HR Peep Show
Three HR and Operations professionals-- Claire Baker (she/her), AnnE Diemer (she/her), and Krista Lane (she/her) bridge the gap between resources and humans, revealing both the deeply human mistakes employers make and how they suggest avoiding them.
HR Peep Show
S2, Ep4: HR at Playboy
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In this episode of HR Peep Show, host AnnE Diemer continues the “HR is everywhere” series by interviewing HR leader David Gaspin about his path from a musical theater degree and years of auditioning in New York to building a long HR career. He explains what was unique about doing HR in early-2000s media, where relationship-based influence mattered more than policy enforcement, and shares what it was like leading HR for Playboy’s New York magazine office, including the workplace “social contract” around content and a sexual harassment case that crossed the line by personalizing comments. HR is everywhere, and trust me, we're gonna find it in some weird places. Subscribe to see where we go next.
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Welcome to HR Peep Show, where we pull back the curtain on life and human resources in the United States. This is HR Is Everywhere. In these episodes, we'll be exploring how human resources actually works across wildly different industries by talking to the real humans doing the work behind the scenes. Whether it's a Fortune 500 company, a political campaign, or your local zoo, HR shows up everywhere. And the people doing it have stories worth hearing. Today, we're talking to David Gaspin. David has built, scaled, and led people and culture functions for dynamic high-growth companies in technology, media, professional services, and wellness. His passion is helping leaders and organizations grow, whether that means designing HR strategies that scale with the business, building leadership development programs that create real impact, or coaching executives and managers to navigate the complexities of leadership with confidence. Right now, he's an HR leader, but we're here to talk about what he did before this. Previously, he's done HR for media organizations, including Playboy, which, as you can imagine, caught my interest. Welcome to HR Peep Show, David.
DavidThank you. I am so thrilled to be here.
AnnE DiemerI'm so excited to have you here. I want to get into this main topic, but I gotta stick with my format. So let's start by talking about your path to HR. Can you tell me about your HR origin story?
SpeakerAbsolutely. So I think um, like most people, I kind of fell into this thing by accident. So, all right, so my original career path, my plan, my undergraduate degree was in musical theater.
AnnE DiemerNo way.
SpeakerWay.
AnnE DiemerThat's awesome.
SpeakerAnd so I moved to New York with my super practical musical theater degree. I'm gonna go and pursue this theater career and I'm gonna audition, I'm gonna do all this stuff. And I did that for about six or seven years. And then what happened was I was temping, right? I was in between gigs. Yep. And actually, the first time I was temping for this company uh in their HR department. And I was like, I don't know what HR is, I didn't know what offices were, like, I don't know anything about anything, right? And so I was temping, and there was something about me they liked, and they were like, hey, do you want to stay and work here? And I was like, no, I do not want to work in an office. I don't want to do any of this. I've got to go like do Oklahoma in Ohio and so see ya. Um and about three years later, I was back temping for the same department and the same company. And they said, Hey, do you want to stay and work here? And at this point, like I had other things going on in my life. I was about to get engaged. I'm like carrying around this engagement ring in my backpack, and I've got like life plans. And I'm thinking, all right, maybe, maybe that I'll try this stability thing and see what it's about. So I said yes. And that was kind of the the beginning of that next chapter, right? So this was in a large media company, big magazine publishing company. And so I started from scratch and just kind of, I don't know, it was a fake it till you make it situation. And at some point I said, hey, like this is much cooler than not much cooler than theater. It's it, but it's better than theater in that all I have to do to be successful is be good at it. And so that was a draw, right? And so I said, let's do this and ended up progressing. I went back to school, went back for an MBA because I had no idea how business worked. And I was like, people are talking these languages of marketing and finance and operations. And I'm like, yeah, okay. And so decided that was gonna be the path. And, you know, the last 22 years have just kind of been an offshoot of that.
AnnE DiemerThat's awesome. So it sounds like you stuck with it for the stability, but also found elements of it interesting. What were the pieces that like stood out to you?
