The Breakthrough Hiring Show: Modern Recruiting, AI, and Talent Strategy

EP 225: From Animal Behavior to Talent Teams: Leading with Positive Reinforcement

• James Mackey

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0:00 | 48:00

Host James Mackey sits down with Jennifer Anker, a talent acquisition executive who has built and led recruiting organizations at Illumio, Twilio, Wiz, and Okta. Long before recruiting, Jennifer studied animal behavior and worked with marine mammals - an experience that shaped the calm, positive-reinforcement leadership style she still uses today.

Jennifer and James explore how to deliver direct feedback with empathy, use positive reinforcement as a genuine management philosophy, and build teams that feel empowered to challenge ideas - including their leader’s. They also discuss overcoming imposter syndrome, creating a culture of “disagree and commit,” and adapting coaching to what motivates each individual.

The conversation closes with a practical look at AI in recruiting, from note-taking tools to custom AI agents, and why recruiters who learn to work alongside AI will have a significant advantage over those who don’t.


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Welcome And Meet Jack

SPEAKER_04

Hey everyone, welcome to the show. I'm your host, James Mackey, and today we have Jennifer Anker with us. Her colleagues know her as Jack. And Jack has been the in talent acquisition leadership roles for company like Twilio, Wiz, most recently Illumio, and even Okta, I think previously, right? So, anyways, Jack, really looking forward to learning from your experiences throughout your career and learning more about you as a whole human being. So welcome to the show.

SPEAKER_00

Thanks, James. Glad to be here.

SPEAKER_04

So where are you from?

SPEAKER_00

So originally was born in New York City and grew up in Pennsylvania. And then I don't know, 25 years ago or so, I moved out to San Francisco and I've been here ever since. But I still am at heart and East Coast girl.

SPEAKER_04

Gotcha. Do you ever visit home at this point or are you full-time upset?

SPEAKER_00

Unfortunately, I rarely do because everybody has since moved west. So both my brothers and my sister and my parents, they're all out west. I don't get home as much as I'm used to.

SPEAKER_04

Ah, gotcha.

SPEAKER_00

Are they in San Francisco with you or or my brother is, and then my other brother and sister actually live up in Seattle with my team. Yeah.

SPEAKER_04

Seattle's a fun city too.

SPEAKER_00

Yes. It is beautiful. If you can, if you can deal with the rain, it is a beautiful town.

SPEAKER_04

Yeah, for sure. Nice, nice. And you so we before we recorded, you were telling me a little bit about how your dad was such a huge influence on who you've become as a person and professionally as an executive. He was pretty supportive of you, right? And yeah, helping you pursue whatever you'd like to.

SPEAKER_00

Yeah, early on, I I knew I had a love of animals and I knew I wanted to do something along those lines. And so in high school, I took a lot of science, took a lot of advanced math. I went to an old East Coast school that had old teachers that, you know, I remember I was in a calculus class, and the it was with about 10 men and me. And the teacher never called on me, never raised, never let me answer any of the questions, and didn't think I should be in that class. And my dad was not having it and gave him the Riot Act and turns out and supported me and helped me through it all. And then turned out at the end that I was the only one who passed the AP exam. So he taught me very early on that there isn't anything I can't accomplish. And that support has very much translated through my whole life.

SPEAKER_04

Do you always say you just helped you develop the psychology where you could bulldoze through any obstacle?

SPEAKER_00

Yeah, I think women have girls and then women have a harder time with imposter syndrome and all of that. And I still have that, but I have him in the back of my head reminding me that it doesn't matter if I'm a woman or a man, I can do it and I can, I should keep pursuing what I want to do, regardless of what anybody else tells me. And that has translated, like I said, into I think I mentioned an early career of animal training versus even just getting into recruiting and not being scared to try something new.

SPEAKER_04

Yeah. Do you feel like to be successful, it's more about not feeling those things to begin with? Or is it really just more of an emotion of overriding it? Right. Like you feel imposter syndrome. Do you does it get do you feel like it gets easier over time to just not feel that way? Or is it something that

Family Support And Early Confidence

SPEAKER_04

you think is just like constant? It's very normal for people to just constantly have to override that.

SPEAKER_00

Yeah. And I think it is a a bigger topic for women. I'm not saying men don't have it, but I, you know, I coach a lot of women, I mentor a lot of women, and and on my team, I have a lot of women and I hear about it a lot. And I think it's not something that there are some people, some women who don't have it, but I think even if it's not about not having those feelings, it's about not letting them freeze you so that you can't move forward. And it's about overcoming them and taking pride when you do, right? Being they say, what is it? Fear is not the is not being scared, it's being able to get past being scared. And that it's the same philosophy. So pushing forward and still doing it because it's what you want to do, and then feeling so accomplished when you do.

SPEAKER_04

Yeah, for sure. It's like courage is a virtue. It's like this idea of virtues wouldn't be virtues if there weren't alternatives. Your alternatives, courage is a virtue because it can be hard to be courageous. It could be hard to hold yourself to a standard to overcome, to push to overcome those things, to try to do your part to overcome those things, right? Yeah. Yeah, yeah. So that's commendable. That's awesome. And you were you were one of four, right? Siblings growing up.

SPEAKER_00

Yeah, I have two older brothers and an older sister. So yes.

SPEAKER_04

So you were the youngest.

