Diversity, Equity & Inclusion Strategist

In this episode of LWWYA, Dia Bondi interviews Angela Roseboro, culture strategist and Executive at Riot Games, about her journey through leadership in culture transformation and startups. Angela shares her operating principles and leadership philosophies, providing valuable insights for founders looking to level up and confront what it means to go from Founder to CEO. 

Listeners will also gain valuable insights into how to bring empathy and grace to their work, create successful human capital strategies, and lead with who they truly are. Angela's peak moments in her professional life, including a failed initiative that turned into a peak experience, offer unique perspectives and inspiration for those seeking to grow as leaders. 

Don't miss this episode of LWWYA and be sure to share it with fellow innovators and leaders who lead with authenticity.

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In this episode of LWWYA, Dia Bondi talks with Angela Roseboro, an award-winning diversity, equity, and inclusion strategist, about her career journey, leadership philosophies, and advice for founders. 

Angela shares her operating principles and experiences in culture transformation, having worked for and with recognized brands such as Whirlpool, T. Rowe Price, and Dropbox. In her most recent role as Chief Diversity Officer at Riot Games, she led the company's cultural transformation from being at the center of a cultural reckoning around bad behavior in the gaming industry to being certified in 2022 as a "Great Place to Work" by the Great Place to Work Institute.

Dia and Angela discuss the key transitions founders experience as they level up and how to confront what it means to go from Founder to CEO. Angela also shares one of her peak moments in her professional life, which surprisingly was a failed initiative, and how she turned it into a peak experience as a leader.

Listeners will gain valuable insights into how to bring empathy and grace to their work, create successful human capital strategies, and lead with who they truly are.

Don't forget to subscribe to LWWYA on your favorite podcast platform and share the show with leaders and innovators who lead with who they truly are.

Find Angela Roseboro on LinkedIn.

Weather her TEDx Talk: The Gaming Connection

Check out all things Dia Bondi here.

Dia Bondi  00:19

Hi everyone, this is Lead With Who You Are. I'm Dia Bondi, and on this show, we are exploring and discovering what it truly means to lead with who you are. And we're doing it with people who do and embody just that. In this episode, we're talking with Angela Roseboro, Culture Strategist and Executive, about her journey through her leadership and culture transformation. And helping founders level up, she drops some real knowledge about the difference between the leadership experience of professional CEOs versus founders who have to CEO and grow into that role right out in public. She shares her operating principles and advises us and you on how to bring empathy and grace to our work so we can have the impact we want. And weirdly, her peak experience when I asked her to share is one where she lost her audience on an initiative she was leading. It was not a win, it was a total fail. And still, it's credited as her peak experience in her leadership life. Hear all about it in today's episode. You can ask for more and get it if you ask like an auctioneer. The book, Ask Like An Auctioneer: How To Ask For More And Get It, is coming soon! So go to asklikeanauctioneer.com and get on the list for pre orders now. In the book, you'll learn the power of asking big, the one idea that holds us back from asking for more and getting it and the nine ideas I learned from the auctioneering stage that you can use as strategies to help you step into every ask with courage and conviction. Get on the preorder list now for preorder bonuses, again, go to asklikeanauctioneer.com now.

Hey, just a quick reminder, you can subscribe to this show on your podcast platform of choice. We're live nearly everywhere and you can always listen to the show at diabondi.com. If there's a leader or innovator in your life, who is it their shiniest when they lead with who they truly are. Please share the show with them. And rate subscribe and leave us a review makes a huge difference in the reach that the show has when you let everyone else know what you love about the show. Thanks so much. 

Angela Roseboro is an award winning Diversity, Equity and Inclusion Strategist. Starting with the premise that companies win because of their people and not in spite of them. She's worked for and with some of the most recognized brands including Whirlpool, T Rowe Price, and Dropbox. She's been a recognized leader in building human capital strategies. And in her most recent role as Chief Diversity Officer at Riot Games. She has been credited as being the driving force behind the gaming giants cultural transformation from the company being at the center of what became a cultural reckoning around bad behavior in the gaming industry to being certified in 2022 as a great place to work by the Great Place to Work Institute. Hello, I'm so glad to see you. I know folks are listening and we're seeing one another but I have to say I'm so happy to see you.


Angela Roseboro  03:47

I have to I've been following your stories on Instagram, you're having a ball. So congrats.


Dia Bondi  03:52

Oh well, I'm glad you it looks like that. I did spend two weeks in Japan. And so that's probably a lot of what you got. But I have to tell you, I am so bad at Instagram. Everyone's so good at it. I'm so bad. I need massive support on my Instagramming I spent a set my courtyard the other day and made one reel and it took me like 25 minutes. And it was literally just like six pieces of text and some scenery of like driving down the i Five. So I don't know. I'm glad that I'm glad that it's catching your attention. Thank you.


