In the Cut Leadership Conversation with Wilma Wallace

A senior executive leader, Wilma brings experience designing and leading global legal, risk, compliance and ESG programs (including equity) and enterprise transformation. As a legal expert, former Corporate Secretary, Corporate Executive and seasoned public and nonprofit board member, she is known as a collaborative, values-driven partner and trusted advisor. Wilma is a champion for social impact, environmental justice, and human rights and a frequent public speaker and instructor on leadership, law department management, business and human rights, and transforming into a more just, equitable and sustainable society.

Wilma Wallace, welcome to In the Cut!

Thank you! I am so excited to be here with you.

Sheila: Thank you! I’m so glad to be reacquainted with you after a few years absence and to catch up with you and feel like we didn’t miss a beat. That’s what sisterhood is all about. I appreciate you being available to me in that way and for us finding ourselves In the Cut.

Likewise.

“My great-grandfather was born two years after the end of slavery so that’s something I sit with.”

My favorite topic is leadership and I think of you in all of that space. I’m really interested in hearing how you make your way through that, how you found yourself in that space, and how life shows up for you in leadership. So, I always like to start with identity, which is a thing. The intersectionality that we represent on this planet informs us in so many ways. As you think about your identity, where do you start and end with that?

I start with being an African American woman who have Black parents who grew up in the Jim Crow south. I wish that weren’t as dominant, perhaps, an identity that I carry, yet is one that I carry with me all the time and the filter through which I look at life and probably increasingly more as I get older.

I’m two-and-one half generations away from being enslaved. My great-grandfather was born two years after the end of slavery so that’s something I sit with. Fast forward, more modernly, I grew up in New England, again of southern parents. And yet chose to move out west so I’m also a woman of the west coast and have been here for 30+ years.

I think of myself as a mother of 2 boys. A wife and partner. A sister and daughter. That’s how I identify myself.

Sheila: The thought that we have to think about that first identity so much and how that will come into this conversation about leadership and the astute awareness we have in that on a daily, minute-by-minute basis. Thank you for bringing that forward.

I know you first as an attorney and saw you ascend in your expertise to an executive position at REI. Talk a bit about the work you did and maybe what you are contemplating doing, if any?

I should have mentioned that I also do think of myself as a lawyer and advocate for human rights, and social impact. Maybe more of that part of me will come out in this conversation.

I started my career as a lawyer in a law firm. I think, again, coming from a liberal arts background in college, and as an African American woman, I felt I needed to have a skillset and street cred to open doors to those who otherwise didn’t know me. I chose to go to law school and get a law degree. I actually enjoyed law school. I ended up practicing as a litigator at law firms for about 5 years before I went to The Gap.

I rose up through The Gap. When I started it was a $4B company and when I ended it was a $16B dollar company. I was one of the earlier lawyers there which gave me a lot of opportunity to take on different roles and stretch my expertise even outside of the legal realm. That’s another theme in my leadership and career, being able to piece together various aspects or disciplines to come up with the right solution to advance the vision and goals of an organization or individual. At The Gap I had tons of opportunities throughout the 20 years I was there and rose to become one of the Deputy General Counsel.

I had the opportunity to go to REI and pursue something that I have a deep passion for which is the outdoors and provide access to the outdoors, particularly spaces where people haven’t had the privilege and ability to access. Marginalized communities that may not live close to nature the way that you and I are able to. I was there for 6 years, first as the General Counsel, then as the Chief Legal Officer and Chief Diversity and Social Impact Officer.

I have a question for you about the transition from the law firm to corporate. Was that something you always thought about? Or, was it an opportunity presented and you thought it made sense for what you wanted to learn and contribute?

I did not expect that I would have a lifelong career at a law firm. It was very meaningful for me and a means to an end. It was a bootcamp of sorts to learn skills and develop the ability to take a craft and apply it to an environment that I thought would allow me to thrive and tap into other aspects of my interests and passions.

Then REI represented a different part of your life. Something you enjoyed doing naturally which is the great outdoors and you could combine it with your legal expertise. Was that part of your decision-making criteria to move from The Gap to REI?

What I would say is that I know many people think of The Gap as just selling jeans. But I was in San Francisco where I started my legal career, and The Gap was a very progressive company and one that had a set of values very early on in its evolution. One of the reasons I was attracted to The Gap was because it was in San Francisco, had such a large footprint and was such a responsible corporate citizen in San Francisco. And the values manifested in the way in which it treated its employees and the integrity with which it operated across the globe.