SPEAKER_00

I was, which probably shaped a lot of my behavior as well. Everybody always says there's birth order issues, and I definitely have them as the baby of the family. But and I hate to give my brothers credit for anything, but I'll give them the credit that they definitely taught me at an early age to have a thick skin, which I think in the business world is really important, not to take things so seriously or personally. I'm not great, I'm not perfect at it by any stretch, but I'm so much better than I think I would be if I didn't have my big brothers in my life.

SPEAKER_04

Oh, yeah. That makes sense. And so you had a really interesting upbringing as a young adult because you took a career path that I think a lot of people would find fascinating, but just for whatever reason they'll get into. So you, when you were in college, you studied marine biology or marine, what did you study?

SPEAKER_00

In college, I studied animal behavior mostly because I went to school in upstate New York. There isn't a lot of marine around there. So the closest thing I could get to was animal behavior. And yeah, because I really wanted to work with animals. Growing up, I was that kid. I remember we had a big mulch delivery one time, and there was like a baby rabbit that got separated from its mom in the mulch. I'm the kid who brought it inside, tried to nurse it back to health. And then when it didn't work, I was devastated. I was just always an animal lover. And it was another example of my dad and my mom really supporting me. 16, they sent me to Kauai for a summer by myself, where I got to work in a lab with a world-renowned animal behaviorist who was training dolphins. And I got to be an intern there for the summer and get really close to the animals and watch him do experiments and all cognition on how dolphins think about things. And it was fascinating. And I was 16 across the country from my parents and having a blast. So that just sealed the deal. That's what I wanted to do. And that's why when I went to college, I very much focused on working with animals.

SPEAKER_04

So, what kind of experiments were they doing on dolphin cognition?

SPEAKER_00

Like what Yeah, the one I always use as an example is so they had hand signals for all the things they wanted the animals to do, including toys that they had in their pool. So they had a clothing basket that had a signal, and then they had a football that had a signal or a ball. And so what they were trying to understand is could dolphins understand syntax? So if they said put the ball in the basket, would the dolphin know to take the ball first, put it in the basket, or would it take the basket to the ball and not worry about the syntax? So it was, he had been doing these studies for decades by the time I got there. So they were getting really complex and learned fascinating things about dolphin language and how they communicate with each other and how really smart they truly are.

SPEAKER_04

Wow. So how how well do they do with syntax? What was the very well?

SPEAKER_00

Like shockingly, yeah, very well. And then other things I've been around where they were training or working with killer whales, learning how they communicate with each other. Killer whales are in pods and they all have different languages. Where I worked, we had a killer whale from the Pacific Northwest paired with a killer whale from Iceland. And when they first met up, they couldn't communicate with each other. And so they watched, and there was a researcher who worked with them that watched and saw how the languages evolved and that the younger one evolved to the older one's language, which was the one from the Pacific Northwest. So it's fascinating work and work that then translated into helping them in the wild, believe it or not, right? Understanding how they use sonar actually helped scientists and researchers advocate for the Navy not to bomb in the oceans because it actually impacted

Imposter Syndrome And Moving Forward

SPEAKER_00

these animals and how they migrated and how they communicated with each other. So it reduced the amount of stuff that the Navy was doing in the oceans. So yes.

SPEAKER_04

So how did you get into that program in Hawaii? How did that something all the way from the East Coast?

SPEAKER_00

Yeah. That was lucky. That was a program called Earthwatch. I don't even know if it's still around, but back in the day, it used to be the concept that you're going to be an environmentalist and give money, but instead go and see the work that you're contributing to. And I applied and got accepted. And again, my parents supported me to go there and they paid the money. And I got to, it was an unpaid internship. I won't make it glamorous. I was definitely not paid, but it gave me so much great experience to do that. And again, I don't know if Earthwatch is still around, but if it is, it's a fantastic organization for kids to go out there and actually experience not just life, but the environment. There was a couple things that it there was one about learning about the great apes in Rwanda that I was very tempted to do, but I'm much more of a marine animal person, and I did that one instead.

SPEAKER_04

So cool. What a cool experience to have growing up.

SPEAKER_00

Yes. Yes. And again, it shaped, then I went to college, and like I said, it shaped everything that I did. I got an internship at a local zoo and worked at the zoo while I was in school, also then trying to get my degree in biology in the middle of New York. So I was very lucky. And then I got a couple internships over the summers. I worked at Cape Cod Aquarium. And then the next summer I worked at the Mystic Aquarium, which was amazing with like feluga whales and everything. And then when I graduated, I was able to parlay all that experience into getting a job out here, actually in the Bay Area, with an organization called Marine World, and got to work with killer whales and dolphins and sea lions and seals. And I was living my best life in my 20s doing that.

SPEAKER_04

That is amazing. Yeah, killer whales, all these animals are fascinating. Killer whales are fascinating. They really are. I they're in the news lately because they're bumping into all these ships, boats. Is that up in Alaska? Or where is that?

SPEAKER_00

No, actually, I believe if I it's over by Morocco, I think, or by where Africa and Europe meet. I think it was in that strait that I've been hearing about them beating up on yachts. I think it's hilarious.

SPEAKER_04

Are they like just curious? Apparently, there's like they have the cultures, right? And it's and it and so it's some scientists think that it's just like a fad. They're just kind of copying behavior from each other.

SPEAKER_00

And they do. They very much copy behavior and very geographically will copy behavior. There's there's in North Carolina, there's a pot of dolphins actually that have learned how to beach themselves on the beach to go after fish and then wiggle their way back in, but they don't see that anywhere else. So it's it's and then they learn it from their mother because it's a very matrilineal group, and then it just gets them handed down. And the problem is that one or two probably started this by accident, but then they're teaching their young, so it's gonna continue to happen. But I think it's hilarious.

