How to Find, Select & Outsource DEI Work to Support Your Inclusion Goals

Welcome to the Inclusion in Progress podcast where we give you the ideas, actions and insights to help you build more equity at your workplace and in the world at large. I'm your host, Kay Fabella, international expert on diversity, equity and inclusion, a Filipina American living in Spain and your guide in navigating this DEI journey. Having worked with teams at companies such as Philips, the IMF, Red Hat, PepsiCo and more, I know firsthand that the work of inclusion only works when everyone has a seat at the table. Regardless of your personal entrypoint into this conversation: your race, ethnicity, gender, ability, age, sexual orientation, country of origin, or educational background, we all have a role to play in creating inclusion for all and it starts with us having conversations we need to create the change we wish to see. So let's dive into today's episode.

Kay: As we shared in episode IIP115, we’ll be interviewing some of our past clients over our next podcast episodes who’ve partnered with our company, Inclusion in Progress, on implementing diversity, equity and inclusion in their organizations. Today’s episode features Regina Lawless, formerly the DEI Head of Instagram, and the current Founder of Bossy & Blissful.

Before starting Bossy & Blissful, Regina served as the head of diversity, equity, and inclusion (DEI) at Instagram. She has worked with Fortune 500 companies across various industries, including Target, Intel and Micron Technology leading equity, inclusion and justice in workplaces.

Now, Regina has built a wellness community for Black women executives and business owners that helps them find purpose beyond their paycheck in order to experience more bliss in their lives and sustainable success at work and at home.

She holds a master’s degree in organizational development and lives in the Bay Area with her partner and teenage son. Her first book, “Do You,” will be published by Greenleaf Book Group, in partnership with Fast Company in February 2024.

Regina is not only one of our client partners, but a dear friend of Team IIP as well. We’re excited to share how we met and her story with you as one of the practitioners we admire most. Let’s dive in!

Kay: Alright! So I'm excited to have our guest on today for this series where we're basically playing catch up with all of our favorite client partners and showcasing what it's like to work with Team IIP behind the scenes. Obviously, we've reached out to several of our favorites, and I am beyond excited to introduce Regina Lawless on this podcast! Welcome to the show, Regina!

Regina: Thank you! And Kay, you know, I'm always excited to talk to you and your team. So I was thrilled when you all asked me to be on the podcast!

Kay: We're so thrilled to have you! And, obviously, we can't wait to highlight a bit more not just about your expertise, but also your incredible work.

Let's go ahead and dive right in!

We're asking all of the people that we're having on this show to share a little bit about their DEI journey which, as we know, is never linear... Whenever you're ready, tell us your story, Regina!

Regina: Yeah… my DEI journey started later in my career. So, I've been in the HR field for almost 20 years now and I started as an HR Business Partner — I was working in the retail sector — back then it was called an HR Representative. I was responsible for coaching and consulting managers on policies and being the go-to person for employees that had various issues in the workplace. But then, over the course of my career, I wanted to do more strategy work because I found that, in the regular course of my HR day, I was doing a lot of reactive work. So people coming to me with every problem under the sun, which was entertaining sometimes, but also draining. Fast forward, I pursued a degree in Organizational Development, which is really a fancy way to say Change Management. So I started down that path. And that led me into the tech industry. And then, within tech, I started to learn more about DEI, because the tech industry is one of those industries that definitely is always in need of more diversity and more representation across the spectrum. I went from having a DEI champion on my team, to eventually moving to my next company where I was Head of L&D and Talent Management, and then I had DEI programs, and then that was the spark. I really enjoyed the DEI programs and the leadership programs we were doing for women.

That's where I decided, like, “Ah, I would really love to do this full-time!” because it would incorporate my level of change management, how do you get organizations to think differently, behave differently, and then you infuse that with DEI — which I've always been a lifelong champion of equity and justice. That's what led me firmly into a global DEI role, And then, in 202, I ended up with Instagram. So they hired me to be their first head of DEI.