Angela Roseboro  04:20

The output has been fantastic. So I look forward to it. So I didn't know all the things that went into it. But yeah, that seems to look a little a little bit laborious, but it looks great.


Dia Bondi  04:28

So bad. It's not my superpower, either. I'm so glad to have you today. Because when you and I first met backstage or in the dinner the night before we did our TEDx, I was like that's a woman who leads with who she is. And I knew that I knew that I would be booking this conversation we're having today. So thank you so much for coming on and gracing me and our listeners with your presence.


Angela Roseboro  04:51

I am humbled and I'm so happy to be here and you and I feel the same way about you like what a powerhouse so much. It's just mutual love.


Dia Bondi  04:58

Thanks so much. So I I want to start with a question, which is like, who are you? If you were to answer that question today, how might you do that?


Angela Roseboro  05:05

You know, it's interesting given where I am in my career, I would say I'm an explorer. You know, of course, I talk about being a mom, being a wife, and really trying to come into my own humaneness. So I'm exploring this next phase of who I am and who I want to be. And I get to do that, and I have to reinvent myself. So I am really loving the curiosity that I'm approaching everything with. And the rediscovering of me of what you know, I don't know, when you have kids, and they grow up and leave the house. Does there's an inflection point where I was mom for such a long time. Who am I when I'm, you know, I'm still wife, I'm still Angela Abdul Executive. But there was such a big part of who I was such a big part of my purpose that I had to rediscover what it is I found, what I loved about myself and what I want to continue to do. And so I'm doing that now. So I'm exploring who I am. I'm, I'm learning some things I love. I've learned some things I don't. So that's how I would talk about who I am today.


Dia Bondi  06:07

That's great. And as you're doing this discovery, like, can you share? Like, is there anything? You're finding that surprising to you?


Angela Roseboro  06:15

Yeah, you know, I always thought that I could live in ambiguity. I really thought that was who I was. But not in this in this journey of rediscovery being okay, not knowing has been tough, something that I have had to accept that I don't have to have all the answers. And you know, when you're in corporate for as long as I have, I'm paid to solve problems. So to sit in ambiguity, and not, and let myself just, just be is very tough. And that has been the biggest learning. I don't know if I do it well. But oh,


Dia Bondi  06:57

it's so interesting that it's like the stories we tell about who we are to ourselves and then to have an opportunity to and go, is that true? Is that actually true? is so interesting?


Angela Roseboro  07:08

Yeah. I, I also never allow myself to be vulnerable. So that's another surprising thing for me is to live in this space of I've always been open and honest about who I was. But the vulnerability to let others in others people see me, which is really interesting, I have found to be a bit scary. Because if we're not in Who


Dia Bondi  07:33

were you not feeling seen in earlier, you know, your high power roles you were being in or you were just so focused on. I mean, I hear that as like, maybe she was just really focused on what was needing to happen, that there was a you know, people could there was some standoff sadness that could happen. I don't know how do you how is it different now?


Angela Roseboro  07:55

I don't think I was raised to be vulnerable. I think that came from you know, never show weakness. And if you're particularly if you suffer from loneliness, which a lot of us do women people of color, that vulnerability is not a strength. And so there is this, what there is this, you know, wall or there is this guardedness that you have. And I used to say, for a long period of time, like, Don't ever let people see you cry. Now, what's interesting is that I've kind of said that to my kids, and having to backtrack that because that's what I thought you were supposed to be when I talked about this journey of discovering who I am and who I want to be the vulnerability. I'm, has been hard for me, because I've always felt that people would use that against me. And so going in being the strong woman, right being the strong woman of color. That was my badge of honor.


Dia Bondi  08:49

And maybe entity, right, yeah, get really invested in being seen that way?


Angela Roseboro  08:54

Yes, yes. And not feeling like I could make that mistake. Or I could show up in that certain way. Or I could show up like it did have the answers.


Dia Bondi  09:02

It seems like that, you know, since launching Project: Ask Like An Auctioneer has been in the way of a lot of women talking about, like really having intimate conversations about their own ambition and the way in which they move toward the things that they want in the world and the armor they put on or don't put on and just sort of the set of operating principles they've developed for themselves and assumptions, blah, blah, blah. And it really stands out to me as a theme. I hear people say, Oh, you have to meet so and so you'll love her. She's a really strong woman. It's almost like it's part of the way in which we make we legitimize somebody who's a woman leader in business. It's like, I'm like, well, she doesn't have do we have to be do we have to identify as such in order to be, you know, amazing to others. It's like a It's in and of itself. It's like a brand of woman nests.