SPEAKER_04

Yeah, it is, it's kind of wild. I yeah, I don't know. Hopefully, they stop so it doesn't become an issue for them, you know what I mean?

SPEAKER_00

Or people don't end up doing something they shouldn't, but yes, that is the fear, but they have not hurt anybody. Yes, they've hurt some votes and they've hurt property, but they have not hurt any people. There is no recorded incident of a killer whale hurting a person in the wild.

SPEAKER_04

Really? Yes, zero, zero. There is a recorded video of a killer whale ramming a great white shark. I don't know if you've said that, but that was wild.

SPEAKER_00

That was great because that solved the age-old question of who is the top predator. No one really ever knew the answer. We had our beliefs, but we didn't really have the answer. And then when they caught that footage, I think that was actually out in the Fairlands out here.

Dolphin Cognition And Animal Behavior Work

SPEAKER_00

It was fascinating. And it confirmed our hypothesis that the killer whales would win every time.

SPEAKER_04

Oh, yeah, for sure. I so I play this game with my girlfriend where we both this is so random. We'll pick teams of five animals and ask Chad and Claude which team would win.

SPEAKER_00

That's a little random.

unknown

Yeah.

SPEAKER_04

We have way too much fun for this. But yeah, it's just, I don't know why that just reminded me of that. But you should play sometime up, serious. Play with your kids. It's it's a great game.

SPEAKER_00

But you always pick the killer whale.

SPEAKER_04

Yeah, I'm gonna pick the killer whale. Let's pick that one next time. Yeah, no, they're just incredibly powerful and strong. It's when I watched that video, I was just blown away. I was like, oh my god.

SPEAKER_00

Yeah, it's incredibly strong. And the other thing about the I don't know if there's more than one video at this point, but I know the one that you're talking about. What they also don't tell you is that it was a mom killer whale that had a baby with them, and you never mess with a mom. I don't care what kind of animal it is, you never mess with a mom. 100%. So I think the killer whale would have won regardless, but you absolutely don't mess with a killer whale mom.

SPEAKER_04

Yeah, yeah, no, that's the same with hiking, right? With bears and yeah, particularly the black bears are like very actually gentle creatures. You still don't want to accidentally get in between mom, right? Baby, yeah.

SPEAKER_00

100% you do not want to get cool.

SPEAKER_04

So, like I I think during this time when you were working with a lot of animals throughout your 20s and doing research. You also you told me about a book you were reading, you had read at the time in college, right? Called Don't Shoot the Dog. Yeah. What's that about?

SPEAKER_00

Yeah, it's a by a woman named Karen Pryor who's one of the pioneers of animal training. And so I knew if I wanted to get into it, there was a book I should read, and I did, and it was fascinating. It's the whole concept of operant conditioning and positive reinforcement, right? It's used to be even just training your dogs, people would smack them if they peed or pooped or whatever. And and this concept is just not to. It's and it works, and I'll tell you how it translates into humans, but it's you just focus on the positive things people do and or animals do, and you don't you just ignore the negative stuff. And what ends up happening is you shape their behavior that obviously they want to be rewarded, so they continue to do the positive things. And so it was very impactful, just not only in like how I think my leadership philosophy evolved, but just in everyday life. Little things when you're trying to get yourself to, I don't want to go to work today because I have to go all the way to the train station, then I have to take the train into work, and then I have to go to work, giving yourself reinforcements along the way, it's small things, but they're impactful and they help to encourage you then to continue doing it. So it's stuff you can use for yourself, but it's absolutely stuff you can use then when you're a leader. I would like to think that's how I manage people. I don't ever get mad when people make mistakes, A, because everybody makes mistakes, but I don't want to focus on those. I try to only celebrate the wins, the big things, right? I don't make a big deal about the mistakes and all of that. And I think that's how that has shaped my leadership because it's very valuable to people. Everybody makes mistakes, everybody wants the gold star by learning. So if you can reinforce that, you're gonna encourage the right behavior.

SPEAKER_04

For sure. How do you handle like serious conversations, feedback situations? And there's like mistakes. There's some mistakes I've learned as a leader. Like people can course correct. I don't even necessarily, not every mistake has to be a conversation to get it. And the solution is obvious. It's a situation where you have to know the person. But like I've had some folks work for me where like I just I know that okay, yeah, they made a mistake, but they know it, and I feel confident that they're how they're wired, they're gonna fix it. Like, I don't have I don't even have to talk about it. There's other times where though, like you have to, I think maybe you don't agree, have to have those kind of conversations to change a behavior or some kind of something that's going on. So, in those cases, how do you do that? Yeah, just like with what you're discussing now.

