A Candid Conversation About Juneteenth

Juneteenth, a holiday commemorating the end of slavery in the U.S., has gained wider visibility in the past year. Listen in on a real conversation about how small business leaders can acknowledge and celebrate the holiday, even if they haven’t in the past.

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A new survey from Gallup found the majority of Americans (60 percent) know “nothing at all” or “a little bit” about Juneteenth, the United States’ newest federal holiday commemorating the end of slavery. While Juneteenth has gained wider visibility in the past year, many small business leaders may be unsure how to talk to their employees about the holiday.

Listen to this illuminating conversation between Zenefits Chief Operating Officer Issac Vaughn joins VP of People Ops Danny Speros for a conversation about what Juneteenth is, how it’s celebrated, and the importance of acknowledging it — even if it makes you feel uncomfortable. You’ll hear how talking about Juneteenth plays into broader DEI efforts and why everyone benefits when small businesses foster inclusive workplaces.

Read more: Racial Equity and Justice at Work: How to Keep the Conversation Going Beyond Juneteenth

Danny Speros (00:00):

Hello, and thanks for joining us. Isaac, it’s great to be speaking with you here about Juneteenth and about how small businesses and HR leaders can talk about diversity in their workplaces. I’d like to have you give a brief introduction about yourself. I’ll do the same here in just a second, and then we can begin our conversation.

Isaac Vaughn (00:22):

Danny is great to have this opportunity to speak with you about Juneteenth and its importance and relevance in the workplace today. As far as my background is concerned, I’m the chief operating officer of Zenefits. And prior to Zenefits, in my previous operating role, I spent over 15 years in the private practice of law as a partner representing companies like Zenefits. And it interesting in thinking back across my time as a lawyer, and even recently as an operator, the importance of diversity equity and inclusion.

Isaac Vaughn (01:06):

And one of the things I will say, just at the top, Juneteenth in all my time practicing law was something that was never specifically discussed or acknowledged, and DEI was more along the lines of just goals of just hiring people to get them in the door. I say all that because I think acknowledgement, recognition and appreciation is really what is the essence of all of this. And from where I sit today, it’s just great to see companies starting to have the conversation, even if they’re uncomfortable, because it does accomplish the most important thing at the outset. And that is acknowledge either events or people, or in the case of Juneteenth, holidays, which I would venture to say most people in the workplace have little to no appreciation or understanding of. Which is okay, now that we’re talking about it, but the whole key is going to be, how do we build on it moving forward?

Danny Speros (02:10):

Yeah. I think a lot of people became aware of Juneteenth in last year. I think we saw a pretty dramatic shift. But for people that are just nominally aware of it, or maybe are just sort of coming to hear about it now, what is Juneteenth?

Isaac Vaughn (02:27):

It is a holiday now celebrated on the 19th of June to commemorate the emancipation of enslaved people in the US. And it was first celebrated in Texas on this date in 1865. This was the last group of slaves to be made aware of the emancipation proclamation, which actually was in 1862. So in Texas, these slaves were finally made aware that they were free. And so, that was June 19th 1865.

Danny Speros (03:10):

Yep. And I guess after the end of the Civil War, that was the last place to hear that the Civil War was over.

Isaac Vaughn (03:17):

That’s right.

Danny Speros (03:18):

People were free now. So fast forward a hundred or so years and tell me a little bit about how people celebrate that holiday.

Isaac Vaughn (03:27):

Yeah, I think the ethos behind the holiday is it really is designed to highlight and celebrate the dignity, freedom and contributions made by Black Americans in the US. And so, for me, growing up and probably in my late teens, early twenties, where I became increasingly not only aware of, but acknowledging the holiday, oftentimes they’re local events. I grew up in San Francisco, and so there’s sections of the city where you had larger populations of Blacks and took on the feel of a street festival, where there would be food and there’d be music. And there would be a local Black businesses showing their wares. So for me, it’s always signified by an opportunity to get out into the community to some of these local events.

Isaac Vaughn (04:26):

And some cities and some parts of the city put on bigger celebrations than others, where you may be seeing hundreds of folks, and then others it’s much smaller. But yeah, it’s a day of celebration and a day of reflection, again, on the many contributions that the Black Americans have made to all aspects of American society, including business.