I felt I could play a meaningful role in ensuring that all the stakeholders – whether it be employees or factory workers, mostly women and people of color internationally – were treated fairly and with respect. The Gap gave me access to influential policy forums, including US Congress, the United Nations and other foreign governments.  Many of my career highlights and the opportunity to make a long-lasting social impact was due to the access a company that makes jeans afforded me

Sheila: It's so important for people to understand that a role that may look like it influences horizontally and up,  actually can influence everywhere. When you sit in an executive seat, it is representative of everyone in an organization. Your decisions touch everyone and that type of leadership holds a lot of weight. And in a global organization, I won’t say more so, but the complexity that a global organization has to address, requires a lot of legal rigor. My hat is off to you even more.

The compexlity and variety of issues that a global organization faces requires operational and legal rigor. It also brings the opportunity to influence policy and brings shared positive impact value for the company; it’s customers and the communities it touches. For instance, I was able to speak to our U.S. Congress when The African Growth and Opportunity Act as part of the legislative process to ensure that corporate America was supporting tariff relief for a trade bill that was going to have a positive impact on millions of people in Africa. My access to forums such as congress to represent other voices and perspectives to bis a privilege and responsibility I take very seriously.

Another example is my participation in the Clinton Global Initiative and other major international forums where I was exposed to thought leaders. I recall one forum where Ursula Burns, former CEO of Xerox, delivered the keynote. She spoke of the obligation that despite your fear, or introspective nature, or feeling like you’re not qualified – when you’re in those types of positions as she was – you must be able to recognize the unique role, obligation, responsibility and honor that you have to represent others in that spaces and rooms that they are not in. This has always stuck with me and has provided moments of inspiration and courage.

Sheila: I just got chills thinking about 360 leadership and how, particularly, women and people of color have a swivel on our heads to see the various constituencies that we represent; but also, those in which we operate. Right? That’s different from some leaders who might not have the same swivel or even understand that there needs to be a swivel. That I need to understand audiences and communities that are not of me. But the requirement that comes to us as women and people of color brings  the grounding to be better leaders with that awareness. It doesn’t guarantee that we are, but we certainly have the perspective that could make us be differently better leaders.

Yes, you’re dancing around the whole DEI conversation we are having in this country that is weighing so heavily on me and so many of us. What you just articulated is one of the proof points of why having diverse voices and perspectives is so obviously a positive thing.

And I also sometimes think about people who don’t necessarily have that swivel and marvel at what they are thinking about.

Sheila: Or not!

Or, not! When you walk into a room and you’re assessing a hundred data points? A thousand? I don’t know what the number is but my brain is snapping. Right? The synapses are connecting. I’ve come to appreciate that this is not an operating mode for everyone. And so, then I think, “what are you thinking about when I’m doing all this? What should I be thinking about that you’re thinking about because I’m thinking about something else?”

Sheila: I remember a bumper sticker that was popular when AT&T would break apart and then come back together. It said, “We don’t care because we don’t have to.” It was surely not an AT&T bumper sticker but was created because AT&T didn’t have to care. There’s so much of this that shows up – particularly now- because some don’t have to care because they don’t have to.

I want to go back to identity for a minute because one of the things you didn’t say was board member. How does board member of a public entity show up in what you’re doing and what you intend to do going forward?

Thank you for mentioning my service on the Baord of Directors of both corporate and non-profit organziations! We have so many identities - it’s easy to omit some!

I retired from REI about a year ago and am what I would call semi-retired. My work now is through a portfolio of board service. I am now serving on 3 nonprofit boards and 1 for-profit board. I really appreciate and am fulfilled with that service. I’ve served on boards for more than 20 years. Up until 4 or 5 years ago, they were all nonprofit boards and a great learning platform to now serve on corporate boards.

I serve on 1 corporate board and am really enjoying the experience. It’s in the health field which is something I have not spent time in professionally. Other than having 3 children, I have not really spent that much time navigating through the health system. So, my board service has been eye opening and sometimes shocking to understand our healthcare policies and practices in this country. And I appreciate the opportunity to think about my board work through the eyes of health equity which is also very important to me. It’s a way to connect my interest in equity and inclusion with my passion around health and wellness.

“I was only going to be able to spike the volleyball so hard, if at all. I’m 5’2’’. So, I had to figure out what’s my role and how do I add value to the team playing that role?”

Let’s talk about when you first knew you were a leader. When was your first known leadership moment?