SPEAKER_00

Yeah, good question. And and I agree with you, there's a lot of people in kind of the recruiter mentality that I try to hire, they're gonna beat themselves up over that mistake way more than I could ever. So, what's the but there are people not like that who end up either through you acquire a team and you don't have a choice in who's on it thing that you have to manage. And I also another book that I believe in very dearly is radical candor, in the concept that being very honest and transparent with people and your feedback actually helps them get better as long as it's presented in that way, right? I'm not a I have worked for CEOs, I have worked for leaders that are very much yellers, I even had one who threw things. It is not my style at all. My feeling is it's not a mistake if there's a thought behind it. And so I have had people on some teams where when I say, Why did you do it that way? I'm just curious about your thought process, and they had no explanation. That's where I do get disappointed when I do. I, if there's a thought process, it couldn't be the wrong one, or in my opinion, the wrong one. But as long as there's a thought process behind it, okay. So let's talk about that thought process and why maybe that wasn't the better way to go, but at least you thought about it and made an educated decision. The ones I struggle with are the ones who come to me and are like, I just thought that's how you'd want me to do it. And I was like, that's not a reason. And so that's where real radical candor plays a part in what I do. And I'm very honest about it. I do say I need you to think these things through. And if you're not going to, then you need to call me and we can think things through together. But you need to think it through and actually think about the outcomes and figure out what the right answer is. And when mistakes happen, my team knows people who have worked with me multiple times now, when they know that they've made a mistake, they always come to me with solutions. Hey, I messed this up, but here are the three ways I think we can fix it. How do you want me to do it? Yeah, I'm very solution-oriented. Okay, great. Let's figure out which is the right one.

SPEAKER_04

Yeah, I feel like the like the best employees are like the ones where like they hold themselves to a high standard and they are going to course correct. Yeah, but also then they don't crumble under constructive blunt feedback.

SPEAKER_03

Yeah.

SPEAKER_04

And sometimes it's hard to find both because some people, if they course correct, they'll they're like hard on themselves, and then and it's sometimes harder to give you give it, have to give them feedback less, but like sometimes it can be hard giving them feedback because they're already riding themselves pretty hard. It's uh it's it's interesting. I I definitely think sometimes with management leadership less is more in some cases. Like it's a balancing act though, right? And it's oh for sure. But yeah, radical candor. And that's actually something I don't know about you, but that took me some time in my career to get comfortable giving really blunt feedback without some people just the Oreos stuff where it's like you do the content and then the and I'm like, well, come on, we're all adults. Let's just let's be respectful, of course, but let's just yeah, I try to set an expectation on my team. Like, I talk about I don't call it radical fandor, I guess. I guess I could because people are familiar with the term at this point, but like, yeah, it's more of just a look, it's it's just be blunt. We're on the same team, we all want to win. I use I typically praise success. And if there's a challenge we need to address, then I'm gonna call that out too. And just keep in mind it's coming from a place of like, I want you to be successful. We have to have clear community communication in order to do that. So that's how I I mean, yeah, that's how I articulate it.

SPEAKER_00

Well, and what you said it a little bit earlier, and this kind of rolls into my animal trainings kind of background, in that not everybody can you can't treat everybody on your team the same way. And you really have to understand what makes each person go. And I have certain people on my team where radical pander absolutely works, and I do that, and I they know that it's coming from a good place, and they know that feedback is only there to help them. Others, like to your point, they need the Oreo, they need the good, the ugly, then the good again, right? And so I know to do that with them and make sure that they know like all the things they're doing really well and kind of sandwich in the negative feedback right in there. And so I think good leaders, just like good animal trainers, you can't train every animal the same way. You can't have everybody on your team, you can't respond to them the same way. You have to really tailor how you are. And that took a lot of learning for me because I'm very for I'll tell you, my previous manager's chief people officer, asked me, I don't know, a year after we've been working together. I had feedback for him and his leadership. And I said it, yeah, you need to give me more radical candor. I can't read between the lines. That's not me. That's not my, I need to just know when I've messed up and we'll talk about it. And then and he's like, oh, and he's so much of an Oreo person. I'm just like, no, don't sugarcoat it for me. Just lay it out and I'll get it done and I'll be upset at the moment, and then I'm gonna go fix it and move on, and I will have learned that's what works better for me. And I think that's where leadership's so important is having those discussions with those people to understand what makes them tick and what makes them. That's where reference checks are great, right? Like, how did you give feedback to this person so that I know how to give them feedback?

SPEAKER_04

Yeah, that's a good, that's a solid reference question. I yeah, no, I agree. I guess I have a slight bias toward like individuals that we can just can we just have like one conversation and move on. I uh and I do, I think, yeah, I am like I do I do situational leadership is incredibly important and management is incredibly important. And I do it to some extent. I think I maybe I do it like a little less than I used to, though, because I I do I still do it, but there's a part of me like in terms of like the culture I want to build when I think about culture building an organization. I again have a bias toward a radical candor kind of culture, and I try to hire people in, but I also need people to understand look, just like if you're on a professional, this is a high performing team, just like in a professional sports team, I'm considering like your coach, right? You got to get in, be clear about what needs to be done. And yeah, and so there have been it's a balancing act, but I actually one of my companies recently had somebody leave, and I think it was because it was more of a radical candidate. Very respectful, but just I think I don't think it's for everybody. And it's like I'm also as I'm trying to find a place to believe of how much should I adapt versus like how much should I also decide the culture I want in the organization

Orca Culture And What Scientists Learn

SPEAKER_04

and kind of stick to that too? Does that make sense?

SPEAKER_00

It does. But one of the Things I'm very clear with my team on is that I don't build the culture, we build the culture.

SPEAKER_01

Yeah.

SPEAKER_00

So I tell them what I like. The one thing that I won't compromise on, and this is to your point, is that open and transparency, right? That radical candor. But I tell them very clearly it has to go both ways. And I expect them to give me the same feedback.

SPEAKER_04

That's hard. Yeah, that's it's hard to convince some people to do that. A hundred percent. People don't want to give their boss feedback.

