Kimberly Wilson is a dear friend and former client who has always inspired me as a human being, strategist, and leader. When I was thinking about starting a series of conversations with people I admired, she was at the top of the list. As the executive director of Hedgebrook, a 35-year-old writer's retreat for women on Whidbey Island, Washington, she's looking to bring their powerful mission into a new era. I hope you enjoy this conversation, the first of many to come with the best, most brilliant people I know.

Please watch the video above or read the full conversation below. 
 

Talie: I'm Talie Smith, CEO and creative director of Smith & Connors, and I'm here with my friend, client, and an amazing human, Kimberly A.C. Wilson. 

I know Kimberly from her time at Meyer Memorial Trust, where she was the director of communications for many years. We worked together closely for at least five years on some really meaty, wonderful work on Meyer’s brand and website and all kinds of other great projects. We're here because I've always been really inspired by you. One of the things that I have witnessed and really learned over the years from you is how to lead from the heart.

I feel like leading with love is something that our world needs. I'm certainly learning how to do it in my own business. First, we have to define our terms. In her best-selling book, All About Love, bell hooks writes that love is “the will to extend one’s self for the purpose of nurturing one’s own or another’s spiritual growth…. Love is an act of will — namely, both an intention and an action.” What do you think about when you hear that?

Kimberly: Actually that book is at my bedside table right now. I've been very slowly reading it. What that says to me is really what we need in the world. For me, at least, COVID offered an opportunity better understand that we get an opportunity to shape the world around us. As leaders in organizations, we're empowered to create spaces where people can show up as their full selves. We can offer each other grace and accept that we're fallible human beings and that we’re drawn together for a purpose and a mission. That purpose and mission has value that's intrinsic, that has nothing to do with what our budgets are, or how many donors we have or clients we have. The work itself should be based in joy and love. In a place like Hedgebrook, which is a writing residency for women who write, the payoff is a space that's unlike spaces that are available to women. 

We call it radical hospitality here, but it's just love. When I applied, I didn't have a name for it. But this is what this is how my mother held her home together. It was through the idea of radical hospitality. It was always being ready for guests — not just to be able to make sure their glasses were full, or their plates were full, but to welcome them with warmth, and love and attention and music and care. I think coming from a place of love helps to create a space that I want to be a part of. I've worked in lots of spaces that I wouldn't want to be a part of anymore.

We can offer each other grace and accept that we're fallible human beings and that we’re drawn together for a purpose and a mission.

Talie: Why is this such a new or fresh idea? I think about the typical definition of a leader in our corporate kind of culture – it's somebody who's at the top of a mountain looking down, not really connected, thinking about the bottom line, leading with an iron fist. Clearly, that's not working.

You see it in any emerging industries and sectors like tech where at least they're trying to make it seem like they care. Sometimes they don't. And that's really clear as well. Why is it so risky to lead with love? 

Kimberly: It's such a great question, because there absolutely are risks. We never ask what the risks are of leading from the top of that mountain. We take those risks for granted. And we assume that those are appropriate risks to take.

I was literally having this conversation today with Marc Moorghen, who is the vice president and director of communications at Lever for Change. We were talking about the boardroom table and how our expectations around leadership are often shaped by what we grew up imagining the boardroom looked like, how you behave, how you dress, and your demeanor. One of the beautiful things about diversity in the business world is you have people who are coming from very different life experiences. Rather than necessarily imagining that boardroom table, I imagine my dining room table or my coffee table or the firepit. The way that I approach people is not from a place of positional power. It is from a place of candor and respect.

The word “love” is kind of loaded. I don't think I work in a family. I actively say, “We're not a family.” This is a business. This is a nonprofit. But I also think it's important that we have respect for each other and for the gifts people bring, regardless of where they are in an organization. You're surrounded by talent, and recognizing that and respecting that is just the first way of exercising that love.

The way that I approach people is not from a place of positional power. It is from a place of candor and respect.

Talie: Absolutely. I was a new leader in my business when we started Smith & Connors 10 years ago, and I really tried to lead with love, but I experienced some of those challenges. What did it take for me to lead with love?

To love, you have to bring openness and vulnerability, which is inherently risky. As soon as you open up, then anything can come and happen. But you can't build trust without it. But in a place where you have a lot of complexity to teams and different personalities, and the culture isn't quite supporting that vulnerability, maybe there's a lack of trust. I have personally experienced that, where I struggled in the culture that I had built, because I didn't really know how to lead truly with love. I became a defensive leader and protected myself, which actually stands in the way.

