Honest Feedback and Hard Truths: Developing Startup Leaders

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, you're going to see the results. The same with, you know, HR. When I was coaching employees internally, I did put more effort into the high performers. And sometimes it wasn't even just high performance, it was potential who are willing to invest in their own development, who are reading the books on the weekends. They're not out, you know, 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 that genuinely took their career and wanted to grow and they had a growth mindset.

Welcome to the Startup CEO Show. I'm your host, 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 inside established kind of incumbent companies and multiple times in technology startups. And one of the true, truly strategic HR leaders that I've met in my career. We unpack everything. Why certain— why CEOs can go all the way, why leaders fail, the importance of culture, communication, having systems, changing how you operate, 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 you doing today?

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

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, 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, actually it always comes down to people. And so that's why I really wanted to have you on, 'cause 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.

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, 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 Nix and was there for 2.5 years. It wasn't tech, but they had the same scaling problems that tech startups had. And, uh, it was a great experience working with Joanna Griffiths.

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 co-founder or solo founder, fundraising shortly before giving birth to twins, like, uh, dealing with COVID honestly, just so much respect. Um, 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 3 or 4 CFO roles, HR reported to me, not to the CEO. And then this, 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, 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, A, what are your thoughts on that? Do you agree? And like, how do we make HR more strategic inside startups?

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, I don't know how to manage this. We've gotta go fully remote. We've never done this before. And and everything kind of shifted. And I think people started realizing, sheesh, you can't run a business without HR. They're not just there to order pizza and, you know, 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 gotta earn it. You can't just say, hey, I'm the head of HR, so I'm gonna 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 it 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 like 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 they just have their own siloed data and metrics, and they're just ready to, you know, report on engagement scores or, you know, 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's in a totally different world talking about their own metrics. And I think that's where you're not gonna be invited to the table because the rest of the business is managing the business. You've gotta figure out a way to support the business as well. And some of the things that I think about is like, HR can be strategic by thinking about, you know, are we 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 kind of the things that the rest of the business would be interested in. And so, I would say tie your HR initiatives to the business outcomes.

I like this, 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?

Yeah, I think every person who's at the table has to think about the business first and You know, from an HR perspective, I think about how can I support the business and each of their leaders so that HR becomes a partner? It's not just 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, and you are making sure that the most expense expensive expense out there, it's payroll. It's the talent function. It's the people. And so, it's a critical role, I think. And for me, you know, 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.

I'm a big Godfather fan, like the movies and, uh, not movie number 3, 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.

Yes.

And what, so did you, did you play that role for your CEOs and, and how did you become that person?

If so, 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 4 or 5 months after joining, we raised private equity money, few million. And everything accelerated really, really quickly. So I had to learn startup overnight. I had to manage, you know, 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 that 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 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. And what I realized was, gosh, there's so many mistakes he's making. And if I don't say something and I don't speak up, this company's just gonna 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, like, you kind of have the courage to speak up to the point where you could get fired. And I've always, always, um, Taken that to heart because I, 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. And 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 like 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 gotta be the one that's gotta speak up? It's created a lot of stress for me over the years. And there are some things now that, you know, I, I can kind of sense that I'm not gonna tolerate. And so I pick and choose leaders that I wanna work with carefully and the kinds of environments that I wanna put myself in because it's gotta be worth it. I'm gonna give it 110%.

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.

Yeah.

And, you know, in some ways, like, 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 to 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?

You know what? I will speak the truth in leadership meetings, and I 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. We can't operate like this. There were a lot of long nights on the phone. I'm up till 12:00, 1:00 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 always, you know, I, I wasn't often like, 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 like, 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, if it's almost like if I make a choice to join a company, I wanna be so good at it. I want the company to do great. I want us to all succeed. And you can't do that unless you're facing the truths and you can take the feedback that comes with it as well.

Yep. Totally agree with that. I'm curious, how did that company turn out?

The company eventually, we did, gosh, it was such a journey. It was like in one year, I think we did 3 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 4 or 5 companies and they, 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, 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 it's you'll never forget your first, you know?

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. And because that's the leverage of the CEO, right? You go in the beginning, you're, 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, um, not everyone keeps up with the growth of the company. Like, in fact, frankly, often the CEO doesn't, and that might be a reason why they come to be coached. Uh, and, but sometimes it's a surprise to the CEO. Right? 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? Is there, obviously people have different degrees of intelligence, different backgrounds, and you know, your second, you had way more experience your second go around than your first, but anyway, just, just riff on, on that, on that observation to the extent that you agree with it. Yeah, I agree with that. And if not, if you don't agree with it, then rip it up, you know, like, floor is, floor is yours.