Danny Speros (04:47):

Yeah, the incorporation of a party, but also the recognition and the celebration of the accomplishments. And then, I don’t recall learning about Juneteenth in school. Don’t recall learning about it early on in my professional career. Actually when my wife and I adopted our child, so our daughter’s Black and that was a moment for us to really learn more. So I’m obviously white and my wife’s white, and this was something that if we were going to raise a Black child in America and white parents, then this is something we needed to get more involved in, and Juneteenth was one of the first things that we got involved in. And yeah, it was great to see the party, but be a celebration of the businesses that are owned and operated by Black people here in the community.

Isaac Vaughn (05:32):

And if you think about it in the context of small businesses, many Black-owned businesses are small businesses. There are very few that are scaled, if you will. And so, we know from our own experience at Zenefits how many small businesses there are in the United States. And we talk about leveling the playing field for the 99.7%. Those are the 6 million businesses in the US alone with less than 500 employees. So you take those demographics, combine it with, I think, increased institutional recognition, because you said something which is important, which is Juneteenth is not, at least for a long time, it was not discussed in school. It certainly wasn’t when I was coming up, and you said the same thing. And so, I think there’s a great opportunity now to raise the collective understanding and appreciation for the holiday, but obviously more importantly, the contributions of Black Americans.

Isaac Vaughn (06:33):

And then, it also for companies in particular, including ours, gives us an opportunity to really know even more so who our customers are, what’s behind the name, and just mathematically we know a good number of small businesses are going to have owners who are African-Americans. And so, that gives us a chance to celebrate and acknowledge those contributions real time and current experience by supporting those businesses in ways that companies can support one another to advance the efforts.

Danny Speros (07:06):

You make a good point. So you’re talking, for us at Zenefits. Our customers, certainly a number of them, fall into Black-owned businesses, and many of their employees may also be Black employees as well. And for other companies too, thinking about how we interact with our customers in our communities, this kind of awareness actually helps us do a better job serving their needs. What are some of the reasons why businesses would want to talk about this?

Isaac Vaughn (07:33):

It will sound trite, but it’s also borne out in the data. It’s actually good for their business. When you look at the data, and it’s more sort of a DEI sort of metric, but the bottom line is companies that are advanced on the DEI spectrum, it’s proven they’re more profitable, they grow faster, they attract and retain a broader base, talented base of employees. And some would say, what relevance is that in a small business? It’s all relative right at the end of the day. And we also know from our experience at Zenefits. Today’s employees, whether they work for a big company or small company, they have an expectation about the employer, employee compact. And this younger generation of employees are much more socially conscious.

Isaac Vaughn (08:26):

So I would tell a small business leader, I would tell an HR professional of companies of all sizes, it is in your near-term and long-term best interests of your company if you want to attract talent, if you want to connect further with many of your customers who are women and minority-owned businesses, having this gene, if you will, or this part of your organization become more and more core to who it is and its values, you’re going to need to do that. And ignore it, and you run the risk of, potentially without knowing it or meaning to, alienating large segments of customers who otherwise don’t want to do business with you, employees who won’t give you the time of the day because they see no commitment whatsoever.

Isaac Vaughn (09:13):

And so, while it may sound like a relatively simple exercise, acknowledging Juneteenth in the workplace, celebrating it, encouraging your employees to first understand why the holiday exists and then look for ways to celebrate or join the celebration will go a long ways because there are going to be some employees in your company who are going to expect that would be the case. And when it doesn’t, it’s going to send a message to them. And then, others are going to shout in a positive way, proudly that their company acknowledges it, celebrates it, and it’s not something they even had to raise in the first instance.

Isaac Vaughn (09:56):

So there’s just so many good reasons. It’s good for business. It’s good for culture. It’s good, I think, for attracting and retaining employees. And I think it also translates, depending upon your business and who your customers are, but odds are it’s going to give you a deeper connection to many of the customers that you’re already serving.

