Start With A Win - Steve Cadigan: Interview With LinkedIn's Very First Chief HR Officer

Episode Date: November 19, 2025

What if everything we thought we knew about loyalty, leadership, and the future of work is about to be rewritten? In this episode of Start With a Win, Adam Contos sits down with Steve Cadigan... - LinkedIn’s first-ever Chief Human Resources Officer and one of the most respected minds in global talent strategy - to explore the shifting realities of today’s workforce. From the rise of a restless generation to the untapped power of learning and mobility inside organizations, this conversation challenges leaders to think beyond old models of retention and success. It’s a provocative look at how businesses can thrive amid constant change - and why the key to keeping your best people might be the very thing that sets them free.Steve Cadigan is a globally recognized talent advisor and founder of Cadigan Talent Ventures, a Silicon Valley firm that has worked with top organizations like Google, Intel, and the BBC. As LinkedIn’s first CHRO, he guided the company through its IPO and shaped its culture, which later became the foundation for a Stanford University course. With over 25 years of HR leadership, he has advised leading VC and consulting firms such as Andreessen Horowitz, McKinsey, and Deloitte. A sought-after speaker and media expert, he frequently appears on Bloomberg, CBS, and CNBC and teaches at major universities. His book, Workquake, debuted as a #1 Amazon Hot New Release in 2021. Recognized annually since 2021 as a top 100 thought leader in talent, he serves on multiple boards and advisory panels, helping leaders craft innovative talent strategies. Having lived and worked in Singapore, Canada, and the U.S., he brings a global perspective to the future of work. Based in California, he enjoys coaching basketball and playing tennis.00:00 Intro02:15 This is my moment…have you found yours? 03:40 This is the last thing companies think about!05:05 Ways of winning without a team that has been together for a long time08:25 The need for this has accelerated! 11:01 A person is loyal to this13:30 CEOs need to do a better job in removing the silo thinking18:30 Would you rather…?20:50 Advice, listen up!23:30 I do this for my twinshttps://stevecadigan.com/https://www.linkedin.com/in/cadigan/  steve@cadiganventures.com https://www.tiktok.com/@stevecadigan?lang=en===========================Subscribe and Listen to the Start With a Win Podcast HERE:📱 ===========================YT ➡︎ https://www.youtube.com/@AdamContosCEOApple ➡︎ https://podcasts.apple.com/us/podcast/start-with-a-win/id1438598347Spotify ➡︎ https://open.spotify.com/show/4w1qmb90KZOKoisbwj6cqT===========================Connect with Adam:===========================Website ➡︎ https://adamcontos.com/Facebook  ➡︎ https://facebook.com/AdamContosCEOTwitter  ➡︎ https://twitter.com/AdamContosCEOInstagram  ➡︎ https://instagram.com/adamcontosceo/#adamcontos #startwithawin #leadershipfactory

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Starting point is 00:00:00 Teams aren't together as long as they used to. People are not staying in organizations or companies or roles as long as they used to. And that's creating a problem because most of what we were taught is that the teams that win are the teams that stayed together the longest. Then he said something different. He said nobody can be in a job in the same job more than two years. You have to move. But what that did was it created an insurance policy for a more fluid workforce.
Starting point is 00:00:25 Because when someone would inevitably go, someone else knew how to do that job. And it turns out when you give someone a new experience, you unlock enormous energy. Welcome to Start With a Win, where we unpack leadership, personal growth and development, and how to build a better business. Let's go. What does the future of work really look like? And what if the biggest challenge today isn't finding talent, but actually keeping it? Today, we talk about that on Start With a Win.