I do agree with it. I think that, you know, we've always had that saying, like, the people that start the company with you aren't gonna be the people that are gonna 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 early stage. They're more of the generalist. They can put on 3 or 4 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 gonna 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 gotta 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's a lot of things happening and there's no processes or rules that are in place yet. If you don't set up the systems and kind of operate like you're in product, you're gonna operate as if you're an IT help desk and you're just gonna pick up the phone and help people put out fires every day, and you're available 24/7. That is not scalable. If you wanna operate like that, you better have a team of 100 HR leaders. But the reality is, um, You've gotta set up processes, you've gotta 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 one sole HR person. I've gotta set up everything. Nothing exists in HR, and then I gotta build out a team. And I've also been that person that 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, you know, my 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 wanna 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 wanna come into a startup because they think it's fun and sexy, and they read so many stories about exits, but they come in and they say, oh my God, it's so dysfunctional and there's no processes and everyone 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 gotta grow at the rate of the company. If the company's 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. Read a few books, go get a coach, watch some videos, talk to your peers, 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 gonna do to develop me? Like, it's your responsibility as my manager." It is not your manager's responsibility. Like, they can support you, but you've gotta manage your own career.

Yeah, I don't, 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, 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, and you just talk about, you didn't use these words, but like Shopify had, they had an HR department, but they also had that talent acceleration department, which was a separate in-house coaching team. And Shopify's 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 at, in C-level roles at the time that they went public. And it's not just 'cause they're smart. Toby's obviously ridiculously smart, but it's because they invested in, and there's a huge luck in timing, right? 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 Toby got a coach early on and at one point he had two coaches and then they brought they had one coach in-house and he built, 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, like that coaching department did play a big role in growing the talent, right? 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?

Yeah, I think that's a great idea. It's very similar to what we did at NYX. We brought in a coach, and we called that person like 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, you know, 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 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 know, you can't just take a ticket and every time someone wants a spot coaching session, you're available. So we thought, let's reserve this mostly for our director level and above. They're the ones that are managing the teams. They face most of the people problems, and they need a toolkit. They need someone to go to. They need to kind of develop themselves so that they could manage larger groups. And it was probably the best idea that we came up with. I know that the service that we used, 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 it, you know, we faced scaling issues. We faced issues where the confidentiality with the embedded coach kind of clashed sometimes with HR because something was—

I was gonna ask, is it a safe environment? Can I truly confide in you, or are you gonna go, hey, you know what, Joe here, he's losing the plot. You need to get rid of him.

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. I'm not gonna 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, you know, there were some like 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 the 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.

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

Yeah, I think coaching is much more— you'll get better results than a leadership development program that you launch out. The leadership programs are so vague, and it doesn't really support individual learning. I think AI, you know, could probably do better. But obviously the, 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 like directors come into workshops and have coaching sessions. Maybe we're talking about like 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 where employees would come to HR and want to be coached by them. It just, it depended, like, the kind of relationship you had with HR or with the coach, and individuals are picky sometimes.

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, 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 like your high potential leaders? And less in your underperforming leaders? Is that a thing?

Yeah, 100%. I think about in 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, you know, 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, you're going to see the results. The same with HR. When I was coaching employees internally, I did put more effort into the high performers. And sometimes it wasn't even just high performance, it was potential. It was like, people who are willing to, you know, invest in their own development, who are reading the books on the weekends. They're not out, you know, 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 that genuinely took their career 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 that 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 I want to work with this person or not? And when I ask coaches, why do you do that? They said, because not everybody's coachable. There are some people that will just go through coaching because their manager or their board told them to. But they're just going through a process. They're not genuinely invested in, you know, taking in the feedback, hearing the hard truths, you know, feeling those paper cuts slide into your soul. Like, you've gotta really feel the pain to be able to work on yourself, and not everybody is genuinely ready for that.

100%. I can tell you, I do that. It's a two-way street. I'm sure the CEOs also wanna know, hey, do I wanna work with Marc? But like, for me, The number one thing I look for is self-awareness because that's the thing that's gonna 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 gonna miss the signals, right? So, and then also I, 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, right? So like, it's just like, life's too short. I wanna be with people that I like, but the number one thing is self-awareness. That's by far.

Yeah. And not everyone has it. I think there's a lot of people that 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's so many people that don't have self-awareness. And I would look at him like, yep, you would be one of them.

That's right.

You had no idea.

Right. Well, there's so much hype in 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 about this, right? Like you catch up, I don't know, like, uh, I don't know, 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 that you haven't done. How's your portfolio? Yeah, we're crushing it. Everyone's crushing it. It, which is mathematically untrue because most startups fail, right? Which means that we're putting on this facade. And I'm wondering, are you, 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, is that a thing?