SpeakerYeah. So I mean, I loved a lot of it, right? So to me, it was there were pieces, there are a couple of pieces that really spoke to me. One was just the human behavior element, which I always found fascinating. I think this is carries over from the acting training and where you're okay, well, what's my motivation and what's happening? And and and kind of bringing that level of empathy into it, right? Trying to figure out what's behind an action or what's behind a decision. Um, and that always really appealed to me. And then when I started, I part of my career I was pretty focused on the recruiting piece, talent acquisition. And that was a whole different kind of thrill because that was like all relationship building and all just like, I don't know, being likable and like being a person that people wanted to work with and work around. And I like I got off on that, right? Like maybe that's the whole like the I don't know, unfed piece of my soul that led me into acting in the first place was like, I need this validation.
AnnE DiemerUm and or connection with people, not just yeah, let's go with that.
SpeakerThat's yeah. Um and like as it evolved and I got into more senior roles, like then there were things I didn't even know existed, right? When you're talking about leadership development and and and coaching and manager enablement, these things that just like unlocking capabilities in people that just like what's better than that, right?
AnnE DiemerAbsolutely. Absolutely. Oh, that's a great way to describe HR. Sometimes they get a little down on us and like make us sound boring, but it is. It's about connecting people, it's about setting people up for success. All those pieces are great. Do you ever miss musical theater?
SpeakerOh, obviously. Um but but the thing is like so, so I miss a very small percentage of it, right? Like I miss the part that is rehearsing and performing shows. That's three percent of the career, right? The rest of it is auditioning and schmoozing and submitting and trying to get an A year agent to do stuff for you. And like that I don't miss.
AnnE DiemerYeah. Absolutely. The actual art of it.
SpeakerYeah, I get to live vicariously. Like, I still have great friends. My wife is a performer, so I get to like live through her universe. And so like it's still around.
AnnE DiemerGood. I think the pipeline of theater or theater adjacent people to HR needs to be studied because I know a lot of people that I can think of off the top of my head. You said musical theater, and I was surprised for maybe half a second, and then I was like, oh yeah, of course, because of that pipeline. Well, let's get to the headline. The moment you told me that you did HR at Playboy, I immediately wanted to know more, but didn't ask too much more because I knew I wanted to have you on here and learn about it here. But I want to frame for folks listening, you know, you did HR for Playboy, but we need to remember that Playboy has a particular reputation, but it's also a media organization. So let's do the zoomed out perspective first and tell me some things that are unique about doing HR for media that you don't see in the other industries you've done HR for Yeah.
SpeakerSo media, and this is going back a ways, right? Like because when I was doing my work in media was early 2000s, and it's not like any other industry I've worked in, right? Because more than anything, it's a cult of personality. And you've got these high-powered editors and publishers, and they are the brand. And like there are no rules, there are only suggestions. Yeah, there are there are suggestions, and there's like that's where it's even more important to, and maybe this is why I did well early on in my career, right? It's even more important to form the relationships and like build the trust and be the little quiet voice in the ear saying, hey, don't you think it might be a good idea to not do that? Uh because there's no ramifications, right? At the end of the day, if someone wants to throw a chair across the office at their assistant, they're gonna do that. True story. And uh not naming any names, but they're gonna do that and like they're gonna get a slap on the wrist and be told not to do it again. And so the whole influence balance is a little bit different in terms of that versus any other industry I've worked in.
AnnE DiemerYeah. It sounds like the the change management in some roles, it's like you write a policy, you roll out the policy, you uphold the policy. Sounds like that's not what it was like. You had to build the relationships to put the suggestions into sub one.
SpeakerYeah, you write a policy because you're supposed to have a policy.
unknownYep.
SpeakerAnd then you address reality as a totally separate piece of the job.
AnnE DiemerInteresting. Did that cause any, I don't know, weirdness at any point of like where you just wanted to be like, no, we have the policy, just stick with it, but you knew that wasn't necessarily how to handle it?
SpeakerWeirdness, but not like that. Right. It was never like, and maybe that's why I am the way that I am, and I've had my wrist slapped more than a few times for not being like policy adjacent enough. Yeah. But the the weirdness wasn't around the policy piece. The weirdness for me was around the human piece, right? Because you've got for every executive that's throwing a chair across the office of their assistant, there's an assistant that's had a chair thrown at them.
AnnE DiemerYeah. Yeah.
SpeakerAnd so the weirdness was how do you balance a level of care with like the pragmatic reality that, like, hey, sorry, but like this is kind of who we are.