Where have you experienced that sense of fear around “Oh, my God, I have to bare my heart and love these people, and at the same time, this is a business”?

Kimberly: When I came on board, I made a policy around COVID and then got feedback from my team, and I realized that I was wrong. So I owned it and changed the policy. And it kind of threw some of my team members because they weren't expecting that.

I was like, “Why wouldn't you expect that I wasn't born as an executive director of a small nonprofit on a rural island in Washington? I'm days old at this work, and I'm gonna make mistakes. And that's not going to be the last time I make a mistake. And each time I do, I'm going to be transparent about it. And I'm going to own my piece. And I'm going to work really hard to put those lessons into place.”

So the vulnerability part is the easy part for me. The harder part is owning up to the positional power that I have and my unwillingness to hold that firmly. That creates uncertainty, sometimes. I'm not a parent, but the parents I know tell me that that is true: If you leave a void that children can step into in terms of positional power, they will, and then you’ll be on the outside going, “Wait! I’m the parent here! How did this happen?”

It’s not to say that working together or leading is about parenting, but my lesson has been that I needed to get over my discomfort with being the boss, and just be the boss and be the kind of director I always wanted to work for.

So the vulnerability part is the easy part for me. The harder part is owning up to the positional power that I have and my unwillingness hold that firmly. 

Talie: Oh my god, I totally identify with that. I think that hesitancy is where I was years ago. People were asking me to step up and do it and I was like, I don't know. I felt that upward pressure from the team, but I didn't trust myself enough. That’s where it started to break down for me. We have to do it to learn it, but that's a really uncomfortable place to be as a leader. 

I had to do a lot of personal growth, to strengthen my sense of self in order to feel like I could trust myself. Then I could be more open.

One thing I read in a book recently was that culture is equal to what you tolerate. If you say, here's what our culture is, but then you tolerate all this other behavior, then that behavior that you're tolerating is actually the culture. The void gets filled.

Kimberly: I think that's really true. I think part of the idea of leading with love, or through love, is really about creating a culture. That is unique from what our expectations are, around business success. It's definitely a work in progress for me, especially as a Black woman leader of a mostly white organization that was founded 35 years ago implicitly for half of the women here to be women of color and Black women in particular. The organization has the most beautiful bones. I am a child of this moment, so I have been really cautious. In an organization that talks a lot about equity and racial equity and hierarchy, I have danced a fine line of not wanting to be a hierarchical kind of person in the organization that I run. That doesn't really make sense because that sentence ends with “that I run.”

So it's been an effort to own it and be comfortable with that and recognize that as, as a Black leader, I also have a level of restraint that I impose on myself, that can make it a little bit more challenging sometimes to have the candor that I'd like to have. I want to make sure that I'm heard and also that I'm not offending and that not hurting sensibilities. It’s a bit of a tap dance, where you're trying to figure out precisely where your feet go.

I don't want to be the angry Black woman. That curtails me from responding sometimes with the candor that I might prefer. I don't feel like I've got a boot on my car, and I can't drive, but I do feel like I have a ticket, and it's something that I have to be cautious about. I hold that, whether or not other people necessarily hold it. That's had an impact on how I deal with conflict sometimes.

But when I step far enough back, what makes the most sense to me is to just continue to lead through vulnerability and love.

In an organization that talks a lot about equity and racial equity and hierarchy, I have danced a fine line of not wanting to be a hierarchical kind of person in the organization that I run.

Talie: Yeah, that makes 100% sense. As a leader, I think it's particularly challenging to show up as our full selves and share that in a team environment, when people are looking at you as the one to set the tone and be the model. For me, personally, I have made it a habit to share with my team when I have really screwed up. That's something I'm trying out, and so far it's working, but there are some serious risks in it.

Kimberly: I don't feel the risks as acutely because I’ve made a conscious choice. I'm a grown-ass woman, and I'm not going to apologize for that. I do think that there's a beauty particularly in women's leadership at that moment when you're comfortable in your skin and you know who you are. I got nothing to lose. What does being vulnerable cost me?

I don't think I always felt that way. But I certainly feel that way now, and it's also coupled with not feeling defensive anymore about, Do I know enough? Am I enough? 

I have stopped believing in imposter syndrome. There is only what your expectations are, and the questions of what you need to do to get to where you are, or or acknowledging that you actually are there, and being okay with the fact that you're there. But I'm not an imposter.