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, it's almost the opposite for me. I felt like a lot of 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, like, you know, 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. They're like, no, 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 gotta 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, I don't get depressed really easily, but when you're constantly told like nothing's good enough and we've gotta do better. Like, I get that we have a high bar, that's the way you wanna operate. But when that bar is unattainable and good enough is never good enough, like it's just nothing is worth celebrating, it just makes you feel like, what's the point? There were a lot of times where 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, like 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 wanna 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 like, there was, the sales team was supposed to celebrate, like, you know, at the end of the day, it was like a Thursday and they were gonna 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, really hard? I think something's missing right now.

Yeah, it's so sad, I think. I think a big part of it is comparison. You're comparing the 100% you know about your company to the 5% you know about your competitor.

Yeah.

Which is, that's never gonna turn out well. Right. And then this hustle porn thing, like we just need to keep grinding. I don't know. It just leads to burnout. Right. Like I tell my CEOs all the time, A, having sold a lot of companies, the number one reason why founders want to sell is they burn out. But especially from a CEO, like some acknowledgement, some praise, some recognition, like not like 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, that's a 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 Toby, uh, on the podcast last year and I asked him like, 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. You know? Um, and he's obviously had a massive success, you know, and still all he's focused on.

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 is, you know, this whole thing about 996 culture. It's like originated from China. You work from 9 to 9, 6 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, you know, early-stage startups that operate like 7 days a week. You gotta be on call. You better be checking your Slacks. But when I see them interviewing candidates for that role, they never tell them that. They just go, you know, we work hard here, you know, 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, you know, this looks like a really intense culture, but I'm curious how intense it is because to be, I'm gonna be honest with you, I have a newborn son. He's really young and I do wanna spend time, you know, after work or on weekends with my child. And in my mind, I was thinking, you're never gonna see that child for 3 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? It's literally like 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. They said there's 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 gonna be surprised and bamboozled when you have the wrong fit as your hire. And so, I think there needs to be some honesty, but I also think, like, this hustle culture isn't sustainable. Like, if you are working 80, 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 minimum 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 cancer diagnosis, you know, high blood pressure medication. This one CRO that we had who was like just killing himself trying to hit his quota suddenly couldn't come into work. And we asked what happened and he said like, I have this strange vertigo. I can't even see, like 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, 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 gonna be faced with if you think you can sustain that kind of culture because nobody is a Superman and nobody is invincible. And you might think you are in your 20s and 30s, but you're gonna shorten your lifespan really quickly like that.

A thousand percent for sure. Yeah. And I've been on both sides of that. I was that person at one point. Point and lived under 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 just unsustainable that was, right? And then I tell my CEOs a few things. I probably just repeat the same 100 sentences all over that. This is when you get old, you just repeat yourself. But like one of them is like, you know, a healthy person has 100 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, is a thing. Like it's so important. And then like you're creating, you're turning an idea into a company. You're creating growth. This company is now gonna be 2x bigger than it was last year. Therefore, you've created, you know, half of it. You can't create when you're stressed, or it's like harder to create when you're stressed. So just trying to get people to unlearn, right? And then like, focus it, 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, I've had to, when I was in a company last time I was operating, like you can't come to a meeting and be like 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, like, like, let's be engaged and get shit done. You know?

That is so true. When I think about, about all the hours that people work, let's say on standard, like 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 in this week, like each day. And a lot of it was just stupid work, just things that weren't automated, processes that weren't implemented. You're 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 like time is the most precious resource that we have. You never get it back, so you've gotta really preserve it, but you've gotta 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 gotta increase velocity. You hear that all the time. What happened? We used to move faster. You, 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, um, clarified what's the most important thing. People are still using that template for the sales meeting that you had 5 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 gotta really change as they do. Um, you can't operate as if this is like, this is how we operated when we started and we're gonna continue to operate that way. This is why companies blow it out with so many people. My opinion. Yep.

No, I don't disagree at all. I'm curious, you could either answer this from the point of view of CEOs specifically, or executive team leaders generally, but like, When you look at the ones that you have had the most success, have kept up with the growth or created the growth, like, what are their habits? Like, what is it? What are the, I guess, actionable, you know, observations you have from those leaders?

Yeah, I think the most successful leaders, they really had great systems thinking. Like, they understood how to scale the company appropriately and ensure that, you know, the stress points are being taken care of. They understood that process was a good thing and that 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 liked, 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 gotta think of it as like, this is your team. I know that a lot of people compare like companies to high-performance, like 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?

It's true.

This is what they signed up for. So, I don't think we can glamorize it by looking at, you know, sports teams or, you know, F1 drivers or whatever you wanna compare it to. But there's 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 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 wanna 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 better share some motivating messages. And 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 that 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, 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. 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.

So many good points there. The systems one. I'm curious on the systems one, right? 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 corporates, but I'm wondering, is there anything you took from that? 'Cause you can't run a company that big without systems, or is there goodness from corporate that at a certain stage, you know, more innovative companies should be embracing?