Angela Roseboro  09:56

Because the burden that comes with that. Imagine some When saying I want you to meet dia, She's a strong woman. How do you become vulnerable in a moment where people see you as this strong woman? branded by? Brandon. Right, right. And so how do I tell you? Oh, I'm not sure all the time? Or, you know, I don't really know the answer to that, or, you know, so it is, it is all as much as I, it was my identity, I'm the strong person, not only in work, but in life, the burden of that as well of not being able to be vulnerable, not being able to feel like you can fail. It's such a hard expectation we place on ourselves.


Dia Bondi  10:38

And what does vulnerability look like to you right now? I know, we might be going down a rabbit hole here. But is it? Is it about the not knowing? Is it about the not being a hyper productive executive right now? Because you're in the in between times? And so it's like, if I'm not doing then who am I? I mean, what is what is the form that vulnerability? Like, what's the vulnerability? What's vulnerable right now?


Angela Roseboro  11:01

It is the ambiguity of not knowing and being okay, in that, you know, it's interesting, I have been in for your listeners who don't know, I took a break, and D and I talked about I took I made a decision to take a break and walk away from a really good job and career still have my career. But I did that because it was, I had to put myself first, right, and I had to think about what the next iteration of me would be. And so making that decision, and I have always been a person who knew what the next step was, or at least I thought I'd like I always knew what was next. So to be in a position where you're trying to figure it out, when people have described you as strong, and you got to know this person. She's very fantastic. She's got a plan. Yeah, exactly. So so then I don't have a plan. And then I'm like, Oh, my God, I'm being so lazy. Yeah. Right. Because I'm not, I'm not hyper productive. And I can't be lazy. So I have to strong women with. Exactly. And so, but but I'm taking this break. And here I'm putting, I'm putting, so I'm filling my days with stuff. And I had to go, I had to take a step back. Like, it's okay, that you don't know. It's okay. And that's the vulnerability for me to tell someone I don't know. Because Is that is that strong? Because everyone expects me to know. So when I talk about being an explorer, it's like, that's what I call it. That's why I said, I'm exploring now. And it's okay to explore.


Dia Bondi  12:30

What I love about that is that you're actually this is the power and folks that listen to the show, you know, will hear me say name and claim all the time. And there's something so powerful in in naming the place you're in right now. Because that in and of itself is a platform for the not knowing explorers are not supposed to know they're supposed to explore, they're supposed to leave. Like that's the actual job of it. And so in that way, when we can name where we are right now, even where we are right now is a nowhere place is really like, like, you know, there's lots of different ways to say it, like I'm in the sandbox, or, you know, I'm exploring or I'm in, I'm in retreat right now, or like, whatever we can name that creates a platform for us focusing on the being and not the doing. Yes, it makes it less feel like for me, it makes it feel a little bit less adrift.



Right. I agree. Because you can't I can't work in this world being aimless, like. But you can like it's okay, like I call it exploring, exploring, right? And so you don't know until you find it. And when you talk about like, that has been the hardest thing for me. And the hardest struggle honestly. Because I've been getting a lot of job offers. I've been getting a lot and it'd be easy to take that because that is that take me


Dia Bondi  13:53

discipline to say no day in the exploring


Angela Roseboro  13:56

Yes. Because then I would know. But I don't know if I will emerge as this more evolved person, I can always do what I do. Right. But I don't know if I have the opportunity to evolve into what I what I think I could be. And even if I don't know what that is, so imagine saying nope to this really good opportunity nope to this good opportunity omics, and they go away, I'm exploring that that just sounds really definitive. But it is that it's being it's being uncomfortable. It's being comfortable in the space of discomfort. That's the hardest part.


Dia Bondi  14:30

And you know, it's a fantasy that I hear a lot in folks early, you know, when I when I'm teaching workshops or doing keynotes and talking to, you know, women in the audience is like, there is an there is an appetite and a fantasy about you know, all of the everything related to something that might feel like a sabbatical, the place where we go inward for a while. And, you know, it's what we think we want and when we're in it, it can be difficult and there are when And early on in their careers that fantasize about doing that at some point. And so, you know, well, it is difficult I, I expect, I could say it's necessary, I did it four years ago for about a year and a half. And while I'm not an in house executive, I took a break from just all things. And you know, that cultivation time, I think is really, you know, what you pointed to of like, who I'm going to be next, to bring to the table of what it is that I do next, a new way of being to apply to what I might be doing. And unless we take that cultivation time, we never let that blossom. So in that I'd love to hear a little bit, I know, we set you up and, you know, outlined a few of your like, very large accomplishments, I think the one that's very compelling to me is the impact that you had in, you know, in the gaming industry, which is one that has been historically hostile towards women and and you made a significant transformation at Riot Games. But as you think about your journey, in your own sort of arc of your career, and I don't know if these are things that will stay with you as you go into your next doing chapter, but like, what are some of this might be just like reaching and grabbing a little bit, but like, what are some of the leadership philosophies that you take with you? When you go to lead with who you are in an organization, community or movement?


