When Deanna Singh appeared on screen on our Zoom interview, I couldn’t help but comment on the unusual, bright yellow beads she was wearing — a cheerful note that reflects her upbeat personality and multi-dimensional background. Singh is founder and CEO of Uplifting Impact, a DEI consulting, coaching, and training company, and she launched a virtual event last year on inclusion and allyship that drew several hundred participants via word of mouth.
The second edition of that event, “How to Be an Ally Virtual Summit” — billed as “three days of bridge-building for DEI leaders” — will be held Oct. 4-6, 2021.
Singh calls her professional background “eclectic,” which is something of an understatement. “I practiced law, I was a middle-school principal, I started and founded an urban prep school, I have taught all the way from the elementary level up to the postgraduate level, I’m currently teaching at the business school for UW Madison [University of Wisconsin-Madison],” Singh said, “and I taught social justice.” Oh, and she also was the CEO and president of three, very large foundations in the financial services and biopharma world.
In addition to Uplifting Impact, Singh runs three other companies under her Flying Elephant umbrella — an inclusive children’s book imprint, an inclusive birth coaching and doula services company, and Purposeful Hustle, based on her book by the same title, with a focus on entrepreneurship and leadership through a DEI lens.
Convene spoke with Singh about six weeks before the second edition of her allyship summit — which is about how long it took her and her team to plan and pull off the first event in 2020.
How did you first get involved in diversity, equity, and inclusion?
What brought me into the DEI space is a couple of different things. I was born into it. My mom is African American. My dad is Asian Indian.
The other part of it is that because I’ve been in all these different sectors and had leadership roles in all these different spaces, I can see with a bird’s-eye view of all the commonality of challenges that we have. And one of the biggest levers that I think leaders can pull in order to get past the challenges that you see in all these different organizations — at growth, at maturity — is the lever of inclusion. I don’t care what your business is, at the end of the day, you are going to fail or you’re going to succeed based on how connected people feel to the mission of your organization. People don’t feel connected to anything unless they feel included.
I think what got me here was my own personal background. I think what keeps me coming back here and so inspired, encouraged, and passionate about it is the fact that when organizations get it right, when leaders get it right, you see this incredible shift that happens and what’s possible. To me, one of the biggest drivers is helping people thrive.
What prompted you to hold a virtual conference last August?
It was a process in and of itself. I’ll start at the beginning. After George Floyd was murdered, we started to get all of these calls, and of course we have been in the work, and so people knew to reach out to us. One of the most pressing questions that I was getting repeatedly, because of the different venues and different spaces that I’ve been in, was, “How do we talk to our children about what they’re seeing on the news? How do we talk to our kids about what’s happening around them?” And this was from educators, parents, community members, just from concerned citizens. We kept getting this question over and over and over again.
I am a service-oriented person, so I would get a message on social media or I’d get an email, or somebody was calling or texting or whatever, they’re sending me one or two or three lines. I’m sending essays back, right? And I was so tired. I was physically drained, I was emotionally drained, and I realized I’m being super inefficient — even though people are coming from different doors, a lot of them are asking the same questions.
So I was talking to my husband — he’s also my business partner. I said, “I keep getting this question over and over again. There’s got to be a better way to do this.” And I said, “What do you think about us hosting a Zoom Room? Just opening it up to anybody who wants to come, and maybe we could just facilitate a conversation?” And he’s like, “Yeah, yeah. That sounds cool. Let’s do that.”
So I put a post on Facebook, not an ad, just a post. I didn’t even look at it again. Monday night at 7:30 was when we hosted the room. When I got into the room, it was completely full. Over 100 people, maybe over 200. Whatever our cap was at the time. I know it was less than 500 because then we increased to 500 and then we had to increase again. So the room is full and now I’m getting messages like, “I can’t get in.” So I’m like, “Okay, I don’t know how to make it bigger in this moment.” We’ll serve the people who are in the room, but then we’ll do it again next week. But then we got asked to do it again from an organization, then again from another — it just kept growing.
Over the summer, we must’ve talked over 10,000 people. So many people said, “You know what? If I’m honest, I need to have this conversation with my team, and I need to have this conversation with the adults in my life.” And we knew that — because that’s the work that we do all the time, but it was this different kind of a moment because it was coming out in a very clear way. There was this desire. And I think one of the things we just realized is people have a desire and want to show up as allies, but really just don’t know what that means.
How did the event come together?
I want to say it was four weeks from, “This is the seed. We should do this,” to “Now we’re really doing this.” Maybe it was six, but in a short time we hosted this really elaborate three-day, full-of-content, rich virtual event. It happened significantly by word of mouth among people who had already worked with us and we had trusted relationships with. One of the very encouraging things is that five minutes after we finished the program, we got inundated with requests — “When are we going to do it again?”