SPEAKER_00

100% to the point where I have at some points actually planted people to challenge me on things in front of other people so they can see that's okay. And I think some of the younger generations confuse my not agreeing or not my in general, a leader not agreeing with them with that they're mad at them and they're in trouble. And it's like those are two different things.

SPEAKER_04

Yeah, it's totally different things. And it's hard, it's it could be hard for people to absorb that. But I do think it's it's important for and we could, I think too. It's like as you could say that to your blue in the face. Look, if I give you constructive feedback, it's because I'm here to enable you to win and you have to have clarity around like how to do it. We can say that all day, but I it's people still sometimes it can be hard. I think it could be hard for all of us, even us, people who appreciate it and want it. It's still not always easy. Here it is.

SPEAKER_00

Oh, it's never easy to hear that you screwed something up and right like it's like, oh my god. We're one of those, we're probably those people that we beat ourselves up more than they're 100%. But I would much rather know and just it be done than try to figure out what did he mean by that? Did he really think, or was she that? I'm not good at that. I'm a very like honest, open, transparent person. And I think for me, what works really well is direct feedback. Oh yeah, and again, I really try to instill that in my team that I want them to give that to me as well. And yeah, based on some of the people who work with me, I think they've gotten the message because they have no problem telling me when I've messed up and I'm like, hey, like there's definitely been a couple of times, but that's right.

SPEAKER_04

Because every once in a while I have to catch myself because there's been a couple of times where I'm like, damn, that was like I was like, wow, I feel comfortable speaking to their boss like that. And then I think it was like, oh yeah, this is exactly what this is exactly what I'm asking for. This is great. Yeah, see, that's but this is the point. It's not necessarily easy for anyone, but it's important, right? Like it's also I feel like creates this culture of like mutual accountability too. I think it goes hand in hand with accountability. We're all in a healthy way, like trying to help each other elevate, help each other be the best versions of ourselves as individuals and as a team member.

SPEAKER_00

Yeah. Someone who worked for me a long time ago was her first job out of college. She was with me all through Twilio and has become an amazing manager in recruiting now. She told me a story that I didn't even remember of when she first started to be a recruiter, where she came and asked me, she wasn't sure how to handle a situation. And so she asked me, What did I think she should do? And so I gave her my opinion and she went out and did the exact opposite. And she said, and this is why she told me the story, she said, most people were like, Oh my God, your manager must have been so mad at you. And she goes, Do you remember your response? And I said, No. She goes, Your response was, I've never been so proud of you because you trusted your gut. You did what you thought was best. Does not always gonna be the same answer as me, but you were so proud of me because I had come so far in acknowledging that I knew my stuff well enough and you were giving me that confidence. And she was right. I didn't remember that story, but she was right. That's a prideful moment when you've helped somebody grow in their confidence, not just their career, but in their confidence to make the right decision. And if it worked, great. And if it didn't, okay, you're gonna learn, but you have to trust your gut and go with it. And so very early on, I was very happy when people disagreed with me, weirdly enough. I know that probably makes me weird, but I I think from disagreement comes really good things.

SPEAKER_04

Honestly, I get a little bit worried when I make an announcement that I know is gonna be somewhat controversial or that everybody's not gonna like it and it's crickets, or everybody seems to free. I'm like, all right, okay. I know that there's some side chats happening on Slack right now. 100% when I don't hear the disagree. I'm like, okay, well, it's like maybe like sales, like what are the objections not in the room, or like that people say on the call on the not on the call. So I almost like I think it's like we should expect, and if we don't have it, it's not that we're perfect or that everything we're communicating everything perfectly. It's that okay, there's some people not even necessarily due to the fault of how maybe I communicate per se, but it could also just be like how they're wired where they're just not comfortable giving their boss like feedback. So yeah, it's something that I think it's important to be aware of that as a leader. Like, yep.

SPEAKER_00

Oh, a hundred percent. And I think that's really where you also can role model it with how you manage your team. And one of the things I do wrestle with sometimes when a company makes a decision that you don't agree

Positive Reinforcement Becomes Leadership Style

SPEAKER_00

with, you have to buzz the head of talent. You have to be out there, lock arms, right? You can disagree and commit, right? You lock arms, you go forward. But sometimes you have to be really transparent with your team because if you walk out there and say this is the best thing ever, they're gonna look at you and be like, you have no credibility with me because I know you don't think that. So there's been times where I haven't and I've gone out and I've said, this is a crappy decision. I don't agree with it. However, we have to do it. And here's how we're gonna make it work, right? Within these four walls, we can vent about it. But when we walk out in front of a business, this is how we're doing things.

SPEAKER_04

But that's I think in a very important thing. There's a lesson here too when it comes to leadership. And I think actually a lot of people get this wrong, and I think it stunts their growth in leadership roles. So it's like understanding that your responsibility first and foremost is to the other members of your leadership team. And regardless of whether or not you agree or not, you are a team. And like we make decisions together, and we have to be focused on okay, the company's North Star, what what we're trying to accomplish and working together. And uh it's not that our team, like folks that you know work on it within a specific function, aren't also our team, right? But it's like what you're saying. It's like regardless if there's a disagreement, it's like that's your your number one, like we're accountable to each like each, like the execute's accountable to each other first before to their department. And I think that that's hard for some folks because it's like they have there's this idea like of and it's genuine, like as a leader, like you want to lead and you want to put obviously we want to put our people first, and like we want to be good to keep managers and leaders, but I think sometimes uh people trip up on this in terms of understanding like how like order of operations, yeah, when it comes to these dynamics, right? But I think you said it was like very well said, it's like transparency and candor is like very important, and then also like being clear on and regardless of that, like here's what we have to do.