Angela Roseboro  16:26

You know, I love when I turned 50. And I'll tell you why. Because in my 20s, I just was trying to I was trying to assimilate or try to figure out who my role model when I was going to be like that person, right? In my 30s. It was like, Okay, what you got this career now? Did you make the right move, and it was about building career and opportunities and learning. And that was my 30s and 40s. Were about like, I wanted to be this VP, I made the VP and I would tell people now like, did it really help? You know, it was a, it was a goal I had. And when I got it, I felt quite empty. It was something that was on my list. Like I wanted to do this, it was always and then I got it was like, Okay, I got a deal with it. So what was that about? In my 50s, I know stuff. I know stuff. And I can stand in my own authentic truth of things. I know my skill set now. And so I can move very differently than when I was in my 30s and 40s. And it is a freedom to that. So when I think about like principles, I get to be authentic, I've grown into who I am. And I I will I think when the work that I do, particularly in di that authenticity really, really matters, and stay true to my values. And I know what they are, and I will ever compromise that. So when I think about what's next, that is something that's really cool.


Dia Bondi  17:58

Can you give me some examples of just Can you name one or two or three of the values that you that feel steadfast for you


Angela Roseboro  18:05

that we win because of people not in spite of them. So a company that, that sees people as kind of collateral or just kind of widgets, that is not a company that I think I can that will be against what I'm what I think I believe and how companies are successful. A culture that is transparent. Another thing that's super, super important to me. Because I think that goes to my authenticity, a company who has stated values that they don't go against, like, I don't believe that a company has to speak on everything that's going on in the world. But I gotta know what we stand for. And I have to align with that. And there was an example where I was with a company and, you know, something that they wanted to do just really did not sit with my values. And I had to either say, Hey, let me tell you why I think we should do it a different way. Or I knew I couldn't be at that company now, thank goodness, we had a conversation and they understood kind of where my point of view was and decided to go that route. And I love that company because we could talk about it. I was afraid that if they didn't go that route, like that was such something that was entirely could I could not sit with that we ended up coming to a really good place. So that's an example. I also think empathy and grace, empathy and grace for me is is so super important, particularly when I went to a place like riot where I had to really look at that culture and and everyone was upset or sad. And the way sometimes people try to talk to you, I had to separate what the essence of what they were telling me from the package the package was that people were upset. So that empathy allowed me to see through kind of how they were packaging the message and I can get to the essence and we can start to move from there. So I think that's super important. And the other thing that's for me is I have to be at a place where I can create space for others. I used to say, I help women navigate. And I don't know if navigate is the word I want to use, I want to create space. So you so you can be who you are having to navigate and overcome things is not where I think we should be anymore. We have to be at places where there are spaces that are created, that people can hear each other. And so is


Dia Bondi  20:26

How is that different? talk to me about how that feels different.


Angela Roseboro  20:29

So navigating is like me teaching you how to overcome how to get past that barrier. Right. So as somebody combat in there some there's something there that you have to figure out how to like how to be heard. So let me help you navigate. So if you want to be heard, let me help you navigate that. And I'll give you an example. So I have two daughters. One is 32. One is 24. And I have always given them voice, I have always given them voice and say, You know what, if you believe in something, you should speak to that. So she came to me maybe two months ago, and she wanted to raise, she felt like she deserved a raise. And she was the way she was going about it. It was like whoa, you're not gonna get a raise that way, pull it back some Oh, and you need to talk this way too, in order for you to be heard. And that was helping her navigate. instead? How do I My job was create space, like the job that I hold is to create space. So she can have the same conversation that a man would have, and not have to navigate it differently to get to a different output, if that makes sense. And so in that moment, it was for me, I was trying to take her voice a little bit away. It's like, nope, nope, you got to you got to be softer. You got to do this,


Dia Bondi  21:45

right? Because you're maybe working as an editor in that moment, but not necessarily in like, what do we need to bring forward instead, in a way of like, what do we need to carve down in order for you to be successful, which, you know, I love the notion of navigating it reminds me of like, way finding it means like, Oh, I see this, I'm gonna go this way. And I see a possibility over there. But I can also understand that what you're talking about here that it can have an edge of editing ourselves. And like an offense defense, kind of like opposing voices place instead of like, a container to see what might Yeah, so how is holding space, help you with the same outcome with a different disposition. Talk about that.


