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Episode 15:

Changing Your Thinking to Change Your Future

Natalie Gillard


On Episode 15 of The Upstream Leader, Jeremy Clopton talks to Natalie Gillard, the creator of FACTUALITY the Game, which simulates structural inequality in America. Natalie shares the origins of FACTUALITY and discusses how she cultivates positivity and practices holistic minimalism to sustain her momentum in her work. 

About the Guest

During her undergraduate experience, Natalie Gillard found that support for individuals from diverse backgrounds was rather limited. The latter ignited her desire to pursue diverse professional opportunities and a self-designed graduate study in Race and Ethnic Relations. Natalie has held various inclusion roles over her 14 year career, including Stevenson University’s Assistant Vice President for Multicultural Experiences. 

Natalie is the creator of FACTUALITY, a facilitated dialogue, crash course, and interactive experience, that simulates structural inequality in the United States. Over the last five years, Natalie has led virtual and in person FACTUALITY facilitations for over 40,000 people, around the globe.

​FACTUALITY has supported the diversity, equity, and inclusion initiatives at hundreds of multinational companies, universities, government agencies, and nonprofits (including Google, Twitter, American Express, Under Armour, Converse, Yale, Princeton, UCLA, Stanford, Boston University, U.S. Immigration and Customs Enforcement, New York City Department of Correction | Rikers, United Way, Big Brothers Big Sisters of America, American Heart Association and more).

FACTUALITY has been featured in Amazon Best Seller | The Memo: What Women of Color Need To Know To Secure A Seat At The Table and Baltimore Magazine’s Best of Baltimore issue. Factuality is listed in the Kellogg Foundation’s Racial and Equity Resource Guide and became an ice cream flavor through a partnership with social justice ice cream brand, Taharka Brothers.

Highlights / Transcript

Welcome to The Upstream Leader. Today’s episode focuses on the journey to becoming a leader and the importance of choosing how we react in specific situations. I was introduced to today’s guest through a mutual friend on LinkedIn and attended an open enrollment of the program she founded, FACTUALITY. Today’s guest is Natalie Gillard, the founder of FACTUALITY the game, a facilitated dialogue, crash course, and interactive experience that simulates structural inequality in the United States. She has reached more than 40,000 people around the globe through the program, working with organizations such as Google, American Express, Under Armour, Yale, Princeton, Stanford, the American Heart Association, and others. Our conversation today focuses on the journey that led Natalie to create this program. Natalie, welcome to The Upstream Leader.

Thank you for having me today, Jeremy. I’m really excited to be with you and dive deeper into the parts of FACTUALITY that many actually don’t really know about.

Yeah, I didn’t know about them. Obviously, when we initially spoke, and I attended FACTUALITY, one of the open enrollment programs, and I can genuinely say it was one of the most experiential learning programs that I’ve gone through in such a long time. And as you know, being in the role that I’m in, in the industry that I’m in, we go through a lot of leadership development and do a lot of leadership development. But FACTUALITY really helped me understand the importance of feeling the situation, rather than simply learning about a situation. 

Yeah, that is also great. It’s accomplishing exactly what I set out to accomplish. I just got to this place where I realized that although I enjoyed consuming that type of content in lecture form, that it wasn’t necessarily the way to get individuals to show up and have the conversation and walk away. And I had grown accustomed to seeing so many empty seats when I would do any type of diversity facilitations. And so when the idea of FACTUALITY came to me, it was designed to allow me to a piece of different learning styles to ensure that everyone walks away with exactly what they need to walk away with to begin to move the needle in this area.