SPEAKER_00

Yes, yes, a hundred percent. It is a challenge sometimes because I know I've had to learn in my career because I'm very passionate about what I do. I care about my reputation, I care about doing the right thing for the business. I've had to learn how to not, I don't want to say not care, but pick your battles, right? Pick the ones that matter rather than picking every single one. And it's still something I'm working on and it's still something that will evolve. I'm much better than I used to be. It's hard behind closed doors not to get riled up and get passionate because you feel so strongly in what you do.

SPEAKER_04

I prefer that. And I again, this is another reason I prefer the radical candor approach because I feel like I can trust somebody. And I know that's not necessarily fair because people are like, I'm sorry, it is it, but it is, but I know that if somebody can is is the type of person give me one feedback, I feel like I can trust. Yeah, like we can have a conversation and I know what matters to you. And you're right, like you kind of have to pick your put context. How important is this? Do I is this really something that needs to be discussed, or do we have to do it? But it makes things so much easier.

SPEAKER_00

Oh, I agree. And I always say, I actually do really well with assholes at work. We all have them. Like I know everybody has the no asshole policy, but assholes always get through. And I, when this is probably going back to my brothers and how much they've helped me learn about it, but I am much better with assholes at work who own that they're assholes. Okay, then they're not trying to be anything but who they are. It's almost radical candor in a different way, but they're being honest. Where I struggle are the people who are actually assholes but pretend to be like, I'm so nice and I'm so great, and everybody loves me, but they're really assholes. Those are the people I struggle with, that fake, right? Like just be who you are and like just put it out there.

SPEAKER_04

And like I can both be an asshole and really care about you.

SPEAKER_00

I know it's very weird, but I really did in Zynga in the early years when I was there, I would was the first recruiter who was did non-technical. So I had all the non-technical roles, and we had some difficult managers back then, and I got all of them because I dealt really well with them. I just I listen, I when I say I'm gonna do something, I do something, and I just built great relationships. And I remember the CPO came to me at one point. She's how are you buddies with all these people? They're so challenging. I was like, I don't know, because they know they're challenging, and they I just ask them what they want and I work with them. And so I'm actually I in my early days when I was actually recruiting, was known for that being able to work with everybody who nobody else wanted to work with.

SPEAKER_04

Oh, yeah, for sure. No, I think I was actually just interesting that you're saying that because I definitely I in the early days of Secure Vision, my RPO, an embedded recruiting firm, that was I this was early days where a lot of what I did was like business one was like primarily referral based before we had more of a GT emotion that we're building these days. Yeah. And I just noticed that I was still the company was smaller, so I was like more hands-on. And most of my I started to notice that a lot of our customers mirrored this energy because we just got each other. And so almost became our customer base was like more of this radical candor, back and forth, very blunt, yeah, nonsensitive sometimes. But we would just and it we would it just worked. And I don't know, it was interesting, and now it's changed because we have it's a little bit different and in terms of how the company is structured, and I'm not everywhere, and it's not just referral-based, but yeah, it's interesting too how you tend to gravitate sometimes toward it's like because it's a it's like a language, right? Like it's a communication style.

SPEAKER_00

Yes, and again, I think people, if you are transparent for the most part, you're transparent and open, people trust you because they know what they're expecting, they know what they're gonna get. It's not a surprise, it's not a oh, everything's great. And then you turn around and say something different to their boss, right? Like I'm a big believer that if I have a problem with someone, I go to them first. In fact, we've all had hiring managers come to me to complain about the recruiters. My first question is always, have you talked to them? And the answer is no, I don't listen. Go talk to the recruiter. And if you two can't work it out, fine, bring me in, but you two work it out first.

SPEAKER_01

Yes.

SPEAKER_00

So I'm a firm believer in that. And I think that just helps the recruiters build the trust, but also helps you build trust. I'm not talking about somebody behind their back. They're gonna know you and I are having a conversation. Very, very transparent about all of that.

SPEAKER_04

Yeah, I think I think the balancing act to the radical candor side is also, and this is something that I would actually have been better at, I'd say the last several years, but I definitely didn't have it starting out. It was like communicating with high empathy, too.

SPEAKER_02

Yeah.

SPEAKER_04

The there's I see it's like

Radical Candor And Tailored Feedback

SPEAKER_04

this, okay. I need to operate in a way where I have really high standards, or you could say else radical candor to some extent, and empathy at the same time, not mutually exclusive, like those both, right? So it's like I can communicate in the way that we're discussing, and I can have really high standards, they can be really high, right? Like technology, as long as the level of empathy and support and that human side that people also really need, as long as that's there too. So I think about it too as a scale. And it's if I'm if my standards and how I'm going to communicate are like extra blunt. Am I also giving the reinforcement, maybe the positive reinforcement? I think is in a sense associated with empathy, like showing that you care and being able to roll up your sleeves or being available for people when they when you need them or when they need you to some extent, right? They go hand in hand, and you can I think it's easier, kind of I think that's an important element of it too, is showing that leading with empathy to some extent. Not over uh I think there's a balancing act for all things, right?

