HR Veteran Christine Song on Building Strategic HR Functions, Speaking Truth to Power, and Launching 5 to 9 Society

Christine Song has sat in the rooms where the hardest people decisions get made. As a multi-time Chief People Officer across corporate and startup environments, she’s learned that everything in business ultimately comes down to people, yet most companies get the people function completely wrong.

In this episode, Christine reveals how to earn your seat at the executive table, why you need the courage to speak truth to power even if it costs you your job, and the specific systems that separate high-performing teams from mediocre ones.

She also shares insights from launching 5 to 9 Society, her invite-only network for elite operators who understand that backdoor references and confidential conversations drive real business outcomes.

Here’s our discussion on building the systems and relationships that actually move the needle.

Mark MacLeod:

This episode is dedicated to the topic of people. If I had a pie chart of the topics that I discuss with my CEOs all the time, by far the biggest slice of the pie would be people. And every issue and opportunity in a company boils down to people at the end of the day. And so I’m pleased to have Christine Song on the show.

She’s a multi-time chief people officer. She’s led HR in established kinds of incumbent companies and multiple times in technology startups. And one of the truly strategic HR leaders that I’ve met in my career. We unpack kind of everything, why CEOs can go all the way, why leaders fail, the importance of culture, communication, having systems, changing how you operate, and being realistic about how hard your culture is. Don’t sugarcoat it and then surprise people after you hire.

So much more topics. She’s building a new thing called 5 to 9 Society. It’s an invite-only network for elite operators and founders. And it’s actually launching this week. So yeah, check this episode out. I really hope you enjoy it.

Christine, welcome to The Startup CEO Show. It’s a true pleasure to have you here. How are you doing today?

Christine Song:

I’m doing great. Thanks for having me, Mark.

Mark MacLeod:

Yeah, my pleasure. You, like me, have been sitting at the right hand of CEOs for a long time. And you know, when I talk with my CEOs, they say a few things. One, it’s like this company would be great except for the people. Business would be easy except for people. And then, when I think about the root of every problem and every opportunity in a company, it always comes down to people.

And so that’s why I really wanted to have you on, because I thought we could just go into that. Maybe let’s just start off for people who don’t know you, just give us a bit of your background, please.

Christine Song:

For sure. I think I started off my career working in large corporate, and I thought that was all there was for working. I didn’t really love it too much, but I was pretty successful. And one day, out of frustration, I applied to a startup, and I said, I’m going to do something totally new. Didn’t really understand what the startup world was like, but I needed a change.

And so for the past 10 years, I’ve been working in tech startups of different sizes and maturity. And my most recent role was Chief People Officer at Knix, and I was there for two and a half years. It wasn’t tech, but they had the same scaling problems that tech startups had. And it was a great experience working with Joanna Griffiths.

Mark MacLeod:

Yeah, she’s a very special CEO. We’ve had her on this podcast. I mean, the size of the company that she built as a solo founder, fundraising shortly before giving birth to twins, dealing with COVID, honestly, just so much respect.

So I’ve noticed this trend. You know, when I first entered the startup world, HR was not remotely strategic. HR, like for my first three or four CFO roles, HR reported to me, not to the CEO. And then this was considered to just be like this back office, hey, we need some policies, blah, blah, blah, we need to write up this offer, like, it was not strategic at all.

Whereas now some of the best CEOs recognize, well, everything actually does boil down to people. And so HR is truly strategic. But I would say many CEOs don’t have a strategic HR function in their company. So I’m curious, like, hey, what are your thoughts on that? Do you agree? And like, how do we make HR more strategic inside startups?

Christine Song:

I think HR took a major shift after Covid. I think when Covid happened, I remember a lot of CEOs reached out and said, oh my gosh, I don’t know how to manage this. We’ve got to go fully remote. We’ve never done this before. And everything kind of shifted.

I think people started realizing, sheesh, you can’t run a business without HR. They’re not just there to order pizza and plan birthday parties. It’s actually a strategic role. I’ve had a lot of HR people reach out to me, and I think the one thing that they always ask is, how do you get a seat at the table. And I always say, if you want that seat, you’ve got to earn it. You can’t just say, hey, I’m the head of HR, so I’m going to sit here with the CFO and the head of sales. It doesn’t work that way. It’s how you operate.

And I think a lot of HR leaders mistakenly go into roles. They’ve got their templates, they’ve got their processes, and they just apply them to every organization that they go into. HR was a very siloed function back in the day, just like finance was. And through the decades, it became much more strategic. And finance definitely was the right hand to the CEO. And I would say HR became the other hand.

There’s a lot of strategy involved, and you’ve got to tie your HR initiatives to the business objectives. And I think the one mistake that HR leaders make is that they just have their own siloed data and metrics, and they’re just ready to report on engagement scores or performance metrics.

But meanwhile, there’s a big fire going on here. You know, the company’s not generating their targets, and they’ve missed quota. You know, are we even going to make payroll? But HR is in a totally different world, talking about their own metrics. And I think that’s where you’re not going to be invited to the table, because the rest of the business is managing the business. You’ve got to figure out a way to support the business as well.

And some of the things that I think about are HR can be strategic by thinking about who we are hiring the right profiles to meet our quota attainment. Do we have the right leadership team for the next capital raise that we’re going to be doing? What needs to change so that we can scale the company faster and increase velocity? Those are the kinds of things that the rest of the business would be interested in. And so I would say tie your HR initiatives to the business outcomes.

Mark MacLeod:

I like this line of having a seat at the table. Would you say to have a seat at the table, you need to be business first, function second? Like, you need to understand the business first. Is that just a prerequisite for anybody who’s at the table?

