation, you have to be competitive in the talent wars. The leadership rules for that used to be simple. Create a compelling culture built around in-person experiences. But how do you lead when a company's culture is no longer built around physical space? Tens of millions, probably billions, of the currency of your choice have been spent by business owners to build offices conducive to collaboration, creativity, and innovation. I've owned some of those businesses and spent some of that money. We did it to create a culture. To provide an environment that would help unleash the creativity of the people that worked for us and convert that into economic return. Physical space wasn't the only element to building a culture. Beliefs and behaviors mattered as well. But all of them were connected by the fact that, day in and day out, human beings came together and shared ideas and experiences, and learned from each other. But without the physical structure of an office to provide the day-to-day container in which culture incubates, the responsibility to create those connections falls squarely on the leader. Who are your people? What do they think, care about, love, loathe? Are they happy or not? Fulfilled or not? Interested, enthused, excited or not? Do they feel connected to what matters to the company or not? And if your answer to any of those questions is "I don't know," then it might be time to ask yourself whether your leadership is adapting to the needs of today's talent. Or not.

Edited highlights of our full conversation. How are you creating your company's culture? Melissa Waters is the Chief Marketing Officer at Upwork. They describe themselves as the world's work marketplace. For any business, if your success depends on unlocking creative thinking and innovation, you have to be competitive in the talent wars. The leadership rules for that used to be simple. Create a compelling culture built around in-person experiences. But how do you lead when a company's culture is no longer built around physical space? Tens of millions, probably billions, of the currency of your choice have been spent by business owners to build offices conducive to collaboration, creativity, and innovation. I've owned some of those businesses and spent some of that money. We did it to create a culture. To provide an environment that would help unleash the creativity of the people that worked for us and convert that into economic return. Physical space wasn't the only element to building a culture. Beliefs and behaviors mattered as well. But all of them were connected by the fact that, day in and day out, human beings came together and shared ideas and experiences, and learned from each other. But without the physical structure of an office to provide the day-to-day container in which culture incubates, the responsibility to create those connections falls squarely on the leader. Who are your people? What do they think, care about, love, loathe? Are they happy or not? Fulfilled or not? Interested, enthused, excited or not? Do they feel connected to what matters to the company or not? And if your answer to any of those questions is "I don't know," then it might be time to ask yourself whether your leadership is adapting to the needs of today's talent. Or not.

Who are you? Nicolle Pangis is the CEO of Ampersand. They describe themselves as a data-driven TV advertising sales and technology company. In a world increasingly dependent on zeros and ones, a world in which AI is moving so fast that some tech leaders are calling for its development to be suspended, it's all too easy to forget the human side of leadership. To forget that, in fact, leaders are human, too. There are so many influences over the decisions that a leader must make. Profit. Loss. Risk. Reward. Future. Past. Hope. Fear. So many, that our understanding of self often gets lost along the way. Finding yourself in the middle of that rapidly spinning vortex is not for the unprepared. You need a map. One that shows you the true north of who you are and who you want to be. If you haven't prepared this map before you step into the role, it becomes harder and harder to create. Instead, you find yourself drawing a path forward that is based on the expectations, the hopes, and the dreams of others. Life is short. Your career is shorter. Live them both on your terms and you'll be able to measure yourself against the most important set of data in the world. Your own.

Edited highlights of our full conversation. Who are you? Nicolle Pangis is the CEO of Ampersand. They describe themselves as a data-driven TV advertising sales and technology company. In a world increasingly dependent on zeros and ones, a world in which AI is moving so fast that some tech leaders are calling for its development to be suspended, it's all too easy to forget the human side of leadership. To forget that, in fact, leaders are human, too. There are so many influences over the decisions that a leader must make. Profit. Loss. Risk. Reward. Future. Past. Hope. Fear. So many, that our understanding of self often gets lost along the way. Finding yourself in the middle of that rapidly spinning vortex is not for the unprepared. You need a map. One that shows you the true north of who you are and who you want to be. If you haven't prepared this map before you step into the role, it becomes harder and harder to create. Instead, you find yourself drawing a path forward that is based on the expectations, the hopes, and the dreams of others. Life is short. Your career is shorter. Live them both on your terms and you'll be able to measure yourself against the most important set of data in the world. Your own.

Edited highlights of our full conversation. Who are you? Nicolle Pangis is the CEO of Ampersand. They describe themselves as a data-driven TV advertising sales and technology company. In a world increasingly dependent on zeros and ones, a world in which AI is moving so fast that some tech leaders are calling for its development to be suspended, it's all too easy to forget the human side of leadership. To forget that, in fact, leaders are human, too. There are so many influences over the decisions that a leader must make. Profit. Loss. Risk. Reward. Future. Past. Hope. Fear. So many, that our understanding of self often gets lost along the way. Finding yourself in the middle of that rapidly spinning vortex is not for the unprepared. You need a map. One that shows you the true north of who you are and who you want to be. If you haven't prepared this map before you step into the role, it becomes harder and harder to create. Instead, you find yourself drawing a path forward that is based on the expectations, the hopes, and the dreams of others. Life is short. Your career is shorter. Live them both on your terms and you'll be able to measure yourself against the most important set of data in the world. Your own.

