What happens when HR starts telling the unvarnished truth? (with Christine Song, Founder 5 to 9 Society)

Christine Song: HR has one of the hardest jobs as a leader because people are unpredictable. They have emotions. You don't know how someone's going to react. If you think you're going to be a really great HR leader because people like to confide in you and you're a great therapist, you're a horrible HR leader. We're not here to be therapists like we are truly here as business leaders.

Kahina Wardain: Welcome back to Leading Culture Building the Future of Work. I'm Kahina Wardain, Chief People Officer at workleap. I've always believed in the power of collective intelligence. How people coming together can create something greater than the sum of its parts. And that's exactly what this podcast is about. We're having real conversations about what it takes to lead in today's workplaces. Today I'm joined by Christine Song, a, uh, people and culture leader turned entrepreneur CEO. Christine's career spans corporate environment, high growth startups and now the creation of five to nine society, a uh, private and vital only network for founders, investors and top operators. She's held several leadership roles including chief people officer at NICS and Notch, and she continues to contribute her expertise as an advisory board member across multiple organizations. Christine brings a unique perspective, uh, shaped by her experience across these very different worlds. Welcome Christine. I'm so happy to have you with us today.

Christine Song: Thank you for having me, Kahina. I'm excited to be here. Super cool.

Kahina Wardain: As I was just saying before, you've seen a lot. From the corporate world to the startup world, to the scaling world, to now being an entrepreneur and a founder yourself. Um, one thing I've noticed through your communications online and so on is that you're very open about being open. Um, so I think being open and transparent is a little bit of um, a hallmark of your career. Have you observed any context in which transparency is easy, easier than others? Whether it's in terms of scale, in terms of stages, of businesses, in terms of industries, in terms of founders led versus operator led. I'm very curious to hear on that.

Christine Song: Yeah, no, that's a great question. I started off my career in large corporate and so to be honest with you, there wasn't a lot you could share out there. And I came from a generation where social media was just starting to launch and so I worked in a very large company. We were told, do not talk to the press. You know, we're a public company. There's nothing that you can share about the, the organization. And also being in a role in hr, I felt like the corporate culture Was that HR must keep things close to their chest. You don't share what's going on, you don't share your tactics, your strategy. It's all very um, confidential. So if you really think about it, the world of HR was very confidential. It was always behind closed doors, it was always hush hush. And people didn't really understand what's going on in the world of hr. What do HR people really do? No one really understood. Ten years ago I branched off to a uh, startup world. Um, back in the day they called it a small business, today it's sexy startup. And it changed my perspective on everything. It really opened my eyes to the fact that when you're building a business with an entrepreneurial spirit, you take risks, you are much more open, you're probably more vulnerable when you're doing that. And I really wanted to share, share what HR ah, was all about, what do we work on, what are the hard things that we do? And we didn't get a lot of good press. Uh, nobody ever said, I admire HR people, I want to be a HR leader when I grow up. Nobody said that. And I thought, but there's a lot of great things that we do, there's a lot of human work that we do and I want to kind of share that. So I started kind of sharing snippets about my day, my work, my world, um, on LinkedIn. And this was 10 years ago, um, I didn't start posting to create this big following. What I wanted to do was build a community, community and network. And I was moving from corporate to smaller, um, startups. And so I wanted to build connection and through some of my posts that were very, uh, transparent, honest, raw, um, there was a huge following. People started following me, they started asking questions. They're like, I've never met a HR person who shares what happens behind closed doors. And there was like a fascination with that. And so I don't know if people are just eager to see what happens behind closed curtains or the world of HR was too compliant to govern by secrecy.

Kahina Wardain: Was, or maybe is to this point I think, uh, yeah, because I'm thinking about conversations we've had with other HR leaders who were kind of saying, I wish I could say what you're saying online. And those leaders are, you know, leading organizations today, 2025, sometimes in tech and they don't feel that they can go out there. So now maybe it's a question of taking the leap and taking a risk, maybe a little bit more also at the personal level.

Christine Song: I think so. And I think that, like, as I started sharing more of my content and my world, um, in the world of social media, I thought that it would eventually, like, deter. Deter leaders from wanting to hire me. I thought that CEOs would be like, oh, she's too risky. We don't want to hire her. No. If, if anything, more founders started reaching out to me, going, I like the way you manage hr. I like your voice. I like the way you lead leaders. I want to bring some of that energy into our organization. I would love to incorporate that kind of culture. And so, if anything, it actually opened more doors for me and kind of created the community and connections that I was looking for.

Kahina Wardain: And you've been able to implement that within organizations as well and to lead your own teams to do the same thing as you were doing?

