The Work of Staying: What Leadership Community Requires
Photo credit via Jean-Luc-Duchene via Unsplash
Leaders grow faster in community. It's something we've seen transform careers over more than two decades of work. When our founder Dede Henley recently reflected on her experience at Henley Live, a full day of leadership content built for and by the HLG community, she captured something essential about what it actually takes to build that kind of community: the willingness to stay.
A personal reflection from Henley Leadership Group founder Dede Henley, on her day at Henley Live, the power of community and the long work of staying.
Recently, I attended a full day of leadership content called Henley Live. I was an invited guest and truly honored to be there. There were leaders there who had managed to set down the crush of work that is their day-to-day and prioritize their own learning and development. They had come to fuel hope and optimism in the goodness of community and gathering. We were there to remember that good leadership makes a difference.
The truth is, I wouldn’t have missed this. I cleared my calendar, which is to say I moved having three of our grandchildren for Thursday sleepover, and left pottery in process on the bench. A staggering, breathtaking amount of rescheduling.
Walking in with Passion
I parked my car and got out, glad to see how close the parking lot was to The Collective – our meeting place for Henley Live in Seattle. A young woman got out of her car next to me. She was dressed beautifully in a dark suit with a bright fuchsia blouse. I noted how regal and stunning she looked. She asked me if I was going to the Henley event. “I am,” I replied. I asked her name. “Passion,” she told me. I smiled. Of course, I would have the privilege of walking into the building with Passion. God has such a sense of humor.
She asked my name. “Dede Henley,” I hesitated to say. I waited for her to do the math. Yep. I’m the Founder of this brilliant group of humans she was about to meet. Twenty-two years of holding onto a vision of what was possible. Lots of difficult moments and conversations along the way. A lot of growing up to be done. Carol Zizzo, Shanon Olsen and I grew the team from four to twenty-four. We did it with grit and determination and a willingness to never give up.
The meeting where Carol cried
But to be honest, Carol always had way more stick-to-it-iveness than me. I remember a meeting in the winter of 2009 when the economy was bleak and organizations like ours were dropping like flies. I call it “the meeting where Carol cried.”
You have to know this - Carol is not easily prone to tears. She is pragmatic and practical. She is a hard-worker and loyal to her bones. She is not dramatic nor sentimental. But my recent clarity caused something to collapse inside of her.
I told her that I would be “going back out on my own.” This meant, in consultant-speak, that I would leave our company and partnership and return to being an independent consultant. I would hang out a shingle of my own.
Carol, seated on the floor with legs crossed under my coffee table, collapsed her head into her folded arms and cried. I waited awkwardly to see what would happen next. She finally looked up at me and uttered the words that would carry us into a future together, “Well, Dede, it’s not just about YOU anymore.” She had named the thing that got to the heart of the matter. My own self-preservation and unconscious tendency when things went to shit to look out for only myself. All my fancy ideas about community and partnership out the window. She was asking me to stay - even when it was uncomfortable, even when it was rough and difficult, even when I didn’t want to. To Stay. And like the Grinch the moment his heart grows ten times its size, I grew up that day. I became ten times bigger. Carol trained me in sticking it out when I wanted to bolt.
A place where people stay
We grew our company together for twenty-two years. And I sold my part of it to Carol last year, when it was finally time for me to go onto my next thing with her blessing. I learned to stay and am so proud of the work we did over the years to grow ourselves, each other and our company up. I am not the same person I was when we began.
It was so fitting that I was there to witness the remarkable team that has gathered and stayed at Henley Leadership Group. And new members keep coming to join in. HLG is a place where people stay. Where they belong. Where they find community and connection and contribution. For some it’s the best place they’ve worked in their careers.
All day, I was teary with pride. I am so glad I stayed.
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This reflection was originally published on Dede's Substack, Connected Families, where she brings four decades of leadership wisdom home — to family life, to relationships, and to the quiet work of becoming. If this resonated, we'd love for you to follow her there.
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The questions Dede raises, when asked inside a community of leaders, have a way of changing things. If you're ready to stop figuring it out alone, we'd love to meet you in the middle of your real work - through executive coaching and leadership development designed around exactly this kind of growth.
Questions for Co-Creating Community
What kind of community do I want to be part of?
What conversation matters most in my community right now?
Where am I being invited to stay, even when the work feels uncomfortable or uncertain?
Who might be willing co-creators (or co-conspirators!) in making this community better?
How willing am I to move from “me” to “we” in service of the whole?
And perhaps most essentially: what would become possible for my own growth as a leader if I stopped trying to figure it out alone?