Christine Song:

Yep. I think every person who’s at the table has to think about the business first. And from an HR perspective, I think about how I can support the business and each of their leaders so that HR becomes a partner? It’s not just an HR business partner, because it sounds good, you truly have to partner with your leaders, and you’ve got to have honest conversations. You’ve got to be pretty forthright and direct, and it’s not as fluffy as people think.

You’re not there to make people happy. You are running a business. You are making sure that the most expensive expense out there is payroll, it’s the talent function, it’s the people. And so it’s a critical role, I think. And for me, I’ve challenged CEOs, I’ve challenged executive team members, I’ve challenged the board.

I’m not afraid to do it because at the end of the day, I think when you think about what’s the most important thing, what am I trying to accomplish? You’re trying to do the right thing for the company. So I’m not in service to the CEO, I’m not in service to the board, or my HR team. It’s really in service to the company.

Mark MacLeod:

I’m a big Godfather fan, the movies and not movie number three, it should never have been made. But you know, this notion of a consigliere, like a trusted right hand, somebody that you go to with issues. Like, I always tried to be that person, but I think the best people leaders are also that person. Like, I think of Wendy from the show Billions, if you ever watched that.

Christine Song:

Yes.

Mark MacLeod:

Did you play that role for your CEOs, and how did you become that person?

Christine Song:

I think I became that person with the first startup experience that I had. I had worked at a company that I had never heard of. It was really small. I think we were like 35 people. And about four or five months after joining, we raised private equity money, a few million. And everything accelerated really, really quickly. So I had to learn startup overnight. I had to manage bringing on an executive team. I had to report to the board for the first time.

And I had a CEO, he was a founder CEO who just didn’t have good emotional regulation. And he used to call it passion, but we called it other things, and it was really, really hard. And what I realized was that a lot of the executive team members were really afraid of him. They were intimidated by him. He was a big guy physically, too. He was like 6’2″, and he bellowed a lot when he got upset.

What I realized was, gosh, there are so many mistakes he’s making, and if I don’t say something and I don’t speak up, this company’s just going to go down the drain anyway. What was the point then? Our equity means nothing. The company’s going to fizzle, the board’s going to be disappointed. I may as well just speak up and make all the changes that need to be made.

And worst comes to worst, you get fired. Big deal. The way I see it was someone said to me, they go, Christine, you kind of have the courage to speak up to the point where you could get fired. And I’ve always, always taken that to heart because I stay up at night, and I think if I don’t say this thing, which is so critical to the business, and things don’t change because everything’s falling apart, this business won’t last long anyway.

So, I’ve always made a decision to be honest and forthright about it. And that’s provided me with a lot of success in my career, but also a lot of stress and heartache for myself because sometimes you go to bed at night and you think, man, am I the only leader at the table speaking the truth? And everyone’s hiding behind me, and I’ve got to be the one that’s got to speak up?

It’s created a lot of stress for me over the years, and there are some things now that I can kind of sense that I’m not going to tolerate. And so I pick and choose leaders that I want to work with carefully, and the kinds of environments that I want to put myself in. Because it’s got to be worth it. I’m going to give it 110%.

Mark MacLeod:

I love it. It makes me think of that old fable, the emperor has no clothes, right? Like, somebody actually has to tell the emperor that they’re naked. And you know, in some ways, that’s the role of a coach, is to shine a mirror and be like, hey, dude, this is what I’m seeing. So, kudos to you for having the courage to do that.

I’m curious, would you do that in one-on-one settings, or like literally in a leadership team meeting, you’d call things out?

Christine Song:

You know what, I will speak the truth in leadership meetings and encourage others to do it as well. And I didn’t do it in an emotional way. It was very civil and just, direct, and honest. But when I was in a one-on-one setting and I was giving the feedback, whether it was to the CEO or one of the executives, it would be more forthright. It would have some emotion in it. I would really like, come on, we’ve got to change this. Like, we can’t operate like this.

There were a lot of long nights on the phone till 1 am talking about something really critical. And sometimes you’re having drinks while you’re on these calls because it’s so intense. But I wasn’t a founding member, I wasn’t a co-founder of the company, but for some strange reason, I always operated as if I was.

And you know, I’ve taken a lot of slack. Some people have said, why do you care so much? Why don’t you just be an employee, put in your hours, get paid, and you know, call it a day? You don’t have to be so stressed out about things. But for me, it’s almost like if I make a choice to join a company, I want to be so good at it, I want the company to do great. I want us all to succeed. And you can’t do that unless you’re facing the truth, and you can take the feedback that comes with it as well.

Mark MacLeod:

Yep, totally agree with that. I’m curious, how did that company turn out?

Christine Song:

The company eventually did… Gosh, it was such a journey. It was like in one year, I think we did three acquisitions. So we acquired a lot of companies in the US, and then eventually they just kind of merged. I think they merged with like four or five companies, and they did well; they’re now a much larger company.

But it was a great experience for me for my first startup to have gone through all of that, and worked really closely with the board. I still have great respect for them today. And, you know, a lot of the leaders moved on to do bigger things, which I’m really proud of. But you’ll never forget your first, you know.

Mark MacLeod:

No, that’s right. I agree with that. You know, when I onboard new CEOs to coach, after we do the initial onboarding, the very first topic is like the leadership team, because that’s the leverage of the CEO. You go in the beginning, it’s your own individual heroic efforts. You’re building product, you’re selling product, you’re taking out the trash, whatever.

But by the time I get involved, it’s a growth-stage company, and you’ve got maybe either a full or a partial leadership team, and that’s who you succeed through. And I find more often than not that not everyone keeps up with the growth of the company. In fact, frankly, often the CEO doesn’t. And that might be a reason why they come to be coached.

