OuttaDeeBox Podcast
OuttaDeeBox podcast is a pre-recorded bi weekly show geared towards supporting former and current inmates and their families in Wisconsin. Our mission is to inform listeners about community resources that can assist them in securing employment opportunities, housing, mental health and substance abuse support, with the goal of reducing recidivism in Wisconsin. We also give listeners and guests the opportunity to share their unique inspirational stories through spoken word and other forms of musical artistry.
OuttaDeeBox Podcast
Recruiting Revolution: Peter Gray's Journey from Wall Street to Social Impact
Peter Gray didn't set out to become an executive recruiter. Still, his journey from Wall Street to Madison, Wisconsin, reveals how powerful it can be when professional expertise aligns with personal values. As a Harvard graduate who still admits to feeling imposter syndrome ("Everyone thinks they're the one who got in by mistake—including me," he laughs), Peter brings refreshing authenticity to the often mysterious world of executive hiring.
What makes Peter's perspective particularly valuable is his willingness to confront uncomfortable truths about recruitment. He coined the term "round peg bias" to describe how employers mentally filter candidates against their preconceived image of who belongs in a role—one of the most pervasive yet rarely discussed barriers to diversifying organizations. Even more surprising is his revelation about LinkedIn, the platform most of us rely on for professional networking: "LinkedIn has a ton of systemic bias just baked right into it," Peter explains, detailing how this seemingly neutral tool can undermine diversity efforts unless used strategically.
The conversation weaves through Peter's significant impact in helping Wisconsin's state pension fund build its investment team (saving taxpayers millions in Wall Street fees), his community involvement with the Boys and Girls Club, and the changing landscape of DEI initiatives. He offers thoughtful insights on trade careers, mentorship, and how AI reshapes recruitment: "AI won't take your job. Your job may be taken by somebody who does what you do and knows how to use AI."
For anyone navigating today's complex hiring environment—whether as an employer, job seeker, or leader concerned with building diverse teams—Peter's experience offers practical wisdom and a reminder that meaningful work often comes from connecting our professional skills with the communities we care about. Connect with Peter on LinkedIn or through his website, petergraysearch.com, to learn how his approach might benefit your organization.
What's up everybody? This is your host, dee Star, here with Peter Gray. Peter Gray, how you doing, man? Not too bad. How are you doing, dee? I cannot complain. Welcome to my humble abode, abo-abord, abode.
Speaker 2:Abode right. Yo, it's great to be here in your lower-level podcast studio. My home office is the lower level of my house, too Awesome. So for the people that don't know you, can you tell us a little bit about yourself? Sure, I'm Peter Gray. I'm an executive recruiter. I run Peter Gray Executive Search. I wasn't actually raised in Wisconsin. I am a New Yorker who married into Madison and I'm coming up on 20 years in Madison. I'm not just a New Yorker. I was a Wall Street recruiter, and so I call myself a recovering Wall Street recruiter, and so I call myself a recovering Wall Street recruiter.
Speaker 1:I've seen that on your website I say recovering Wall Street recruiter. What does that mean?
Speaker 2:I recruited on Wall Street. I recruited for all kinds of investment positions. I got to tell you D didn't love Wall Street culture. So I enjoyed the opportunity to leave New York, move to Madison with some different people and different businesses.
Speaker 1:So tell me a little bit about your experiences.
Speaker 2:Oh sure, Well, I mean New York's fantastic. I was born in Queens, I grew up in the suburbs, I went to college and met somebody from Wisconsin and we moved back to New York City. So from the early—I'm in my 50s, so from the early 1990s until 2005, I lived in a few different places in Brooklyn in. Manhattan. We started our careers, we started our family and I love New York.
Speaker 1:On your website I've seen that you actually went to Harvard.
Speaker 2:Yes, that's where I yeah, that's where I met Jen, my wife. She is from Oregon, wisconsin, here outside of Madison, and I believe she was Oregon High School's first graduate to go to Harvard.
Speaker 1:So both of you guys must be wicked smart.
Speaker 2:I don't know. There's actually a fair amount of imposter syndrome. I'm still in touch with my Harvard alum friends and everybody thinks that they're the one who got into harvard by mistake really including me, and that's.