It really is an action-based learning style, it felt to me, and it definitely put me in an uncomfortable situation. One of the things you said at the very start is, you know, experience this through the lens of someone else, not just through your lens. I remember that early on, and that and when I decided to go through the experience and go through that open enrollment program, I told myself, you know, if it gets to the end, and and she says, All right, we’ve got to share this experience, I’m not going to cop out. I’m not going to say, oh, you know, I’m just going to listen, it’s going to be passive, because one of the things that I loved about it is, it was such an action-driven learning style. And rather than just as you said, consuming the content, it was, how do you take at least just one step? And that really resonated with me. Something you said at the end of the session is look, this, you know, the problems that we’re trying to solve are not new problems. They’re long standing problems. So it’s not a fast solution. What’s one thing you can do? And that really resonated.

Well, you have a really great memory, because that’s definitely part of the main components of the program. And the experiential piece truly is just designed to allow people to empathize. We need people to feel, if we want or have expectations for people to move, you have to feel something. And even if it’s short-lived, because oftentimes, many participants are feeling this level of empathy for the first time. It’s so disruptive, that you can’t walk away acting as if those 90 minutes didn’t occur. The next step is to think about what else can be done, even if it’s something as little, if you will, as telling someone, Hey, check out the next open enrollment or you might want to contact this person, this is a great way to engage people in meaningful dialogue. But I do know after hearing from participants and taking a look at the response on social media, survey feedback that it’s a really strong program that gets people to feel and a lot of people begin to act after that.

It really does. And it’s interesting that, you know, we’re talking about how it makes you feel and it’s your feelings, I believe, as I recall, in a certain situation early in your journey that really led to the creation of FACTUALITY. And we were talking before we hit record, and I said, you know, one of the questions I always ask everybody when we start this podcast is, how did you become the leader you are today? And Natalie, I’m gonna take a totally different approach with you. And let’s just turn that into an episode because how you ultimately got to the creation of FACTUALITY, which is, again, a program we can talk at length about. And I would like to learn more about what led to you creating FACTUALITY? Because it sounds like it really was how you were made to feel in a certain situation in an exchange with a colleague that gave way to this. So I don’t know. Do you want to start there with that exchange or do you want to give a little background as to what led to that exchange as to how you became the leader?

I’ll do a combination. So it was a cold January day in 2015 when…

—I love the storytelling!

You know, that is a big component of the FACTUALITY program, the storytelling, but it was a cold January day in 2015 when my coworker just barged into my office, and I had grown accustomed to that. She was the meanest, cruelest, inconsiderate person that I have ever worked with. And not that I need anyone to substantiate this claim, but I can easily pull 10 people that could say, yeah, these things are true. I even had this conversation with her in a team meeting, like I’ve confronted this person before. And she barges into my office and starts talking at me, which was also not uncommon. And she says to me, you need to train my staff. And this time, it needs to go below the surface, and seeing how I had trained her staff quite a bit in the past, I knew that she was speaking negatively towards my past facilitations with her staff. And I got so mad, and I am from Massachusetts, and I guess we are known as people who cuss a lot. So I do cuss a lot. And I called her a whole bunch of things and went right to Google. 

And I began searching. I had this idea after that brief exchange, I was so mad with this woman, and me getting mad—I’m a pretty calm person—me getting mad was, I’m going to find a game. That was me getting mad, I’m going to find a game, I’m going to find the best diversity game out there. So I’m on Google. And I’m searching, searching, searching, typing in things. And I’m not getting, not receiving what I’m looking for. And so everything is on Google, I thought to myself, if it’s not on Google, then perhaps it doesn’t exist. 

And so I remember seeing a Monopoly board and began thinking, Well, how would that game shift if, if I was a pawn as a Black woman, and if the rules were based on the history of structural racism in the United States? Would I start at the same place as the other pawns, if all the pawns were people? And just based on research and statistics and facts, we will realize quickly that we are not all starting off in the same place. And so I obsessively began to dive into this journey. But the best part about that experience with that co worker was realizing that it is so critical to always seek and extract the silver lining in every encounter that you have that doesn’t seem the most favorable. And so I began to dive into building out FACTUALITY, but it put me on this life journey because as soon as I began that research, I realized that so many of the things that I believed in and subscribed to, like my base, was baseless. And so it set me on this path of self-discovery, in addition to the creation of this body of work.

