Wilma Wallace (Gap & REI) on Nurturing Future Leadership With Values & Purpose

Executive leader and board member Wilma Wallace joins Roy to discuss her experience recruiting and mentoring leadership teams at Gap and REI during her extensive career at both legacy brands. After spending over 20 years in senior roles at Gap, Wilma served as Chief Diversity and Social Impact Officer, as well as Chief Legal Officer at REI. In 2024, she retired to focus on impacting change, particularly from an equity, access, and justice perspective, on several boards. Her work centers social impact, environmental justice, and human rights in both the for-profit and non-profit sectors. Wilma and Roy discuss accounting for and addressing changing levels of trust across organizations, internal succession planning versus seeking external candidates, the link between alignment of purpose and successful performance in leadership teams, and much more.

Highlights

(4:18)
How Wilma evaluates candidates’ leadership abilities

(6:48)
Creating an environment that fosters high potential future leaders

(8:26)
Recruiting external talent

(11:08)
Leadership assessment practices at Gap & REI

(14:01)
Ensuring that an organization’s culture stays dynamic and resilient

(17:35)
Leading and hiring through periods of growth and change

(20:30)
Ways in which leaders should be vetting culture and values before taking on new leadership roles

(23:00)
What gives Wilma hope about the next generation of leaders

Transcript

[00:00:00] Roy: Hello and welcome to How I Hire, the podcast that taps directly into the best executive hiring advice and insights. I'm Roy Notowitz, founder and CEO of Noto Group Executive Search. You can learn more about us at notogroup.com. As a go-to firm for purpose-driven companies, we've been lucky to work with some of the world's most inspiring leaders as they've tackled the challenge of building high performance leadership teams. Now, I'm sitting down with some of these very people to spark a conversation about how to achieve success in hiring and create purposeful leadership for the next generation of companies. Wilma Wallace is an executive leader and board member. After more than 20 years in senior roles at Gap, Wilma served as the Chief Diversity and Social Impact Officer and Chief Legal Officer at REI. Today, she's a member of multiple boards and continues to champion social impact, environmental justice, and human rights. Today, we're going to talk about recruiting at Gap and REI through growth and change, ensuring that culture is dynamic, meaningful, and values-aligned, and what boards are thinking about in this moment. Wilma, thanks for being here. It's great to have you on the podcast.

[00:01:20] Wilma: Gee, thanks, Roy. It's my pleasure.

[00:01:22] Roy: I'm interested in having you share some of the highlights and reflections on your vast career journey.

[00:01:29] Wilma: I mean, I feel like looking back over the past 35 years, I've just been so fortunate to have been able to build a career in a corporate setting that is purpose-led and aligns with my values and the impact that I hope to have in the world. And I'd always been fascinated by the law, the role of law in changing society, in molding culture, so felt that the law was the mechanism through which I could have impact. I started as a corporate litigator in a law firm, but I actually thought that I was going to end up joining a nonprofit organization as a lawyer, most likely, but that I wouldn't have a 35 year career in, in a corporate setting. So, started at the big law firm, and a friend worked at the Gap and told me about a position at the Gap when I was about a fifth year. And so, started a 20 year career at the Gap in their legal department when it was about a $4 billion company. There were about six or seven lawyers outside of the real estate attorneys, so I had the privilege of starting in an organization that was in growth mode. Old Navy had just been founded. Baby Gap had just been founded. We'd not yet gone internationally. I mean, it really was a very, very special time, and I just feel lucky, and privileged, and blessed, and humbled to have been a part of Gap'S growth and to have been there at a time when I was able to take advantage of a lot of opportunity that came my way.

[00:03:09] Roy: What a great experience. After Gap, you worked for some great brands, and I'm curious how those aligned with your focus on mission and how you wanted to make an impact.