We had pulled this together so quickly, there was no thinking of, “Oh, are we going to do it again?” it was just like, “Let’s get through this.” I literally, on the third day, when it was finished, we still had the camera crew, everybody was still in the room, and I just laid down face-first on the floor. I was so tired. I was like, “I know. This is so weird, but I have given all I have.”
I think the other thing that we realized was that there were some groups that were very significantly impacted and knew that they could go back and impact their organizations. And those were people like our HR professionals, our DEI specialists, business owners.
How do you think your allyship summit is different from other DEI conferences?
I think the other thing that we really realized was that a lot of the work that’s being done in this space is like … it’s almost got this feeling of heaviness. And I think one of the things that was just really important for us in everything that we do — it’s one of our core principles — is that our operating system is joy.
We need to be able to look at the work that we’re doing, not as this is a punishment or that you should feel guilty. It’s acknowledging that some of those feelings are there and that’s par for the course, but that, really, what we’re trying to do here is think about this idea of joy and how you use the powers that you have to create positive change. We definitely are trying to seek people who are solutions-oriented, who want to learn, who have a thirst for that kind of knowledge and want to be happy about it.
What kinds of session formats do you use at the allyship summit?
It’s a group effort. We really do have a phenomenal team of people who spend a lot of time thinking about what it feels like to be in the audience. What does it feel like to engage? How much time has going to pass before somebody gets the chance to really talk to somebody? All of those things. So we invested in dissecting what that schedule was going to look like with intention, and really with the user at the end.
I think the other thing is that we infused joy through everything that we did because, again, that’s part of our DNA. We had a musician and we had a poet, and they did independent things, but they decided they loved what each other was doing so much that they actually created a collaboration.
My kids came on and read a story. We just try to do things that, again, got to us moving and infusing that sense of joy. I think the most important thing that we did, though, and it’s, again, a part of our philosophy of pedagogy and good pedagogy, is that everything was based in story. So as we moved through the sessions, everything was really based in story, and everything was based in practical tools. So there was never a session where you walked away being like, “Wait, what did we talk about? I don’t know.”
You could always tell the story. There was always something you could go back to the dinner table with or the boardroom table or your staff with something, because there was a story. And the other part of it was, “These were some really practical tools that you could try today. You don’t have to wait. You don’t have to have a certain title.” It’s like, “No, you can try this right now. In fact, let’s go try it.” And that, I think, also was really important.
Everybody got swag boxes. One example of something we did for the swag box that was so much fun is we invited people to try different candy from all over the world. We curated all this candy from all these different places and put together these little bags for everyone so that they would be able to try the candy while we were having our social hour.
What is your definition of allyship?
I think allyship is more about a journey. It’s about how am I showing up? I don’t think that allyship is a destination, and so I think that’s a really important part of the way that we talk about allyship, is that you have to be vigilant. You have to be committed. You have to be very intentional about where you are and how you are showing up in relationship to other people.
This is an opportunity to spend some time in self-reflection. I think a lot of times, one of the challenges that we have is people want to move right to a solution. They’re like, “Tell me what I need to do and I will do all the things because I’m passionate and I believe in this and I care about it. So give me the checklist and I’ll just go through, boop, boop, boop, and I’ll get it done.”
And I appreciate that energy, and part of what my job to do is to be like, “Okay, one second. Let’s just stop for a second and let’s first just spend a little bit of time giving you an opportunity to acknowledge and understand where you’re at in all of this stuff and where your comfort level or discomforts actually are.” Because I do think too often we gloss over or we try to run through some of these conversations because it’s uncomfortable, right? And so it’s not like, “Let me make you uncomfortable.” That’s not my goal. But my goal is to give you the gift of having some space to really think about where you sit in all of it because I think if you jumped through it too quickly, that’s where people make mistakes and they come off inauthentic.
What can participants expect at this year’s event?
We’re super excited about the fact that people who have participated in some of our other trainings and other spaces are going to get to be part of it, too. We have a number of people who have been part of the summit in the past, who are not on the team, but who are volunteering and going to be able to help us facilitate some of our conversations.
From the very beginning, I was committed to making sure that we would have a really high-value production. We had about 15 people in the background making it work to make it a very professional event.
We also created a really awesome resource page. It’s very easy for people to go and get resources in real time. We do a lot of writing — I don’t think a lot of people use writing as a tool. We use it significantly, so people do a lot of journaling with us during the sessions.
We keep it very simple. On our backend, it’s a little bit more complicated. But on the front end, it’s just Zoom, and we’re not using any other platform. But there’s lots of interaction with one another, which is also very cool.
If you make allyship and inclusion heavy, people feel like they can’t lift it, so they move away. That’s why we’re called Uplifting Impact, right? We really are about, “No, you can do this. And in fact, not only can you do this, but we absolutely need you to do this in order for us to be successful.”
Michelle Russell is editor in chief of Convene.