Angela Roseboro  22:31

I think it's, it's, I always tell people, particularly young women, if you're at the table be at the table. Because sometimes when we're sitting at the table, we are censoring ourselves, we're the negative talk like Don't, don't say that thought, don't share that you won't be heard. And so you may have the best thought out there. But because we are self censoring, and we're and we don't know how we should be at this table, then we kind of pull back. If you are there, the biggest currency I have is my thoughts. You don't have to accept it. But it is what you hired me to do. So


Dia Bondi  23:12

The biggest currency I have is my thought.



yeah, like, that's what, that's what I bring to that table. And so if I'm holding that back, I'm not helping the company be better. And if I'm so you know, if I'm filtering because this is how a woman should say, here's our perfect color should do. If I'm looking at all those filters, then it stops me from saying what I need to say. And so as scary as it is to get that point of view out there. If I'm sitting there, it is my duty to do so. So I tell people that all the time, like this notion of you know what's interesting with this notion of imposter syndrome, and I am I have this love hate relationship with it. Because on one hand, I love that you were able to, to kind of put into words what I was feeling when I didn't feel I belong. On the other hand, I don't want you to claim it. Because if I'm being authentically who I am, if I'm showing up authentically with my currency and how I'm helping this company, how can I be an imposter, you may have more experience, you may have more influence, but I get to bring me you know, and so I switched to be unapologetically me versus imposter syndrome. Because if I go in thinking, I'm an imposter, then that's the thing that holds me back from saying the thing that I should bring to the table. So this notion of when I'm sitting there, and I and I'm always in rooms, and I tell people all the time I suffer from only this like, like the only person who looks like me in the room. To the point that when someone else comes in that looks like me, I don't even know how to react. Like saying like, Oh, you know, is this a threat is this I don't know. I don't know, if I'm being honest. And you know, it's it's shameful to say that we're still pioneers, women in these in these executive roles. But again, if I'm bringing my authentic thought, my authentic currency, my authentic self, then I can't be anyone but me. So I can't, you know, I don't I, when I hear people say I have impostor syndrome, I just I drill down why? Because this person has more experience, but you can only do what you do. And so I want people to be unapologetically like, I can say, Yep, he has more experience, she has more experience. But when I show up, I'm authentically and unapologetically going to be who I am. And that is me.


Dia Bondi  25:31

I hear. And this, you know, sort of these driving values and principles, just to recap, around, you know, authenticity, transparency, knowing our point of view as an organization, and maybe even as an individual, like, you don't have to say everything about everything, but to have a, you know, a point of view. And what we stand for is really critical, maybe individually in our own leadership, but also collectively as an organization was we try to, like have an impact in our space. And then I hear you talking about, what did you say grace, and grace and empathy and empathy as a really critical component to be listening, I heard you talking about listening there, if you're going to cause a transformation, because the package that something comes in, doesn't necessarily mean that is exactly representative of the essence of the message inside of it. All really beautiful leadership lessons that we can apply to how an organization functions, maybe how a team functions, and also how we individually lead in our own spaces. As you think about, you know, the founders that you've worked with, particularly in the tech space, go through their own transformation of being, I was a product guy, now I'm a CEO, you know, they're still who they are. But there is a material leveling up that happens, that you as you know, a grown woman in an executive position working with founders that are, you know, considerably younger than you or less, even just less developed, right, in their leadership. How, you know, knowing that we share, you know, my that's my client, you know, for my, for my communications work, and that has been one of your key stakeholders, I think, as you've gotten into organizations to cause the transformation that you've caused, how do you think about those key trends, transition moments for founders as they level up? And how do you advise them as they confront what it means to go from Founder, just Founder, to CEO.



it's a growth path. It's just, it's a growth. So what I love about founders are, they are brilliant innovators. And then when you build a company, you're focusing on the thing, like, we have the thing that we're hyper focus, and in my work with founders, no one wants to have a crappy culture. And in essence, I think they are trying to create a great culture. So we're gonna do basketball courts, or we're gonna give food and all those things that in their minds are what great looks like. So the transition comes when you scale. And when you think about best, and what I say to founders, it was best that was confined to the seven people. And as you grow in scale, you have to continually figure out what's best. And that's why I think the listening, I don't think that when when when companies get in trouble, that these are isolated incidents, people are telling you what's happening. And it is hard as founders are growing. So I think there's a couple of things when I grew up, you know, in, in finance, CEOs are grouped. So there's a set of experiences that you go before you even get to that level, and are ...


Dia Bondi  28:40

deeply supported with a group of champions around you who have chosen you chose even years before you're in that role.



So you know, how to listen, you know, the organization, founders are innovators. And so I always I used to say this, jokingly, like, it's almost like Britney Spears, you're like growing up in public. So everything you do is a learning, but you're learning and everyone gets to see it.


Dia Bondi  29:08

Yes. Not in the safety, not in the safety of the group of people who have a plan for you. Yes, that are blocking, protecting. I mean, later, I think when when founders build a more, I'm gonna use the word sophisticated and mature leadership team around them, they start getting the benefits of that kind of support that CEOs who are groomed for a role get earlier in their career, but it happens almost after the baby's born.


