The Process of D&I Self-Education 

Welcome to Crescendo Chats: Scaling Diversity & Inclusion. In this series, Crescendo co-founder Stefan Kollenberg hosts conversations with HR and diversity & inclusion practitioners, sharing valuable insights from their work. 

This week’s conversation is with Jessie Wusthoff, the HR, culture, inclusion, and diversity director at Clover Health.

Listen to the podcast or read below for the edited transcript. 

Stefan: Can you share a bit about yourselves to get us started?

Jessie: I came to Clover Health about two and a half years ago. Before that, I did a little consulting support, and I worked in tech companies and nonprofits. I bring those different points of view toward my current culture, inclusion, and diversity work, on our employee engagement and D&I teams. Then I started supporting the HR partners, which is really all about integration.

My role is about making sure all of our people processes integrate D&I. There are pros and cons to the integration, but so far so good. We’re feeling good about that. I’ve been in the Bay Area doing this work for global companies for a few years now and what I like most about where I’m at is that a mission-driven company is really important to me. As someone with a disability being in a place where they’re serving the Medicare population is particularly awesome for me.

I didn’t think I’d get the chance to do the role I wanted at the kind of company I wanted, so that’s been great. 

Stefan: What motivated you to get into D&I work?

Jessie: As someone with a disability, I spent my whole life fighting stereotypes, proving them wrong, and proving that wasn’t me. And then I had some pretty explicitly bad things said to me, and I felt like I was held back at my job. They tried to let me go, which they found out you can’t do just because you doubt someone if they are doing their job. And I worked in people operations at the time. 

I can’t change the world necessarily, but it motivated me to see if I could reduce one or two of these conversations happening, it would be great. The big pivot then was that I was already doing D&I, but at that point I decided to start doing public talks about disability specifically. 

Stefan: What challenges did you face early on with D&I work?

Jessie: One thing you have to understand with D&I work is you will never know everything. You will always be learning and always be making mistakes. I think when you expect that you won’t make mistakes, it becomes paralyzing when you do. 

And when other people assume you’re never going to make mistakes, it’s setting the work up for failure because we all need to learn and progress. And I think people need to remember that messing up isn’t about some atrocious thing you did. It can be something said in passing that was still quite harmful. 

People talk about microaggressions. They’re still hard for people to wrap their head around sometimes. 

For example, we as a leadership group had people from leadership present different things about the group at our yearly update. I had tapped out of some of the planning because I was working on other parts of the event, but I was still watching them happen. I missed the opportunity to point out that everyone presenting was white. And I’m still disappointed in myself for that. It’s a tangible example because it was a group of diversity people. It was a problem. But sometimes you’re just tired and you don’t speak up - and that is no excuse. It did not register well with people in the room who were asking why we had all white people presenting at a diversity group meeting. 

I think the other thing to flag too is that what we see as the problem is often the results of the actual problem. So people were asking why it happened and the actual issue was the pool of people to pick from were almost all whites. Those who weren’t white were out of town that week. So when it’s a smaller number of people, being out of town means all your presenters are white and you don’t have people of color presenting. That to me was the real problem that manifested in the representation of the speakers in the group. 

Stefan: How do you balance doing all the work without beating yourself up?

Jessie: A lot of emotions come with this work. Especially because so many people who are motivated to do it are motivated by personal experience. It’s personal. 

Early on I took on too many things. I think that’s common. People say the problem is trying to boil the ocean and you can’t prioritize. But I think the problem is that everything is equally important - how do you pick one group of people being discriminated against over another?

I think I have gotten better at prioritizing now, but it’s understanding who will change and who will not change so you can preserve your energy. I don’t necessarily need everyone on the boat to move it forward, but no one can be pulling us down as an anchor. So I invest energy into making sure no one is pulling us down. But if someone just wants to chill on the pier, it’s not my favorite, but I only have so much energy at the end of the day. 

It doesn’t mean you dismiss everything else, but it helps. You can’t spend 80% of your time into your bottom 20 causes.

Stefan: What are the different stages of learning people go through with D&I?

Jessie: I think there’s a lot of reflection and general learning. You start with you not knowing what you don’t know. Then you know what you don’t know. Then you actually start over again. In D&I there will always be things you don’t know. 

I’m grateful when people point out or ask me questions that help me understand a little bit more about the topic. They’re humbling. And that’s an important thing to understand when you’re going into this work, too. A lot of people just feel so uncomfortable talking about these things. 

If you’re in a Black family for instance, raised in America, you are aware of what it is to be Black in America. But if you were a white child growing up in a white family, you can easily not have those conversations ever. 

I didn’t go to a diverse school. I felt very much like an outsider because of my disability and under-representation at school. So I clung to people who I knew felt the same, so I did have a very diverse group of friends in high school that really helped me quite a bit. 

Learning can be frustrating and uncomfortable. People ask why I’m comfortable talking about race, and really it’s just that I’m always uncomfortable but I’m just powering through and trying to make it work. 

Stefan: How can you push people to start learning?

Jessie: It depends on the person, but some of the more common ones is closer exposure. If you grew up in a homogenous geography, then moved to a diverse area, the general exposure will start making you ask questions. You hear personal stories or things you’ve never thought of before. Those kinds of realizations get people caring a bit more, but I think what holds white people back is fear of saying the wrong things. But if you can understand where they’re coming from, they’re going to engage because I think everyone deserves empathy and meeting them where they are at. 