Danny Speros (10:15):

Yeah. I think on the people operations side, where I sit, I’ve watched diversity be such an important thing in the workplace in the last year or so. From where I sit, it’s been important to me and to a lot of the professionals that I work with for a long time, but to see the emphasis put on it in the last year or so, but you touched on what I see as the glue. It’s one thing to attract people to a company, but if they don’t feel included, if everybody doesn’t feel included in the workspace, then you don’t have the glue that essentially holds that diversity together. And so, Juneteenth can be an incredible opportunity to demonstrate to employees that this is something we’re open to talking about. This is something that’s important to us as a company, and we value the people in the contributions from all of the different walks of life that come in here.

Isaac Vaughn (11:05):

That’s exactly right. Especially, Danny, in small companies in particular, where they just are not of a size and scale where they can have a diversified leadership. They may not even have a leadership team, but they have-

Danny Speros (11:17):

Leadership team is the owner, yeah.

Isaac Vaughn (11:18):

Exactly. And this is a way, I think you said it well, to convey to those folks that you are aware, or as [inaudible 00:11:27] like to say, that you’re woke and you are going to acknowledge this holiday because it celebrates the contributions of Black Americans in this country, and that’s an important thing. Irrespective of whether you’re white or Asian or Black or Hispanic, these are important things. One of our values, in it together, that’s in it together. It’s acknowledging and recognizing everyone’s contributions and how that plays into our own life experiences and our own personal and business success.

Danny Speros (12:01):

Black history is American history.

Isaac Vaughn (12:03):

That’s right.

Danny Speros (12:03):

The contributions of people across all of the different backgrounds in America, our American history. And to the extent we may or may not have had the opportunity to learn those things appropriately in school, life is one big learning opportunity. And to the extent employers can share in that with their employees, I think that creates, I don’t know, some stickiness to the employee experience and as attractive to people of all backgrounds.

Isaac Vaughn (12:29):

Agreed. And one maybe final thing or the elephant always in the room is that people are not comfortable talking about it. And that oftentimes means it doesn’t get talked about because people are not comfortable. And my advice on that point in particular is it’s okay, especially in the beginning, that you’re not comfortable and you feel uncomfortable. It still doesn’t mean that people won’t see value in your acknowledging the holiday. Even if you admit that, one, you didn’t know about it growing up, or you weren’t aware of it until recently. It really comes down to your intentions for it. And if you are intentional and authentic. And authentic doesn’t mean you have known it and have lived it all your life. Authentic means your natural voice.

Isaac Vaughn (13:19):

So your natural voice in the beginning may be, “Hey, I wasn’t even aware of it. I should’ve, but I didn’t. But now I do. And now that I understand it.” I’ll tell you, on the other side of that, if I hear that as a Black person, I’m not hung up on the fact that they’re just now acknowledging it. What I’m really listening to is are they doing it because they feel they have to, because that’s what the current thing is, are they doing it because they understand what the holiday represents and why that’s important, and then are able to translate for themselves what that means to them personally, what it means for their business. So let the awkwardness subside and just embrace the opportunity to bring people together.

Danny Speros (13:58):

Yeah. I think that’s great. With some topics like this, some people do either stay away from it or come at it knowing everything. And the reality is you don’t have to do that. And if anything, coming at it with a level of vulnerability and authenticity helps everybody else come to the table as well so that nobody feels intimidated by the conversation and the level of the conversation. It’s important to us when we have conversations like this within our company and within our teams that essentially we meet our people where they’re at, and it creates an environment where people are okay being a little uncomfortable, but not so uncomfortable that they don’t participate. But what are some ways that leaders, HR leaders, can get employees involved in this?

Isaac Vaughn (14:42):

Yeah. So I think that something that every company can do of any size or scale is make it a holiday, and in advance of the holiday remind people that the holiday’s are approaching and we’re taking this time out for these reasons to celebrate this particular holiday, and encourage your employees then to spend that time or part of it going to an event in their community or talking about it with people in their broader narrative. So just the acknowledgement, because I think, again, for me, first it starts with acknowledgement and recognition and we can build on that. And then over time, it evolves and it may become such that companies are doing more and more things beyond the holiday to drive it home in the workplace.

Isaac Vaughn (15:29):

I think the other thing too, to make it more than just the holiday itself, I think use it as a lightning rod to do what I would call sort of a DEI assessment. And again, small companies probably not as relevant as companies of some moderate size and skill, meaning look at your makeup at all levels of the organization. And is that reflective of the broader world we live in? Is it reflective of the broader customer base that you’re serving? Take inventory of who your customers are. At least have it be top of mind and not something that is in the recesses.