Speaker 1:That's like the culture. Yeah, it's like man we kind of sneak by.
Speaker 2:I don't know, maybe not everybody, they're probably. They're probably some people who feel a sense of entitlement about being there. Right, because there are some people who, like, the legacy model was strong, so there were people who were like whose father's father?
Speaker 2:yeah multi-generations of their family had gone there. And there are people who've gone, who went to um, some of the elite private schools where, like you know, several people from their private school class would go to harvard every year, and so they'd get to harvard and they'd be surrounded by friends and people they know. Was that your experience? That was, that wasn't me. I was the first person in my family to go to Harvard. I went to public high school and it's an amazing place. It's beautiful, it's very historic. It feels like you're kind of in the center of the world, because whatever's happening at Harvard, it makes Boston news and it often makes national news.
Speaker 2:So you felt like you were in the center of things and I never lost that sense of wonder. Corn Ferry is one of the big global executive search firms and I started my career there, my career as an executive recruiter. That was in New York City. I was there for about three years. That was a great learning experience. That was just my, you know, learning the business.
Speaker 1:For the people that don't know what is an executive recruiter.
Speaker 2:An executive recruiter people sometimes call us headhunters is someone who helps companies fill positions, and the model is when an employer has a position that is senior enough or is strategic enough or difficult to fill enough that they want to hire an outside consultant to help them search for candidates and to help them manage the recruiting process. That's what a recruiter is. So how did you get into that type of work? When I graduated from Harvard, I didn't know what I wanted to do, or I thought I wanted to. Actually thought I wanted to go into film and television production and I did that for a couple of years in New York. It was a struggle.
Speaker 2:I went to business school and when I graduated from business school I still didn't know what I wanted to do. So I went into management consulting. That was what my classmates if we still didn't know what our career path was, we often get hired at management consulting firms Did not enjoy that. But at the same time as I was management consulting I was kind of the unofficial class secretary for my business school class. So I was the guy who was kind of keeping us all connected and in doing that I kind of became the person who was helping people hire and helping people find jobs. So I was running this is again.
Speaker 2:This is the late 1990s I was running a list serve which at the time was like I guess I feel really old saying this, but managing a list serve in the late 1990s was actually a pretty the cutting edge of community building. Okay, this is before social media, and I got just so deep into that that I I discovered that there was a profession where people actually do this and get paid, which is recruiting and executive search, and so I I went pro I went pro.
Speaker 1:What inspired your transformation from wall Street recruiting to social impact hiring and what key lessons did you learn in the corporate world that you would now apply to the nonprofit and social impact hiring?
Speaker 2:Well D, there were two things the first part of your question there were two things that were happening at once. One was Jen and I felt ready to leave new york city. Okay, we had two toddlers in diapers in a small new york city apartment. That was getting tough. They were. We were starting to have to look into preschools and kindergarten for them. We were in new york through 9-11 and post 9-11. New york was actually a lot harder place to. There was a lot more security and a very different vibe and at the same time I did feel I told you I was not a fan of Wall Street culture. So it was a great time to move to Wisconsin and to say let's change my focus.
Speaker 2:Coming from that background of investment recruiting, coming from that background of investment recruiting, my first big recruiting client here in Wisconsin was actually SWIB, the Wisconsin State Pension Fund, state of Wisconsin Investment Board. Swib was expanding its in-house investment team and I became SWIB's recruiter, which was a fantastic experience. Over the course of about three years or so 2007, eight, nine, 10, I helped Swib hire 15 investment professionals from around the country, including from wall street, and growing that in-house. And what? What that enabled was growing. That in-house investment team enabled Swib to take billions and billions of our taxpayer dollars that Swib was sending to Wall Street firms and Wall Street firms were charging us millions of dollars in fees to manage those funds. Swib was able to bring those funds back, manage those investments in-house and save our Wisconsin taxpayers tens of millions of dollars. So that was a great project, thank you.
Speaker 2:Peter, sure, don't thank me, but it was actually an amazing time for Swib to have embarked on this investment strategy, because this was, like I said, 07, 08, 09, 10. Wall Street was collapsing, so I'd like to think like I was a great recruiter and I did a great job and I did work hard. But we also we got a big tailwind out of the fact that Wall Street was getting crushed and suddenly a lot of investment professionals were looking for jobs and across the country, they were seeing oh my gosh, I didn't know, there was a. One of the biggest public pension funds in the world was in Wisconsin, and so we recruited people from all over the country. Some of them are still there, so you also train diversity, hiring outcomes.