I’m going to go way, way back! I think there’s some connection with how I lead and these first leadership opportunities which were around team sports. I was always active in organized sports starting in middle school through college. I was a collegiate athlete. I found that by junior high, most if not every team I was on, I was selected to be one of the captains. Track, volleyball and gymnastics. I was never the best athlete! I was good, but I was never, ever the best athlete. I came to understand that being the best wasn’t why I was selected and started thinking about what inspired others to seek me to step into those roles.

Sheila: What did you figure out about that?

I had team spirit, was super optimistic and a hard worker. And I still am. Never say never. Where there’s a will, there’s a way if you work hard enough. This attitude is a strength and like most strengths it can also be a blind spot. I have grit. I think I also have an ability to connect with individuals in a way that makes them feel important and seen. They may not be the smartest or fastest, but they have a role and that’s really important.

My own personal experience informed how I treated others. I was only going to be able to spike the volleyball so hard, if at all. I’m 5’2’’. So, I had to figure out what’s my role and how do I add value to the team playing that role? I think I apply that thinking as a leader. “What are other team member’s roles and how do they add value to the unit or organization?” And I work to respect, appreciate and acknowledge their contributions. I try to treat people fairly and will speak out when I see inequity. I’m a bit of a justice warrior. Unfairness really bothers me! I think I’m a pretty thoughtful person. I’m not a reactive person. But if I see someone being treated poorly or unfairly, it triggers something deep in me and rational thought may sometimes go out the window.

I think those are some of the traits that folx saw. I’m articulating it in a much more concrete way than I ever thought of at age 13, 15, 17 or even 22 but in hindsight I think those are some of the qualities that I hope I engendered that were noticed.

Sheila: And then later you said…

And then later which goes to the leadership moment when I realized I needed to step up and be on my A game because my team needed me. That was the pandemic.

For those of us who weathered through the pandemic, and are on the other side of it, and particularly for leaders who needed to set a north star and lead teams through an incredibly challenging time – emotionally, personally, professionally, physically, mentally – that is the leadership moment that I’m most proud of. To show up in a sustained way and flex my leadership style to meet the needs of my team when, in some respects, their survival was at stake. To make decisions to keep them safe physically. To make decisions about how to support them mentally and how to create an environment and culture where we could lean on each other and still operate optimally which was required of all of us. I know I am not unique in that way as a leader. We all had to show up differently in order to be the support and leader that was called for. It also required very intentional adjustment and reflection over an extended period of time.

Sheila: Some of which is still being experienced.

The pandemic has had a long tail.

Sheila: Yea, I started a new job on the day that San Francisco went on lockdown. I met 3 of my 8 team members in person, ever. To this day. That’s a good call, Wilma.

Leaders need to continue to flex because this is the new normal. It really is the new normal so how do we help people continue to thrive and grow professionally in ways that many of us had the benefit of. I worry about those entering the job market now, how we are supporting them and flexing our expectations as leaders to help them thrive.

Sheila: I was talking with someone yesterday about a colleague they are working with and how they are someone who needs eyes on them every day. Not that you’re hovering. But they need to know that you’re watching what they are doing. They need to have the presence of someone seeing what they are doing. They need that kind of connection.

I think about the phrase “I see you” and how powerful those words were for so many people during COVID and after. There is something to being physically seen and not on a tile in a video conference.

Sheila: Even if you think about things like our visual backgrounds on a video call. I always make sure that my background is tidy when I’m in meetings. But if you were in my office, it’s a hot mess. If I were in an office in a building, it would not be this neat. This is a false pretense! Behind me is a pile of my journals and notes and my floor is strewn with project folders.  

In one of my recent jobs, we were interviewing consultants who would come on video calls with offices with big brown bookshelves loaded with books and windows with views of their lawns. And then you think about the person who is in an apartment who has a false backgound up because they don’t want you to see that they are in their bedroom or kitchen. And how the juxtaposition of wealth gets tweaked even more when we are not present together.

My apparently clean office is a story that is only partially true! And it gets twisted as we meet regularly in these on camera environments. But I have to be “this” to present on screen. If I was in an office, you’d see pictures of my family and what I had for lunch. We’re not there anymore! It’s an entirely different thing.

There’s some connection to the show “Severance” which I just started. It’s bizarre. The set is perfectly sterile. Devoid of messiness, which is the image we sometimes feel compelled to adopt in professional settings. That sterility evokes the opposite of authenticity and vulnerability that I think are, or can be, superpowers for a leader.

Tell me. Identity. How does your identity inform your leadership style? You’ve talked a bit about it in terms of how you seek to see individuals that is part of your instinct of people first. How do you as a Black woman, child of Jim Crow south parents, educated, double degreed – all of those things – show up in your leadership style.