Christine Song: Yeah. I think when you think about being a leader, there's no book that you follow. There's no playbook. What I used to tell leaders is if you want to be a great leader, you do have to be authentic. There has to be a part of you that's real. You can't copy mimic Obama, or you've got to be yourself. And when you're authentic and you show the human side of leadership, people tend to believe in you more. We have instincts. Formative leadership really turned me off. When people stand there and they're using the perfect words and they're speaking the corporate talk to me, that was just a speech. Someone wrote that for you. But I really loved, um, people who can speak from the heart. I used to work for a CEO who used to say, win hearts and minds. And it was the perfect eulogy to say, like, you want people to be inspired and respect you, and you've got this vast knowledge that you want to share, but you also want to lead by the heart. You want to show a part of you that's human. You want people to believe in you as authentically as possible. And that's when I think that, um, people are truly inspired by that leader.

Kahina Wardain: And how do you think an HR leader or any leader in an organization really can bring, uh, his. His peers to walk out of the fueled by fear approach when it comes to these things? Because sometimes you are fueled by fear by default. How do you bring that? How do you use your power of influence to kind of bring, let's say, an executive committee, your colleagues, a C suite to take that leap and to go to the other side?

Christine Song: It's not easy. I think we're all born. We're cut from a certain cloth we operate the way we do. And when you think about the startup world, there aren't a lot of roles. The earlier stage you go into, you kind of are in this very open. You could call it dysfunctional, you could call it creative. It's a very innovative space and you need that innovation. You need authenticity to kind of grow a culture, grow a product, grow, grow a service. But you're going to get different personalities as leaders. And I think that what you want to do is encourage the parts of leadership that bring out the best in people. So I've worked for leaders who are very blunt and direct. Sometimes they could be what you might call fierce, fierce leadership. Um, and we've seen entrepreneurs like that in the past. We've seen big personalities kind um, of come out of these entrepreneurial roles and we look at them and you either admire them or you loathe them. And I always used to say every person has a personality where there's parts of you that are probably ugly. There are parts of each one of us that have ugly sides. That's not what you want to become as a leader. But you can fuel a lot of energy and desire through those parts. So I'll give you an example. If you're someone who's super direct, you can be direct in a way that really turns people off. You can use the wrong, um, ways to motivate people through fear. But in other ways, your directness can really cut through all the fluff that sometimes we hear leaders talk about. You can cut through all the performative talk and get right to the point. You can actually encourage people to respect that directness. And I've kind of seen both. I've seen the fluffy leaders who soften everything and you don't know what they're talking about. And I've seen the blunt leaders who are a bit too fierce and people are a little bit afraid. Find a balance. Find a balance in what you're trying to achieve. And I try to do that with my own leadership as well because I can be blunt sometimes and it could rub people the wrong way. Mhm.

Kahina Wardain: Throughout my career I've observed a lot of executives sugar coating when they speak to CEOs because they are worried that or they believe that the CEOs don't want to hear the raw truth. I'm curious to hear your thoughts on that.

Christine Song: That is such a great question. I think that the more junior you are, the more you think that when I speak to the CEO, I've got to say the things that they want to hear. And I guess there's a power dynamic. There is a little bit of intimidation and fear when you think about speaking to someone who kind of is leading the organization. But if you truly understand a CEO, the CEOs that I've worked with want to hear the truth. They want you to be more direct. They don't want to hear verbose, um, you know, flowery language. They don't want to read long emails. They're like, get to the point. They don't have a lot of time on their hands. And so for me, I've always been pretty direct. Just say it like it is. And I don't mean in a rude, condescending way, but just get directly to the point. And a lot of the founders and CEOs, particularly founders, like, compared to operating CEOs, they do. Tell me, Christine, be as brutally direct with me as possible. I'm like, I shall do that. I shall. You don't have to ask me twice. I've worked with, um, big CEOs with big names. Um, early in my career, I worked for a billionaire CEO. He, um, I won't mention his name, but there's not a lot of billionaires in Canada. He, um, he loved to hear the truth. And he would always ask me, what do people think about me? What are people saying about my leadership? What did they say after town hall? I want to hear the brutal truth. I want to hear the, the, um, the kind of things that I could be doing better. Because they're hearing the flowery all the time. All the time. And I think that the truth is what they seek, but it's hard for them to get it. And so, um, I encourage any leader, particularly as you're moving up, to report to the CEO, get right to the facts.