Talie: I am so glad to hear that because you are one of the most visionary people I know. Tell me a little bit about where you're heading with this organization. What's your vision?

Kimberly: So, I'm standing at my desk, and I'm looking out at a field that used to be a garden ten years ago, before the last dot-com boom. There’s a storage shed. If I could see through it, I could see the house where Gloria Steinem wrote most of her last book. There are six cottages on the land. Behind me is Deer Lagoon, which has a bird sanctuary. On a clear day, I can see Mount Rainier and downtown Seattle. Here's the farmhouse, and right now one of the chefs is in there preparing dinner for our six writers that are on the land. We have six cottages and one little house. That roughly works out to be about 70 writers who come on the land each year.

Last year, we had 1,800 writers apply. I am not from the school that says that’s a sign that were so fantastic. To me, that’s really sad. What it means is that there are infinitely more people who need this space than we can accommodate. And the world doesn't accommodate them. These are caretakers. These are parents, these are people who are working and trying to have a writing practice, and they look to Hedgebrook as a dream and apply year after year.

My vision for this organization is for us to be able to fully accommodate the needs that exists in a world where women's voices are shut down. Where the list of banned books, includes writers like Jacqueline Woodson (a Hedgebrook alum) and other writers who are writing about race and gender and environmental issues and what families are and can be and artificial intelligence and the justice system.

These are writers who people are intentionally trying to shut down their voices out of fear of the power of what those voices hold. So my vision for Hedgebrook is to be able to offer more platforms so that writers can have the time to create the stories and the narratives and the ideas that really shape what our future should look like and can look like — nationally, internationally, and here, on this beautiful little 48 acres.

My vision for this organization is for us to be able to fully accommodate the needs that exists in a world where women's voices are shut down. 

Talie: What a dream that you are leading this organization with your incredible past as a journalist, as a global citizen and visionary. Does this feel like you’ve stepped into what you always were meant to do? 

Kimberly: It really does. I was probably 9 when my mom handed me The Color Purple. I remember reading it and being blown away. In the barn that's just across the walk here, there's a little blue rustic table. That was Alice Walker's. And it's the table on which she wrote The Color Purple. This place feels like full circle for me. I just wish my mom was alive. This would be meaningful to her in ways I can't even fathom. She was such a huge reader and a student of words and ideas. So I’m thrilled to be in a space that is was created to bring to life Virginia Woolf’s “room of one's own,” to have the role that allows me to help bring that vision to full fruition.

Virginia Woolf talked about financial autonomy as well, that a woman needs to be able to create and have her full creation realized. I'm trying to rebuild this organization to be sustainable for the long term. Part of that formula has to include being able to provide some kind of stipend for the writers who come so they don't pay anything to come here. But their lives are big behind them, and what would it look like to be able to support them so that they can be as fully present here, as they as they need to be for two to four weeks? Maybe that's covering their mortgage, maybe that's covering their rent, maybe it's covering their childcare or dog sitting, whatever it takes.

So, yeah, my vision is to fully realize this place beyond the cottages that we have with the online classes and the in-person events that we have to be something that attempts to provide what we offer so that it can be provided in other places. Not just here.

Talie: Amazing, beautiful, Kimberly. What an incredible gift that you are leading this organization because I know that you're going to achieve everything that you want. You're just a force. Thank you for doing this work. 

Kimberly: Thank you for having me. Please check out hedgebrook.org and support this amazing organization. If you're a woman writer, apply! This is your space. 

Talie: Thank you so much, Kimberly. It really struck me that there's a continuum in how you talk about your work in the organization: it's the past, the present and the future. That continuum is the meaning behind our work, any organization, anything we're doing. It gets our head up and out of the numbers and details and reminds us of what it's all really about.

You've got to be preparing the organization for the next leader to bring their vision. 

Kimberly: When I look out at the meadow, I see three trees that we planted shortly after I got here. Everybody wrote little comments and we stuck them in the soil when we planted them. They are shade trees. (We're a nonprofit, so we don't have any air conditioning!) One day, the trees will shade this office for someone. They will shade an area outside where staff will be able to sit and have coffee and eat meals and stuff together or do some work outside. That was one of the first things I wanted to do to to pay into that future. A leader is here for five or ten years. You've got to be preparing the organization for the next leader to bring their vision. Your staff will be here longer than your leadership. What are you doing to make sure that they still have a home in this organization?

Talie: So you planted seeds. Really amazing. Thank you.