AnnE DiemerYeah.
SpeakerSo that part was the challenge.
AnnE DiemerI think that's something that no matter which part of HR you're in, you do always have a little bit of that. You know, someone wants to do things a particular way, and you're like, I get why you'd want that. This is not the org where that can happen. And that's a tough conversation no matter what, especially if you kind of agree with that other person, but you have to uphold the business.
SpeakerI mean, that's look, like that's 70% of the time. It's like, I get it. Like what you are saying makes absolute sense. Yeah. Um, but sorry, like here's why we can't do that. Um and and, you know, and I think part of the HR, like, I don't know, uh the the stew that we find ourselves in, right? Is like we're where the the buck gets passed to. Yep. And so we also can't turn around and be like, well, yeah, I think you're totally right. But like, hey, this is uh No, like can't really do that. You can't say, hey, well, the CEO wants it this way, or because that's not the job, right? Like the job is to an extent party line. And like, I hear you and I get what you're saying, and I understand why this is important, but here's where we stand as an organization, right? And like you have to be a part of that. You can't be separate from it.
AnnE DiemerNo. You have to hold those multiple truths at once, but know what you're prioritizing, which is a tough part of our job for sure.
SpeakerBetter than uh being an unemployed actor.
AnnE DiemerI absolutely. Um, although that brings up a whole other conversation about like how are we supporting artists in this world because we need them so desperately. But we're not gonna solve that um in this 20 minutes. So let's let's get into the thing that piqued my interest when we first were talking. What was it like doing HR at Playboy specifically?
SpeakerSo funny. Like, literally no one's asked me this question in 15 years. Um because when I was interviewing, like when I was looking for new jobs, like in the years following that, that was always the first. Like I got interviews because that was on my resume, right? Because people just wanted to ask about that experience. Um but so so let me set the scene a little bit. So I was leading HR for Playboy's New York office specifically, which was primarily the hub of the magazine group, right? So magazine editorial, sales, marketing, and then we had some other things that we had a little bit of digital, a little bit of TV, but mostly it was the magazine. So this was a media product, right? What I will say about my time at Playboy is this it was all right, so it sounds cheesy, right? Like, and people like they take punchline, like the I read it for the articles thing.
AnnE DiemerI was waiting to when I could bring that up.
SpeakerYeah, yeah. But legit the most talented, creative, brilliant set of content creators and editorial folks like that I've ever seen, ever worked with, hands down. They were making a brilliant magazine that happened to have pictures of women without clothes on.
unknownYep.
SpeakerUm and so that experience was amazing, right? Like just interesting, smart people doing what doing something where they had a lot of freedom, right? More than other media brands, because like where are you gonna draw the lines? Now, where that created a little bit of, you know, a little bit of issue, a little gray area that's grayer than it would have been in other places is like because that's the content, because you go, you know, so we were on two floors in the building, you go up to the editorial floor, and like the walls are the layout of the magazine. And so there's just like skin, right? And in a normal office, that's not acceptable. Like that's not gray area, that's black and white. Nope, we don't have naked women on the walls. Um but we did, because that was the subject. And so there was a very interesting and very firm line that was drawn, right? And this was both I don't even think this was written anywhere, right? It was like kind of the social contract, which is anything goes as long as it's referring to our content. The minute the focus shifts and it's referring to the world or a person in the office or whatever, like then that's the hard line and no one crosses it. Right. And I while I was there, we had one case where there was a sexual harassment complaint. And it was about a person who personalized a statement, right? It was like they were talking about a layout or an issue, and like an element of a photo. Actually, the term I think it was like about like side boob was the the topic in question, right?
AnnE DiemerYeah.
SpeakerAnd somehow someone said something that kind of redirected the idea of side boob toward a person in the room. Oh no. And it was like, there's the line. Because, yeah, like you have to have it somewhere. It's just not the same place as it is most other organizations.
AnnE DiemerOh, that's so interesting. So did this person know when they said that they had crossed the line, or was there like a feeling in the I don't know if you were in the room. I'm sure you probably just heard about it afterwards. Was there a feeling that it crossed the line? How did it evolve from there?
SpeakerSo I don't know. I can't say what they thought or what they knew.
AnnE DiemerTrue.
