To Everyone Who Used To Work For Me: I Apologize!

My Epic Fail at leadership—and what you can learn from it.

Some years ago, I was promoted to be Regional President of a fast-growing Internet marketing agency. I went from running an amazingly talented, hand-picked Creative department of two dozen or so superstars to having 200 people reporting to me during a time of tumultuous growth and change. Since then, I have, hopefully, grown not just older but wiser. From where I stand today, something has become crystal clear to me: I owe you all an apology.

I’m sorry that I didn’t truly get what leadership is, didn’t fully embody it myself or facilitate its emergence in each of you.

I worked hard, sure. And I cared. But I lacked some crucial distinctions, understanding, insight. I’d like to share a few of these here, in the hope that this may help you unleash the leader I believe is inside you.

Let’s start with a definition of leadership, offered to me by Bob Dunham, founder of the Institute for Generative LeadershipLeadership is the capacity to declare a future that other people commit to. That commitment comes willingly, happily, even enthusiastically, because the future is connected to the things people care about.

Think about it: Without caring, there is no commitment. Without commitment, people will only work so hard for so long. They won’t tackle the difficult conversations or demand integrity from the people around them. Trust gets broken. Values disrespected. The organization’s culture sinks to the lowest common denominator rather than rising to its highest aspirations. This is what happened to us.

The executive team at the agency was made up of good, smart people. We got the memo: We read all the right books, did Vision statements and Values exercises. We were sincerely, and financially, invested in training and development. But, as Bob points out, leadership is “a performance art, not a domain of scholarship—you can’t get it from books, it is only expressed through practice. Knowing about leadership does not make you a leader.”

In my assessment, we lost our connection to what our people cared about. Instead of identifying, bringing forward and honoring the values of the tribe, we tried to tell people what we wanted their values to be. And then, when the heat was on, we failed to live up even to those values.

We suffered from a blind spot all too common in modern workplace culture, the belief that what you produce matters more than what you care about. While I felt uneasy about this at the time, clashing frequently with my boss, nothing productive came of it. A sense of resignation crept through the ranks. Resignation is a killer. Under the weight of this mood, people give up on the possibility of making things happen and the potential of an organization is squandered.

To truly make a difference, what I needed to do was to find out what you cared about. To foster conversations for creating possibility and value. To generate an offer to realize a future that was meaningful to you. To find out what commitments you were willing to make to take care of those things you cared about. And then to give you the tools to skillfully manage those commitments.

As Bob Dunham explains, “Leadership is not having a title, power or authority. Leaders have a quality they bring forward in other people, a sense of possibility for the future and a commitment to take action on behalf of that future. Leadership is about being in service to others, to a promise, to a standard of excellence.”

I am sorry I wasn’t a leader back then. I am also grateful to all of you for the incredibly valuable, and beautiful, lessons that experience taught me. I’ve learned a bit since then, and I’m still learning. I offer this experience in the hope that it will spark some insight into your own relationship with leadership. Call it karma, or irony, but I can’t help it: My core values include Growth, Mastery, and… Making A Difference.

Five Insights That Would Have Made All The Difference For Me (and still can for you):
  1. Explore care and the gap between what the people around you care about and what you are doing to take care of what they care about.
  2. Know your big hairy noble cause, but focus on the small steps needed to get where you want to go, constantly exploring the edge and taking the next single step.
  3. Keep tabs on what conversations your organization is having—and not having
  4. Give yourself permission to learn, to experiment, to play, to fail, to ask for help.
  5. Get a great coach and/or mentor. (They’re called blind spots for a reason: You can’t see them on your own! See Feedback Loops Are A Critical Key To Long-Term Growth and Fulfillment.)

About Us

The WYSIWYG Co. is the coaching partnership of Caroline Sugarman and Aaron Sugarman. We are members of the International Coach Federation (ICF), with more than 40 years of combined coaching and consulting experience.

We work with individuals and organizations, through a mix of one-on-one coaching, workshops and group work that builds leadership and communication skills and improves team performance.

We support our work with assessments that generate insight, highlight strengths and areas for development, and help organizations make better hiring decisions.

Learn More


An occasional digest featuring the best of our blog and curated reading list.

Connect With Us