Sometimes it’s a surprise to the CEO. Like someone who used to be great, no longer is. And you don’t even realize you’re tolerating. Like, why do you think that? Is that like that some people just can’t keep up? Obviously, people have different degrees of intelligence, different backgrounds, and you know, you had way more experience your second go around than your first. But anyway, just riff on that observation to the extent that you agree with it. If you don’t agree with it, then rip it up. You know, like, the floor is yours.

Christine Song:

I do agree with it. I think that we’ve always had that saying, like, the people that start the company with you aren’t going to be the people that are going to stay with you in series C or D. And there is some truth to that. Not 100%, but there is some truth. I’ve seen that some people operate much better at an early stage. They’re more of the generalist; they can put on three or four different hats. They love learning something new, and they’re not really focused on process and scalability. It’s just whatever you need them to do; they’re going to go out there and do it. And it’s a beautiful thing because not a lot of people can do that.

But you know, I think about when a company needs to scale and it needs to grow, you’ve got to set up the processes. And I’m not saying set up bureaucracy for the sake of it. It’s really creating scalability. Like, I think of chaos in a company starts in HR because there are a lot of things happening, and there are no processes or rules in place yet.

If you don’t set up the systems and kind of operate like you’re in product, you’re going to operate as if you’re an IT help desk, and you’re just going to pick up the phone and help people put out fires every day, and you’re available 24/7. That is not scalable. If you want to operate like that, you’d better have a team of a hundred HR leaders. But the reality is you’ve got to set up processes, you’ve got to have the rigor to do it. And some people do it much better than others.

I’ve been at early-stage companies where I was the sole HR person. I’ve got to set up everything. Nothing exists in HR, and then I got to build out a team, and I’ve also been that person who could have a team of 20 people, and it’s running smoothly like a machine. So I’m not saying I’m perfect, but I’ve kind of gone through these stages, and there are some stages I enjoy more than others, just preference-wise.

But I think a lot of people kind of struggle when they get to a certain stage, and they also come to a realization that they’re not happy either. So, being on the HR side, I’ve done exit interviews. I’ve had to let people go because, you know, you try and try to get that person to scale into their role, and it gets to a point where they’ve hit their ceiling.

And when I talk to them at the exit interview, they just say, you know what, in hindsight, I look back and I think my happiest times at this company were in the early years. I really liked it when we were 30 people and a dog in a small room, and it was just divide and conquer. And I want to go look for something like that again. And that’s a beautiful thing that you can recognize that.

But there’s also a lot of people that come from corporate, formal structures, banking world, and they want to come into a startup because they think it’s fun and sexy and they read so many stories about exit, but they come in and they say, oh my God, it’s so dysfunctional and there’s no processes and everyone’s just running around like hair on fire and they can’t handle it.

And you’ll have a CEO going, we never should have hired someone from corporate. They can’t handle this kind of environment. They’ve never seen growth like this before. There is an environment for some people and a non-environment for others. But most importantly, if you do want to continue progressing, you’ve got to grow at the rate of the company.

If the company is growing 30% per year, you can’t just sit back and be busy for the sake of being busy. You do have to work on yourself and read a few books, go get a coach, watch some videos, and talk to your peers to create a network. For all the scaling that you could do just being a good leader, I think some people are really good at it, and they’ll teach themselves, and other leaders will go to their manager and say, what are you going to do to develop me? It’s your responsibility as my manager. It is not your manager’s responsibility. They can support you, but you’ve got to manage your own career.

Mark MacLeod:

Yeah, I’m old and crusty now, but I wouldn’t have reacted very well to somebody coming and telling me it was my responsibility to grow them. I’d be like, no, you’re actually here to give me leverage. I’m here to support you in a purely self-interested manner so that you can give me leverage. So no, you have it entirely backwards.

I’ll probably circle back to this question about the leadership team and how they keep up, but you made me think about Shopify. You didn’t use these words but Shopify had an HR department, but they also had that talent acceleration department, which was a separate in-house coaching team.

And Shopify is obviously an exceptional company. Certainly, the biggest tech company in Canada and the only company I can think of in recent memory where all three active co-founders were crushing it in C-level roles at the time that they went public. And it’s not just because they’re smart, Tobi is obviously ridiculously smart, but it’s because they invested in it, and there’s a huge luck in timing.

Like, the single biggest thing you can do to grow yourself as a leader is to unlock revenue growth and then hang on for dear life. And their business was growing, but Tobi got a coach early on, and at one point, he had two coaches, and then they brought one coach in-house, and he was coaching all the founders, and then they built a coaching function.

And so it’s maybe not the manager’s job to grow you, but that coaching department did play a big role in growing the talent. Because by definition, no one in Canada had seen the scale that they had, and so they had to grow their people.

So, what do you think of that as a concept? Is that something that growth-stage, kind of scale-up companies should be thinking of, not just HR, but talent acceleration?

Christine Song:

Yeah, I think that’s a great idea. It’s very similar to what we did at Knix. We brought in a coach, and we called that person an embedded coach in the organization. The reason why we felt that was better than just giving someone a stipend and they go out there and find their own coach was that when the coach was embedded in the organization, they knew the pace of how we worked, they knew what problems we were going through, they knew the leaders that they were working with and they were familiar with the environment.

So it wasn’t just someone telling their coach, oh, I have a horrible manager, but I’m like a superstar. And the coach doesn’t really see what’s going on. This embedded coach knew all the players. What made it challenging was that we had to figure out how do you have one coach for, let’s say, our head office was, like, 200 people. One coach for 200 people. You can’t help everybody. And you can’t just take a ticket, and every time someone wants a spot at a coaching session, you’re available.