As it relates to that experience, you said, you know that she’s one of the, easily one of the meanest people, you know, you have ever worked with. And it sounds like that’s a very shared thought. What was different about this exchange? What was it about this exchange that stirred something inside of you that instead of saying, You know what, that’s just who she is. And I’ll just, you know, just keep doing what I’m doing or change just a little bit and try to essentially appease  that cruelty, that meanness, what was it about this exchange that was different, where you said, You know what, I’m going to take this for the good and I’m going to go make something out of it.

That is such a great question. I have a great friend named Dexter and Dexter will say to me, as it pertains to FACTUALITY, that this was divine, the way the idea just kind of popped up. And it wasn’t so much that the exchange led me immediately to extracting the good in a negative situation. It was just that quick window where I had to do this training. I couldn’t say no, like, I had to do this training. And I felt like she was attacking my work. And so that created the desire to dive deeper, to go below the surface. So there’s that piece. But after I gained some traction with this, and realized, oh, my gosh, like this, I knew within the 30 minutes after she stepped out of my office that I found something. I knew right away, it was a feeling that I can’t even begin to explain. But when something so good came out of something that was so perpetually negative, it forced me to shift my outlook on every other negative thing that presented moving forward. So it was like a catalyst. 

How do you now apply that going forward? Because I tend to be optimistic. And at times, you know, folks view that as, Oh, you’re, you know, rose colored glasses, you can’t see the negative in anything. Natalie, it doesn’t sound to me that’s the approach that you take—you recognize now there was a lot of bad here. 


But there’s also good, it’s not like there’s—no, everything has to be good and pollyanna and all of that. How do you apply that in situations going forward? As you’ve grown your company, as you expanded your work with all of these amazing organizations that you work with worldwide—how do you apply that in a way that balances both looking for the good opportunities, but also, in a way recognizing the risk and balancing it against the negative?

I have a good friend named Jean, he tells me that I don’t brag enough. And I’m not about to brag right now. But I’m going to tell you a little story that’s like, okay, okay, we’ll see how this comes full circle, just the patience, like there’s an algorithm here. 

Now, when I first had this exchange with the coworker, I went to Google to search for some diversity game. And fast forward. It was supposed to be April of 2020 when I was going to do an in person session with Google, they found me on LinkedIn. And they reached out and we began to have these conversations, and I kept it so quiet, because I was so excited. And then COVID hits. And they have to pull out of the facilitation. And actually everyone did—it was a revolving door of cancellations and postponements, obviously, and then someone asked me—I had an exchange with someone—can you run FACTUALITY virtually, and I was able to extract the core components of the program and move it into a virtual program called Just the Facts.

I decided to take a chance and tell Google, Hey, I found out a way to move this program into a virtual space. And they wrote back to me almost immediately and said, we would love to explore it. And this is like right after George Floyd. And so here I am searching on Google, back in 2015, to find a way to—to find a diversity game. And now five, six years later, Google is emerging as one of my biggest clients. 

And so when they had to cancel in April, I didn’t—I promise you I didn’t, I wasn’t upset, I didn’t cry, I didn’t feel bad. I just said, if this is going to present as an opportunity, it’s going to find me just like everything else finds me. And so extracting the good there is just being able to be thankful for the fact that Google found me. And that if I had to cancel on this date, that something great always comes in its place. That’s just the way it works. 

And so instead of lending myself to all these negative feelings—I can’t believe it got cancelled—it’s just move on to the next thing. Keep your energy in a positive space, and the good is going to find you. And I just had another session with Google last week. And there’s been so many that I’ve lost count, but I can’t focus on counting all the negative things. I need to keep that space clear. When you keep everything light, it increases your capacity to receive. I fully believe that and that exchange with that co worker was that catalyst for me.