[00:03:20] Wilma: Yeah, so I then had the opportunity to go to REI. Again, it was another organization that did align with my values, being able to spend time outdoors and working to ensure that the outdoors is a place where everyone feels they can thrive. So, joined REI as general counsel, and then 2020 came, and I was given the opportunity to take on a role establishing our Diversity and Social Impact office at REI and was elevated to the Chief Legal Officer role.

[00:04:00] Roy: Wow.

[00:04:00] Wilma: And I had that role until about a year and a half ago when I left the organization, retired, and am now working on boards and using my skills, and experience, and passion for access and equity in the board setting.

[00:04:18] Roy: In the context of hiring and promoting individuals into senior level roles -- I'm sure you've had lots of different teams and groups that you've worked with -- how do you evaluate a candidate's leadership? And what do you look for in a leader for your team or for the company that you've been working with?

[00:04:35] Wilma: I think it depends on whether you're promoting from within or hiring from the outside. And, if you're promoting from within, you've had, presumably, time to evaluate skills and Gaps. You have colleagues who've worked closely, if you haven't, with that leader in their existing role. And you also understand how they're perceived by other leaders. And I do think that so much of a leader being successful in role, particularly if you are promoted from within, is how you engage and interact with other leaders. And are you able to use your influencing skills -- your superpowers -- to actually be impactful and effective? These people have been on your radar. You, as a leadership team, have invested in upcoming leaders, and they have a documented track record of driving positive change in a way that is consistent with the purpose and the values of the organization. They must have been doing something right over the period that they've been there, such that they are aligned with the values, the way of working, and are able to have impact.

[00:05:43] Roy: In thinking about that from an internal perspective, did you participate in or lead any succession planning with your team or other teams across the organizations?

[00:05:51] Wilma: Absolutely. In both of my primary roles at Gap and at REI, succession planning was, ultimately, something that each organization came to understand was critical for the sustainability of the organization. And, ultimately, spent concentrated, intentional time creating succession plans, but, more importantly, aligning and agreeing as a leadership team that we each had a responsibility to invest in those leaders and break down the silos, break down whatever false competition you might feel to, as a team, recognize the importance of each of us committing to the next generation's success, and, in particular, those leaders who've been identified as our successors.

[00:06:48] Roy: How did you create that environment or support those high potential future leaders? What are some specific things that you personally did to coach or help mentor people up through the organization?

[00:07:02] Wilma: So, formally, we would have succession plans and identify where there might be gaps, or blind spots, or opportunities for those leaders to excel. And, personally, each one of us, including myself, would commit to using some of our strengths to support that individual. So, if there was someone who was not thoughtful around executive presence, and how to be succinct, and get to the point. And, as a lawyer, I probably lean a little bit more in that direction to being direct and having a message that you try to make sure is clear. And so I would offer up to mentor that person on that element. So it was very personalized in so many regards. It wasn't just, "Okay, let's slap together a individual development plan and hope for the best." It really was, "How can each one of us personally support the success of this individual, given our strengths and our experiences, and frankly, what we may have struggled with as we were coming up?" You then are very acutely aware of what it takes to perhaps be able to fill that gap.

[00:08:26] Roy: If you needed to recruit somebody externally, what were some of the things that you looked for in a leader when you were searching for your own team or for the company?