So we thought, let’s reserve this mostly for our director level and above. They’re the ones who are managing the teams. They face most of the people’s problems, and they need a toolkit. They need someone to go to. They need to kind of develop themselves so that they can manage larger groups.

And it was probably the best idea that we came up with. I know that the service that we use they were sending out embedded coaches to different organizations, and it was like a matchmaking system. So that was a great opportunity to invest in our employees and promote their leadership.

It wasn’t perfect by any means because we faced scaling issues. We faced issues where the confidentiality with the embedded coach kind of clashed sometimes with HR because something was…

Mark MacLeod:

I was going to ask, is it a safe environment? Can I truly confide in you? Are you going to go, hey, you know what? Joe here, he’s losing the plot, you need to get rid of him?

Christine Song:

Well, what the coach did was she was pretty honest with her clientele, as you can call them. And what she said was, look, what we talk about is sacred. Like, I’m not going to share that, but there are some themes that I’m going to share with your manager, because if I share the themes that are happening in the organization, it’s going to help you.

And so everyone understood what that meant. And there were some 360 reviews that we would do. The coach would manage that, and obviously, the manager and HR would get the results. So there were some things that we shared together, but for most part, the conversations that occurred, if someone went to the coach and said, look, I’m intimidated by the CEO and I don’t know how to manage conversations with her, the coach would coach them and it wouldn’t be shared with the HR team and obviously not with the CEO.

Mark MacLeod:

So, you’re a fan of the notion of internal coaching in some fashion?

Christine Song:

Yeah. I think coaching, you’ll get better results than a leadership development program that you launch. The leadership programs are so vague, and it doesn’t really support individual learning. I think AI could probably do better, but obviously, the luxury product is having a coach that understands you and can work with you, and you can build trust with them.

It’s just difficult to get a coach for every single person. So we tried to have coaching sessions. We would have directors come into workshops and have coaching sessions. Maybe we’re talking about direct feedback. How do we do that? And we may launch it just before a performance review session occurs.

But there was also the one-on-one coaching, which was valuable. It was just with one person. It was difficult to find the time. But they did trust her. And there were times when employees would come to HR and want to be coached by them. It depended on the kind of relationship you had with HR or with the coach. And individuals are picky sometimes.

Mark MacLeod:

Yep, that is true. I wonder, like, venture capital comes up as an analogy. Let’s say I’ve got a portfolio, right? Like, theoretically, if I’m focused on maximizing returns, I should put all of my effort into the high-potential and ignore the underperformers.

Would you take a similar approach? Not in the coaching as a service, hey, let’s learn how to give feedback, that’s probably available to everyone. But like, would you invest more in your high-potential leaders and less in your underperforming leaders? Is that a thing?

Christine Song:

Yeah, 100%. I think about the olden days, HR was kind of responsible for performance management and discipline management, that horrible word. And HR spent a lot of time working with the underperformers. And quite honestly, a lot of these underperformers never made it. They were eventually moved out of the company, or they chose to move on.

So I think nowadays, focusing on your high performers is the way to go. Put the coach in front of the high performer, get them to kind of grow exponentially in the next year or two, and you’re going to see the results.

The same with HR. When I was coaching employees internally, I put more effort into the high performers. And sometimes it wasn’t even just high performance. It was potential. It was like the people who are willing to invest in their own development, who are reading the books on the weekends, they’re not out having fun and partying. They’re the ones that are coming to me, going, look what I built over the weekend. Can you take a look at it? I need a sounding board.

These were people who genuinely took their careers and wanted to grow, and they had a growth mindset. Those are the ones that obviously I spent the most time with. And it just seems really unfair when you think about it. But it’s not unfair because they were the ones who cared the most.

And it kind of goes back to coaching. I’ve heard about a lot of coaches who kind of vet their clientele, and they’ll have a conversation with them and they’ll decide do they want to work with this person or not. And when I asked coaches, why do you do that? They said, because not everybody’s coachable.

There are some people who will just go through coaching because their manager or their board told them to, but they’re just going through a process, and they’re not genuinely invested in it. You know, taking in the feedback, hearing the hard truths, feeling those paper cuts slide into your soul. Like, you’ve got to really feel the pain to be able to work on yourself. And not everybody is genuinely ready for that.

Mark MacLeod:

A hundred percent. I can tell you I do that. It’s a two-way street. I’m sure the CEOs also want to know, hey, do I want to work with Mark? But like, for me, the number one thing I look for is self-awareness. Because that’s the thing that’s going to enable you to see the signals all the time and grow faster than your business.

If you think your shit doesn’t stink, you’re going to miss the signals. And then also I call it the Tokyo test. Would I be happy or unhappy sitting next to this person on a plane going to Tokyo for 14 hours? So like, life’s too short. I want to be with people that I like. But the number one thing is self-awareness. That’s by far.

Christine Song:

Yeah. And not everyone has it. I think there are a lot of people who genuinely think they have it, they do not. Like that first CEO that I talked to you about, the founder, when we talked about self-awareness, he would always go, oh, I know there are so many people that don’t have self-awareness. And I would look at him like, yep, you would be one of them. He had no idea.

Mark MacLeod:

That’s right, yeah. Well, there’s so much hype in the startup world, right? And there’s a risk that you could end up believing your own hype. And that actually brings up a thing for me. I’m curious about your thoughts on this. Like you catch up, you’re at some big event, Collision Web Summit, whatever, you’re catching up with people, and you ask everyone how they’re doing, and the answer is they’re crushing it. Catch up with a VC, how’s your portfolio? Yeah, we’re crushing. Everyone’s crushing it, which is mathematically untrue because most startups fail, right?