Speaker 1:What makes your training different from your typical DEI programs?
Speaker 2:Oh, that's a great question. D. This is a great topic. Should we get into it? Let's get into it. Okay, first of all, I'm work is DEI adjacent, because hiring absolutely hiring has a huge impact on what organizations look like and so how people think about people's attitudes about diversity and diversifying their organizations have a huge impact on hiring. So that's what I mean when I say my work is DEI adjacent.
Speaker 2:Two things One, here in Madison I'm a business consultant. Employers sometimes come to me and sometimes come to recruiters and say hey, peter, I'm a white CEO, I have an all-white leadership team. We are a mostly white workforce in our company and we are interested in and motivated to, diversify our organization, make it look more like America. Now we have an empty seat at the leadership table. We want to use that as an opportunity to diversify our leadership team. So that's a conversation that I found coming to me and I thought to myself oh, I really need to improve my competencies and my skills to be able to respond to that conversation. And that's look, that's better than nothing when someone comes to a recruiter with that conversation. But sometimes it's more strategic and thoughtful than that. Sometimes it's kind of superficial, like, oh, we have an empty chair, let's use that as an opportunity to diversify our hiring. Of course, it's better if the employer is being more thoughtful and strategic and taking a more holistic approach. So, dee, that's one thing.
Speaker 2:As I like I said, I wanted to improve my skills and my competencies around helping employers diversify their hiring. I had a light bulb moment when I discovered that LinkedIn, which is the biggest you know online and software tool that employers use for recruiting and hiring, has a ton of systemic bias just baked right into it. So I was trying to help those employers diversify their hiring outcomes and the primary tool I was using was LinkedIn. I was struggling and that's when I realized that, that I realized that LinkedIn has a lot of bias issues in the way that LinkedIn is organized and the way we use it. So my again, I'm not a DEI consultant. So again, I'm not a DEI consultant. My biggest sort of move in helping employers diversify hiring outcomes is recognizing that LinkedIn is biased and if we change how we use LinkedIn, we can change that. We can flip LinkedIn from not helping us diversify hiring outcomes to helping us diversify hiring outcomes in the people we're finding in LinkedIn.
Speaker 1:So I don't want to give away too much of your secrets because I know it's a lot of secret sauce in there. You do serve on the Boys and Girls Clubs board and have won multiple community service awards. How has community involvement shaped your perspective on leadership? Oh boy, Well, d.
Speaker 2:First of all, I love the Boys and Girls Clubs. You know I went to the Boys and Girls Clubs growing up as a kid, so this is an organization that I, that I you know, helped shape me, that I have a love for I'm also people who know me in Madison and in Wisconsin know that I'm a big cyclist too. So when I got to Madison, wisconsin, and discovered that the local Boys and Girls Clubs, that its annual fundraiser, was a big bike event, I was like great, count me in, I'm in and we're going back 20 years. But first couple of years signed up and participated in that event and my kids did, and they asked me to be on the event planning committee. And one thing led to another and then I chaired that summer fundraising event campaign for several years At the same time and also I got to help recruit Michael Johnson to Madison and I think the world of him, and it's a real honor to serve on his board.
Speaker 1:I didn't even know that you were the person that recruited Michael Johnson.
Speaker 2:I wasn't the person who recruited Michael Johnson. It was actually another recruiter at the firm I was at. I was there, so I have known Michael Johnson from day one. That he's been in Madison, but okay, we'll see. If Michael hears this, michael sometimes likes to say I recruited him to Madison. That's a little exaggeration, but I was there when we recruited him to Madison at my firm.
Speaker 1:So you're guilty by association.
Speaker 2:Yes, at the firm that I worked at at the time.
Speaker 1:Yes, guilty by association. Blame me. Absolutely Well, after people hear this, they're going to be like. So that's the guy. So I wanted to talk about biases in the hiring process. So biases in the hiring process is a huge issue. What are some of the most common biases you've seen and how do they affect hiring outcomes?