SpeakerUm I will say that they defended themselves.
AnnE DiemerOkay.
SpeakerUm and that's that's where the trouble started, right? Like kind of double down on I didn't do anything wrong. And there was a whole investigation, and there was a whole thing, um, and ended up that nobody was happy, which is usually how those things end up.
AnnE DiemerAbsolutely. Oh, that's an interesting one. Not something you would encounter anywhere else, that's for sure.
SpeakerYeah, I mean, and that's funny. Like, because I worked there when did I start there? Like 20 years ago is when I started there. But I still remember like side boob will stick in my head forever.
AnnE DiemerWe've all got a couple of those stories of just like the things that define something. And I feel like what I'm hearing from this one is the social contracts and workplaces really matter. And I don't I don't know if that's like what you intended to have me take away from this, but that's like what I want to be thinking about is yes, we're talking about something that's going to like pique people's interest for various reasons, but it's still a workplace. And how to navigate that workplace is going to depend on so many things. And in a place that's publishing content like Playboy does, that social contract is going to be that much more important.
SpeakerYeah. And there's more reliance on individual, uh, I guess both individual people, but also the collective to like enforce that social contract. Because if you're in a regular workplace, like you're nowhere close to the line for work. But at Playboy, you live just on the edge of that line for work all day, every day. And so like there's that much more onus to like really be committed to that social contract, right? So kind of what we've said is all right.
AnnE DiemerYeah. And I think that's such an interesting place that HR has to sit because you know, people think of employee handbooks as something you just like print off of a SHERM website, PSA, don't do that. Um, and that like it applies to everywhere, but it really doesn't. And it really couldn't. The policies for what's appropriate in a workplace, I work with a lot of nonprofits, that could not be applied to your workplace, but you have to adapt it to make sure people are still protected and the work that you're doing can be done.
SpeakerExactly. And like even this is an extreme example, right? When you're talking about, you know, a Playboy type organization. But even so I moved, like my progression was starting with, you know, traditional media companies, and then I moved into, you know, smaller earlier stage, like tech startup world. And even from there, like so different, right? Because when you're talking about a tech startup, you need to have fundamental like rules isn't the word I want to use, but I'm gonna use it because I can't think of a different one. Fundamental rules in place because a lot of times people are not like you have a lot of early career folks, you have a lot of people who don't have, you know, experience in the workplace, who are super talented, super smart, super well paid, and feel like they don't actually know how to operate in the world, right? Or at least in the professional world. And so you have to have these foundational things, but then within that, it has the scaffolding has to be loose enough that people can do what they need to do and not leave because there's so much like war for talent, blah, blah, blah. Um, and so like we used to have dress codes. Like the dress code is wear clothes. And so like things evolve, but it's all, yeah, it's who's your audience. Yeah, figure it out. Figure out what's going to keep people there and what's gonna not get you in trouble.
AnnE DiemerAbsolutely. And this feels like it comes back to, you know, your HR origin story of building those relationships. That's how you figure out how this needs to be is building those relationships. You come into a new startup, you see what the founders are trying to build in terms of culture, and then build that HR foundation that can reflect that and hopefully set people up for success.
SpeakerYeah. Uh it's it's so fun. Like the fact that we're sitting here having like a policy conversation is the wildest thing to me. Um because it's not, it's not something I usually even talk about, right? Like I'm policies are there when they need to be there, right? Because the rest of it is what it is. Like you can't have you, you can't manage by policy. Yeah. Because you can't have a policy about every single thing. And so it has to be that social contract. It has to be like the who are we, what's okay here, and how do we live that um so that somebody coming in has a quick understanding of like, all right, what's the vibe? Who are we? Okay, got it.
AnnE DiemerYeah. And I I'm hoping that's what this series does is like hearing from so many different perspectives, as we can realize that. That human resources work, which is stereotyped to be like one particular thing, is also just deeply human. And I think this is such a good example of it of like it wasn't the handbook violation that was the issue. It was the human violation that was an issue in this particular circumstance.
SpeakerYeah. And and that's, I mean, but isn't it always, right?
AnnE DiemerLike Always. Always.
SpeakerSame thing with policy. It's like you break a rule and nobody knows or cares. Did you?