Which means that we’re putting on this facade. And I’m wondering, do you get your CEOs to take the mask off and stop bullshitting and just confide in you, kind of how they really feel, and actually share their fears with you? Like, is that a thing?

Christine Song:

Yeah, I’ve been really privileged. Like, behind closed doors, I have always had such a close relationship with the CEOs that I’ve worked with, and they’ve been very honest and forthright. When they know their baby’s ugly, they’ll admit it. And it’s almost the opposite for me. I felt some of the founders and CEOs that I work with always talked about the negative. Oh, we’re just doing horrible, right? And it’s like, they’d be like we’re doing the worst, and everyone’s doing so well.

Like, no, a lot of companies aren’t hitting their targets right now. It’s a very difficult time. Like, no, we could be doing so much better. I don’t know what’s wrong. And I’m like, what about that win we had? We just won that logo last week. Oh, who cares? I can’t think about that. I’ve got to think about all the things that we’re not winning in. And to be honest with you, it started to make me depressed. And I don’t get depressed easily.

But when you’re constantly told, like, nothing’s good enough and we’ve got to do better, like, I get that we have a high bar. That’s the way you want to operate, but when that bar is unattainable and good enough is never good enough, like, nothing is worth celebrating, it just makes you feel like, what’s the point?

There were a lot of times when I used to think, like, can’t we work hard and have fun? Like, would that be such a sin? I thought about, like, some of the companies I worked at where we worked so hard, and at the end of the day we couldn’t afford to go to the Ritz, but, hey, let’s have a beer together. Let’s sit down and tell some funny stories. And it’s like, those are the memories that I’ll never forget. Or, let’s go to that cheap pub across the street. It’s happy hour.

Like, celebrating the little wins just made us all want to work even harder the next day. And I don’t feel that a lot of companies do that very much anymore. I was at a company recently where the sales team was supposed to celebrate, like at the end of the day, it was like a Thursday, and they were going to celebrate with beer. And like the whole sales team left, and there were two guys left drinking beer by themselves.

And the guy said like, oh, it was so depressing, everybody left. I thought we were supposed to stick around and have beer. This is what we did when I worked at my previous company, and I was like, I didn’t even hear about it. Like, why didn’t anyone invite me? I said, I’m coming for that beer next week. I mean, why can’t we celebrate and have fun and still work really hard? I think something’s missing right now.

Mark MacLeod:

Yeah, it’s so sad. I think a big part of it is comparison. You’re comparing the hundred percent you know about your company to the 5% you know about your competitor. That’s never going to turn out well. And then this hustle porn thing, we just need to keep grinding. I don’t know, it just leads to burnout. I tell my CEOs all the time, having sold a lot of companies, the number one reason why founders want to sell is that they burn out.

Especially from a CEO, some acknowledgement, some praise, some recognition, not like a participation ribbon, like, oh, great, you showed up today. But like something truly exceptional, and you recognize it. Man, that fuels people. Like, that’s jet fuel in terms of motivation.

And so, yeah, these little rituals, acknowledgements, just super powerful and they don’t happen anywhere near enough. And I had Tobi on the podcast last year, and I asked him, dude, do you ever stop to smell the roses, or are you always focused on the gaps? And like, instantly he’s like, yeah, yeah, just focused on the gaps, and he’s obviously had a massive success, and still all he’s focused on.

Christine Song:

I just think that culture is glamorized a little bit too much. And so what happens is no one tries to make it better. And what I mean by that is this whole thing about 996 culture, it’s like, originated from China. You work from nine to nine, six days a week. Fine, I get it. Some early-stage companies, sure, you gotta do that to get off the ground, but if you’re hiring someone into that environment, you better be forthright and honest.

I’ve seen early-stage startups that operate seven days a week. You gotta be on call. You’d better be checking your Slack. But when I see them interviewing candidates for that role, they never tell them that. They just go, we work hard here just like everybody else, but that poor person at the other end has no idea what they’re signing up for.

I remember talking to one candidate who said this looks like a really intense culture, but I’m curious how intense it is, because I’m going to be honest with you, I have a newborn son. He’s really young, and I do want to spend time after work or on weekends with my child.

And in my mind, I was thinking, you’re never going to see that child for three years if you work here. But no one would tell him that because they wanted to hire him. And there’s a rude awakening when that person gets in and they’re like, what the fuck is going on? Literally, they are shocked.

And of course, the first person to hear about it will be HR. And I’ll be like, what did they tell you at the interview? Oh, they never told me this. I asked them, and they said there’s a relatively good balance, and we just work hard. That’s too vague. I think you have to be upfront and honest about what people are coming in for, and that way, you’re not going to be surprised and bamboozled when you have the wrong fit as your hire.

So, I think there needs to be some honesty, but I also think this hustle culture isn’t sustainable. Like, if you are working 80 to 100 hours a week, you might be able to sustain that for a quarter. Maybe something important and critical is happening. But if you expect all your employees to work like that for 365 days a year, that is not possible.

And the reason why I say that is, like, I always worked a lot. I worked a minimum of 60 hours. 80 hours was normal. But as I started getting older, I started seeing people in the leadership team at my previous companies, I started seeing them go through a cancer diagnosis, high blood pressure medication.

This one CRO that we had, who was just killing himself trying to hit his quota, suddenly couldn’t come into work. And we asked what happened? And he said, I have this strange vertigo. I can’t even see. I can’t even stand up. And he said, I can’t even drive to work. And so we said, well, why don’t you go see a specialist? And he goes, there is a waiting list to see a specialist. I can’t even function. I’m literally in bed right now.