Kahina Wardain: There's a story that I like to share that I read one day about leadership. And it talks about John F. Kennedy and, uh, Winston Churchill. I don't know if you've heard about this story, but it says that JFK's advisors were in love with him. Right. Everything that JFK was touching was turning into gold when his presidency started in 59, and then in 62, there was the missile crisis in Cuba. Uh, but no one, apparently in his circles, was advising him. Uh, what they truly believed, which was that it was going to be a mistake because they were kind of in awe and they were in love with him. Yeah. Um, and so that created one of the biggest incident, diplomatic incident of the 20th century in the States. And, um, the opposite of that is Winston Churchill, who apparently had built a department of people whose job was to contradict everything that he was saying and that he was saying. That's the only way that I can sleep in two years. If I have people who will unturn every turn, every stone to make sure that whatever I believe, there's someone who's checked the opposite of that and who will challenge me and contradict me. And that's something that I've be, You know, I've been bearing in mind in my. Throughout my career.

Christine Song: I think it's a disservice if you can't speak the truth. You're truly not a leader. Um, you can't sugarcoat things. You're right. Your CEO is going to make the wrong decisions if you can't speak the truth. I had, um, CEOs where I shared the brutal truth to them. And sometimes they would say, christine, that was a lot. Like, that was a lot for me to take in. And you could see their eyes glaze over. And they would say, I'll get back to you in a week. I really need to absorb this. And it was almost like they went through PTSD or something, and they had to kind of, like, put it through their system. They would come back after about a week or two and they would say, okay, I thought, thought it through. Uh, this is what I'm going to do. Thank you for sharing that with me. I really needed that kick in the ass. And I'm thinking that's the greatest thing you could do with the leader, is just be honest so that you could put the business first, do the right things for the business, versus trying to be liked. Right.

Kahina Wardain: I agree. And talking about raw truth that you were talking about being a leader, uh, bringing our whole authentic self at the table as a leader and showing our ugly parts as well. It's also true for an HR leader or people leader that you're running a business and you're looking at everything, the good, the bad, and the ugly. Can you talk to us a little bit more about that and your experience of bringing all that to the table?

Christine Song: Yeah, I think HR has one of the hardest jobs as a leader. Like, leadership itself is difficult. Anyone who's ever become a people leader for the first time, they always say, christine, like, I thought my job, the hard skills were hard. It's nothing compared to leading people, because people are unpredictable. They have emotions. You don't know how someone's going to react. But being in HR and having to manage all of that is even harder. People think that because you manage human resources, you're the owner of every people problem in the organization. And it takes um, someone with a really good critical eye, someone who can be extremely objective and someone who has to be business minded to be a really good HR person. If you think you're going to be a really great HR leader because people like to confide in you and you're a great therapist, you're a horrible HR leader. You have to be able to speak the hard truths, you have to bring things back to logic and being objective. And that doesn't mean that you can't have empathy. But you've got to make sure that you balance that. Because if we lead a business all through feelings, we're doomed. We won't be able to manage, um, any of the data, the functions, the wins because we'll be thinking about people's feelings all the time. And we're not here to be therapists like we are truly here as business leaders.

Kahina Wardain: Exactly. And it's interesting because I think that chief people, officers or HR leaders in general do share something, do have something in common with CEOs, which is the holistic view of the business. Because we oversee everything and we can see the interdependencies and the links between the different departments. And that's something that, what I've observed is that the best partnerships between HR and CEOs is the partnerships where they can kind of take advantage of each other's holistic view of the business.

Christine Song: It is so true. I, um, always used to say the CEO's job is the most similar to the Chro's job. And people used to go, what are you talking about? Like they're so worlds apart. And I said no, if you really think about it, the hr, ah, leader comes in. So the Chro is part of the executive team. That person reports to the CEO just like all the other executives. But that Chro is also in charge of performance and talent management. That includes all the executives at the table and that also includes the performance of the CEO. So in a lot of ways the Chro is also kind of indirectly reporting to the board and they're making sure that this ship is, you know, operating at the pace that it should be and we're hitting the goals that we need to hit. And so I think that I've had the moments of vulnerability the most with CEOs. I remember behind closed doors, we've had moments where you're just on your knees and there's nobody else you can share insights about regarding the business or regarding performance except with the CEO. Because you could be talking about one of the executives. They're leading a function, maybe it's the cfo. You can't talk about it with anyone else except for hr. You can't talk about salary, um, and rewards except with hr. There's a lot of things that you can only talk about with the CEO. And so holistically, you are looking at the business as a whole.

Kahina Wardain: I agree. You've talked, uh, a little bit throughout our conversation already around founders, and you talk about operating CEOs. And I'm curious to hear you, because you've worked in the corporate world, and then you've worked in the startup world. So you've worked with operators and you've worked with founders. What are the main differences that you've observed? What are the strengths and weaknesses of both camps? Because obviously, no one's perfect. But I'm kind of curious to hear you on that.