And that's, of course Kay, where you and I met!

Kay: Yes, it is! And we'll make sure that we touch base a bit on this next chapter of your journey that we’re finding you in today… but we were very excited when we first had a chance to connect with you officially as IIP, and obviously I was very thrilled to connect with you before that. And, like you said, 2020… it feels like forever ago!

Regina: It does! I almost said 2000, if you heard that! That’s how long ago it feels like it was.

Kay: Oh my goodness! No, it's the pandemic time warp, for sure!

I think one of the things that Team IIP and I… we were all trying to figure out, well, what do we want to highlight on the show when we reached out? And one of the things that we hear often is we've covered so many things on the podcast about diversity, equity, and inclusion; but one of the things that we haven't really shown the behind the scenes of is what it's like to work with, in our case, as external contractors and what that partnership looks like when you're with an internal champion or a stakeholder who is leading that particular… whether it's a program or initiative internally.

And I know that you've worked with several external contractors before. With us, obviously, when you were with Instagram, but also before at Micron and in other capacities. What have you gained from partnering with external contractors?
Regina: Yeah, absolutely!

Yes, throughout my career I've worked with external contractors. When I was leading L&D and Talent Management at a company called Flex — Flextronic — that's where I really got to see the power of that external engagement. I had a team, but my team was mostly focused on project management. I had some internal consultant roles on my team, but I didn't have a lot of facilitators and we didn't have the capacity to actually design programs, not full scale for the organization. We partnered quite a bit with external firms and external consultants to help us to design our programs and, in some cases, to help us deliver them. That was my first experience of, like, okay… this could be a really good way to not only augment my staff from a numbers standpoint, but also bring in expertise that I didn't have in- house. And so that worked really well.

And then I continued to do that at Micron… brought on some vendors to help us build out our inclusive learning portfolio. At Instagram, we as a company — because Instagram is owned by parent company Facebook, now Meta — we had a ton of resources. So, initially, I didn't have to go outside. But here's where I think external partnerships still comes in play: Even though, technically, I could have gotten almost everything I needed to be done in-house, I found value in the external perspective.

Kay, when you and I originally connected when I was at Micron, I wanted to partner with you and IIP at Instagram because you had a global perspective that, I think, at the time we were lacking. We were very US and North America-centric. That's the other power, I think, of bringing in external partners, is that they have the benefit of not only working with multiple companies — they can see what's best-in-class — but also, in your case being a global firm, being based overseas, I felt that you all brought in that perspective as well for us, which was really valuable.

Kay: Yeah, and we loved working with you all… I think it's something, to piggyback off of what you said, it really is a privilege when we get to come in and offer support. And I've jokingly referred to it as when your favorite aunt comes to visit: everybody behaves a little bit better with somebody else in the room.

Regina: So true!

Kay: And so when it comes to some of the facilitation or some of the harder conversations or even, as you said, when a learning and development program needs a little bit of external support or a perspective that's not currently offered, there really is a beautiful symbiosis that comes out of a partnership. Where you have somebody who can really focus on what their remit is in-house with the supportive and external partners.

I'd love to hear a little bit from your perspective more of, when somebody is considering embarking on working with an external contractor or vendor as an in-house practitioner, what are the benefits that they would gain from that kind of partnership? And what are the ways that they could advocate for that internally as they're trying to build, say, for example, a business case or gain buy-in from stakeholders internally?

Regina: For me I've found the benefits are opening up, as an internal person, the aperture of what's even possible. I think, oftentimes, it's easy to get insular. And it's easy to get just bogged down in this is the way we've always done things or, especially larger companies, you have your legacy programs that you may have run for years and years… and you start to, I think, lose some competitive advantage when you're not consistently updating those programs and looking for how to make them best-in-class.

For example, when we worked with you, Kay, at Instagram, when we brought your team in, you all did a fantastic job of doing some virtual facilitation for us. Taking a program that would have been logistically difficult to do during the pandemic, it would have been hard for us to do ourselves, to pull that off virtually — you already had the expertise of running virtual programs and you all pulled it off extremely well.