And he had an appointment for a specialist in 30 days, and we were scrambling trying to find someone that he could see. This is what you’re going to be faced with if you think you can sustain that kind of culture, because nobody is a superman, nobody is invincible. And you might think you are in your 20s and 30s, but you’re going to shorten your lifespan really quickly like that.

Mark MacLeod:

A thousand percent, for sure. And I’ve been on both sides of that. I was that person at one point and lived in the world of should: I should be doing more, I should work harder, blah, blah, blah, and should just imply somebody else’s expectations. It’s not actually true, but I came to realize how unsustainable that was.

And then I tell my CEOs a few things. I probably just repeat the same hundred sentences. When you get old, you just repeat yourself. But like, one of them is like a healthy person has a hundred priorities, and a sick person has one, which is to be healthy.

Like, your health is literally your most important thing, and it’s the foundation of your performance. Like, today’s performance began last night based on when you went to sleep. Like, sleep is a thing. Like, it’s so important.

Then, like, you’re creating, you’re turning an idea into a company. You’re creating growth. This company is now going to be 2x bigger than it was last year. Therefore, you’ve created half of it. You can’t create when you’re stressed, or it’s harder to create when you’re stressed. So, just trying to get people to unlearn, right?

And then like, don’t focus on the 80 hours. That’s just an input. Like, so many hours are wasted, so many people are checked out. You know, when I was in a company last time I was operating, you can’t come to a meeting and be doing emails and messaging. If you’re in a meeting, you’re in the meeting. And if I catch you doing that, you’re out of the meeting. Like, let’s be engaged and get shit done.

Christine Song:

That is so true. When I think about all the hours that people work, let’s say on average your leadership team works, let’s say 60, 70 hours. And I did an exercise at one of my companies, and I said, I want you to jot down what you spent your time doing this week, each day. And a lot of it was just stupid work. Just things that weren’t automated, processes that weren’t implemented. You’re just trying to work as if you’re still that 30-person company, but you’ve scaled to 300, and you’re just doing everything manually. You’re wasting so much time.

And I think about how time is the most precious resource that we have. You never get it back. So you’ve got to really preserve it, but you’ve got to work on the most important things. And the danger of companies that get more mature and grow, people always say, oh my God, we lost our agility. We’ve got to increase velocity. You hear that all the time. What happened? We used to move faster.

It’s because you’re still operating as if you’re 30 people, but you’re 300. You’re not communicating properly, you’re not building out the right channels. You’ve not clarified what the most important thing is. People are still using that template for the sales meeting that you had five years ago. And now it’s like a bloated 150-slide deck because no one’s cleaned it up and said things have to change.

And so I think that’s the most important thing for a company to grow and to scale. They’ve got to really change as they do. You can’t operate as if this is how we operated when we started, and we’re going to continue to operate that way. This is why companies blow it out with so many people. My opinion.

Mark MacLeod:

Yep. No, I don’t disagree at all. I’m curious. You could either answer this from the point of view of CEO specifically or executive team leaders generally. But when you look at the ones that have had the most success, have kept up with the growth, or created the growth, what are their habits? What are the actionable observations you have from those leaders?

Christine Song:

Yeah, I think the most successful leaders really had great systems thinking. They understood how to scale the company appropriately and ensure that the stress points are being taken care of. They understood that the process was a good thing and allowed us to be more agile.

They were great communicators. Like, they understood that not everybody’s going to be in the room at the same time. Now you’ve got to figure out a way, how do you share the most important message with the whole organization so we understand what our North Star is, that we understand what the executive team finds most important.

You bring that down all the way to the coordinator level, and it spreads across the company. And I also think that the best leaders were people who could give direct feedback. They were honest and direct, but they knew how to balance that with humanity. And what I mean by that is not being fluffy and not caring about being light.

But you also have to think about you can’t be hated either. Like, if you are a CEO and you’re being so stern and you’re telling people to just fucking work harder, don’t expect to be liked, but you will be hated. And you’ve got to think of it as like, this is your team. I know that a lot of people compare companies to high-performance sports teams. And I know some of those coaches are swearing and yelling at their guys, but they’re getting paid millions of dollars, okay? This is what they signed up for.

So, I don’t think we can glamorize it by looking at sports teams or F1 drivers or whatever you want to compare it to. But there have been really great leaders out there who are very direct, but they understand how to work with human beings. They know how to share feedback that gets that other person to understand where that person’s coming from.

And they don’t just tell them what to do. They’re not giving a directive. They’re saying, like, how can we do this together? Tell me how I can help you. I know that you’re better than this. You know, you’re performing here. I know you can make it up here. Like, let’s do this together. Like, there has to be some sort of motivation.

And I know some CEOs are like, oh, I hate giving the motivating message. I just want to get shit done. Well, too bad you signed up for a CEO. Everybody’s looking at you. Everyone’s listening to what you say. You are the leader of the all-hands meeting. You’d better share some motivating messages.

It’s the same thing with HR. There are some things I don’t love doing. Do I like being the problem fixer? No, I don’t. But sometimes those are the things that I have to do. And you have to do it really well. And so I guess some of those leaders who were really great at doing that just had more experience in life.

I think that there was a maturity there that you couldn’t just be technically smart. You also had to go through life, you had to work with a lot of different people, you had to interact with different personalities, and you had to build lots of teams. And when you get to that point, and you kind of look back, like, you talk great. You know, you can talk to anybody and resonate with them. People will listen to what you have to say. You kind of command the room. You do have that gravitas, and you don’t have to try that hard. And I’ve always found that really fascinating.