SPEAKER_00

But I think they're not they're definitely not mutually exclusive in the book. That's what the point is. And I think that by having radical candor, you are showing empathy because if I didn't care about your career, I'm not gonna waste my time telling you how you can be better, right? I'm telling you how to be better because I care about your career. I want you to grow, I want you to stay, right? I want you to be all these things. Whereas if I didn't, I'd let you go, but I that's not who I am. So I actually think that having radical, to me, having radical Panda shows that you do have empathy and it shows that you do care about the person and you do want them to grow. Yeah when it's on the right way. And I think that's super important that they don't they should not be mutually exclusive.

SPEAKER_04

Yeah, it's interesting. I think like one of the the the personality traits, I guess you can call it personality trait of a lot of people who come on this show, they have like different personalities in a lot of different ways, but like one thing is that they're very intellectually curious and they're very curious about how to continue to improve. I think like they appreciate radical candor. They they not they're the type of person that they want to know like what they're not doing as well at so that they can optimize. And I'm talking about like the top TA executives, like VPs at all a ton of the different companies like we've had on the show. Like I would say that's fundamentally one of the similarities is their desire to learn from others and to like really seek to understand areas for improvement.

SPEAKER_00

Yeah, that's why we get into the business, right? It's building that relationship with the candidates too, understanding their drivers, why do they want to make moves? How can our company help you get to where you want to go? And if not, where is the better place? The best recruiters that I know of don't always place the candidates with them. Sometimes the best recruiters go, you know what, this actually isn't the right opportunity you're telling me about, I think that one's actually better for you. And that's another version of radical candor, but that builds trust where you're not just trying to fill a seat, you're not just trying to push somebody into something that you're actually thinking about them. And that's where I think recruiting is heading. We haven't talked about AI yet, but with everybody's talking about AI, and I think that with all of the kind of advancements that we're making there, what that's going to do is push recruiters into having to relearn how to build that trust and those relationships with candidates. It's not texting them, it's not emailing them, it's picking up the phone and calling and really having more time to learn what their drivers are so that we can put them in the right roles.

SPEAKER_04

And that's, I feel like everything around revolving around what we automate, what we use AI for, how we're leveraging different workflows should be around like protecting and improving and just increasing the amount of like those human conversations that we're having with candidates and also hiring managers.

SPEAKER_00

Hiring managers, yeah. Yeah, no, 100%. Yeah.

SPEAKER_04

If they find an AI that can automate what three different hiring managers want to like align, that'll be the day that like recruiter life is going to get easier when you get everybody on the same page easily, consistently. Damn, I'm looking for it. If someone could sub make that tool, that would be pretty cool.

SPEAKER_00

Yeah, I don't think AI is that powerful, but I am.

SPEAKER_04

I don't know if it's 100% of the time. Yeah.

SPEAKER_00

But I think that plays into recruiters' fears about AI replacing them. I what I always tell my team, and what I think my role to help make them more comfortable with it is I don't think, and maybe I'm a Pollyanna, but at least right now, I don't think that AI is going to replace recruiters, but I do think that recruiters are going to be replaced with recruiters who embrace it. And so my job as a leader is to help my team embrace it, learn it, feel comfortable with it, and help the company grow with their AI usage to then be able to focus more on the relationships.

SPEAKER_04

Oh, 100%. It was like it's all about it's just other forms of automation, but the again, it's it's all about there's huge productivity gains that can be earned. There's certainly cost savings as well that that can be implemented with uh but yeah, the the whole uh point is to free up time so that recruiters can focus on candidate relationships, hiring manager conversations, feedback, alignment. And frankly, operating more kind of almost like a talent engineer scope overseeing a tech stack and optimizing the AI and different workflows too, which is I think fascinating. And I'm like seeing become more like a bigger part of a recruiter role too.

SPEAKER_00

Yeah, for sure.

SPEAKER_04

For sure.

SPEAKER_00

Learning how to, I just found out prompt engineering is a whole new category and and how important that is. And I'm still in the whole learning phase. I think I said I'm not I'm not a dial it up to 11 AI person, but I'm not a zero. I'm somewhere in between. And I think there's some amazing tools out there that I have demoed. We over in Ashvy Shop, and Ashby is amazing with the AI that they're embedding into their ATS so that you don't even have to go out and create your own. You can just use that. But there's some out there that I think is a little maybe too soon yet to be using. I'm a little unsure about the bots uh that will do the initial phone screens. I think it could work maybe with some more junior or repeatable roles. But do I think if I'm trying to hire a VP of talent that someone's gonna talk to a bot as their first interview? No. So I think we're somewhere in between. And I'm talking to me again in six weeks. I won't even say in six months, that'll change, but it's constantly evolving. And part of my role as a leader is to make sure that I stay on top of it and stay very, very understanding of what's out there.

SPEAKER_04

Are there anything like specifically any use cases for AI and talent acquisition that really excite you the most at this point?