AnnE DiemerOkay. I love this story. I think this is such a good example of what we're trying to talk about here, which is, you know, HR is everywhere, but that doesn't mean it's done the exact same way everywhere. We have to adapt to our environment and adapt accordingly. So as you have seen, I mean, you've seen HR across several different industries, had to adapt to the different ones. Is there now an HR hill that you will die on? It can be a hot take, it can be an unpopular opinion, it can also just be incredibly normal.
SpeakerYeah. Um, I don't know if it's a hot take or not.
AnnE DiemerOkay.
SpeakerBut there's been a lot like middle management is not dead. That's my thing. Middle management is vital. Um your line managers are the most important part of your organization, and they are worth way more investment than you're probably giving them.
AnnE DiemerYes.
SpeakerUm that's you live or die by those people, right? Like they're managing their teams that are doing the work, that are making your business your money, and they're probably were never taught how to do that. And so, you know, and may or may not have had good examples coming up. So like if we're talking about getting rid of middle managers and it's going to be replaced by like AI or whatever, that feels to me like a bad recipe. We should be doubling down on those line managers, train them, invest in their development, make sure that they know what they're supposed to be doing, how they're supposed to be doing it, they know what decisions they can make, they know how to apply judgment and when to apply judgment. Like that's where you're gonna find success or failure.
AnnE DiemerWholeheartedly agree. And I think that's important. Like no matter the size of the organization, you know, we've been talking about media organizations, which are huge, that makes middle managers, line managers even more important because that's how you as HR or you as leadership are connected to the majority of the organization. They're so crucial.
SpeakerAbsolutely. Well, and in the smaller companies that I've been working with lately, whether that's you know, by full-time work or some of the consulting and fractional work that I've done, like one of the conversations that I have with founders a lot is like it's not too soon to start thinking about this. As soon as you have your first layer of managers, like that's when it's time. Like, you know, you're super early stage, everybody reports to the founder, whatever you can get away with it, right? As soon as you've got a layer between the founder and your most junior employee, like that's when it gets important. Yes. People need to understand how to help the business run, because also that lets your founders and your leaders like get out of the weeds and like build the business, right? Because that's their job.
AnnE DiemerAbsolutely. That investment makes a big difference. And I think speaks to other things you've talked about, like building that social contract within an organization, building that foundation. A lot of that comes from line managers. Maybe we're directing it as HR or as leaders, but upholding it and sustaining it, that comes from the line managers.
SpeakerA hundred percent. And that's who lives the values, right? Whether you have them written down or not, like that's who lives your real values. That's who demonstrates your culture. That's who defines like what is acceptable and normal and rewarded and tolerated.
AnnE DiemerSo now we're gonna move on to the lightning round. This is where HR is everywhere really comes to life. I'm asking every guest the same question so we can see how different HR looks depending on the organization. There's no right answers, as we've been talking about. There's no one answer in HR. It depends on your circumstances. So let's have you answer these questions from a media organization perspective for HR. And if there's a different example for like Playboy specifically, we can go into that. But otherwise, generally, I think, because ultimately it's still a workplace. As you were saying, like people joke about reading it for the articles, but like there are articles are really good. Yes, yes. It's still there's writers there. That needs to be part of understanding the overall business.
SpeakerYeah. So, okay, uh I'm just like taking all the time, but quick like side quest. So while I was I was working at Playboy when my son was born. And so, of course, like I'm thinking, preparing for this seminal moment 18 years in the future. I'm like, here's the issue from your birth month, and it's saved and like, you know, encapsulated in plastic and blah blah blah. On his 18th birthday, I present him with this, I tell him the whole thing, and he could not care less. He's like, What? Like, kids don't even know what Playboy is. It's not like a cultural, culturally relevant thing. So, like 18 years of anticipation for this moment that just like nothing.
AnnE DiemerJust nothing. Okay, well, um, this episode is for millennials and above. Gen Z, we'll catch you on the next one. You don't know what we're talking about here, and that's fine. That's totally fine. I love that you did that though. That's such a special thing to say for him.
SpeakerI thought so.
AnnE DiemerYou tried, and that's what matters. I mean that's what HR comes down to sometimes. Let's go with this lightning round. First up, most common worker classification, exempt, non-exempt, or contractors?
SpeakerExempt.