[00:08:36] Wilma: So, in my experience, it's less about evaluating the functional and technical skills. There's so many ways to be able to assess that independent of engagement with that individual candidate, the prospect. By the time they're relatively senior, they may be well known in the industry or the sector, if your orbit is their orbit. There's LinkedIn, there are podcasts that, perhaps, they've participated in, there are articles they've read. I mean, there's so many ways in which to assess their technical and functional capability and even, to some degree, how they think. Unless they're writing about leadership skills and their belief system, that's what's more difficult to get a handle on through desk research. And so that's what I've found I tend to gravitate to, "What are your softer skills? What's your mental model for leadership? Are you command and control? Are you servant leader? Do you like to take up a lot of space? Do you ask a lot of questions first?" Things that are a bit of a signal as to how someone tends to lead. And then, do they believe in the mission and the purpose of the organization? Are they passionate about it? Integrity is key for me, both personally, but I think also probably informed by my legal background. Other things I've looked for, because it's the culture. I mean, it's my inclination too, I think, but it's the culture of the organization, both at Gap and at REI. Are you collaborative? Are you inclusive? Are you committed to a team approach to problem solving? Or do you believe that you have most of the answers, and you're just validating them or testing them against your team? How important do you think it is to bring in different voices? Or, again, do you think your voice is the largest, loudest, it's the biggest, and it's the one that counts the most? Obviously you want people who are strategic thinkers, but, beyond that, are they looking at trend? But are they able to see around the corners? Are they curious enough to see around the corners? And then, adaptability and resilience. I don't think you can leave those two characteristics or competencies out, given how volatile, and uncertain, and complex running a business is. And then, I think, finally, can they actually inspire and empower others?

[00:11:02] Roy: Those are all great leadership qualities. I'm interested in what methods or ways that you, whether it was at Gap or REI, assessed and evaluated those leadership qualities. Was there a certain methodology or practice in place at either of those companies?

[00:11:19] Wilma: So, the first was being very careful and thoughtful about who would be the interview cohort, and certainly wanting to have diverse perspectives represented on that panel because everyone comes with their own bias, their own preferences, and want the candidate to feel comfortable in that space. And so, being very thoughtful about who was on the interview panel. And how do you just ensure that you're creating a very curated experience for the candidate, and one that is going to be meaningful as it relates to providing feedback? And we had competencies against each of our values and expectations, and each member of the cohort would be given one or two of those questions to ask. And we did then provide written or verbal reports back to the recruiter. But I also think that a best practice is to come together as a team and have a conversation around strengths, weaknesses, what you saw. It forces you to challenge your own assumptions, and I truly believe that's the most fulsome way to engage with a candidate and their ability to thrive in a role. It's very easy to just send in your notes, or leave a voicemail, and call it a day, but I really think that's missing a large part of the value of having an interview process.

[00:12:58] Roy: So you've highlighted how rare it is and difficult it is to form a truly effective leadership team. And so, what are the essential ingredients that make leadership teams truly click and perform in your opinion?

[00:13:16] Wilma: I think it starts with alignment and a deep, selfless commitment to the purpose. Is everyone at the leadership level bought into the purpose? At REI, it was: we exist to inspire and enable a life outside for everyone. Those are really aspirational, heavy words, and we used that purpose and other values and action documents to gauge and influence decisions along the way. So, I think that's one of the essential ingredients that make a leadership really click.

[00:14:01] Roy: How have you worked to ensure that culture stays dynamic and resilient within the organization?

[00:14:06] Wilma: You have to live it every day. When I say "it every day," culture, particularly as it's articulated in the values and the purpose of the organization. Whether it's documented or not, every organization has a culture. The advantage is to get ahead of it, or around it, and make sure you're developing an articulated statement of the culture and expectations in a way that brings out all the goodness and tries to slough off some of the, perhaps, negative aspects of a culture. Then it just is a, I think, constant drumbeat--

[00:14:48] Roy: Yeah.

[00:14:48] Wilma: --to remind people what the culture is, the actions and the behaviors that are expected, and bring it to life so that it's not a piece of paper that sits in a desk.

[00:15:04] Roy: Yeah. Over the course of your career, how have expectations around leadership, especially related to things like values, transparency, and accountability shifted?

[00:15:17] Wilma: I think the bar's just been lifted, raised, particularly as it relates to transparency, authenticity, accountability. I think many organizations would say in 1995, and in 2005, that they had values, but values that transcend the organization around people and the planet has changed.

[00:15:47] Roy: Yeah.

[00:15:48] Wilma: You know, no people, no planet, no profit. It's that simple.

[00:15:52] Roy: It really is. How do you account for the diminishing or changing level of trust in institutions and organizations?