Christine Song: I've worked with a lot of founders, um, and I love working with founders, and I think I've worked with six or seven in my entire career. Worked very closely with them, not just as leaders and partners in the business, but as humans and friends. And, um, I've also worked with the operators. And there's good and bad that both sides bring. I think that something that founders bring is the creativity, the innovation they will push through because they will care about this baby, their business, sometimes more than their own children. I'm going to be honest with you. This is like their life's work. And that passion that they feel, that dedication is unlike anything you'll ever see that you'll learn at an MBA or a Harvard School of Business. And I've been in organizations where we have removed the, uh, it's time for the founder to go. Got to bring in, you know, the operating CEO. And there were times where I thought, okay, maybe this is good for the business. We've operated in dysfunction and chaos for a little bit too long, and now we need to, like, scale. And maybe this is the right thing we need to do. And, you know, you also lose something from that. And what I realized that I lost was I remember when we replaced our founder and we, you know, the board brought in, uh, a operating CEO. One thing that one of my og, um, executive and I were talking about was, do you feel something? Like something got lost? And he said, yeah. He goes, it's the essence of only the founder would truly care about culture the way he did. And we used to say, like, this operating CEO comes in with the data. You know, the okrs the, everything that you could think of, the dashboard. But there was no essence of culture. There was this lost, organic feel of what it meant to build something from scratch and to care truly about the people. And so when you lose something like that, it's lost forever. And it's really hard for, um, boards to understand that.

Kahina Wardain: But do you think that operating CEOs can have. That, can have the essence of the culture?

Christine Song: Uh, I'm going to be honest with you, I'm not sure. I'm not sure because they're coming in and adopting the baby. So they're kind of coming in and their job is to come in and say, like, okay, these things we've got to remove. Like, sure, it was fun back in the olden days, but these things don't serve the business anymore. It's very. No nonsense. It's very objective and logical. And so that essence, that feeling that, you know, that cultural drive is not as important because the board's not looking at that. The board wants to see results.

Kahina Wardain: It's interesting because it's making me think about, like, how compelling is the mission and how attracted to the mission the operator CEO is. And maybe most of the time we don't hire CEOs based on, you know, their alignment with the mission more than the revenue numbers that they're going to drive to the board. And maybe that's an issue. I don't know. I'm thinking out loud.

Christine Song: I think the, the mission shifts a little bit because I think about when we brought in new operators, the new CEO. What typically happens is they'll say the culture has changed. It's been now, you know, four or five, and we've gotta change the values. That's the first thing that comes up. Like, the values aren't the same. What got us here won't take us there. And so they change the values. They start to change the team, they start to say, hey, this head of was good in the early years, but they're not gonna take us to the promised land and we're going for bigger, we're going after the whales. And so a lot changes. And you don't realize what's changing, what you're losing, until it's kind of gone. And what the company was in the early years was morphs into something else. And so you get different customers, you get new types of employees. You don't get the types of OGs that were attracted to that original company mission. Things do change. And I've seen a lot of great leaders that took the company from the early years, five, six, seven years in. And then they go, I think it's time for me to move on. It's time for me to go. The glory years are done, and I just don't want to be part of that new phase. Whether it's going ipo, they'll say, I'm not going to be that publicly traded company anymore. I kind of want to keep my memories from the olden days. And I mean, it's a choice you make, and it's beautiful. But there are things that I lost when we kind of morph, which was kind of sad. And it's kind of like an ex boyfriend. You're, like, moving on to better things,

Kahina Wardain: but nostalgic about what you're nostalgic about it.

Christine Song: It's kind of sad when I think about that. And so even when you look at established businesses that are large corporations, they always have that book, the dusty book about the early years and the story. And I love hearing the myth can

Kahina Wardain: be so powerful in a venue, people who are not even around or telling stories that, you know, it's fascinating.

Christine Song: How did you get the company name? Where did the idea come from? There is a story to all of that, and it kind of starts with the founder.

Kahina Wardain: That's interesting. And so now you're a founder yourself. And I'm curious, like, are there things now that you understand that you weren't understanding when you were a chief people officer advising a founder?

Christine Song: Let's say yes and no.

Kahina Wardain: Tell, um, me.