Definitely. You’ve mentioned a couple of your friends—Dexter and Jean. It sounds like you’ve got a community of people around you that also help you keep a focus on the positive and keep the negativity at bay. How has that benefited you as a leader as you’ve grown your company?

When I tell you—I mean I mentioned those two quickly, but goodness gracious like what the support is unbelievable from people. I have a friend Amanda who will send me messages almost every day like hyping me up about the work that I do. By the way, she’s dropping a book tomorrow called Right Within. It’s about racial trauma in the workplace and a great solution after you learn about FACTUALITY—just wanted to throw out that shameless plug. 

But it’s an arsenal, maybe a smaller arsenal, but it’s an arsenal of people who want me to win so bad, you would think that they are doing this themselves. And what I can say is that, for my relationships that didn’t shift in that particular direction, I extracted what was good about it, and realizing that I need to move into a space where I do have that support system that really holds me down. Because this is really heavy work. But I have a friend who also says that, for this type of work, that we are the subject as Black women, the subject and object of what it is that we are researching. And that’s pretty complex to do every single day. It’s heavy.

Yeah. You mentioned relationships, I’m going to kind of go a slightly different direction with this. You mentioned relationships that you’ve extracted the good from, and then kind of moved on. And I know I’ve heard you use the phrase in the past holistic minimalism, which includes not just the idea of not having a lot of things in the house, but you really apply this in your professional life as much as in your personal life. Is that an example of that holistic minimalism? Talk a little bit about that, as a leader.

Yes, I did a TEDx talk a few years ago. And of course, I spent so much time on this TEDx talk, I knew every single word verbatim. And of course, the camera cuts off during it. So there’s like no record of this anywhere. But I had this TEDx talk called holistic minimalism. And it opened up with me saying, to release yourself of the people, places, things and beliefs that fuel your discomfort. And I talk about realizing that, for all the issues that I ever faced, I realized that I was the cause and the cure of the grief in which I routinely encountered because if I’m not taking the time to seek out and extract the silver lining, then it becomes—Natalie’s issue becomes a problem for me, because I’m not doing the work. So yeah, it’s just something—it’s hard to do to release the entities that fuel your discomfort, it’s very hard, but I’m realizing that it is one of the most—It’s so essential to my ability to thrive, I have to trim away all the fat, if you will, and keep the lean.

In a way that brings us a little bit full circle to what we talked about on this idea of consumption versus action-based learning as well. Because we can consume, consume, consume, consume. But if we don’t do something with it, we aren’t going to grow at the same time. We can surround ourselves with people that help us grow our network, per se, but especially those that are closest to us if we aren’t intentional about who that is. We’re just in consumption mode. We’re not in action mode. Is that a fair assessment based on your experience?

I know you can see my facial reactions over here. Yes. Undoubtedly, undoubtedly. I read some statistic and I know it’s a little controversial, but I read some statistic that said that we are the average of the five people that we surround ourselves with. And when I started looking around, I mean, no harm or disrespect. But I was like, Yikes. If I think about growth as ascending to the top of a pyramid, there is space at the top of the pyramid for several. But at the very bottom of that pyramid, that base is where you’re going to find a lot I will say. You’ll find a lot there. So if you want to go out drinking all the time, if you want to eat unhealthy, I’m not talking about active things. If you don’t want to excel in your career, you’re always going to have company, you’re always going to have company. 

But as you ascend to the top of the pyramid, things have to be a little bit lighter. And there’s not a lot of space up there because it takes a level of determination, dedication, a willingness to be misunderstood, being excluded, it takes so many of the things that remove us from our social experiences to ascend and lightly at that. 

And so at this place now where who I’m surrounded by, it’s just like, I feel so inspired. I feel so motivated. I feel even more dedicated because everyone around me operates in the same capacity. So it’s a hard decision, but it is one of the most essential ones I’ve made in life.