Starting point is 00:00:52 Coming to you from Area 15 Ventures and Start With a Win headquarters, it's Adam Contos with start with a win. If anyone has this answer, it's Steve Kattigan. He's a world-renowned talent strategist, speaker, and the first ever chief human resources officer at LinkedIn. If there's somebody that should know about people and talent, it's LinkedIn. He's helping shape the culture that made it the powerhouse it is today. From advising companies like Google and Manchester United to teaching at Stanford. Steve is the go-to expert for navigating the evolving workplace. We're diving into his insights, his book, Workquake,
Starting point is 00:01:32 and what leaders need to know to stay ahead. Let's get into it. Steve, welcome to start with a wind. Great to be here. I love this topic because this is probably the number one thing that I see in any workplace survey amongst leaders and business leadership or owners. and that is about the environment of the workplace and how people play into this.
Starting point is 00:01:57 And I mean, this is your playground, man. You know, you were the chief human resources officer at LinkedIn. You wanted the, you know, founding people back in creating this juggernaut around human resources and people management. How did you get into this, first of all? And let's get into the future of this that you've been talking about. Yeah, I got into the world of talent because of my love of sports. I love not only competing, but I love watching how people handle themselves in different situations. Now that we're recording this in the middle of March Madness basketball playoffs, and I just love seeing how do teams handle being behind?
Starting point is 00:02:33 How do they handle victory? How do they handle different styles of coaching? How do they handle I was the star and I'm no longer the star? Or I am the star, but someone else is on fire. So am I going to give that player the ball? And that when I found that I could parlay that interest into a professional career in recruiting, and organization development, it was love at first sight for me.
Starting point is 00:02:54 So I feel really lucky. I found it probably a year out of college. And since then, worked in a bunch of different industries, different countries, lived and worked in Singapore and Canada and so forth. So, yeah, we've never,
Starting point is 00:03:06 as you were saying, we've never seen a more complex universe in the world of work. So I'm just, this is my moment. I love it. And obviously, you know,
Starting point is 00:03:15 the talent on a team is created during, you know, recruitment season and then the development of coaching. And that seems to happen in the workforce constantly. There's never this moment where we're like, all right, we're perfect. We're not going to change anything. I mean, are you still seeing across the board, this being the key challenge that the workforce is facing? Because it seems like this is far more than taxes and far more than, you know, product development or supply chain. It always comes back to people. Is that,
Starting point is 00:03:47 Is that consistent still? Yeah. I mean, how does any organization create values through the people? And unfortunately, for most businesses, it's the last thing they think about. It's more like, hey, what's the sales plan? What's the product plan? What's the customer growth plan? What's the business strategy?
Starting point is 00:04:02 And it all has to start with people. And unfortunately, it's not been something that's gotten as much weight, I think, as it should. Obviously, I'm converted like I'm in a talent business. But I will tell you what, the biggest thing that people are struggling with right now is what you said, which is teams aren't together as long as they used to. People are not staying in organizations or companies or roles as long as they used to. And that's creating a problem because most of what we were taught is that the teams that win are the teams that stay together the longest. And this is playing out.
Starting point is 00:04:29 I mean, look at college basketball. Used to have a player stay four years. Now, you know your best player is staying one year. We have several teams now that the entire team is already in the transfer portal. And so coaches have to think differently around, okay, I'm going to have to constantly recruit. I'm going to have to have a simpler offense and a simpler defense because I don't have four years and I have to have a different philosophy around building teams. And so I'm seeing that being a really good canary in the coal mine for what business leaders
Starting point is 00:04:57 are facing today is I've got a lot of examples of companies that are creating incredible value with teams that aren't staying a long time. So I think that myth of the best teams are the ones that stay to the longest is being under attack right now. And I'm trying to encourage my leaders like, hey, there's ways of winning without people staying a long time. And so let's try to reimagine a different way of building value. So many questions come out of what you just said, man. Do you think this is a generational thing? Because I think you and I are probably Gen Xers. Our generation was like, I might have two or
Starting point is 00:05:33 three jobs maximum during my working career. Now you got Gen Z who's coming in. They're like, I'm going to hop around every year or two until I find something I want. Is this generational or am I just reading too much into this? I think it is, but not for the reasons that most people think. I think the generation that's entering the workforce right now has been presented with a window of opportunity and transparency to what they can do, where they can work more than any generation history. And that's causing enormous confusion because not only do I have the benefit of seeing a lot of choices, I have the curse of worry that I might make the wrong choice. So let's take, for example, new industries. We have more new industries that have been born in the last 10 years
Starting point is 00:06:16 in any 10 year window in history. That's a fact. And if you ask anyone, do you think that's going to slow down? Everyone's going to say, no. And so what happens with the new industry is new career pass. Look at cryptocurrency. Look at blockchain. Look at electric cars. Look at, you know, gig economy, the Airbnbs, the Uber's. Those are relatively new. And they're causing a lot of churn in the workforce. Like, what should I study? Where should I go? How do I prepare myself for that? And that's leading to, I think, a lot of decisions that my generation, like, I couldn't see all those opportunities when I entered the workforce. So it just, it changed the psychology of how I'm thinking about careers. And what, you know, one interesting stat I'll share with you, Adam, more students are changing majors in universities faster than any time in history.