Christine Song: So when people used to say, like, you don't operate like a typical chro. You're. You're a little bit different. And I always used to say, I'm a lot different. I think that I operate as a HR leader as if I'm the founder. And I know that sounds really arrogant for me to say, but for me, it was very much about. I became obsessed with, like, how we operate the business, how we hire people, how we groom people to scale up in their roles. And it became an obsession to me. Like, you become obsessed with it. And m. People used to say, like, Cristine, you need to tone it down. Like, I see it in your eyes, you look a little bit psychotic sometimes. And I'm like, it's just, I want this company to do so well, and I care so much about its success. And then I thought, man, what's wrong with me? Like, why am I taking it so seriously? I'm not a co founder. I don't have the equity that they have. But it was almost like, for me, if I'm going to go in and I'm going to commit to something. I'm going to go all in. And so I always understood how founders led the business. And sometimes I would say, okay, you and I need to tone it down. Like, we need to calm down a little bit. But there was something beautiful about that obsession because you, you would do anything to allow the company to win. Transitioning into an entrepreneur wasn't that difficult. Um, you know, people always say, like, oh, the luxury of it all is you don't have a boss anymore. You get to do whatever you want. And I don't really see it that way. When I worked with founders, I didn't actually see them as my boss. And I know some of the founders out there are probably like, what? What's going on, Christine? But it's true. I didn't see them as a boss. I didn't see myself reporting into them. I truly saw it as a partnership. And I always used to tell them that. I said, you and me are partners. We're going to, like, partner together and build this business. We're going to build the culture, we're going to build the strategy. And they will go, yeah, yeah, we're partners. And it wasn't like I was, like, hypnotizing them, but it was how I truly operated. If I saw the founder as my boss and CEO, I could never work for them. There's just no way that I could operate that way. My therapist says I can't handle authority. Maybe that's true, but. But if I see it as a partnership, I'm willing to go all in as well. I'm willing to do all the hard things, get the dirt in my nails, do whatever it takes. And I've had many conversations with founders where I said, okay, so we got this big life and death problem to solve tomorrow. What do you need me to do? Like, just tell me. And I would be on calls at midnight, two o' clock in the morning, talking to them, and we would come up with these wild, crazy, like, strategies, and I would actually do it. But you wouldn't think that way if you weren't operating like a founder.

Kahina Wardain: It's interesting because I think that language, uh, words, the choice of words, has a huge impact in life in general. And like, working for versus working with is something that's like a world of difference. And I remember in my consulting days, I was at a townhome meeting with the whole company, and the managing partner of the consulting firm that I was working with mentioned something about people working for you. And I kind of. I stumbled upon that. And I said to him, if you want a new generation to be, like, all in, it's not working for you. It's working with you. And then we, uh, started having this whole conversation. But I'm very sensitive to this choice of words because I think that it makes a world of difference, especially as a leader. Do you want people to work with you, or do you want people to work for you?

Christine Song: I love that you brought that up, because I've worked with leaders who do want people to work for them. They do want the authority. They want to have all the answers. They want to kind of be on the pedestal, and they want to have these very junior people looking up to them. So they want to be this mentorship figure. And I remember with every organization I went into, if I was introduced to introducing myself, let's say, to the new HR team, I would say, this is how we're gonna work together. And they used to go, this is so great, Christine. Like, I. You know, I admire you. I want to. I want to learn from you. I want you to be my mentor. And I will go, whoa, whoa, whoa. Like, let's not go there. Let's talk about how we can work together. It's a partnership. And they used to go, I've never reported into an HR leader who called it a partnership. And I said, but if we can partner together and kind of divide and conquer, there's a lot of things I don't know how to do either. There's parts of your job that you're going to do way better than me, but what can I do to help you? That's a partnership, right?

Kahina Wardain: And, uh, do you think that maybe there's not enough of that in leaders? And that's why we're talking about lonely at the top. That's something I've heard you say. That's something I've heard a lot of people say. Is it because of that, that leaders tend to want to be on their pedestal for some type of, like, ego?

Christine Song: I think some leaders do want that as an ego, which is why they tend to hire people that are, um, much more junior than themselves. So, I mean, now, this is going to get controversial, but, you know, they say, A, players will bring in A players, B, players will bring in C and D. There is some truth to that. And I don't mean like these.

Kahina Wardain: I believe in that.