AnnE DiemerExempt. Okay. I thought it might be contractors for media.
SpeakerNot in my world. I think there are a lot of contractors. Like there are a lot of like freelance writers and reporters and things like that, but that wasn't the world that I touched. Totally.
AnnE DiemerUnion or non-union?
SpeakerIn my organizations, they were all non-union. One of the reasons that I was never able to move into newspapers was the union factor. They did not want anybody that didn't know how to deal with unions.
AnnE DiemerInteresting. Wow. Follow-up conversation about that. We'll save it for another time. Okay. Performance reviews. Annual, quarterly, continuous, or never?
SpeakerAnnual is most common. Okay. And I like annual.
AnnE DiemerYeah.
SpeakerIn conjunction with continuous feedback. Which was not always there.
AnnE DiemerNo. That's a common answer I think I'm going to be getting from HR folks. Onboarding. Week-long process or longer? Or sink or swim?
SpeakerUh so most common in the media industries where I worked, sync or swim. Not what I would design if somebody asked me.
unknownNope.
AnnE DiemerYou're just executing. I hear that. Exit interviews. Essential or a waste of time?
SpeakerWaste of time.
AnnE DiemerCan you think of someone who you fired who you would rehire?
SpeakerEasily. Many people.
AnnE DiemerSo many people. So many people.
SpeakerPeople get fired for all kinds of reasons. Most of them are not that they're not good at what they do.
AnnE DiemerOr made a deeply inappropriate comment about sideboob.
SpeakerYeah, I mean there's that.
AnnE DiemerVacation time. Unlimited PTO or accrued PTO?
SpeakerAccrued. Accrue that shit. Unlimited PTO like just takes away PTO from people.
AnnE DiemerThere's value in that. We need to track it.
SpeakerYeah. I can see how many days I have. I'm going to take them.
AnnE DiemerTime tracking. Time sheets or YOLO?
SpeakerTime sheets for billable work, right? So I have worked in professional services organizations. Time sheets, absolutely, right? Like but otherwise, especially when you're talking about largely exempt population, no, do the work. I don't care when.
AnnE DiemerAwesome. Love it. Background checks. Specifically interested in this one for Playboy, if you remember. Standard, extensive, industry specific, something else?
SpeakerStandard. Criminal aliases, national watch list. Like, are you convicted of something bad? Is the one question.
AnnE DiemerDress code. Not so much a thing anymore, as you said, but when it is in place, formal, business casual, or anything else?
SpeakerSo in my like if we're going media, it's always been business casual. Um which like also evolved over the years in itself because business casual when I started was like was meant no tie and an unbuttoned top button.
AnnE DiemerYeah.
SpeakerUm and then it evolved, right? Yes. But now like I'm a like anything goes guy, right? Like, yeah, nothing crazy. Don't have like swastikas on your hoodie, but like the hoodie is the is not the problem.
AnnE DiemerAbsolutely. Um Slack Teams, G chat, signal, something else. How are you keeping in touch with people?
SpeakerGive me Slack all day.
AnnE DiemerAll day. It's so good. And then lastly, what is your favorite state in the United States to deal with?
SpeakerI'm gonna go with New York because it's familiar, because I know it, right? Like I don't have to Google things when I'm dealing with New York regulations and figuring out what we need to do.
AnnE DiemerThat's a good enough reason for me. Okay. Thank you so much, David, for this fantastic conversation, giving us a little bit of insight into a workplace that we have stereotypes about, and some maybe can be upheld, but also reminding us that workplaces are workplaces and HR is a way to see what's happening behind the scenes. I really appreciate it.
SpeakerIt's been my pleasure. This was really awesome.
AnnE DiemerWhere can people find you or learn more about working with you?
SpeakerFind me on LinkedIn. That's where I don't shut up. Um, I tend to post relatively often. Uh, you know, and so hear about what I'm thinking, what I want to do, how I approach things. And if that resonates, then like let's have a conversation.
AnnE DiemerAwesome. If you want to hear about why line managers are so important, then you're checking out David on LinkedIn and probably some other important things too.
SpeakerNo, that's all I talk about.
AnnE DiemerNo, just line managers. Thank you for listening to HR Peep Show. HR is everywhere, and trust me, we're gonna find it in some weird places. Subscribe to see where we go next.