Starting point is 00:07:01 Pre-pandemic, it was about 1.2 times to 1.5 that people would change a major. And now we're seeing north of two, two and a half times in a four-year window. And that, I think, is a direct connection to the fact that, whoa, there's so many choices of places I could go work. It seems like we've become a little bit ADHD in this whole environment, chasing the next shiny thing. Is that, I mean, is that becoming cultural or are there any solid norms that we in business can latch on to and go, okay, these things are going to stay the same while the rest changes around it? Or is it just all constant change and people chasing the next thing? I mean, if that's the case, then we need to build a strategy around change instead of a strategy
Starting point is 00:07:47 around our pillars, right? Yeah. And I think the answer is much to the disheartenedment of many leaders is there's more in flux now as a leader than any time in history. And that's hard. That's really, really hard. And I have a lot of, you know, as a parent, I'm excited. My kids have a lot of career choices as an employer.
Starting point is 00:08:06 I'm just not happy that my team has. so many places that they can see. Not only do they see opportunity, they can see how people are paid, they can see what the culture is, they can see what the turnover is, they can see what the leadership style is, they can see the selling habits of the executive team. Think about all the things that talent can see right now. And so, you know, I think it, you know, is there, are there anchors that we can hold on to, you know?
Starting point is 00:08:28 And the anchors are, go back to the point that you made in the first question, which is we can build value with talent. That is the number one thing that we need to invest in. But we have another big trend that we haven't talked about yet, which is the need for new skills has accelerated. Look at AI, the hottest skill right now. That wasn't even talked about five years ago. And here we are. Everyone's need.
Starting point is 00:08:51 I need a senior experienced AI engineer. Like, do they even exist? Right. And so that is compelling organizations to do things that we've never seen before. We see more companies laying people off while they're recruiting. It used to be put the foot on the brakes, freeze the recruiting, times are tough. let some people go. Now it's like, we need to let some people go. We need to get some new skills in here because we weren't built as a company that I'm speaking in generalizations. Companies weren't built to upskill talent as fast as they need it right now. And so that's leading me to say compelling and things that are scaring business leaders, which is your business is going to have to become a business school because you are not going to recruit your way out of the talent deficits and the skill deficits that we see in the marketplace right now.
Starting point is 00:09:34 So if you're not going to recruit your way out of it, then you're going to need to upskill your way out of it. Is that you're going to need to upskill and you're going to need to hire people that have high learning velocity, right? I need to know that you can grow and change because I know my business is going to need to grow and change 100%. All right. So as a leader, I mean, we do see this stagnation of leadership at the top of organizations quite a bit. we need to bring in some some fresh ideas and some fresh talent even at the at the leadership level. Is that correct? You do. But I will say I finally got my hands on CEO turnover report last year. Hydrican struggles, one of the biggest search firms for CEO talent around the
Starting point is 00:10:17 world published a report that said, and they did a study since 2015 of 10,000 CEOs and they found something really interesting because all the CEOs I talked to ago, they want to say, that young generation, those disloyal people that don't stick around. And what the Hydric and Struggles report showed was that over a like a seven year window, 15,000 CEOs, 10% left after one year, 20% left after two year, and almost 40% of CEOs left after three years. This is not a, and those weren't all like young generation CEOs. This is across the board.
