Ep 269: Heather Freeland - In 25

Fearless Creative Leadership

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.