Christine Song: Well, like, these leaders aren't going out there going, I'm going to find the lowest, you know, performing person to be on my team so that I could look like a star. But in some ways, there is some truth to that. I've seen a lot of leaders who would say, I don't want to hire that person that we interviewed. And I said, why not? They're a superstar. Like, they can help you to really achieve your goals. They go, no, that person, I think they're going to take my job in like six months. That insecurity would come out and I would go, I would love to hire stars on my team. The amount of things that you can accomplish if you have all star team. And there's a lot of people that are insecure about that. And so I think that's a travesty. I think that it tells you a lot about the person, what's going on deep down inside. I've never wanted to be on the pedestal. I don't want to be the person with all the answers. I always used to think, if I'm the smartest person in the room, I am certainly in the wrong room. Uh, I want to be in a room full of really smart people that are all trying to win on behalf of the company. We're trying to hit our mission, we're trying to hit our goals. And that means that you got to leave your ego at the door. You cannot feel insecure. Like, you've got to focus on what's the right thing to do for this team, this company, and how we can all achieve together. Um, and I think that people who are afraid to do that because they're so afraid that they're going to get. Become irrelevant or get canceled out need to kind of work on themselves a little bit.

Kahina Wardain: I totally agree with that. And I think that it's actually surprising how difficult, uh, some people find it to build or build partnership with their team, with their peers. I don't know why, but I've seen that time, uh, and time again. And that brings me back to isolation and leaders. So why do you think aside from that? So maybe some leaders like to be on the pedestal, and then they have to live with the consequences of their own decisions. But what are the other reasons for leaders to feel isolated? And is there a way to go differently about it aside from meeting peers and working in five to nine society? But I mean, how to go about that, like, within the realm of work?

Christine Song: I think there are people who truly believe, um, that they might not be good enough. I think that sometimes you reach a certain level in your career goals. That kind of happen through luck, maybe through connections, through hard work and Then when you get there, you feel like you need to prove something. You need to have all the answers. You need to, like, I think about, think about founders and CEOs. They're typically quite young. Uh, they didn't go to management school. They typically don't have an mba. But they kind of made it as a founder and CEO because they had a vision, they created a great product, they were able to build their, um, founding team. And investors are like, we believe in you. Here's like, couple million we want to throw into the business. That's a huge responsibility. And suddenly you're thrown into the spotlight. Now this person, you know, raised this many millions. All eyes are on you. It's that feeling of, I've got to prove my worth. I'm relevant, I'm here because I've earned it. And when you're kind of in that position, the spotlight's on you very suddenly. And if you don't have a peer network, one that you could really rely on, um, that OG that you could call at midnight on a weekend when you can't sleep and, and you know something's keeping you up at night, you're going to be extremely lonely. So my experience has been working with a lot of founders and executives of these high performance, high accountability roles in companies. And I've seen them on their knees, I've seen them balling their eyes out. I've heard from CEOs who said, I don't want to be a CEO anymore today. Like, I wish I could just, like, leave my job. I've heard other founders say I'm the only person in the company who can't just quit. Everyone else has the privilege of just quitting when it's a really hard job. Um, I've seen CEOs crying and telling me that, um, they can't talk to anyone outside of myself, and they feel comfortable because I'm HR confidentiality, cone of silence. But I say, who do you talk to, like, when you're feeling overwhelmed? Well, I have a therapist. I am, um, on prescription medications. Sometimes I talk on ChatGPT. Like that. That's really lonely. You've got to have humans to talk to. And if you don't go find them, it will make a world of difference sitting in a room with a real human being who can share insights with you versus talking to a machine.

Kahina Wardain: For sure. You're talking about, um, executives waking up in the middle of the night. On weekends, you meet a lot of executives and a lot of leaders through your work. What would you say are the top three concerns they have on their minds that are keeping them up, up at night these days.

Christine Song: I think when you're building a company, it's building as quickly as it is, especially if you've gotten investment in funding M, you're building it faster than you can learn in the role. And so you are really trying to scale yourself as quickly as you can. And every founder I know has read stories about how this founder was replaced. I mean, come on, even Steve Jobs was replaced, Sam Altman was replaced and then brought back in. But, but there is this fear of you're going to become irrelevant if you can't keep up with the growth of the company.

Kahina Wardain: Mhm.

Christine Song: Um, I think every leader CEO that I've ever worked with hits a point where in the early years, when you're building a company, everyone loves you. You've hired a great team, they're loyal to you, they love the founder. There is this mission that everyone feels streaming through their blood. But what happens is as the company starts growing and you start bringing in more leaders, and now the leaders are leading these OGs, it's not all about the voice of the founder anymore. They start to lose their identity and the culture starts to shift. And it's no longer just a room full of OGs, now you've kind of bringing in people from larger organizations, people who have seen it all, people who have been at, ah, more mature companies and they kind of come in and they scoff at how dysfunctional things are or how scrappy things are. And you lose that romantic vision of what that startup was like. And that kind of kills the soul of the founder a little bit. And I've heard many founders say to me, you know, like, I don't admire the culture anymore. It's shifted, Christine. Somewhere along the line when we went from 0 to 50, now that we're at like 250, 300, um, people are mean. You know, they go on Glassdoor and they see these rotten things about leaders and like, what happened to that essence of what the, the founding culture was in the early years? That's always something that they reminisce about and they're like, ah, I guess there's nothing I could do about it. I've got to shift into this new culture. But they don't love it as much as the early years. And I've heard of a lot of founders who are in these large tech companies now who want to create these incubation labs, these little innovation labs within these larger organizations because they want to go Back to the olden days. There's something beautiful about that.