Starting point is 00:10:53 I do agree that one of the challenges most, let's say, a large enterprises face is that they're being led by a generation that didn't see the world of work the way the workforce sees it today, which is, you know, I'm probably got two or three years here, then I'm going to go do something different. And I'm, I'm loyal to learning, not necessarily loyal to your company, like in a world that's changing really quickly. And I think a lot of businesses are to blame Adam for creating this dynamic because they've been saying for the last 20 years, we're going to go digitally transform. You know, we've got to digitally transform and we care more about the technology than we do you. So good luck figuring out those new
Starting point is 00:11:31 skills. And now we're telling them, AI is coming to take your job. Can you teach the technology how to do your job so I don't need you anymore? And that's just fundamentally causing people to say, well, I'm going to take control of my career. Like you're not looking out for me. You're looking to save money. So I need to go find something on my own or something different. And that's, that's again, information a lot of leaders don't like to hear. I want to unpack something you said in that statement. said, I'm loyal to learning. Is that, I mean, it seems like that is a common attractor for new talent, for people who are looking, you know, obviously was it like 51 to 50% of the current workforce is looking
Starting point is 00:12:15 for another job or something like that? One more, right. I mean, it's crazy. Is that something we should be leaning into as a good organization to help these, I mean, for, you know, obviously, retention of these employees, because if they're constantly learning and they're feeling the satisfaction of getting better, are they likely to stay longer based on that statement? Yes, they are.
Starting point is 00:12:38 And that, and that I think is a big challenge for leaders. They're seeing the turnover go up and they're seeing talent wants to learn more. So you've got the CFOs saying, wait a second, we're paying all this money to teach these people and they're leaving. Why would we do that? And then the CEO says, or someone who's, you know, more evolved in their thinking says, well, what if we don't teach them or grow them and they stay? You know, like, what happens there?
Starting point is 00:13:02 And so, you know, that's really challenged because we were not built as a business community, Adam, to teach and deliver. Most of our business models are like, you deliver an output. That's what I need you to do. My business plan and all my investors are expecting that if you're in that position, you're delivering an output. But now with the need for new skills, I need to dedicate new projects and assignments and challenges to you that you don't have experience in that are going to allow you to grow.
Starting point is 00:13:30 And so I'm working with a company right now is really interesting. They're a large insurance company and they've figured out a way to map every employee to every job in the company and say, Susan, Adam, you know, Jerry, here's how you're in human resources, but here's how qualified you are for a job in PR and marketing, investor relations, and accounting, and finance, and engineering, and product, and legal. And so you have an unbelievable roadmap to help you say, well, if I'm not loving what I'm doing or I don't like my boss or things are slow here, I'm 20% qualified over there, but I really want to go over there. So here's classes I can take. And that we have to do a better job of removing the silo thinking.
