463 episodes

We talk to leaders of the world’s most disruptive companies about how they are jumping into the fire, crossing the chasm and blowing up the status quo. Leaders who’ve mastered the art of turning the impossible into the profitable.

Fearless Creative Leadership Charles Day

    • Business
    • 4.9 • 8 Ratings

We talk to leaders of the world’s most disruptive companies about how they are jumping into the fire, crossing the chasm and blowing up the status quo. Leaders who’ve mastered the art of turning the impossible into the profitable.

    Senator Kirsten Gillibrand - "The Senator"

    Senator Kirsten Gillibrand - "The Senator"

    Here’s a question. What is your leadership for?
    This week’s guest is Senator Kirsten Gillibrand, the Junior Senator from the State of New York.
    Running for public office places you in a spotlight that is white hot. Being clear why you’ve made the choice to run in the first place is table stakes for creating the life you want to live and the legacy you want to leave behind.
    In too many companies and for too many people, leadership is seen as the thing that comes next for those who are willing to stick around. The inevitability of rising up the org chart into a role that comes with more everything is too rarely challenged by company or individual.
    Leadership is a privilege. An opportunity to make the biggest difference for the most people, that most of us will ever have.
    Marty Baron of the Washington Post described it as a responsibility.
    Mark Thompson, when he was at the New York Times, described leadership as the act of running towards the gunfire.
    Cecile Richards, formerly of Planned Parenthood, described herself as blessed to have been one of the really privileged few that could do what she thought needed doing.
    In industries where awards, wins, and results are to the fore, and success is often measured by how many and how much, I’m hoping that some of these conversations will also stir thoughts of what.
    What do I want to make better? What do I want to change? What difference do I want to make for the people around me?
    Because, as my work continues to evolve and my understanding continues to deepen, what I increasingly know to be true is that the awards, the wins, and the results are directly connected to the whats.
    That the leaders who are clearest about what difference they want to make are the ones who have the most evidence of having made it.
    Literally and figuratively.
    So, what is your leadership for?

    • 34 min
    Senator Kirsten Gillibrand - In 20

    Senator Kirsten Gillibrand - In 20

    Edited highlights of our full length conversation.
    Here’s a question. What is your leadership for?
    This week’s guest is Senator Kirsten Gillibrand, the Junior Senator from the State of New York.
    Running for public office places you in a spotlight that is white hot. Being clear why you’ve made the choice to run in the first place is table stakes for creating the life you want to live and the legacy you want to leave behind.
    In too many companies and for too many people, leadership is seen as the thing that comes next for those who are willing to stick around. The inevitability of rising up the org chart into a role that comes with more everything is too rarely challenged by company or individual.
    Leadership is a privilege. An opportunity to make the biggest difference for the most people, that most of us will ever have.
    Marty Baron of the Washington Post described it as a responsibility.
    Mark Thompson, when he was at the New York Times, described leadership as the act of running towards the gunfire.
    Cecile Richards, formerly of Planned Parenthood, described herself as blessed to have been one of the really privileged few that could do what she thought needed doing.
    In industries where awards, wins, and results are to the fore, and success is often measured by how many and how much, I’m hoping that some of these conversations will also stir thoughts of what.
    What do I want to make better? What do I want to change? What difference do I want to make for the people around me?
    Because, as my work continues to evolve and my understanding continues to deepen, what I increasingly know to be true is that the awards, the wins, and the results are directly connected to the whats.
    That the leaders who are clearest about what difference they want to make are the ones who have the most evidence of having made it.
    Literally and figuratively.
    So, what is your leadership for?

    • 19 min
    Senator Kirsten Gillibrand - In 10

    Senator Kirsten Gillibrand - In 10

    Edited highlights of our full length conversation.
    Here’s a question. What is your leadership for?
    This week’s guest is Senator Kirsten Gillibrand, the Junior Senator from the State of New York.
    Running for public office places you in a spotlight that is white hot. Being clear why you’ve made the choice to run in the first place is table stakes for creating the life you want to live and the legacy you want to leave behind.
    In too many companies and for too many people, leadership is seen as the thing that comes next for those who are willing to stick around. The inevitability of rising up the org chart into a role that comes with more everything is too rarely challenged by company or individual.
    Leadership is a privilege. An opportunity to make the biggest difference for the most people, that most of us will ever have.
    Marty Baron of the Washington Post described it as a responsibility.
    Mark Thompson, when he was at the New York Times, described leadership as the act of running towards the gunfire.
    Cecile Richards, formerly of Planned Parenthood, described herself as blessed to have been one of the really privileged few that could do what she thought needed doing.
    In industries where awards, wins, and results are to the fore, and success is often measured by how many and how much, I’m hoping that some of these conversations will also stir thoughts of what.
    What do I want to make better? What do I want to change? What difference do I want to make for the people around me?
    Because, as my work continues to evolve and my understanding continues to deepen, what I increasingly know to be true is that the awards, the wins, and the results are directly connected to the whats.
    That the leaders who are clearest about what difference they want to make are the ones who have the most evidence of having made it.
    Literally and figuratively.
    So, what is your leadership for?