Kahina Wardain: So the fear of being replaced, the fear of losing the culture that they, they've built.

Christine Song: Yeah.

Kahina Wardain: And if you think about executives, not necessarily founders, the leaders, you know, the C suite in general, what, what concerns them these days, what, what, what worries them?

Christine Song: I think there's something very similar. I think that when you think about leaders, they come into an organization based on where that company is at the moment. So you'll early stage companies, you'll typically attract leaders or executives who like that early stage. Get my hands in everything. I'm really involved in the work. And then there are leaders who want to join in the later stages. In the series C or D, after you're about 1,000 plus employees, they want to delegate, they want larger scope. Maybe they don't want to get their hands as dirty, but there's always that feeling of you're eventually going to be replaced. It doesn't matter if the company's doing really well. There's always this fear of you're no longer going to be the star of the show anymore. And when you first come into an organization, no one thinks about their end days. They're thinking about all the great things that they're going to build. But those end days do catch up with you. And eventually you see the shift. Your CEO doesn't communicate you as with you as much anymore. Uh, suddenly the board is a little bit more icy with you at board meetings. Like, I've heard executive talk about this. Like, oh, I know I'm going to be on the chopping block soon. I can feel it. There's an iciness to how they, uh, respond to me. And I'll say, like, where do you think this is coming from? Oh, it's probably the company's maturing and I was good for this phase of the business, but I'm not that seasoned person that can take it to the next level. So there's always this fear of, like, sure, nothing lasts forever, but it kills the ego thinking that you're only good for a certain stage, that that expiry date is kind of just around the corner.

Kahina Wardain: Uh, 100% people are human.

Christine Song: Yeah.

Kahina Wardain: So for sure it affects everyone. Um, you're talking about stages of companies. I want to touch a word on scaling a business and what that entails. And most of the time, it entails bringing in top talent. We talk a lot about top talent. What have you observed that's maybe a common denominator and the top talent that you've recruited throughout your career to help a company skill.

Christine Song: Yeah, I think when I think about the best talent that I've ever brought into organization, whether it was like early stage or later stage, they are great leaders. If you can't lead people, communicate well, um, be able to allow people to understand your vision, you're not going to succeed. You can't just be good at your hard skills tapping your keyboard. So there is something to be said about. Some people are much better leaders than others. If you can give a, uh, great speech, you can show people that you're in the trenches with them. You can share how you're feeling about what the vision is going, where the vision is going to take us. You're going to succeed being able to scale the company because your team is going to continue to get larger. What I find is an issue is when you bring in leaders who come from these large organizations, sometimes they have beautiful logos and they graduated from great schools, but they don't want to get their hands dirty. And I don't mean you need to sit there and do SQL coding at night, maybe for some organizations, but you also have to get involved in the work. You do have to get involved in the work to some degree. Otherwise, how are you going to inspire your team? How can you help them solve the problems that they're facing? If you're just sitting there, uh, in the ivory tower, telling them what to do, you do have to be involved. So I love companies where I've seen larger companies who kind of take a step back and say, you know what, when we hire that executive leader, we want them to get on calls. We want them to understand what the customer issues are like. I remember Doordash, the famous story about when they hired their, um, executive team members, they made them go do deliveries, go do the delivery, think about the issues that you face, go talk to some of the customers. And when you experience that, it's almost like you're a founder yourself. You're going back to the roots of the company and, and you feel the startup feel within your veins. And I think sometimes when companies mature, you lose that. So you start to hire people who maybe worked at $200 million AR companies. But is that really what you need? You really have to understand the person's motives for wanting to come to your company.