When was the last time you admitted you were wrong? In this episode, we're going back in to the archives for a conversation I had with Mark Thompson, early in 2019. Mark was the Director General of the BBC before becoming CEO of the New York Times in 2012. One of his many claims to fame is that he brought both institutions into the digital age, establishing the New York Times as one of the most successful digital news platforms in the world. To me, his leadership is marked by a self-effacing honesty and personal courage. Early in our conversation, Mark talked about walking towards the gunfire. Literally. He was a journalist before he became a leader of institutions. Most of us, hopefully, won't be asked to demonstrate courage of quite that level during our leadership lives. Leadership is complex. It's like playing four-dimensional chess as we try to find the places of intersection between what is needed of us by a host of moving parts, and our own ability to provide them. For almost every leader, saying 'I was wrong' challenges our essential sense of who we are and what leadership is about. It's not easy to find that place on most people's leadership chessboard. But, as the nature of leadership changes, as people come to demand less defensive behavior of their leaders and more humanity, finding the courage to say 'I was wrong' will be the surest test of your leadership potential. Think of it as the leadership equivalent of walking towards the gunfire. And if you turn and head in the other direction, what does that say about you?

Edited highlights of our full conversation. When was the last time you admitted you were wrong? In this episode, we're going back in to the archives for a conversation I had with Mark Thompson, early in 2019. Mark was the Director General of the BBC before becoming CEO of the New York Times in 2012. One of his many claims to fame is that he brought both institutions into the digital age, establishing the New York Times as one of the most successful digital news platforms in the world. To me, his leadership is marked by a self-effacing honesty and personal courage. Early in our conversation, Mark talked about walking towards the gunfire. Literally. He was a journalist before he became a leader of institutions. Most of us, hopefully, won't be asked to demonstrate courage of quite that level during our leadership lives. Leadership is complex. It's like playing four-dimensional chess as we try to find the places of intersection between what is needed of us by a host of moving parts, and our own ability to provide them. For almost every leader, saying 'I was wrong' challenges our essential sense of who we are and what leadership is about. It's not easy to find that place on most people's leadership chessboard. But, as the nature of leadership changes, as people come to demand less defensive behavior of their leaders and more humanity, finding the courage to say 'I was wrong' will be the surest test of your leadership potential. Think of it as the leadership equivalent of walking towards the gunfire. And if you turn and head in the other direction, what does that say about you?

Are you happy? Nils Leonard is the co-founder of Uncommon London. Nils has been on the podcast before. I ask him back pretty regularly because every one of our conversations expands my understanding of leadership. I think he keeps saying, "Yes," because each time he learns something about himself. In this week's episode, we covered a lot of new ground. In truth, I could have highlighted a number of areas as worthy of close attention. But this is the one that really stands out for me. Life is short. Careers are shorter. I find myself saying this quite often these days as a reminder that within the maelstrom of running a business, we are also, and more importantly, living a life. Leadership comes at you hard and fast. It is demanding and unrelenting and it is easy - very easy - to get swept along in the expectations that are placed on us. Managing those expectations are hard when they come from other people. But the more important and consequential challenge is to manage the expectations we have of ourselves. The first and critical step is to define what you mean by success. In all its forms and attributes. Personally, I believe that one of those definitions should include the word 'happy'. Too many people think doing that makes them selfish. But in my experience, the people that are clear that they want to be happy are also the ones who have given the most thought to what that means to them. Often, most often, it includes the desire to help others unlock their potential. So, are you doing something that makes you happy? And how do you know?

Edited highlights of our full conversation. Are you happy? Nils Leonard is the co-founder of Uncommon London. Nils has been on the podcast before. I ask him back pretty regularly because every one of our conversations expands my understanding of leadership. I think he keeps saying, "Yes," because each time he learns something about himself. In this week's episode, we covered a lot of new ground. In truth, I could have highlighted a number of areas as worthy of close attention. But this is the one that really stands out for me. Life is short. Careers are shorter. I find myself saying this quite often these days as a reminder that within the maelstrom of running a business, we are also, and more importantly, living a life. Leadership comes at you hard and fast. It is demanding and unrelenting and it is easy - very easy - to get swept along in the expectations that are placed on us. Managing those expectations are hard when they come from other people. But the more important and consequential challenge is to manage the expectations we have of ourselves. The first and critical step is to define what you mean by success. In all its forms and attributes. Personally, I believe that one of those definitions should include the word 'happy'. Too many people think doing that makes them selfish. But in my experience, the people that are clear that they want to be happy are also the ones who have given the most thought to what that means to them. Often, most often, it includes the desire to help others unlock their potential. So, are you doing something that makes you happy? And how do you know?

Edited highlights of our full conversation. Are you happy? Nils Leonard is the co-founder of Uncommon London. Nils has been on the podcast before. I ask him back pretty regularly because every one of our conversations expands my understanding of leadership. I think he keeps saying, "Yes," because each time he learns something about himself. In this week's episode, we covered a lot of new ground. In truth, I could have highlighted a number of areas as worthy of close attention. But this is the one that really stands out for me. Life is short. Careers are shorter. I find myself saying this quite often these days as a reminder that within the maelstrom of running a business, we are also, and more importantly, living a life. Leadership comes at you hard and fast. It is demanding and unrelenting and it is easy - very easy - to get swept along in the expectations that are placed on us. Managing those expectations are hard when they come from other people. But the more important and consequential challenge is to manage the expectations we have of ourselves. The first and critical step is to define what you mean by success. In all its forms and attributes. Personally, I believe that one of those definitions should include the word 'happy'. Too many people think doing that makes them selfish. But in my experience, the people that are clear that they want to be happy are also the ones who have given the most thought to what that means to them. Often, most often, it includes the desire to help others unlock their potential. So, are you doing something that makes you happy? And how do you know?