[00:16:00] Wilma: Gen Z. They're not crazy. Institutions have not been very trustworthy, and so I think that they have a healthy cynicism of organizations. I also think that as government does not provide the safety net that it may have provided for you and me, whether it's student loans, or low interest housing loans, or healthcare, the workplace becomes more important for those who are employed. Your employer is stepping in, in some regards, to fill that void. And so, I do think that there's more at stake for employees because you're relying on your workplace for mental, physical, and financial stability, and not many other organizations are-- including the government, are guaranteeing that. So, I think, with that comes obligation and, perhaps, a higher expectation of those employees. The good news is they are telling us what they want. So, it's a matter of, I think, listening to this expectations and then figuring out how you shift to be able to address them.

[00:17:30] Roy: Yeah.

[00:17:30] Wilma: And maybe meet them, maybe not, but definitely address them.

[00:17:35] Roy: So you've worked through major transformations at REI and Gap, and I'm curious what lessons you've learned about hiring and leading through periods of growth and disruption and change.

[00:17:49] Wilma: So, I think, when it comes to hiring, you need to know the assignment. What are you looking for? What are the capabilities, the skills that you're going to need for the future? AI is presenting a really interesting dilemma for us right now, right?

[00:18:05] Roy: It is, yeah.

[00:18:06] Wilma: Is everyone looking to hire tons of AI expertise? Should they be looking to hire tons of AI expertise? Is there tons of AI expertise? Or do you bring in consultants? Do you develop people internally? That's just one example of something that is glaringly, blaringly out there that companies are trying to grapple with. Knowing the assignment and what you're looking for is really important during periods of growth, disruption, and change. I also think, when it comes to leading, it's just important to recognize the moment for what it is and how transformative it is or isn't. And is it going to require different capabilities? Covid, I guess, is a great example. There were very specific capabilities that we needed to lean on as flurry of different regulations are coming out and trying to create safe spaces for our employees. Healthcare options, behavioral health options, and recognizing, again, when it comes to leading, who do you need to lean in on who perhaps has not been front and center in problem solving or at senior leadership team meetings? When you're talking about product, all of a sudden, you're talking about risk management, and you're talking about health and safety. So how do you lead in a way that brings those voices in to be able to deal with moments of transformation or change?

[00:19:36] Roy: And, from your perspective as a board member, I'm curious, what are boards thinking about and what's the priority these days?

[00:19:43] Wilma: Businesses like certainty. They can deal with bad news, "Just tell me that it's going to be this way for how long?" And so, it's predictability and certainty that so many businesses are modeled upon, and this is not a certain time.

[00:20:01] Roy: Right.

[00:20:02] Wilma: There's a lot of volatility right now, so it's helping organizations right size their reactions and not get distracted with the chaos and all the change, and yet, do bear down on more scenario planning, risk management. What is-- what are the worst case scenarios? And how do we, at least, contingency plan for that?

[00:20:24] Roy: You've been intentional about aligning with organizations whose missions you believe in. How should leaders today think about doing their own due diligence on culture and values before taking on new leadership roles?

[00:20:38] Wilma: I think it starts from within. And again, this is if you're taking on a new role in a new organization. What do you need to be successful? What environment do you thrive in? What are your short and long-term goals? And get really clear. Have an honest conversation with yourself about that. Bring in your friends, consult with them, but really dig deep and try to have an honest conversation about the kind of environment that you thrive in and can be successful in, because that's, ultimately, what you want. You want to have a successful career, and the people who hire you want you to be successful. Then you can assess whether or not those conditions exist in the company.

[00:21:26] Roy: Yeah.

[00:21:26] Wilma: And then, really have a conversation with yourself around if there any flags that you should be alerted to, either to be able to prepare to deal with them once you're in the organization, or recognize that maybe it's not the place for you and to have an honest conversation.

[00:21:45] Roy: Yeah.

[00:21:45] Wilma: I attribute the success that I have had to being, I think, pretty selective about the organizations that it was prepared to align with.

[00:21:56] Roy: Yeah.