Kahina Wardain: That's an interesting takeaway that I'll take. I'm thinking of an onboarding of leaders, maybe that there's something to it to bring them, do the groundwork. There is a lot early on for

Christine Song: every role that you're in. So even for myself, if I think of it from an HR perspective, when I joined Organization, I said, I'm going to spend the first 30 to 90 days meeting with as many employees as I can, and the CEO will go, well, you don't have to meet with them all. Just have an executive meeting and, uh, talk to the leader of leaders. I said, but you're going to hear a common theme from these leaders. I want to hear from people who are on ground zero. I want to hear the people who are picking up the phones. And so I would try to meet with people from all different levels. I would never deny a meeting to someone who books in my calendar. And they used to say, like, when are you taking meetings, Christine? And I would say, my calendar is completely open. Like, if you need to book a time, book whatever's available to you. And I would love to chat with you. So I got to speak to a lot of people who had different viewpoints. I would encourage them to be honest and tell me, like, the ugly parts of your job, because that's where you're going to figure out how to solve those problems and fix things to make it better.

Kahina Wardain: Um, and there's always beauty in the ugly.

Christine Song: Oh, there is.

Kahina Wardain: It's like, ugly is rich.

Christine Song: Yeah. This is where problems are created, and then you find the solution. And it's a great story that you can share, right?

Kahina Wardain: No, I very much agree. Um, we're almost at the end of our conversation. I have two last, uh, questions that I really want to hear you on. What do A, organizations and B, the world needs more of?

Christine Song: I think there needs to be more truth and honesty. I think that, um, and this goes for, you know, leaders, companies, organizations, if you really think about it. Why is Joe Rogan's podcast so famous? Why is he making $100 million from the podcast? Because he speaks the truth. He asked the hard questions. Why was Oprah Winfrey so famous at the height of her, um, you know, TV shows? Because she asked the questions. We were all thinking. When I do interviews, when I meet with people, I want them to speak the truth, the unvarnished truth. Because then you get to the essence of the person. What motivates you? Why do you want this job? What salary are you looking for? What's, uh, your end goal? Do you want an exit? Do you want to be promoted to a certain level? Do you want to leave a legacy? Like, you've got to ask the raw questions because we're all individuals inside, and I wish people did a lot More of that. I wish there was less judgment. I think that if people could put down their guard and be able to share more, the world would be a better place. I know people that are even afraid to post One post on LinkedIn, I said, what are you afraid of? And they said, you know, people are going to criticize me. What are people going to think? I'm, um, like, no one cares. The world is so big. You're like a dot in this universe. And the reality is there's too much performative stuff out there. Speak the truth. People want to hear it. Um, UGC content is way more valuable than, uh, the marketing budgets that we give to agencies. Like, there is a movement going on where people want to see the real thing. And I think it all starts with being human.

Kahina Wardain: And do you think that it's happening, that people are showing more their true selves, or do you think that it's performative? True selves, hashtag vulnerable. But there's not both.

Christine Song: Yeah, there's both. And I think you can tell when you see it. There is the performative. I'm going to share my story. And you're like, this, this sounds very scripted. And then there are people who are sharing the truth. And when you share the truth, there's an ugliness to it. So you think about Instagram and TikTok. So Instagram is supposed to be very visually beautiful. Everyone wants to live the life of that Instagram person. And, um, then you look at TikTok, it's raw. People are crying on there. They're sharing the truth, they're sharing real stories. And recently I wanted to kind of tap test the two, um, platforms out. So on TikTok, I kind of looked up what are VCs saying? What are CEOs and founders saying? There are raw stories in there where, um, there's one VC that I follow and she talks about right now. I just opened up my VC studio and there's. My name's up there and I just moved to sf. It's a beautiful story, but she goes, I don't know if any of you know my real story. I grew up with food stamps. I was the seventh child in the family. I grew up really poor and I didn't know where my next meal was coming from. When you hear a story like that, you're like, oh, my God, I'm enamored. I want to learn more about her. And this brings a lot more attention to her business as well. But she's not doing it to gain clout. You can tell in her eyes when she tells the story, how hard it is to share that. But I think the world is shifting in that direction.

Kahina Wardain: Interesting. Last question. What's the uncomfortable truth we have not talked about in this conversation?

Christine Song: I think the uncomfortable truth is that because I'm so Forward in, um, LinkedIn social media, and I do a lot of, um, standup talks, people kind of have this idea of who I am, but only my true friends or real people who know me behind the scenes know the real me. Um, I'm a little bit of a clown. I am not as polished as I might come off. Uh, I'm very raw and honest. And if you've ever had a dream drink with me after work, I'll tell you the whole truth in the first five minutes, and I'm not as, um, you know, it's true, you know?

Kahina Wardain: Right.

Christine Song: And I think, um, even with the dinner that we had yesterday, a lot of truth came out. But again, this is where I've made lifelong friends through it all, and they were friends that I worked with as well.

Kahina Wardain: Yes. Thank you so much, Christine, for joining us today.

Christine Song: Thank you, Kaena. This was so much fun.

Kahina Wardain: Thank you.