Ep 269: Heather Freeland of Adobe - "The 'Is That Good?' Leader"

What does your company reject? Karl Lieberman is the Global Chief Creative Officer of Wieden + Kennedy. Wieden is a reference point among creative companies in many industries. For almost 45 years, they'd been impacting culture and driving business for their clients by unlocking the creativity of their people. . Creating the kind of environment in which people feel safe to put all their ideas on the table is the easiest thing to aspire to. And the hardest thing to do, in my experience. It means giving people a voice. It means being open, genuinely open to another way of looking at the world. And to the possibility that being criticized is much more desirable than being ignored. These criteria are at best challenging for most leaders to accept. Control and predict are much more natural. But predictability and conformity are creative kryptonite. To unlock creativity and unleash its power to maximum effect, you have to be willing to break the norms, to encourage the irrational and sometimes even the absurd. You have to reject predictability for possibility. And when you're yelled at, because no one has ever done it like that before, you have to be willing to shrug. You'll hear all that and more in my conversation with Karl.

What are you willing to compromise? Lina Polimeni is the Chief Corporate Brand Officer at Eli Lilly and Company. This is a business whose work is often the difference between life and death, where they are trying to cure cancer, and where the outcome is very personal. In the middle of that reality, your own leadership journey is fueled by a lot of food for thought. No one can lead effectively without compromise.  But what we choose to compromise has a huge part to play in whether we’re successful. If what we end up sacrificing is a pathway to discovering that we are already enough… If what we end up sacrificing is a road to realizing that the best version of who we are can help others become the best version of themselves… If that is what we are compromising, then the cost of that will be the realization that we behaved as others wanted us to. And when they are a part of our past, remembered or forgotten, what we will be left with is a journey that is not the one we started out on. A destination that is not where we wanted to go. And a dream that is always around the corner. We can be what others want, or we can be who we want to be. We always have that choice. 

Edited highlights of our full length conversation. What are you willing to compromise? Lina Polimeni is the Chief Corporate Brand Officer at Eli Lilly and Company. This is a business whose work is often the difference between life and death, where they are trying to cure cancer, and where the outcome is very personal. In the middle of that reality, your own leadership journey is fueled by a lot of food for thought. No one can lead effectively without compromise.  But what we choose to compromise has a huge part to play in whether we’re successful. If what we end up sacrificing is a pathway to discovering that we are already enough… If what we end up sacrificing is a road to realizing that the best version of who we are can help others become the best version of themselves… If that is what we are compromising, then the cost of that will be the realization that we behaved as others wanted us to. And when they are a part of our past, remembered or forgotten, what we will be left with is a journey that is not the one we started out on. A destination that is not where we wanted to go. And a dream that is always around the corner. We can be what others want, or we can be who we want to be. We always have that choice. 

Are you centered? Kerry Sulkowicz is the Past-President of the American Psychoanalytic Association, and the Founder and Managing Principal of Boswell Group. They provide leadership advice to boards and CEOs. Kerry and I have been friends for a long time, and he has taught me much about the psychodynamic aspects of leadership. Whenever we talk, his advice strikes me as clear and straightforward, and always very human. Being centered doesn’t happen through accident, chance, or hope. It happens by intent.  And that intent is driven by recognizing two obvious truths.  Leadership is lonely. And leadership is stressful. Much, much more so than many are willing to admit publicly. The old-world view is that leadership demands that you project strength, certainty, invincibility. Even in the face of threats that can feel like they are existential - because these days, for many businesses, they might be. If some days that means you feel like you’re a leader in a fight for survival, well, that’s not surprising. Because that’s exactly how your brain responds to that set of circumstances.  And under that kind of stress, the part of your brain that’s responsible for executive function, for risk assessment, and problem-solving, and for planning, suddenly starts to develop tunnel vision. And at the same time, our amygdala kicks in and suddenly survival gets added to the emotional maelstrom, and then finally comes the impulse to hurry up and do something. Anything.  Being centered is the shelter in that storm. It’s held up by a strong sense of self, by awareness and honesty about how you respond under stress, and it’s helped by having a clear and multi-faceted definition of success.  Those foundations, when combined with a willingness to take a little time to turn down the short term noise, and dilute the adrenaline fueled feelings of urgency, will give you the ability to lean on yourself and think things through. Leadership is sometimes about taking action and it is sometimes not. But it is always about being centered. So, how well do you know yourself? 

Edited highlights of our full length conversation. Are you centered? Kerry Sulkowicz is the Past-President of the American Psychoanalytic Association, and the Founder and Managing Principal of Boswell Group. They provide leadership advice to boards and CEOs. Kerry and I have been friends for a long time, and he has taught me much about the psychodynamic aspects of leadership. Whenever we talk, his advice strikes me as clear and straightforward, and always very human. Being centered doesn’t happen through accident, chance, or hope. It happens by intent.  And that intent is driven by recognizing two obvious truths.  Leadership is lonely. And leadership is stressful. Much, much more so than many are willing to admit publicly. The old-world view is that leadership demands that you project strength, certainty, invincibility. Even in the face of threats that can feel like they are existential - because these days, for many businesses, they might be. If some days that means you feel like you’re a leader in a fight for survival, well, that’s not surprising. Because that’s exactly how your brain responds to that set of circumstances.  And under that kind of stress, the part of your brain that’s responsible for executive function, for risk assessment, and problem-solving, and for planning, suddenly starts to develop tunnel vision. And at the same time, our amygdala kicks in and suddenly survival gets added to the emotional maelstrom, and then finally comes the impulse to hurry up and do something. Anything.  Being centered is the shelter in that storm. It’s held up by a strong sense of self, by awareness and honesty about how you respond under stress, and it’s helped by having a clear and multi-faceted definition of success.  Those foundations, when combined with a willingness to take a little time to turn down the short term noise, and dilute the adrenaline fueled feelings of urgency, will give you the ability to lean on yourself and think things through. Leadership is sometimes about taking action and it is sometimes not. But it is always about being centered. So, how well do you know yourself? 