So that's something where I could have just struggled in-house and we could have just muddled through and tried some things. But I think the real benefit of partnering with someone externally is bringing in a fresh perspective, but also bringing in expertise in areas that you don't have. And, if I was trying to make a business case that those are the two things I would anchor to because no company, no matter how big you are, no matter how many resources, you're not going to always be able to cover every angle. There are people that do things better than you can as an organization so it, to me, makes a ton of sense to go and hire for that expertise when you need it, or new perspective.

Kay: I love that! There's so many different conversations we could have about that collaboration, but I wanted to kind of zoom out again and ask you a little bit more about DEI because another common thing that we hear from listeners on the show is, “I'm considering getting into DEI work… what do I need to know?”

And I know, for you specifically, at the time that we're connecting, you just founded your own company [Bossy & Blissful] as an extension of your mission in equality and equity and inclusion and justice, I would really love to hear — if you were speaking to Regina maybe 20 years ago or a version of you 20 years ago, what advice would you have given her at the start of that journey and what would you want her to know?

Regina: Oh, my goodness! So much!

First thing would be, “Pace yourself.” I think that's the biggest… when I'm asked by, particularly, college students now. I say, “Pace yourself.” I had a lot of angst earlier in my career about, “Oh, by this stage — by this many years or by this age — I should be a Director or a VP. And as I know now, and as many of us seasoned professionals know now, it does not happen that easy. And I would say, especially getting into DEI, it's one of those fields that is challenging to get into because there's… I have not met anyone that has a direct path. It usually is: you come in through some HR lane, typically, but not always.

But that, in and of itself, I'd give myself the, not only, “Pace yourself,” but, “Follow your instincts.” Because when I first got a taste of DEI — but at that point in my career, it wasn't a full-fledged function. It was one diversity officer that was working through the other functions within HR to do a program here or there, or to have some goals for the company. Now, of course, DEI has matured into a full-fledged function. But it still is a difficult field to be in because, for most of the folks that are in DEI, typically, you're from an underrepresented background. So you already have the historical barriers and real-time challenges that underrepresented folks face in majority organizations. So you're dealing with that, plus trying to advocate for other people who are underrepresented or marginalized in your organization or in your community. So it's definitely not for the faint of heart. But it's super rewarding.

And for me, what I found… I think, in organizations, it's easy to get bogged down because there are all kinds of stakeholders and laws and policies that you have to navigate. It takes a really long time to get traction. It takes a lot of consistent effort and a lot of people rowing in the same direction to make progress in DEI. But once you do, it's amazing.

So I think for me, having been in corporate for almost 20 years, I started to get tired of having to navigate all of that corporate structure, so I decided I wanted to leave corporate and work for myself. But I still kept the mission of DEI and equity in my business. I founded a company called Bossy and Blissful. Our mission is to help high achieving black women executives balance their success with joy and peace. So to find sustainable success, because of my experience of growing up in corporate as a Black woman leader, and all of the burnout and stress and overwhelm and lack of support. And, even at the height of my success, I found that I was still burnt out and tired and unfulfilled.

In recent years, I've done a lot to cure that and find a better way to exist and be, and that's my goal — is to help other women of color generally, but Black women leaders specifically, find that sustainable success.

Kay: That's something that we didn't even touch on earlier in the conversation… we connected and were partnering in the height of just the wildness that was anything post-2020. And you were right smack in the middle of that. I really admired even from when we were in the trenches together, as it were, on that collaboration, how you continued to show up and lead your people with grace even though, I'm sure, you were holding space for a lot of heavy [things] at the time we connected. So I just wanted to highlight that as well.

Regina: Thank you, thank you so much! Yeah, that time was really heavy, because I got hired a few months after the murder of George Floyd. So that was the, I think, height of the fervor to make some sort of progress on racial equity. And so there was an immense amount of pressure on organizational leaders, and of course DEI leaders to help them to undo some of the historical wrongs.