[00:21:57] Wilma: And you have a fighting chance despite, you know, your foibles and the organization's foibles. So, it's just, I think, doing some real internal reflection, and then matching that against what you learn through very standard due diligence.

[00:22:19] Wilma: And it's hard, right? I mean, it's hard to have that kind of deep conversation with yourself. The benefit, I think, of being a seasoned leader is you've had enough experiences that you begin to understand, with some clarity, the kind of organization you enjoy being a part of, can thrive in, and the kind of organization you can't. But then, holding yourself accountable to that is a whole 'nother thing.

[00:22:48] Roy: Yeah.

[00:22:48] Wilma: As you want them to, like you and you--

[00:22:51] Roy: You have an opportunity.

[00:22:53] Wilma: Yeah. And it's an opportunity, and you've invested a lot of time and energy in it, and maybe it's the only opportunity you have.

[00:22:59] Roy: Right. So, looking ahead, what gives you hope about the next generation of leaders and how they'll build organizations that are both courageous and true to their values?

[00:23:09] Wilma: So, I do think, in the times we're in, it really is important to find those bright spots. And what I'm encouraged by is my sense -- and a part of this is my lived experience having young, adult children -- is that they seem to have a commitment to building organizations, and to being in organizations that are true to their values, and hold those organizations accountable to it. So, leaders coming in, that's the population you're dealing with. They have high expectations.

[00:23:43] Roy: Yeah.

[00:23:43] Wilma: I know when, in the early 2000s, we were conducting consumer studies and surveys at Gap, and then, even later in the 2000s, 2016, 2017, '18, '19, at REI, it was a little unclear whether or not customers shopped their values. They said they did, but when you looked at what they actually purchased and how they-- their behaviors, they didn't. Fast forward, I was looking at the study from 2020, and it revealed that 73% of Gen Z consumers are willing to pay more for sustainable products, and that surpassed millennials, Gen X, and it way surpassed Baby Boomers, of which I am one, at 42%.

[00:24:31] Roy: Wow.

[00:24:31] Wilma: Less than half really shopped their values, as compared to 73% of Gen Z. That gives me hope.

[00:24:39] Roy: Yeah, that's amazing.

[00:24:41] Wilma: And I'm just seeing growing emphasis on empathy, on vulnerability, on, again, the connection that this generation's leadership is making between people, planet, and profit. And I hope that's influencing and impacting their leadership style.

[00:25:03] Roy: Yeah. That's fantastic. So what are you most excited about as you think about what's next or what you're working on currently?

[00:25:12] Wilma: Most immediately, I'm spending a fair amount of time engaging, and counseling, and speaking up in the organizations where I sit on the boards or networks that I'm affiliated with, navigating through some of the recent executive orders, tariff issue, and now judicial decisions that are coming down. And so, using my legal skills in a pretty unique way to better understand the environment that those organizations are in. So, that's fulfilling, and I always appreciate being able to use the experience and the training that I've had. And then, I'm excited to continue to serve on boards and volunteer organizations where I can use that platform to be able to impact change, particularly from equity and justice perspective.

[00:26:17] Roy: Yeah, that's fantastic. Any board that you're on, they're lucky to have you, so.

[00:26:21] Wilma: Oh, you're just saying that.

[00:26:23] Roy: No, it's been really great getting to know you better, and learned a lot in this conversation, and just really appreciate your perspectives on leadership, and building teams, and values, and culture, and all of those things. So thank you so much for joining me today, and appreciate you being here.

[00:26:41] Wilma: It's been a pleasure. Thank you, Roy.

[00:26:45] Roy: Thanks for tuning in to How I Hire. Visit howihire.com for more details about the show. How I Hire is created by Noto Group Executive Search. To find out more about us, visit notogroup.com. You can also sign up for our monthly email job alert newsletter there and find additional job search strategy and hiring resources on the website. This podcast was produced by Anna McClain. To learn more about her and her team's work, visit aomcclain.com.

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