So it’s finding what encourages people. If they feel there’s a safe space where someone’s going to meet there where they’re at. There are a lot of people who care and don’t engage because of that fear. So trying to help people get past that is really important. 

Stefan: Do you recall a mistake or misstep, and how you handled it after?

Jessie: Sometimes we say things that hurt people, and it’s not that person’s job to surface it to us. But we’re fortunate if they do. I think going back to my theme of little things making a bigger impact. 

I will say one of the microaggressions I struggle with is my southern California dialect which includes things like ‘dude’ or ‘girl’. I had gotten feedback that was telling me to stop calling a group of people ‘girls’ and I realized I did need to stop. 

It’s such a small thing. It’s one word to change. But I had to spend a lot of time and a lot of focus on it. I think it’s important to have an example of something little like that because the paper cuts can add up. 

I think the one thing is to not make the other person do the emotional labor when you mess up. Don’t make a big fuss with ‘oh I’m so sorry, oh my god.’ I think there’s a balance. When that happens, the person who provided the feedback about being harmed ends up feeling like they need to make the person feel better - it’s the social programming we’ve been submitted to. I see it a lot in that context with white guilt. It’s particularly frustrating when you see white people just starting to notice trends about people of color being shot and they’re so upset - but this is a thing that’s been happening for a long time and it’s not Black people’s jobs to walk you through that emotionally. 

There’s also a whole other layer of people needing to maintain work relationships, so it’s a question of how honest you can be. And people think about the different labels that are going to be associated with them if they speak up. That kind of stuff. 

Stefan: How have you helped others navigate uncomfortable emotions?

Jessie: I think coming from a place of curiosity. People might ask questions as though they are curious but really they are frustrated and you have to keep yourself in check and come from that place of curiosity. That’s helped people take a breath and be able to engage in harder things. 

But it requires a lot of self-care and is extremely hard. It’s not done nearly as much as it’s talked about. 

But generally I just like to call things out to say yeah, this is uncomfortable. It’s ok, though, you can process things so much more and can deal with so much more. I also try to bring humor to it. I learned as a child to keep it real, it didn’t come from the happiest place. But I think it serves me well in my work. Not everyone thinks I’m funny but when someone does it helps people. 

Stefan: How can you help really excited people come in a bit more slowly instead of jumping all-in at first?

Jessie: I think you sometimes need people to do that. But it’s about encouraging people to focus on the desired outcome. Think about the desired outcome you want to see then think about the best way to get that outcome. Very rarely is it calling someone out in front of a bunch of people. That’s probably not going to teach someone something new - it will likely shut them down. But if someone is insisting upon saying harmful things, then maybe you need to. 

So it’s about looking for the harm being done and how you can shut it down. Think about what will allow you to have your best outcome. 

There is such a thing when you’re trying to focus on the outcome of over-coddling. I worry sometimes that I do that. You can overcompensate for fragility and then no one wins. But keeping my eyes on the prize is important. 

Stefan: Clover Health uses Crescendo - what got you initially interested in our platform?

Jessie: Well, you reached out to me because you wanted feedback on the product. I’m glad I could do it at the time. Just talking to you through the Crescendo model, I was already struggling with some things related to D&I and L&D, so the whole integration into daily workflows is pretty important to me. 

The customization was also pretty key. I can’t build everything for everyone. I wanted something that was going to make it easy for people. That was the big appeal. 

Stefan: Any major pain points you’ve seen the platform help with?

Jessie: Yeah, people engaging with it. I know specific people engage because they came with a specific question. I’ve seen them start conversations. It’s not just the people in our D&I working group or people who have already attended trainings. It truly has impacted a different group of people. Not everyone wants to go to an in-person training on a topic they are uncomfortable with. 

The platform is meeting people where they are, in a way that I literally could not have. And that makes me so happy to hear. Cause that’s the goal - meeting people where they are at. It’s in Slack, bite-sized, and I’m focused on those stories. 

Stefan: Where could we improve Crescendo?

Jessie: Two things: There’s always information to be updated and you’ll always be building out your library. The world’s changing. One of the biggest selling points was that people could come at beginner or advanced learning - I never could build enough trainings to accommodate for that. 

Customization needed to improve and has improved, which has been great, like sending from Slack to email. Everyone’s daily work streams at not what they used to be. 

(Note: Crescendo is also building for Microsoft Teams as well!)

Stefan: Lightning round: Favorite quote?

Jessie: Do whatever you feel in your heart to be right, for you’ll be criticized anyway - Eleanor Roosevelt. 

Stefan: What motivates you in life?

Jessie: Making things a little less painful for people. 

Stefan: What’s a book or movie that changed the way you look at the world?

Jessie: Poster Child by Emily Rapp.

Stefan: Coolest tech product you’ve ever come across?

Jessie: Old school wearables. And Spire, a company that came out with a breathing monitor that tells you if you’re holding your breath because you’re stressed. That’s pretty cool.  

Stefan: How can people connect with you?

Jessie: LinkedIn is best!

Stefan: Amazing, thank you!