Kay: And I also, thinking back on our specific collaboration, how I love that it's come back to making sure that you're getting leaders who are in those rooms to continue to make space for themselves. The heart of DEI work, as you said, it isn't for the faint of heart. But I think in community and remembering that we can hold space for one another. In this way, and like the way that you're striking out now with Bossy & Blissful, and the way that you've led throughout your career, the way that IIP hopes to continue leading in the future, it really just depends on what we've been talking about throughout, right? Which is this idea of collaboration and remembering that we can't all do it ourselves. And we do need help and we do need external support, we do need people to hold us up.

So I'm really excited to see what this next chapter holds for you. And I can't wait to continue supporting you. And, obviously, Team IIP feels the same way!

Regina: I love it. You all are wonderful!

And it’s… I'm grateful to have you in my support system, because we absolutely can't do it alone. And, even as… now that I have my own business. I will continue to need help and support from external partners and friends. So I love it!

Kay: Amazing. You know, you've seen, really, every iteration of DEI over the last 20 years, and especially over the last 3 since we first connected… What would be your final words to somebody who was listening to this? And they were like, “Alright, I've listened. I've heard the lessons. I'm in it! What do I do next?”

What would you share with them as a final word before we sign off?

Regina: That's such a great question. Gosh, I… we could do a whole episode on this question, because there's so much advice I could give…

Kay: True!

Regina: But I would say… probably two things: I would say, 1) Don't get discouraged. DEI is very much a long game. And it's going through a transformation. The pendulum is swinging back. There's always a backlash to progress, and we're seeing that. So, I would say don't get discouraged. DEI might need to look a little different than it had it at the height, following 2020. But [that] does not mean we let our foot off the gas.

Secondly, I would say what I find really exciting, and where I think practitioners should kind of lean into is the equity space. I think that if you can work with the company, and whether you bring in an external partner that is really experienced in this, but it's really that equity. And I would also say inclusion because, to me, they go hand-in-hand. But focusing on the experience of everyday employees. I think DEI… it's easy to — particularly from business leaders, I think — practitioners, we know when things are becoming performative. But it's hard sometimes to get leaders to see that. But, oftentimes, there's a focus on the flashy and the big and the events and the recruiting side of things, which are all part of a comprehensive strategy. But I think, moving forward, if we can continue to focus on the everyday experience… So, how do we get leaders to behave more fairly? How do we change policies and processes that affect employees, like salary negotiations, performance management systems, Even time off policies, things like that, that we know have an uneven or inequitable impact on underrepresented groups. If we can focus there, that's how we move the needle long-term.

Kay: I love that! And, ultimately… it's like you said, right? That these are steps. Progress takes time. There will be different iterations but, as long as we keep moving, it'll still move forward.

I really appreciate you taking time with us today, sharing your experience and your wisdom with us. I wanted to make sure that folks knew where they could reach out to you and where would be the best place to follow the work that you're doing.

Regina: I love it! So you can always find me on LinkedIn: Regina Lawless, you can follow me on Instagram: @regina.lawless, and then you can check out my website: bossyandblissful.com or reginalawless.com.

Kay: Amazing. Thank you so much for spending time with us today!

Regina: Thank you Kay!

Kay: So there you have it! That was Regina Lawless, the former DEI lead at Instagram and Meta, founder of Bossy & Blissful, and one of our esteemed client partners. We’ll be diving into more examples of folks we’ve worked with over the years, so stay tuned for those stories in the coming episodes.

And as always, if you’d like to learn more about how you can partner with Inclusion in Progress to deliver strategic guidance on diversity, equity and inclusion for your team or company; to create greater psychological safety, inclusion and innovation; head to the link in the show notes or email us at info@inclusioninprogress.com to schedule a no-pressure consultation call with our team.

Thanks for tuning in and see you in the next episode!