Speaker 2:D, bias in hiring is a huge issue and the different dimensions of bias that I see. For the most part they don't even have names, they go unnamed so I try to name them. I feel like the biggest bias that I see, the biggest one of all, is a bias that I call round peg bias. Right, we all think like employers think of their job openings as round holes. They're looking for round pegs that fit in those round holes. Bias just means that an employer generally has a picture in their mind of who they see for this job, like literally who they see, maybe, what kind of person they are and what they look like. But also boxes they check on paper. And when someone applies for one of those jobs or interviews for it, employers, I feel like in their brains they do this thing where they go okay, in their brains they do this thing where they go okay, how closely do you look like my preconceived notion and that's round peg bias. There are a lot of others, but I feel like that covers a lot.
Speaker 1:So how do you see the future of DEI?
Speaker 2:evolving in hiring and leadership. D I don't know, I don't know, I don't know Because it's a lot going on. Right now it is. We're in a very interesting moment. A lot is happening and changing fast. You know, in this country we take steps forward and then we have a reaction, we take steps back. I don't have a crystal ball, I don't know. What do you think?
Speaker 1:Just to be honest, I felt like DEI. There was a time that it was clear, cut and defined what it was. And then, once it started to take off, I felt like it just got so murky that people kind of lost what it was all about in the first place. And then it was like all of this new DEI it used to be DEI, then it's not the new dei, and then I just feel like it's. It keeps updating, updating, updating what it is, and now I think it's updating again, I think it's shifting again and I just think that there's a lot of confusion. We don't, I don't know where it's going to go from here, because it's just so murky. I don't even If I was to say define DEI for me and you could give me your take on it, but then when you look at the main recipients of DEI, then it's like, okay, is this what you see, what I'm saying?
Speaker 2:Yeah, maybe I think so. It's hard to define and I don't know where it's going. I just D I have to believe that companies and employers win in the marketplace and at delivering their services when they look more like America, when they look more like the society that they're a part of.
Speaker 1:I've seen a study on that that says that companies thrive more when they have a more diverse workforce. I've seen them too yeah. Because of the different thought patterns and different ideas and different cultures and how people share information different cultures and how people share information.
Speaker 2:It unlocks creativity and innovation and it makes companies better able to reach different markets of people. And I also have to believe that our communities win when all kinds of people in our communities are doing all kinds of work and doing all kinds of things and mixing it up with each other right.
Speaker 1:Right, and that's what I was saying. Like you know, about the DEI thing, it's like I thought it was for one thing, but then when I see the outcomes and how much the outcomes has changed from what they said it was originally for, I get confused, to be honest.
Speaker 2:Well, they say okay, there's something that I've heard which I don't know if this is what you're saying Affirmative action was conceived, as I understand it, to benefit primarily people of color, Correct, and they say that primary beneficiaries ended up being mostly-. White women, white women, right. So I don't know, maybe that's what you're saying.
Speaker 1:That's exactly what I'm saying, and White women Right. So I don't know. Maybe that's what you're saying. That's exactly what I'm saying, and maybe I shouldn't have danced around that. Maybe I should have just been more direct with that, and I apologize to the audience for that, because I don't feel like I should have to speak in code.
Speaker 2:It's all good, but you're right, we don't know where this stuff is going. We don't know where this stuff is going and we can talk about meritocracy in theory. In reality, it's kind of messed up because not everyone's had the same access over generations. So, just like you know, talking about the, you know the example that you know, banks love to hire bankers who are multi-generational bankers. Well, you know what? There aren't that many multi-generational bankers who aren't white men.
Speaker 1:And just to prove my theory of what I was saying is when a company comes to you and say, hey, we have this open seat, we're looking to diversify, so we want a DI hire. I don't think they'll probably say a DI hire, but you get it right Is the first thing that you're thinking of when you're having that conversation is a white woman.
Speaker 2:No, not at all. No, usually, when people come with that intentional conversation, they're generally, generally that's a white leader who wants to hire the company's first leadership team member of color. I think that example about affirmative action benefiting white women more than people of color I feel like that's. I mean, affirmative action goes back to what like the 80s or even earlier 60s.
Speaker 2:I feel like that's that played out, and I feel like I do feel like many of our industries are more have more gender balance, a lot more gender balance than they used to, more so than racial diversity.