Starting point is 00:14:09 Like if you're an account and you're always an accountant. No, they could go work in data. They could go work in other more analytical places, right? And I think that's the challenges in a world where there's more fluidity is we have to get a little more fluid in thinking how to apply our. are people. Well, it seems like today, I mean, especially with, you know, the emergence of these large language models and how we can educate them internally on our organization, as much as they are externally, that you can take somebody from legal and teach sales to that person or teach marketing or something like that. And I mean, obviously people are rather
Starting point is 00:14:44 territorial when other departments start kind of infringing upon what they're doing, you know, break that down for me. How do we overcome those barriers and make it more across the board accepted where you're allowed to play other people's games? Yeah. And human nature is what we're talking about. Why would I give my best employee to that department over there? Because what that means to me is I'm going to get home later. I'm going to screw up. My weekends are all screwed. I'm going to spend more time recruiting. Why would I do that? Right. And I've worked in big companies where we tried to do that and employees and managers would block it and say no I have no I have no I invested in this person I want to mine my investment opportunity over the next few years I'll give you an example of a company that's figured this out Spotify Spotify is you know up in the Nordics they're a great music streaming service and they had a problem with a lot of their young talent was leaving and so they did a lot of research and they said why are you leaving said well because I'm stuck here and I want to go do something different and so the CEO this guy Daniel like super interesting dude. He says, okay, we're going to allow you to interview anywhere in the company. And so
Starting point is 00:15:55 he opened the doors to, you don't need to stay in your job a year. You can, you could be in six weeks an interview for another job. That's fine. But nothing's changed. Okay. So then he said, why is that? Because managers are blocking it. Okay. Like, you can make that move, but I'm going to totally crush you. And so then he said something different. He said, nobody can be in a job in the same job more than two years. You have to move. Okay. Now, that's not to see if. and, you know, there's some pretty deep, you know, technical experience roles. You couldn't do that. So what that did was it created an insurance policy for a more fluid workforce because when
Starting point is 00:16:31 someone would inevitably go, someone else knew how to do that job. And it turns out when you give someone a new experience, you unlock enormous energy. Think about your own career, Adam. When have you had the most energy and excitement? Was it doing the same thing for three or four years? Or when someone came to you and said, hey, Adam, I think you can do this job over here. and you're like, I'm not sure I can do that. Is this kind of a setup?
Starting point is 00:16:52 And they say, yes, you can do it. You do it. And you go, oh, my gosh, I'm so fired up because I learned I can do something new and I've got this new toolkit and I'm more valuable. Right. And so that's what, you know, more and more organizations I think need to lean into, as you say, which is this notion of people really, a lot of energy is unlocked when you give people new stuff to do. And maybe it's not as big of a leap or a risk as the traditional thinking on this subject has been for most of us. Yeah, it's, and it's fascinating because, you know, the, comparing this to the past, we always said a good salesman doesn't necessarily make a good sales manager. Right. But if we
Starting point is 00:17:30 approach them as a good salesman and say, I'd love to see you as a good sales manager as well, how do we get you there? Let's upskill your position or let's train you to get there together. You know, you're, you're, you're really unlocking, like you said, a lot of energy in order for that person to say, wow, they're putting some faith in me. I'm not going to let them down. I'm going to go do my very best. And I mean, you're right, Steve. You look at retention. This company trusted me. They put their faith in me. They invested in me. That's right. It makes a big difference. And now, and now you're caring about me for my career, not just when I work for you. You're making me better, you know, and the enterprise of me. The sales leader going to managers is one that always falls
Starting point is 00:18:13 apart when they realize they make less money as a sales manager. Right. But, and I've tried that. I've learned the hard way. Like, wait a second. I'm making less money and I'm influencing the business more. Like we have to figure out and they're like, yeah, but you're getting more stock now. It's not all about cash. And like, yes, I love the cash. But that that is something where we say, hey, listen, you know, you've got this skill set. There's all these other places you could go. Would you like to
Starting point is 00:18:36 take on a project over there and just see how it fits? See how it feels. I think you'd be great at it, but you know, you got to try it on, you know, and we need to do that more because I'd rather, you know, wouldn't you rather take six months to train someone in something they've never done before than nine months of a vacant job that you're trying to, you know, grind out in the open market? And I will tell you this. And even at LinkedIn, okay, here we are a company whose product is recruiting and we couldn't recruit effectively against these companies that could pay more and out culture us, how benefit us, out on-site childcare center us, we finally realized that the only way we're going to get out of this is on-campus
Starting point is 00:19:16 recruitings and we're going to have to build the talent because the open market is really, really hard to find mid-to-senior level talent. It's really, really hard, especially if you're an early enterprise or a small enterprise, it's not sexy compared to all the other choices that they have, right? And so we went all and we could crush on campus. Like we were really good on campus. And our offer acceptance rate was really high. It was like 95% of our interns accepted our offers. Whereas in the open market, 35, 40% were accepting the offers. So it's just a matter of time and investment, right? That's why I say businesses are going to need to become business schools and we have to get a lot better at this. And leaders, to your point, are going to have to become better
Starting point is 00:19:56 coaches and mentors than just operational delivery experts, right? This is a fascinating topic. And I want to I want to kind of pull this down to on the street level in, you know, in the U.S. or in North America or, you know, the first world countries where you drive down the street. And if you spend five minutes, you're going to see at least a dozen franchise locations and small businesses without a doubt. So now we're talking about, you know, these SMBs, these smaller business ventures that might have 20 to 70 employees call it that. We relatively have an unsophisticated leader or owner who hasn't been, they don't have an MBA. They haven't run enterprise level operations, things like that. But they're still responsible for what would seem like a very strong team in a larger company. They're just operating on a small level here. What advice do you have for these managers and leaders to go out and upskill themselves to deliver this culture to their company? Yeah, the big mistake, and I've made it, and a lot of leaders I coach have made it, is assume that because you're the business owner, that you should know more how to run the business and the people who are actually in the roles.