Angela Roseboro  29:09

It does. And so then you and then there's this conversation that that I have around what does great look like now, and also not looking at founders, like they're humans to write. So I tried to talk about the human side. So I want to know what they what they're trying to cultivate. And my role is to say, Hey, if you do that, then that might happen is that the outcome you want, and having that voice that can help you think things through and keep that calm, I think is super important. And so allowing them to grow is the toughest thing. And you know, I've worked with a founder who has like 18 people, and I said, you have a lonely job like you are this, you can't, you know, you are the CEO. And there's a point that you can't be like one of the others like, and that's a hard concept. I have, I have a hard concept,


Dia Bondi  30:33

I had a client say to me, like, Whoa, I just realized that I'm wearing a microphone on my face, and I can't take it off. Exactly, everything I say, has so much weight, and I have been massively underestimating. If I look to the left, or I scratch my nose when someone's talking, or a yawn, because, you know, whatever, there's not enough oxygen in the room. It has so much meaning to everyone around me that taking on the sort of recognition or I'm here you say is it like taking on the recognition that your voice has weight and also, like, what the world needs from me is not what the 12 people I founded this company, who are all my besties needed from me, my role is different. I'm my, my, who I am maybe is not changed materially. But my role is different.


Angela Roseboro  31:32

It's It's a lonely place. So I say to CEOs call me, like, if you have to have difficult conversations, call me because you do need to have that safe space. And I think that's the best thing I can do is provide that safe space on a space for them to say whatever they need to say, but because you know, I have a CEO who says that tweet is a lot, right. And then it's like, well, you can't tweet the same things you used to tweet, because now people are not looking at you as kind of a, you know, just a person on Twitter, they're looking at you as a CEO of a company. And that's a hard transition. Because they're innovators. They are creators. And so to make that transition from being doing building something you'd love to now I have to be a I have to be the CEO. And what that means that means that I have to change some things that I'm the way I'm behaving or moving, could be hard for for them. So being able to create that, that safety to say, hey, look, we can do that. But if you do that this might happen. And I think they need that. Because to your point, when you grew up in finance, or more mature organizations, everyone's blocking and tackling for you. And you're learning that way, as a founder of a company, you don't have that safety. And the safety is probably the people that you trust, who are going to tell you the things that probably are not always because they don't may not know either. So So you have to get that outside, I think the one thing that founder can do is get somebody outside the circle, to be able to help them kind of build their company.


Dia Bondi  33:05

And know, that is, like I have a very explicit relationship and agreement with that is the thing that you are in and around here for is to help me do this thing. Yeah. What are your thoughts about founders who are facing that transition of like, Wow, I can't show up in this role the way that I did when we were, you know, two to 100 employees. Now we're at 500 to 1000 or beyond. How do you advise them when they think about putting together their leadership team? Like what are the three four things they should be thinking about, as they put it as they they invite people to that table,


Angela Roseboro  33:46

I think there's a couple of things one, I would say be diverse on purpose. And that is looking for people with different backgrounds, different skill sets, and not just the people that you are comfortable with. So get uncomfortable and get the people that you need to help advise you through. I also say you know, get people that are in there that may have more experience in different industries or or skill sets that you might need. I we're all creatures of comfort. It is easy for me to say okay, do I want you to be my coo because I know dia we can have this conversation we can have but dia might not be the best person to be my see my CEO Oh, I may have to get someone that is from that has deep experience in taking a company public or no operations and putting process in place. And that's not my not going to be someone that I know. And so getting out your comfort zone and getting one or two people that you know will give you dissenting views if need to the be but have the best interest of the company. So I when I say be diverse on purpose, I'm not I'm talking No, I think you should have gender, I think you should have ethnicity. But I also think you should have experience. And that's going to make you so super uncomfortable because you're going to be used to being in your bubble of people who are telling you who are who you're who all have the same groupthink mindset.


Dia Bondi  35:17

Yeah, that'd be just feel cozy. I mean, there's something we talk about, you know, in my leadership communications work is that you are not your venture anymore. You are not your venture? Well, you are the face of it. You know, people want to conflate the venture with you as the founder. And it is important that you're speaking and showing up in a way that you recognize, well, while you travel together, you know, next to one another, you are not your venture, meaning, what I'm hearing you say is like, it's more about what the venture needs and less about what you need. Exactly. Because you got to get it doesn't mean you don't get to get that need met somewhere else. But it can't always be with the people who are the ones driving the business, that are sitting around your executive table, their job, and what we need them for is to take the venture to the next place. And you have a different ball team for what you need.