Mark MacLeod:

So many good points there. I’m curious about the systems one. Like, you began your career working for Galen Weston, one of Canada’s most successful entrepreneurs. Built a pretty big company, and we often in startup land like to poo poo the big corporations. But I’m wondering, is there anything you took from that? Because you can’t run a company that big without systems. Is there goodness from corporate that, at a certain stage, more innovative companies should be embracing?

Christine Song:

I think that a lot of people kind of criticize corporations, but there are some things that they got right, and when I think about what those things were, they were very good at communicating things, they were very direct and clear. There were some things that they said they weren’t going to tolerate. So you couldn’t push, like kids pushing their parents. You knew you could never get away with it, and they drew a line about things that they would not tolerate.

So if you did cross that line, you were removed from the company, and you weren’t surprised because you were told that’s what was going to happen. Having worked in startups and some of them being very dysfunctional, there was a lot of tolerance for bad behaviors, a lot of dysfunctions, a lot of things that shouldn’t have been tolerated that wasted a lot of time. A lot of people, leaders’ time, a lot of HR people’s time, like just things that, I mean, are borderline illegal.

And I’m just like, why are we tolerating this? Why? Because we got some OG who’s been with the company for five years? Who cares? This person is going to bring this company down. And once you have bad PR and it gets out there, you can never erase that. The Internet lives forever.

So, corporations really understood that well, and people understood that. Going back to Galen Weston, he was probably the first founder that I worked with, and there was something very genuine about him. He was so powerful, and when he came into the room, you couldn’t miss him. The guy was like 6’6″. He was so tall and lanky, and he would wear his gorgeous, tailored Tom Ford suits.

Mark MacLeod:

It had to be tailored at that height. That’s not off the rack.

Christine Song:

Tailored with his silver hair and his perfect posture. But he operated the company as if it were still like his own, that it weren’t a publicly traded company. Every weekend, he would go visit the supermarkets and he would go to every stand. He would go to the fruit stand, he would go to the butcher, he would talk to every single person, and he would pick a different store each month.

And I was fascinated that he would spend his weekends doing that, but he loved it. And if he walked into your supermarket, everyone would gush, oh, my God, Galen Weston Senior is here. He also did the same thing when he was going to open the Loblaw location at Bathurst and Lakeshore. It was going to be like two floors. And he had never opened a Loblaw store that was two floors.

There were all these agencies that drafted up like, this is what it should look like, and it’s state of the art, and he didn’t like it. So he would tour around the US and go visit all these other kinds of concept stores that had two floors. So he would go see a Home Depot that had two floors, or he would go to a supermarket in the UK, and he would really look to see what I can incorporate, what do I want Loblaw to look like?

And we were delayed almost a year opening that store because he wanted it to be perfect. And this is like a founder who cares. This is like someone who truly treats the business as if it were his own. And I learned a lot from him. He would start his Monday executive meetings flying in bagels from his Philadelphia plant, and the executives had to sit there and eat the bagels every morning to make sure that they were high quality.

But when you really care about your business, you will operate as if you’re always a founder. And I really appreciated that. So, I did learn a lot from corporate. I learned that processes are important, and how you communicate is important. And I think there are some lessons that startups can learn from that.

Mark MacLeod:

I love it. You’ve highlighted, both in this answer and in previous answers, a really important thing, which is communication. I tell my CEOs all the time, basically, the bigger your company gets, the more your job is actually just a communications job. And both the US and Canada have recently gone through elections, for better or worse, and politicians are a bad connotation, but I tell my CEOs, look at a politician, they’re on message, right? Like, they’ve got the same bullets, and they’re just hammering them over and over again so that you know.

I tell my CEOs, basically, you’ve got to do the same thing, all the time hammering vision, mission, North Star values. Why are we here? What matters? Helping every person connect their work to the overall context. So yeah, that’s super important.

And then with that story about Galen, what came up for me there is actually the true org chart. The customer is at the top of the org chart. But often as companies get big, the CEO gets to get more and more removed from the customer, and then they lose their way. So yeah, just staying really close to the customer is really important.

Christine Song:

He did stay close to the customers when he went into those supermarkets. He would also walk up to customers and he would say, hello, nice to meet you. And they would be like, oh my God. And he would say, are you a shareholder of Loblaw? And a customer would say, why yes, I am, sir. And he would say, that’s wonderful. So, where do you buy your groceries when you’re not at Loblaw? And the person would say, Walmart. He would say why? He’d say, the prices speak for itself. So it was kind of funny.

But he did speak to customers all the time. And at that time, he was well into his 60s, and he reveled in it. He loved speaking to them and listening to their opinions. And I thought that was a really lovely thing.

Mark MacLeod:

I love it. I do want to hear about your new thing. I want you to be able to tell folks about your new thing. But I got one more question before we go there, which is just around, I guess, this balancing act with like how comfortable people, individual contributors, are in an organization, and is that good or not? Like, I have very mixed feelings about ENPs.

As an example, I think back to when I was operating, and I think my third CFO gig, I called it Boot Camp. It was 18 months of torture where the CEO would send these martini-fueled flame mails at 2 in the morning, telling me everything that I was doing wrong.

But he toughened me up, and I grew to this other level. We sold the company for a 10x return. At the end, when we were exiting, there was the buyer with the buy-side investment bank, and it was just me and him, no investment bank. And we beat them up and got a crazy deal.

So when I was in the moment, it was torture. I was stressed. I had a one-year-old and a newborn. I barely saw the newborn. But when I looked back, I was like, wow, that was an amazing experience. So, maybe that’s extreme, but what are your thoughts on how hard we push people? And do we want to have them be fat and happy, or do we actually want to push them out of their comfort zone?