    • 10 min
    Tom O'Keefe & Jeff King of BarkleyOKRP - "The M&A Leaders"

    Tom O'Keefe & Jeff King of BarkleyOKRP - "The M&A Leaders"

    Here’s a question. What do you think and why?
    This week’s guests are Tom O’Keefe and Jeff King. They are two of the four partners who have just merged their respective businesses, OKRP and Barkley.
    Mergers are a forcing function for open-mindedness. And for doing things differently.
    The ability to accept the need to do things differently, to truly change perspectives, is a never ending leadership challenge.
    In my experience, you have to be pretty clear about your own point of view in order to embrace new ones.
    Worry too much about providing strong leadership, and the temptation to stick to our beliefs — even in the face of evidence or views to the contrary — becomes almost like a drug. An addiction to being right or first or better.
    This is perhaps the most damaging characteristic that any leader can possess. And too much of it will ensure you’re not a leader of very many or very much for very long.
    When we are clear about why we think what we think, when we are free of insecurity or hubris or ego, then we can assess an alternative path with an open mind.
    Mergers provoke the need to lead through this lens. Tom’s outline for unleashing the creative potential of the newly formed business is filled with best practice.
    But regardless of external forcing functions — like mergers — being clear about why we think what we think is table stakes for the most fearless leaders.
    So what do you think? And what will it take for you to see things from a different perspective?

    • 38 min
    Tom O'Keefe & Jeff King - In 20

    Tom O'Keefe & Jeff King - In 20

    Edited highlights of our full length conversation.
    Here’s a question. What do you think and why?
    This week’s guests are Tom O’Keefe and Jeff King. They are two of the four partners who have just merged their respective businesses, OKRP and Barkley.
    Mergers are a forcing function for open-mindedness. And for doing things differently.
    The ability to accept the need to do things differently, to truly change perspectives, is a never ending leadership challenge.
    In my experience, you have to be pretty clear about your own point of view in order to embrace new ones.
    Worry too much about providing strong leadership, and the temptation to stick to our beliefs — even in the face of evidence or views to the contrary — becomes almost like a drug. An addiction to being right or first or better.
    This is perhaps the most damaging characteristic that any leader can possess. And too much of it will ensure you’re not a leader of very many or very much for very long.
    When we are clear about why we think what we think, when we are free of insecurity or hubris or ego, then we can assess an alternative path with an open mind.
    Mergers provoke the need to lead through this lens. Tom’s outline for unleashing the creative potential of the newly formed business is filled with best practice.
    But regardless of external forcing functions — like mergers — being clear about why we think what we think is table stakes for the most fearless leaders.
    So what do you think? And what will it take for you to see things from a different perspective?

    • 20 min
    Tom O'Keefe & Jeff King - In 10

    Tom O'Keefe & Jeff King - In 10

    Edited highlights of our full length conversation.
    Here’s a question. What do you think and why?
    This week’s guests are Tom O’Keefe and Jeff King. They are two of the four partners who have just merged their respective businesses, OKRP and Barkley.
    Mergers are a forcing function for open-mindedness. And for doing things differently.
    The ability to accept the need to do things differently, to truly change perspectives, is a never ending leadership challenge.
    In my experience, you have to be pretty clear about your own point of view in order to embrace new ones.
    Worry too much about providing strong leadership, and the temptation to stick to our beliefs — even in the face of evidence or views to the contrary — becomes almost like a drug. An addiction to being right or first or better.
    This is perhaps the most damaging characteristic that any leader can possess. And too much of it will ensure you’re not a leader of very many or very much for very long.
    When we are clear about why we think what we think, when we are free of insecurity or hubris or ego, then we can assess an alternative path with an open mind.
    Mergers provoke the need to lead through this lens. Tom’s outline for unleashing the creative potential of the newly formed business is filled with best practice.
    But regardless of external forcing functions — like mergers — being clear about why we think what we think is table stakes for the most fearless leaders.
    So what do you think? And what will it take for you to see things from a different perspective?

    • 8 min

Customer Reviews

4.9 out of 5
8 Ratings

8 Ratings

CDNCoyler ,

Incredible

I stumbled upon this series and now listen to it daily. It's incredibly insightful, useful and inspring. Charles Day is a fantastic host, and his selection of guests are fantastic.

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