Angela Roseboro  36:10

And that is a tough transition, because you're so used to your safety bubble, of the people that you know, so that's the hardest adjustment I think, that founders have to make is like, Who do I bring in? How do I listen to them differently? And how do you know what is my role as founder, which I founded the company, I'm been at the company to now CEO, which means that's a whole nother, that's a whole nother skill set that you have to create. That means, you know, I say to the founder, sometimes you're not the CEO for the 12 people, you're the CEO for 500. And, and a company is different from when they're 200 to 500. A company 500 to 1000 is different. And knowing when those inflection points of when you have to shift and change is going to be super important. So the the type of people you need when you're 200 is gonna be very different than the type of people you need when you're 1000. The type Alicia team you need is 1000.


Dia Bondi  37:06

So you know you did you had an incredible impact at Riot Games, you've been in other tech spaces came out of the world of finance. As you look back, can you name like, one or two, no matter how like public or private, they were, like one or two peak experiences that you could point out and say, That was that was peak for me. I mean, I can think of ones in my life. One that was very early. I tell this story a lot when I'm on stage that, you know, the first time I traveled internationally for doing professional development, communication stuff, I went to Hong Kong and I remember staying at the JW Marriott and I went to the 400 floor what it felt like and I pulled the curtains back and I just looked out over there. Nobody was there and plotting for me. But I had this moment of like, oh my god, I'm doing this. I'm doing and it wasn't about where I was like Fancy Pants JW Marriott in Hong Kong, it was about halfway around the world getting to do the work that I love in a very intimate environment with people who are having huge impact in the world. I just, I was so taken with that moment. And it was a moment of recognition. For me that felt very peak, even though nobody was applauding, nobody could see. So as you look back at your own career, tell it can you find one or two stories of peak moments for you?


Angela Roseboro  38:25

I can tell you when I first started to do this role, Chief Diversity Officer, which I rejected. I did not want to do I thought this was a fluffy role. I thought it was not a role that had substance in it. And and because you don't really own anything. And so you can't you really are successful in change management by how you get others to do. And the first time I went in, and you know, I researched this thing, like, these are the five things we need to do. And we need to do these and I didn't listen. But also I was right and what we need to do, but I didn't win the leaders over to do what I needed them to do. So in that moment, I lost them. And I was ineffective. And even though that was the right approach, I made the right the right answer. I didn't take them with me. I didn't hear their concerns. Because what I knew is that this was the plan that was going to get us from point A to B. I lost that audience. I didn't get them back. And what I learned in that moment is it wasn't about being right. Even though I love being right, it was really about getting people to follow you and getting people to see what you see. I'm a great strategist, but if I don't get people to see what I see, I can't move and that was a big lesson for me.


Dia Bondi  39:56

So how is that a peak experience if it feels like A loss that you couldn't get back as such, this is the first time in my career, I've asked somebody to share a peak experience, and somebody tells me at a time when they lost control of something,


Angela Roseboro  40:10

because for me the peak experience is what I lost. Like for me failing is my are my biggest times, because I can tell you that was an experience, because I had I didn't even know that happen until maybe a year later. And I knew how to go. And even without thinking about it, I knew how to do it better the next time. So that was even though it was a loss. For me, it was something that changed the trajectory of how I did this work. It was something that said, okay, it wasn't about that. So I think for me, my biggest lessons is when I don't succeed, and that is an experience that I never forget, I reflect on, and then I can and then I it's just, it's just more in my toolbox. So I would think that I can talk a lot about, you know, you know, and I don't see those as peak experiences, which is interesting.


Dia Bondi  41:02

Yeah, like, literally, my brain is going (insert robot sounds)



We have a, we have, we have a woman like look at Riot, something came out today, where we have more women in leadership positions, we have a woman that leads into one at least entertainment, she probably has the largest game, you would think that would be inexperienced, because getting leaders to, to really be diverse on purpose, was a hard thing to do. But because of that experience of you're going to do this, it that's not how I approached it. So that that's why I don't define that as a peak experience. I love to see it. But the peak experience happened when I learned how to do that. So that's how I think about it. You know, I always will often ask people, particularly in this work, because you know, I can talk about all the data and all the things in which I've moved the needle. But it only matters to me, when an employee says this place is better. Like all the data stuff I don't like that's fine. But when someone says this place is better. Because of the things that we puts put in place, that warms my heart, that is my biggest driver of success. So my peak experience has happened because of something I've learned not not the not the actual accomplishment of the thing. Right, if that makes sense.


Dia Bondi  42:22

And so is there. Yeah. So I hear that as like, is there some satisfaction in being able to look back at and be able to name the moments where a shift happened that produced fruit 1218 months later, three years later? And then that way, you know, there may be there's pride in that of like, I actually took that lesson. Good. What? Good for me. And look, look what I could do with it. Yes.


Angela Roseboro  42:51

yeah, I learned how to do this. And it caused these these great things to happen that I expect to happen anyway. Right? Because, but it wouldn't have happened, had I not had the experience that I had.