Starting point is 00:21:10 And the best advice I could give is spend time working the line with the team, spend time sitting there learning how they're doing it and ask them, hey, you know, how do you think you could do this better? The best question I've ever asked in any company I've ever worked for, and I didn't come up with this. someone else did, a friend of mine, John Schuller, who does employee surveys, is, are you as productive as you can be? And if not, why? What could we do to make? Because that drives high performers out the door. If there's something or some process or some person who's cultural kryptonites just messing up the whole amount, like, I'm not because it's too loud, it's too noisy, or we could just tweak this one thing in this system that you're making me right to support. It has no value. Ask the people what you can do to help them be more.
Starting point is 00:21:55 successful in their role and you will unlock not only magic but the earliest studies of organization are all about like asking a factory worker what we could do and they said make the lights brighter in the factory it was called the hawthorne effect and just because they asked the factory workers what they could do productivity one of 20 percent they never made the lights brighter they just asked them a question and no one ever asked them and so I think that's that's something like I would promise you listeners if you go to some of your people and you ask them they will be shocked because no one's ever asked them that question. Amazing.
Starting point is 00:22:31 Steve, this has been a masterclass in 23 minutes on how to grow business and how to do that through your people. So huge, huge kudos to you for all that you're doing to help grow with businesses. Where can we find you online for all of our listeners to follow you and listen to more of your wisdom? Yeah, thanks for having me, Adam. You can find me on LinkedIn, obviously. You can also find me in my website, Stevecadigan.com. I also have it for humor. I have a TikTok channel with a series called True Stories from corporate America for fun.
Starting point is 00:23:03 But yeah, and if you want to email me, Steve at Cattigan Ventures.com, I'd love to, you know, help you out. Awesome. Great information today, Steve. Everybody, make sure you follow Steve online. Reach out to him if you have any questions. Let's boost his audience because I'll tell you what, he's got a lot of value to deliver to our businesses for all of the listeners here. I'll start with a win. Steve, I have a question.
Starting point is 00:23:24 I ask all the great leaders. on this show. And that's how do you start your day with a win? I have two twins who are seniors in high school right now. And it is an absolute joy for me to make them breakfast every single morning. And I get up before they do and I serve them eggs. It's usually a sausage and eggs bagel. And I feel so good about that. And I can't tell you how sad I am about the prospect of not being able to do that when they head off to college next year. But that's, that's, I mean, a joy for me. I love that. And there's nothing like family time and that quality time kind of fades away as time goes on.
Starting point is 00:24:01 So thank you for being such a great father and family man. That's amazing. Everybody, make sure you follow Steve at stevecadigan.com and on all the socials. He's got some great stuff. Steve, thanks for all you're doing to help us grow businesses. And thanks for starting your day with a win. Thanks for having me. You know,

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