I’m going to start with respect. It’s definitely a part of my origin story, for sure. I was taught that there’s a right and wrong way to engage with people and demonstrating respect for one’s humanity was drilled into me at an early age. No matter who the person is, or the privilege you have, you respect them. You respect the job they are doing. You respect their humanity. That’s one of the things that drives me to connect with people as individuals. The unique qualities they bring.

Part of this is aspirational! I mean, I hope I do this. I think I do this. I work to do this. I don’t want to suggest that I’m any more human than anyone of us who on some days is not exhibiting the qualities that I hope I do. But I strive to, for sure.

Respect and trying to find connections with individuals. Making connections to be able to advance against a vision.

“No matter who the person is, or the privilege you have, you respect them.”

How do you take the presence of the c-suite and situational power and ensure that it doesn’t get in the way of making those individual relationships? How do you keep your human-ness in your function as an executive leader?

I’ve had the privilege of working, and intentionally seeking, organizations that value authenticity and respect. The values that I hold. It starts with that. Understanding what is important as a person. What is important for me in order for me to thrive in an environment. That’s why I chose San Francisco as one of the places where I wanted to start my professional legal career. That’s why I chose The Gap and REI. They were environments that allowed me to be authentic.

I suppose I may put on certain armor and masks, but I don’t feel like I did in those environments. I showed up pretty authentically. I also acknowledge that I entered all of those environments with positional authority, as a lawyer.  

It allowed me to speak with authority and confidence. It allowed me to show up, maybe a little more formally. A little bit more bluntly. A little bit more directly than maybe some other positions which is more in keeping with who I am. So, I didn’t feel like I had to cover up a lot because I was in roles that required and expected that persona and work style.

Sheila: That’s so good. I always say that I wish I was Benjamin Button and I was born knowing what I was good at rather than taking so long to figure it and understand why. That is what this conversation gets us. It affirms why you’re good at what you do and how you show up in leadership is consistent with that. It can’t be an imposter way of showing up to be a good, valued and inspired leader.

As you’ve matured in your leadership, what over the course of time has surprised you, or continues to surprise you about leadership?

I think how welcomed real leadership is. When you’re doing it well, it’s appreciated. And leading doesn’t always mean doing it from the front. In fact, the more senior you get, you’re leading from behind and asking questions that you don’t really know the answer to. Nor should you if you’re asking. As a leader, you seek input, for different perspectives – not to be right.

That kind of leadership when done well is welcomed. Clearing obstacles and taking on tough conversations and not delegating it are welcomed. It takes finesse and understanding the role and capacity that each of your team members have. When and under what circumstances they can show up as their best selves.

Sheila: I wish leaders could hear you say how welcomed good leadership is, and appreciated. I don’t think we get that we hold people’s lives in our hands – their livelihoods in our hands. I didn’t get that any better than when I had 40 employees that I had to feed their families, and keep roofs over their heads, and get new houses and put their kids through college, that how they felt and worked was important to how they were going to exist outside of their jobs in their lives. That was a huge revelation to me in running my business.

And for that reason, transparency, as much as you can and should provide, is an important aspect of trust. Trust is the foundation of any relationship. I keep reminding myself of that when I think about why a particular relationship isn’t working. Why is this person asking me these questions? Why are they treating me this way? I try to remember to ask if there is a trust issue. Do I think that they are not going to follow through? Do I not think they have integrity? Like which part of trust is the issue? What element of trust is the issue?

As leaders, there can be a lot of distrust by employees and people who are depending on you. That creates a very strangled dynamic when you’re the person that they are depending on and feel like they can’t trust you.

Sheila: The other part is not knowing how to earn it back if you’ve lost it. There are all kinds of things in that dynamic of trust. I always say that I give 100% of trust at the beginning and it’s yours to lose, and then I can tell you why I’ve lost it. As opposed to telling people how to earn it. I’d rather be able to say, “Here’s a moment that made me question some things, so let’s work through that.” Versus let me tell you the 10 things that you need to do to earn my trust.

It's the lightening round... what is your superpower?

Building connections.

What talent are you not using?

That’s a hard question.

Sheila: Okay, I can ask  you a different one about talent. What talent do you wish you had?

Singing. And I wish I had more ability to think dramatically differently than I think for the purpose of coming to an understanding. I’ve had to work on being able to flex from what I see as being so clear. How could anyone think differently? I’ve learned over the years that not everyone thinks like Wilma Wallace! So, I need to explain and communicate more about why I’m reacting or approaching an issue a certain way. 