Christine Song:

So I would say it depends on the company that you want to build for. And the reason why it depends is that I’ve talked to founders who genuinely want their employees to be happy. And it doesn’t matter if they’re not performing. It doesn’t matter if they can’t give the real feedback because employees there have never received feedback, and they can’t handle it.

They don’t want to see bad Glassdoor reviews. If that’s what you choose, then you can’t complain. You’ve actually done a disservice to your employees because they will never grow beyond that. They’re going to have to go through a rude awakening.

I don’t typically choose companies like that. I can’t work in a company like that. I really want to work in a place where people are challenged. And I don’t mean push them to the brink, but really challenged. Because if we can operate here at a normal pace, most people can go up from that, and that’s where I want to be.

I love seeing people who said, I look back now, one year ago, the way I operated and how I am today, I’ve learned so much. I think about myself when I first joined startup and suddenly had to pick up the pace because corporations were much different. And I was like, wow, this is great. I always thought everyone else was in slow motion, and I was in fast, and I was like, I finally found my place.

But working directly with the CEOs and founders was harsh. They weren’t very kind. They just said it like it was. And yeah, they gave me feedback right in front of the executive team, in front of eight other guys. And you either cry on your pillow at night or you pick yourself up and go, you know what? A lot of what he said was right. I could do better.

And so I think you need to build your culture the way you want your employees to work and how you want your work culture to be. And I typically want to work with founders who want to create a high-performance work environment.

But if you want to do that, you’ve got to do the hard things. Starts with the CEO. You’ve got to share the message at all the all-hands, it’s not just once. You’ve got to repeat it, rinse and repeat over and over. You’ve got to give the feedback to your direct reports, your executives. You can’t push it to HR.

I recently talked to a CEO who said, I need to hire an HR person. And I said, well, you’ve gone six years without one. Why do you need one now? And he said, because of these fucking people’s problems.

Mark MacLeod:

Oh, yeah, they’ll just magically go away.

Christine Song:

I mean, I’m sorry, but if you have direct reports, you are also an HR manager. And you know what, we’re going to partner with this, but you’ve got to create the culture that you want your company to have. And it takes a lot of work and commitment. And there have been times where I’ve said to founders, look, if you really want me to join, we have to be partners.

These are the hard things I can tell you right now that we’re going to have to do to turn things around. Because right now the culture is very mushy. And I can tell that even your leadership team can’t handle feedback.

Like, I’ve had executives with C-level titles who couldn’t handle a little bit of feedback. They would like literally crawl up in a ball and cry. And I’m like, this is not going to serve them. You’ve got to build the culture that you want and do the hard things. And not everyone wants to do that, is the truth.

Mark MacLeod:

Yeah, that is for sure. For sure. So, final thing. Tell us about the 5 to 9 Society.

Christine Song:

So I think about four years ago, I was already thinking about doing my own thing. And 5 to 9 Society was something organic that my co-founder, Mandy Gruel, talked about. We said, why don’t we just build our own network, a secret society? And that came about because I think I was always living in it.

I was living in this kind of echelon society, where it was very exclusive, and it was very confidential. When you’re at that level, you’re talking to people about backdoor reference checks and I don’t care how many people say it’s unethical, when you run your own business and you’re hiring and you need the best of the best for some of these leadership roles, you are going to ask for backdoor references because otherwise, why don’t you just look at LinkedIn and look at recommendations and make your hire? Like, it doesn’t make any sense.

You’re trying to fill confidential roles because there’s a silent search going on, and someone isn’t going to make it six months down the road, and you’re looking towards your network to find the right person. And I just thought, I’ve connected people with opportunities, I’ve asked for references and given them myself.

And there’s this network where people genuinely want to help each other. And I thought I could formalize this, I could build it out, bring in the right people. And when I announced this on LinkedIn about what I was building, in the first 30 days, 600 people signed up. And I thought, okay, there’s interest there.

And out of the 600, I sent out a survey, asking if I could get some feedback. And 300 completed the survey. And a lot of people were saying post-COVID things have never really gotten back to connections, relationships, and people. And they need a community where it’s with the right people. It’s very curated.

Even if you’re planning a dinner, it’s only 12 people where you get to know everybody there, and you can actually help someone who’s working on a problem. And this is what I do in my spare time anyway. This is how I’ve always networked for the past 20 years. And I thought I could actually create a society and bring in the right people.

So, that’s the thing that we’re launching, which officially goes live on June 26th. So if anyone’s interested, DM me. But yeah, a lot of people have signed up.

Mark MacLeod:

That’s really cool. I love it. Sounds very needed. That’s super cool. And now. So this is the third chapter for you. You had corporate, you were inside startups, and now this.

Christine Song:

Yeah, my life has been in thirds, and every chapter has been an eye-opening experience. I’ve learned so much and met so many great people. I have no regrets, and I think everything happened very naturally for me, so I’m excited about this new chapter and see what can happen. But not forgetting the past either, and everything that I went through brought me to where I am today.

Mark MacLeod:

100%. That’s right. It was all for you. Even the challenging bits.

Christine Song:

Yeah, especially the challenging bits.

Mark MacLeod:

Yeah, exactly. This has been amazing, Christine, thank you so much. I mean, if I had a pie chart of my coaching calls by topic, people is like by far the biggest slice of the pie. So there’s way more we could have talked about. But I love this. Thank you so much for coming on.

Christine Song:

Thanks for having me, Mark.

Hey, thanks for listening to the Startup CEO Show. If you’d like to connect with me, be sure to visit my website at markmacLeod.me, or follow me on LinkedIn at The Mark MacLeod, or X account @markmacleod_, and if you want to tune in again next week, be sure to subscribe on YouTube, Spotify, Apple, or wherever you get your podcasts. We’ll see you next time!