What is your pain for?  Taban Shoresh is the Founder of The Lotus Flower, a UK-based charity that supports women and girls that have been displaced by conflict, and helps them to build sustainable futures. Since 2016, the charity's projects have impacted more than 60,000 women, girls, and community members.  Every now and then, you meet someone whose story stops you in your tracks. Taban’s story starts with her being arrested in Iraq at the age of four. Three weeks later, she's ordered onto a bus that will take her to the place where she and other members of her family will be buried alive. At the end of 2021, before Russia invaded the Ukraine or the war in Gaza, the number of forcibly displaced people worldwide stood at 89.3 million. There were 27.1 million refugees globally, half of whom were aged under 18, which makes Taban's story one of millions and completely unique.  She has experienced staggering trauma, she has known realities that I'm sure I would not have survived, and she has taken all of that pain and turned it into creative leadership of the most consequential kind. As you'll hear, for reasons both global and personal, she's in a hurry.  All of us have suffered pain. What we use it for is a question that will stay with me for a long time after this conversation. 

Edited highlights of our full length conversation. What is your pain for?  Taban Shoresh is the Founder of The Lotus Flower, a UK-based charity that supports women and girls that have been displaced by conflict, and helps them to build sustainable futures. Since 2016, the charity's projects have impacted more than 60,000 women, girls, and community members.  Every now and then, you meet someone whose story stops you in your tracks. Taban’s story starts with her being arrested in Iraq at the age of four. Three weeks later, she's ordered onto a bus that will take her to the place where she and other members of her family will be buried alive. At the end of 2021, before Russia invaded the Ukraine or the war in Gaza, the number of forcibly displaced people worldwide stood at 89.3 million. There were 27.1 million refugees globally, half of whom were aged under 18, which makes Taban's story one of millions and completely unique.  She has experienced staggering trauma, she has known realities that I'm sure I would not have survived, and she has taken all of that pain and turned it into creative leadership of the most consequential kind. As you'll hear, for reasons both global and personal, she's in a hurry.  All of us have suffered pain. What we use it for is a question that will stay with me for a long time after this conversation. 

Is that good? Heather Freeland is the Chief Brand Officer at Adobe, a business that, as Heather describes, is undergoing significant change to prepare itself for the future to come, and the one that is already here. In a company long known for providing powerful tools to creative people, the advent of Generative AI is both a threat and an opportunity. How human beings maintain our relevance sits at the very heart of that tension. Is that good? In the quest to become leaders that make a difference, there are many powerful questions to ask ourselves. What do I want to find out about myself? What is success? Both of these are intensely personal, and can be answered, albeit with some serious and honest reflection, from within. But, “Is that good?” usually stretches us out into the world. We are inclined to ask, through what lens? Against what criteria? Measured by what result? Based on whose experience? But at the end of that journey of data collection, consultation, and analysis, the answer to, “Is that good?” is still waiting for someone to decide. Michelangelo, when asked how he had created such perfection from a piece of rock said, “I simply removed everything that wasn’t the David.” If human beings are to create a dividing line that AI can not cross, the question, “Is that good?” may be the beating heart on which that barrier depends. “Is that good?” is heavy lifting. It requires clarity and confidence. Muscles we should probably start building today.

Edited highlights of our full length conversation. Is that good? Heather Freeland is the Chief Brand Officer at Adobe, a business that, as Heather describes, is undergoing significant change to prepare itself for the future to come, and the one that is already here. In a company long known for providing powerful tools to creative people, the advent of Generative AI is both a threat and an opportunity. How human beings maintain our relevance sits at the very heart of that tension. Is that good? In the quest to become leaders that make a difference, there are many powerful questions to ask ourselves. What do I want to find out about myself? What is success? Both of these are intensely personal, and can be answered, albeit with some serious and honest reflection, from within. But, “Is that good?” usually stretches us out into the world. We are inclined to ask, through what lens? Against what criteria? Measured by what result? Based on whose experience? But at the end of that journey of data collection, consultation, and analysis, the answer to, “Is that good?” is still waiting for someone to decide. Michelangelo, when asked how he had created such perfection from a piece of rock said, “I simply removed everything that wasn’t the David.” If human beings are to create a dividing line that AI can not cross, the question, “Is that good?” may be the beating heart on which that barrier depends. “Is that good?” is heavy lifting. It requires clarity and confidence. Muscles we should probably start building today.

Why are you doing what you’re doing? Gabriel Schmitt has just celebrated his one year anniversary as the Global CCO of Grey. Grey’s proposition is that they have been coming up with famously effective ideas since 1917. Gabriel is somewhat younger than that, but over his career, has learned one of the most important leadership lessons that I think often gets overlooked. The importance of context. A few years ago, I wrote an article for Fast Company called The Four Weapons of Exceptional Creative Leaders. I got some pushback on using the word “weapons” in the context of creativity. My response was that if you’ve ever done battle with the status quo, then you already know that you need to bring some serious weapons to that fight. Context is the beginning and the end of the leadership journey. Without it, you have no ability to answer critical questions, like where are we on our journey? How much further do we have to go? Context is the reason why you are trying to make that wild idea. It is why you hire that person. It is why you invest in that technology. It is why you make that decision. It is why you come up with the answer. It is why people follow you. And without it… everything else is just a guess. So why are you doing what you’re doing? And are you sure?