Now, I’ve come to the realization that there are people who have dramatically different views and values. Rather than judging, I’m trying to seek to listen. 

Sheila: Are you looking for agreement or understanding.

Understanding! And then maybe we’ll see if there are points of agreement. I’m all about compromise. But when something is so existential, apparently to both sides, there may be no compromise. First, I hope to develop more capacity to better understand.  

What do you know your life’s purpose to be?

To speak for others whose voices can’t be heard.

I’m still working on my purpose because it’s important. But as I sit here today, and hear what I shared with you in the conversation we just had, I’m gonna go with that for now and see if I can live up to it.

Sheila: We are a work in progress. We get better at our life’s purpose is as it becomes more clear to us. Particularly, how we do it. For example, for me, I feel my life’s purpose is to help people dream bigger. To think about the bigger possibility. Whether that’s a business or I’m coaching or talking with a young adult or child. When I work with clients, I encourage them to dream differently about what they could possibly be. Let’s take off the guardrails and think about what we could possibly be, then define it  and get about being it. It’s situational but it’s always about how we dream beyond the place we are right now. And it continues to evolve how that gets manifested.

How do you elevate yourself above – how do you have a purpose that is elevated – and not in the moment or in the weeds? That’s an evolution that I’m going to assign myself as an ongoing project. To take that vison or life purpose and massage it and elevate it.

Sheila: It’s life lifing. That’s exactly it.

It's 5 years of your life right now, what’s this chapter about?

This chapter is about trying to become more physically, mentally and spiritually healthy after devoting many years to a day-to-day job and children who are now adults. That’s a large part of what I’ve given myself the grace to spend time on in this chapter.

And, reconnection and exploration. To not rush the process at the risk of not making it meaningful. Whatever the future is to be. Not rushing the current chapter which feels transitional because it is meaningful to be in it. And allow the future to unfold. But it takes work. I’m not sitting watching Netflix waiting for the future to unfold. I’m working hard to spend time in a meaningful way that advances the life purpose we just talked about.

Sheila: It makes me think about the fact that I eat by myself a lot, being single, and I don’t always taste the food because I eat it so fast. I have to tell myself to slow down and savor the moment. Savor the moments. Savor the moments.

What’s a song, quote or poem that gets you going when you have a big thing to face? What gets you ready for the big stuff?

It depends but one that is super random is Shakira’s song “Try Everything”.   

One of the quotes, is from Martin Luther King, who like many of us, I was taught to revere and study from an early age. His quote, “The arc of the moral Universe is long, but it bends toward justice.” is a source of strength for me, particularly in the context of my human rights and social impact commitments. Recognizing that it’s a journey. It’s not a moment; it’s a movement that we are engaged in and movements take time. There’s the ebb and flow. That quote gives me hope when it’s hard to feel hopeful. Or when it’s easier to feel frustrated, I try to adjust my approach and expectations according to where we are in the arc.

And Toni Morrison’s poem And Still I Rise, is an inspiration and reminds me of our ancestor’s journey. I saw on a t-shirt something about the assignment we have. Have you seen that t-shirt?

Sheila: I have an assignment t-shirt that says, “Dear ancestors, I understood the assignment.”

It’s a year from now, and other than still being on the planet, what are you celebrating?

I am celebrating people coming together and resisting. I’m also looking forward to balancing that with joy and feeling that I, and loved ones around me, feel joy. That I brought them joy. The act of resistance is hard and the place we fall on the arc today, we need to find joy in the places we can in order to play that role. Fulfill the assignment.

Is there anything else that you’d like to share with me?

I think we covered a bunch of things. I hope that you have something to work with that is intelligible from my side.

Sheila: I have you to work with. These conversations are designed to go wherever they go. And what’s revealed is always incredible. When you hear yourself in this form, it’s pretty amazing – the connections of how you got from here to there and why it’s so ingrained in you. From beginning to end, Wilma, it’s about justice. It’s about that scale that is what you do. It is who you are and it shows up across the board.

The idea that your leadership started in a team, in a team sport, not an individual sport. And not where you were the best but at what you were good at made people go, “her”.  And that’s a thing. Sometimes leadership is anointed and sometimes you step right into it because it was the next thing. But how we find ourselves getting to it is our own story and they are all beautiful.

Wilma, thank you for taking time to sit with me In the Cut!

Please leave Wilma a comment below! Thanks for stopping by.