And it’s an ongoing decision at that. I would assume that it’s not like I’ve picked my five. And now, because I agree with that—you’re right, it is controversial. I agree with that premise as well. And if you don’t believe it, I would encourage somebody, surround yourself with five different people that you think are where you want to get to and see how different everything is. To your point, Natalie, it’s those friends that you’re surrounded with, those people that you’re surrounded with, that want you to succeed as much as you do. And you feel like they’re working as hard as you are on your behalf, even when you don’t think about it. 


But you can’t do that with everybody. It does take a small group of folks that you—that not only are giving to you, but you’re also willing to give back to them.

Exactly, exactly. Yeah, I always, I try really hard to replenish what I take. And it doesn’t have to be in the same exact exchange—like you give me a podcast, well I’m giving you a podcast—but replenish what you take. It just has to be these beautiful reciprocal relationships where the foundation is, I want you to win, I want you to grow, and how can I assist you with that if you require that assistance?

And it’s very much this idea that everyone can win. We don’t all, we don’t have to have a zero sum game here, where well, Natalie, if you win, I’m going to have to lose. So do I really, am I really okay with that— we can all win, we can all grow. And I think it was Simon Sinek, if I recall correctly, that wrote the book The Infinite Game, and he talks about that idea of, you don’t win at business. Business is ongoing, there isn’t a finish line. So therefore, having this win-loss mentality is very finite, right? It’s very short term thinking. But if we all recognize, look, business is going to go on as long as we’re here. So let’s figure out a way for everybody to win. And that’s that mentality that you’re talking about is, how can I surround myself with people, the right people, in a way that we can all help each other win?

Yeah, that feels like that just goes without being said. That is like a core component of this for me. And it’s also important to note that some of the people that I talked to the most are all in this DEI space. So we’re all doing very similar work. And at no point is it ever like, Oh, you’re trying to hop into my lane, there’s—Have you ever seen a highway in Atlanta? Like there’s just like, there’s like 12 lanes on one side? There’s space for all of us. Basically, there’s space for all of us to win and thrive even though we are doing pretty similar work.

Yeah, I agree completely. Natalie, before we go, I do want to talk about one more thing. I almost always ask guests for a book recommendation because I’m an avid reader myself. I love to consume content that is actionable content. You mentioned a book Right Within—I believe Minda Harts is the author of that. Is that your recommendation for folks as a great book to read? Talk a little bit about it.

Yes, that is my—that is 100% my recommendation. Minda dropped a book two years ago called The Memo: What Women of Color Need to Know to Secure a Seat at the Table and is following up this fall with Right Within: How to Heal from Racial Trauma in the Workplace. And I recommend that book so much because as she begins to talk more and more about it on social media, I’m realizing that although I’ve only known Minda for a couple of years and my work history extends beyond that, that she’s capturing my story because it demonstrates how pervasive structural inequities are, not only in the workplace, but in our lives in general. And so the memo introduces us to the inequities and Right Within, it’s like a spin off of Lauryn Hill’s, “How you going to win if you ain’t right within?” it’s all about that. So we’re going to air out these traumas. And we’re going to begin to figure out how to reconcile these traumas. And it’s for everyone to read, everyone should pick up a copy, and it drops officially tomorrow.

All right, and tomorrow is October 5, for those of you that are curious, so that by the time this goes live, that book should be out and available to you wherever you get your books. And Natalie, I just want to thank you so much for taking the time for this conversation. And I absolutely have enjoyed this conversation around looking for the positive and your approach to it with balancing it against the negative to me is really summed up with how you define holistic minimalism, which is to release yourself of the people, places, things that fuel your discomfort—that is so well articulated. I absolutely love that definition. If you’re open to that I’m going to use that as I work with leaders and encourage them to adopt this idea that it isn’t this mentality of, if we have more the positive will come, but it’s cultivating that intentional space where the positive can thrive. And Natalie, you’ve really helped me to see that. I hope you’ve helped all of our listeners with that as well. So Natalie Gillard, thank you so much for joining us on The Upstream Leader.

Thank you for having me, Jeremy, and take great care.

You as well.



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