Speaker 1:Some companies are scaling back DEI efforts. What's your response to critics who say DEI is no longer a priority?
Speaker 2:I think it is a priority and I think there are different cases. There's a moral case, there's a business case. I feel like it makes sense for someone who is a critic, who thinks DEI shouldn't be a priority. I think it actually makes sense to lead with the business case and show that employers that have more creativity and innovation on your team and being able to reach a broader, more diverse customer base.
Speaker 1:And just to slide off a little bit. You know I was thinking I'm like man, you do so much for the Boys and Girls Club. I didn't put this on our sheet, but I wanted to get your views about mentorship and how important it is to you and how do you feel like. Did mentorship play a part in your success? Part in your success.
Speaker 2:It did. It did to some degree. I mean I was. I grew up in a home where, you know, my parents went to college. I was the youngest of four kids. We were expected to advance to college, where I see tremendous mentorship impact at the boys and girls clubs. I've been a tops mentor and and I'm now a mentor through rotary of a rotary. Scholar is scholar is mentoring kids for whom that might not be the story. You know young people, high schoolers, who might be first person in their family to be applying to college. It's confusing, man. It is the applications, financial aid, choosing a school.
Speaker 1:It is confusing and that mentorship really is really an important, important thing the Boys and Girls Club does, you know it's funny because you said it was kind of like your mother and father went to college and they told you you know, it's pretty much expected. You know you don't really have a choice. You're gonna go, and I always tell my kids you don't have to know what you're going to go for, I just want you to go.
Speaker 2:I feel the same way and at the same time D I'm also opening myself to a better understanding that college isn't for everyone and that we need to have great life and career pathways for people who don't choose college and college isn't for them, and I'm glad we're doing that. You can see the Boys and Girls Clubs doing that with the McKenzie Regional Workforce Center and focus on trades education. You know we have a big labor shortage in the trades.
Speaker 1:Yeah, we're going to get hurt here soon if we don't get on that.
Speaker 2:Well, we're getting hurt now. I mean, did you ever have you had an emergency call to a plumber or an electrician? Yeah, Just recently. Oh yeah, I hope someone was able to come promptly.
Speaker 1:Yeah, but it cost me big time. You know, we're talking about the emergency calls, like 450.
Speaker 2:Yeah.
Speaker 1:You know, just for them to come in and not taking away from anything that they do. But I was like man. If I would have known just to pull this lever, I would have saved myself $450,000.
Speaker 2:We have a big shortage, and I mean John McKenzie has talked about this. You know he is a real estate developer. He and his family business is apartment buildings, so he builds buildings and it's hard for builders to build on schedule because they have trouble staffing their construction sites and their trades. And he's gotten up and talked about the fact that a bunch of pretty much white men got into these trades, set up unions, made it harder for the next generation to get in after them, and now they're aging out of the game and they're not being no one's backfilling them because it's hard to get into the trades and so we need to make it easier to get into the trade, and people recognize this. We need to make it easier to get into the trades and we need to be making the trades more accessible to more young people, including and especially our young people, who college might not be for them.
Speaker 1:But I also think that I want to tell the kids that if they think that college isn't for you, that it's never too late to change your mind, because I thought college wasn't for me until I went and I loved it and I was a 4.0 student and I was assistant to the dean and I loved it and I was a 4.0 student and I was assistant to the dean and I started the chess club. I started just so many different programs and got so many different opportunities and I never thought that I would go to college. I was like I'm not going to college. I didn't even like high school that much and as time went past, it's like I started college late. I went to college at 26.
Speaker 1:I just don't want people to think that just because you feel like right now that college isn't for you, don't close your mind forever, because you can always go back. But the trades is a great alternative, if not, in some cases, a better alternative than college, because a lot of times when you go to college you have an idea of what you want to do, but nine times out of 10, that's not probably what you're going to end up doing. But with the trades is, once you get into the trades, you're instantly making money doing what it is that you say that you want to do.
Speaker 2:Yes, you are.
Speaker 1:A significant amount of money to take care of a family or take care of yourself versus going to college. And now you're paying a bunch of money. You'll never hear the Department of Labor workforce saying hey, we have too many plumbers and carpenters and roofers. You know what I mean.