Isaac Vaughn (16:05):

All of these things, I think, are ways in which you can reinforce what is really is all about, which is recognition that contributions are made by many. And that just sets you up to embrace the increasingly diverse workforce that we have ourselves in. But at least we’re more informed about many of the people that are coming through the doors, actually or virtually, on a daily basis. And that’s going to be to everyone’s benefit because you said it, which is we’re going to do better. We’re going to feel better when we’re acknowledged and we’re included, when we know that we actually are part of a community that knows you and values you and has a little more understanding and appreciation for if not your specific background, general conditions that affect all Americans, good and bad.

Danny Speros (16:55):

Yeah. When in some of the inclusion efforts that we’ve done at Zenefits, what we found is people from all different backgrounds appreciate it. It’s not just the specific group that you’re looking to include. Everybody appreciates the fact that we can learn from each other, we can partner with each other, and that they see that this is a company that does these kinds of things. And if they do it for one group, they’ll do it for other groups. And in fact, everybody can be more involved in that sense. So yeah, the impact goes well beyond any one specific group and ends up helping. And we’ve seen there’s a number of statistics out there around employees want to work for companies that take this kind of approach more and more. And increasingly younger generations are actually demanding it, which is fun and exciting to see. Yeah. So it creates some additional opportunities beyond just the goodness and the appropriate response to these kinds of things.

Isaac Vaughn (17:48):

Yeah and we know that not all cultures are the same. And if you build a really healthy culture where everyone for the most part feels included. There’s always going to be people no matter what that won’t, but that can become a barrier in the switching costs. So we also know that in the workplace, yeah, how much I get paid and what are my opportunities for advancement are important, but who you work with and under what conditions, it also plays into it as well. And so, at the margins, it makes a huge difference. And sometimes it can make a material difference, meaning people will stay versus just take another opportunity because it’s significantly more money.

Isaac Vaughn (18:30):

Now, of course, there’s a whole bunch that goes into that and everyone’s at a different place in their life where they can make those decisions. And I’m not making the point around retention as much as I am. There’s more good that’s going to come than downside by investing in the kinds of things that drive inclusivity because I think that also helps drive engagement, and engagement drives actual results that matter in the business context across every key performance indicator you can think of.

Danny Speros (19:02):

Yeah, and it’s free. All you got to do is talk about it.

Isaac Vaughn (19:05):

Talk about it. Right.

Danny Speros (19:07):

These are things we can do. And I know June 19th falls on a Saturday this year, so I expect that, as the pandemic restrictions are being lifted in various levels across the US, I assume there’ll be some good parties out there to the extent any one particular neck of the woods doesn’t necessarily have that. There’s all kinds of neat stuff that can be done virtually and some learning opportunities out there.

Isaac Vaughn (19:29):

100%. I will actually be at a party on June 19th, except this will be a wedding.

Danny Speros (19:33):

Oh, okay, well.

Isaac Vaughn (19:35):

For the daughter of a good friend, but otherwise I will be celebrating. And I know the people in that room, we will have a good.

Danny Speros (19:42):

Right on. And what kind of a neat thing to be able to celebrate their anniversary on June 19th every year from …

Isaac Vaughn (19:48):


Danny Speros (19:48):

… here on out.

Isaac Vaughn (19:49):


Danny Speros (19:50):

That’s a neat thing.

Isaac Vaughn (19:51):


Danny Speros (19:52):

All right. Well, thank you, Isaac, for taking this time to talk with us, and I hope you enjoy that wedding. And I appreciate truly from the bottom of my heart the work that you do for us here at Zenefits in your professional capacity and you side capacity and helping us come together and rally around the important things in life. It’s a great partnership.

Isaac Vaughn (20:11):

I appreciate your thoughts. They humbled me and I too enjoy working with you and others in a place where it was just collection of fine individuals doing good stuff for all the right reasons. But it’s a lot easier to tackle our problems when I get the shoulder up with people like you. So thank you very much. Really enjoyed having the opportunity to talk about, so thank you.


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