SPEAKER_00

Yeah, we just use, and I'm I swear I'm not a commercial for Ashby, but they just rolled out a few months ago they're at their note taker. And to me, that was a game changer because I'm constantly, because I'm a recruiter, because this is what I do, I always make sure to have notes so that I remember everything and remember the don't have bias creep into the memory of the interview. But to be able to just sit back, not have to take notes, just engage with the candidate because I know that the note taker is going to take it all for me and then shape it into feedback. And if I can add to it and everything, but I don't have to write everything down. I can just stay engaged in the conversation. That to me was awesome and

AI In Recruiting And Real Use Cases

SPEAKER_00

remains awesome, right? Even having it on Zoom calls, because I, as I'm getting older, I forget things and if I don't write it in my book, I won't remember to do it. And so having Note taker on my Zoom calls, so then I can look through those at the end of the day and go, okay, what did I miss? What do I need to do? It's been game-changing for me. So that's one of the things that I think I was most excited about. But they're coming out with all sorts of things, just and having the agents in general. One of the things we did as a team is in Q4 last year, I had them all do agents. We did it as a whole people team. We had everybody build their own agent. And I didn't really care if they worked or not. I just wanted people to get fundamentally comfortable to build it, figure it out what worked, what didn't work, and then we can iterate over time. But I had one person on the team who actually built a great one that helped automate and increase the pass-through rates of resumes to one of our hiring managers who was very prickly. Whereas 20% were going through before when he built the agent, trained it, now 80% were going through to the point where the hiring manager came and said, you know what, I don't even need to see the resumes, just go ahead and start doing some were very impactful, some didn't work at all. And that's okay. And we all learned from each other. And we had sessions where everybody talked about what they were doing and what worked and what didn't work, and now we're iterating on that through the next few quarters. Like I said, just getting them comfortable with it was a big step.

SPEAKER_04

I'm starting to see the companies add like AI fluency testing into their interview process, which I actually am here for as long as the scope of what they're asking for is appropriate. Yeah. You don't want people to have to build a whole house just to interview for a role. But I just something like, hey, show us something you've built with Claude or put something together that could make your, if you haven't already, just put something light together that you think would be helpful for accelerating your workflow. And again, it's not necessarily about it being robust or working incredibly well. And I think it's even okay to set that expectation with candidates. Look, we're we're looking for baseline proficiency and your understanding of how these things can work, right?

SPEAKER_00

Yeah, yeah. It's one of the things I argue, not argue, but discussed with with our head of engineering, Metalumio, which was around, hey, we're hiring for AI skills, but we're not allowing AI in the process. And so I think that's where I think a lot of hiring managers, I don't think he's abnormal in that they're wrestling with that because they don't want to interview the AI. They want to interview the person. Sure. So where do you draw that line? So we did build a I built an AI transparency statement for Illumeo about where we want you to use it, where we don't want you to use it. But I think people are going to continue to use it how they want.

SPEAKER_04

But I do think it is important. I think it's like in projects where there's aspects. I of course nobody wants somebody just be reading from chat or Claude when they're answering questions.

SPEAKER_00

But they do.

SPEAKER_04

They do.

SPEAKER_00

They do. We saw one person that was interviewing had glasses on, and we could see it just typing out on their glasses.

SPEAKER_04

Yeah, I that's I don't know if I'm not gonna get into the ethics of that exactly. I'm not saying it's unethical per se. It's not that, it's just again, we're trying to understand the actual candidate, and that's not what we mean by AI fluency. Reading from a script, it's not what we mean.

SPEAKER_00

Right, that's not fluency. Yes, yeah. It always bothers me when people do that because I'm like, you do realize if you get the job, you will then have to do it. So if you're not qualified and you've portrayed yourself as being qualified, great, you'll get the job, but you'll get it for six weeks and then you'll get fired. Well, why not? I guess that goes back to my like crazy transparency stuff. But I'm like, I want to get the job because I'm qualified, not because I faked it.

SPEAKER_04

I don't, I still don't know. I guess maybe some ways, maybe sometimes these folks don't get caught, but it can it still fortunately is it's somewhat obvious if somebody's reading just like a can to general everybody knows how chat and club talk now. It's gonna get probably harder though to identify.

SPEAKER_02

Yeah.

SPEAKER_04

Um that's super interesting. I do want to get into the final segment of our conversation. Talk to you a little bit about just we've already touched on this, but like over the next few years, like really what's gonna be your focus in terms of your own evolution as a leader.

SPEAKER_00

Yeah, everybody always asks me, like, what's my next step? Do I want to be a CPO? And and I don't right now. That will change. It could talk to me in six weeks, six months. Maybe that will change. And I think with AI and everything that it's gonna do, I think the role of the head of talent is going to evolve. I think the time of really massive TA teams is going away and the scope is somewhat not shrinking because the scope is still there, but like the size of the team is going to get smaller. And so I've started to think about investing in other parts of HR, broadening my skills, and maybe CPO is the next kind of iteration of it. But I've always been very happy as the VP of talent. I love what I do. I think it's the best job in any company because you get to work with everybody across every discipline. I work with sales, I work with engineering, I work with GNA teams, and I have to understand how that all works together. And I have to understand our future plans and how I can be strategic with talent and help bring that company into that next evolution and scale. So I've always loved my job, but I think it is evolving over time. And like I said, that's where my head is now. Ask me again in six weeks. That question is going to be different. That's the crazy thing about AI. Literally, it is changing. It probably just changed and we didn't even know it, right? Like everything's just evolving so quickly. So I don't have my feet buried in the sand that I am staying where I am, and that's it. I'm thinking about the world around me and how it's changing.

SPEAKER_04

I love it. I love it. Jack, look, this has been incredible. I've really enjoyed this conversation. It's been pretty fast-paced, and I've been like super engaged. I actually remember I was telling you like before we hit record, I was like, like, sort of my goal as a host is to help my guests forget that we're recording. And there was a few times in this conversation where like I forgot. So I definitely had a really good time. It was a fun conversation. Thank you.

SPEAKER_00

Yeah, thank you. It was fun. It was a good conversation.

SPEAKER_04

All right. Well, thanks for joining us and come back sometime.

SPEAKER_00

Absolutely.

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James Mackey

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