Speaker 2:Yeah, no time soon.
Speaker 1:No time soon. So a lawyer, yeah, you know, with the emergence of AI, Well, here's what I heard said about AI.
Speaker 2:Your job is not going to be taken away by AI. Your job may be taken by somebody who does what you do and knows how to use AI. So I'm trying to learn how to use. I'm trying to get better at using AI in my business as a recruiter. There are some different ways Do you use AI?
Speaker 1:I was afraid of AI at first because I was like, I was just afraid. You know, because, like you said, like you were having that imposter syndrome, I had the same thing. I'm like I'm not smart enough to use this, I don't know what I'm doing. But as I got more and more comfortable with it, I find myself leaning into it a lot more.
Speaker 2:I'm starting with. You know I use Zoom a lot. I'm just trying to get better at using the AI tools that are now built into Zoom. You can capture a transcript and you can actually you can have an AI summary of a Zoom call. And I just so Dee, in fact, just yesterday, of a Zoom call, and I just so Dee, in fact, just yesterday or two days ago, I sent my first AI summary of a call to the group that I was on the call with. But I also learned I shouldn't have just grabbed the summary and sent it without reading it first, because it summarized the whole call and the first few minutes. We started with small talk and someone was like, yeah, I was like, oh you, oh, did you get a haircut? Your hair looks great. And oh, and we just took a family trip and went all these places, and that was in the summary too.
Speaker 1:So that reminds me of one of my favorite shows, the Office, yeah, and there was a scene when he was like they were doing this called the nights of the night, and they were going over the minutes from last week and he was, like, you know, just saying all of this like just crazy stuff, like, oh yeah, we tested out our flashlights and we did this and we did this. It's just like little stuff. I was like it's really funny. But yeah, I had to learn that the hard way too. Like you need to actually read it, like it'll do a lot for you, but you need to manage it. You know you still need to go in there and okay, sorry, I kind of went down a rabbit hole.
Speaker 2:It's all good, you know, this is stuff we're all dealing with every day.
Speaker 1:So if you could change one thing about how hiring is done today, what would it be?
Speaker 2:Well D. I would like to see employers overcome that, those biases, and particularly that round peg bias, and just open their minds to hiring differently. I feel like the biggest change that that would that that wouldn't be needed is you should hire someone who's right for your business, who cares about the work that you do, even if they don't have a certain specific experience-based skill. My experience as a recruiter is employers don't want to hire people to train them to do the work that they're hiring for. That's why there are recruiters, that's why I have a job, because employers they don't want to hire someone who's a good learner and is willing to learn. They want to hire someone who already knows it and often they want to hire someone who's ready to teach it, and that's why they're coming to me. And coming to recruiters is because they have a knowledge gap. They don't know how to do something. So let's hire someone in who can teach us how to do the thing we don't know how to do.
Speaker 1:So what's next for Peter Gray? Executive Search, recruiting, social impact leaders. What is next for the company? What is?
Speaker 2:next Well, d, okay, so I've been a recruiter for a long time. Peter Gray Executive Search is five years old. Okay, I launched it at the very beginning of the pandemic. I feel very fortunate. I've had great success. I'm having a lot of fun, I think next about do I stay Peter Gray Executive Search? Because I'm solo, it's just me and I actually enjoy it and I think I'm pretty good at it. But I wonder if I should be getting together with some others to form a bigger firm. I don't know where I'm going with that, but that's something I think about. So have like a super packed of people that can find you.
Speaker 2:So maybe, but it's like I think more about just how it would affect my work, because I don't aspire to like lead a big team and have people working for me, but if I'm teamed up with other colleagues who do what I do, we could support each other. We could share the work. When one of us is busy, one of us who's less busy could help them out. We might have some backend processes and resources that we could leverage together. That's more what I think about.
Speaker 1:So how can people get in contact with you?
Speaker 2:You can always find me on LinkedIn, peter Gray, and you can find me through my website, petergraysearchcom, and my website has a contact form right there on it.
Speaker 1:Well, Peter, thank you so much for stopping by the podcast. We really appreciate you.
Speaker 2:D. I love what you do, I love the podcast, so thank you for having me on.
Speaker 1:Absolutely, I'm D Star Until next time, guys.
.jpg)