Dia Bondi  43:03

What's next for you? I know you said you're exploring. And so I don't want to squash that. But do you have any hints at all? Do you have any interests that are peeking for you? Do you have, you know, what's a little on fire for you right now,


Angela Roseboro  43:19

what's really what I've really recognized my purpose is, you know, and I think this is probably true for you, when you have these experiences is you know, particularly women in how we had to kind of build our careers, I think it's upon us to make sure that the next generation is prepared. And sometimes when you see, you know, people who get to the pinnacle of success of their careers, you just think they ascend there, we never talk about the battle scars. And I want people to know the battle scars, not in a way to dissuade them. So that they were probably more I would say prepared than I was. So maybe they don't have to go through the going in saying, here's how we should do and do it now. And their peak performances will be different from mine, there's won't be the learnings of how to navigate through this or how to create that space. It'll be more about I understand it now. And I know, I tell people all the time when they when they say I don't like to play political games, like you're in the game, whether I asked for it or not learn how to play. And so being able to help people understand and still be authentically who they are through this because I don't think you lose yourself. Like that's the one thing I would say if you if I were to say peak times I never lost myself, I discovered more things about me, but I never lost myself and sometimes not losing myself meant that I had to walk away. And that was okay too. Because you know, and I could talk about that too. But So what's next for me is helping people which is I'm a servant leader. So helping the next generation understand. But also I love this idea of talking to founders and helping them build great cultures. When I when I look at the top 10 reasons why startups fail culture is not anywhere in that conversation. And which is interesting is product mix is leadership, but it's not culture. And I think culture is such an indicator of how successful a company can be. And from my experience with founders, they want to have this great culture, they just don't know how. So I want to be able to be in that space. Because I really love to see the transformation. I really love the intentionality of what you can be when you have a great culture and to see that fruit come to bear. It's just it's is fantastic. For me, it's, I'm driven by it, I'm all I'm here for it.


Dia Bondi  45:46

I love this notion you're talking about you know, not not losing who we are. And, you know, it seems that culture in an organization is a component of who that organization is collectively. And so being able to cultivate that in a way that it's aligned with its sort of best self I can imagine is so satisfying when it works.


Angela Roseboro  46:08

Yes. But lots of work to do. Yeah.


Dia Bondi  46:12

So what does it mean, I know this might feel a little redundant to where we started, I started with the question of like, okay, who are you? You said, You are a, you said you were, you know, an explorer now? What does it mean? You know, pulling the lens back, not just focusing on maybe this time in your life and your career trajectory and your own personal and professional development, but just overall, what does it mean for you to lead with who you are?


Angela Roseboro  46:39

You know, we talked a lot about this, I think it you know, one of the reasons I stepped away is because I got so caught up into the work that I lost me. so caught up in making sure that the company I work for, they got to 300% of me, my family probably got five. So part of this taking a step back and leading from where I am, is having more balance, whatever that means for me, and not being so caught up. Like I built a career for 30 years. And now I think it's who I am now is making sure that, you know, there's this quote that someone said to me, like you will, people are never on their deathbed, she said I should do more work like something like that. And, and I want to make sure that I have the balance of who I'm learning to be and who I'm embracing to be, and the executive piece, and I have to figure out, I'm still figuring out what that looks like.


Dia Bondi  47:35

Angela, you're a boss, thank you so much for being with me today. I'm so thrilled, and I can't wait to be connecting you with the founders in in my world that can use a lot of what you have to give when you're ready to give it


Angela Roseboro  47:50

I know, you know, I learned to play pickleball the other day, so I'm like, I can just do this.


Dia Bondi  47:56

Pickleball is like it is sweeping the nation. Let me just tell you,


Angela Roseboro  48:01

and I would never have learned to play pickleball if I was still working on like, Oh, I found this new thing I can do. So I got roller I got roller skates. I got all kinds of stuff I'm exploring right now. So it's just it's been a fun time.


Dia Bondi  48:13

Angela, thank you so much. Where can people see you? Where can they find you?



I am on LinkedIn. I have Twitter @aroseboro, website to be coming soon. We're working on that. But just reach out on LinkedIn.


Angela Roseboro  48:28

Fabulous. Thank you so much for being on Lead With Who You Are.


Dia Bondi  48:32

Thank you. Lead With Who You Are is a production of Dia Bondi Communications and is scored mixed and produced by Arthur Leon Adams the third. Have a question or an inquiry? Reach out to us at hello@diabondi.com. You can like, share, rate and subscribe at Apple podcasts, Google podcasts, Spotify or wherever you get your favorite shows. Go to diabondi.com for the show notes to find our tools, frameworks, content and programs to help you and your team speak powerfully and lead with who you are.

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