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 about what were those things, they were very good at communicating things. Like, they were very direct and clear. There were some things that they said they weren't going to tolerate. So you couldn't push, you couldn't, like, you know, like kids pushing their parents. You knew you could never get away with it. And they drew a line about things that were, like, 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' times, a lot of HR people's time, like, just things that, I mean, 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 5 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. And so corporations really understood that well and people understood. And, you know, going back to Galen Weston, he was probably like the first kind of like founder that I worked with. And there was something very genuine about him. He was so powerful. And when he came into the room, like you couldn't miss him. The guy was like 6'6". He was so tall and lanky and he would wear his gorgeous tailored, you know, Tom Ford suits and you couldn't miss him.

It has to be tailored at that height. That's not off the rack.

Tailored with his silver hair and his perfect posture. But he operated the company as if it was still like his own, that it wasn't a publicly traded company. He, every weekend he would go visit the supermarkets and he would go to every stand. He would go to like the fruit stand. He would go to the butcher. He would talk to every single person and he would pick a different store each 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 Sr. is here." He also did the same thing when he was going to open the, the Loblaw location at Bathurst and Lakeshore. It was going to be like 2 floors and he had never opened a Loblaw store that was 2 floors. And there were all these, these, you know, 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 kind of concept stores that had two floors. So he would go see like a Home Depot that had two floors, or he would go to like, you know, a supermarket in the UK and he would really look to see what can I incorporate? What do I want Blah, Blah to look like? And we were delayed. Almost a year opening that store because he wanted it to be perfect. And this is like, you know, a founder that 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 it's like, you know, when you really care about your business, you will operate as if you're always a founder. And I really appreciate appreciated that. So I did learn a lot from corporate. I learned that processes are important, you know, and how you communicate is important. And I think there's some lessons that startups can learn from that. 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, you know, both the US and Canada have recently gone through elections for better or And politicians are a bad connotation, but I tell my CEOs, like, you 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, right? And like I tell my CEOs, basically you gotta do the same thing, like all the time, hammering vision and mission, North Star values. Why are we here? What matters? Helping every person connect connect their work to kind of 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, right? 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 was really important.

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 LaBla? 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 LaBla? And the person would say Walmart. He would say, why? He'd say, the prices, you know, 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 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.

I love it. I want to, 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 are, like individual contributors are in an organization. And like, is that good or not? Like, like I have very mixed feelings about ENPS as an example. Like I think back to when I was operating and I think my third CFO gig, I called it bootcamp, is 18 months of torture where this, I had this, the CEO who 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 like I grew to this other level. We sold a company for a 10x return at the end when we were exiting. There was the buyer with an, with the buy side investment bank, and it was just me and him, no investment bank, and we beat them up and got like a crazy deal. Love it. So when I was in the moment, it was torture. I was stressed. I had, a 1-year-old and a newborn, and 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 yeah, like, what are your thoughts on how hard we push people? And do we want to, you know, have them be fat and happy, or do we actually want to push them outta their comfort zone?

So I would say it depends on the company that you want to build. And the reason why it depends is 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 gonna have to go through a rude awakening. I don't typically choose companies like that. I can't work in a company like that. For me, I really wanna work in a place where people are challenged, and I don't mean like push them to the brink, but really challenged because if we can operate here in a normal pace, most people can go up from that. And that's where I wanna be. I love seeing people who said, "I look back now, one year ago, the way I operate 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 like everyone Everyone else, it 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, it was harsh. They, 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 8 other guys. And you know, you either cry in your pillow at night or you pick yourself up and go, you know what? A lot of what he said was right. I, I could do better. And so I think there, you need to build your culture, um, the way you want your employees to work and how you want your work culture to be.. And I wanna work with, I typically wanna work with founders who want to create like a high-performance work environment. But if you wanna do that, you gotta do the hard things. Starts with the CEO. You've gotta share the message at all the all-hands. It's not just once. You've gotta repeat it, rinse and repeat over and over. You've gotta give the feedback to your direct reports. Yes, you're executives. You can't push it to HR. I recently talked to, um, a CEO who said, I need to hire an HR person. And I said, well, you've gone 6 years without one. Why do you need one now? And he said, because these fucking people problems.

Oh yeah, they'll just magically go away.

I mean, I'm sorry, but if you have direct reports, you are also an HR manager and you know what, we're gonna partner with this. But it's, you've gotta 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, you want me to join. We have to be partners. These are the hard things I can tell you right now that we're gonna 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 gonna serve them. It, it— so it's, you gotta build the culture that you want and do the hard things, and, um, Um, not everyone wants to do that is the truth.

Yeah, that is for sure. For sure. Um, all right, so final thing. Yeah, tell us about 5 to 9 Society.

So I think about 4 years ago I was already thinking about doing my own thing and, uh, 5 to 9 Society was something organic that me and 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 kind of society where it was very exclusive, it was very confidential. When you are at that level, you're talking to people about backdoor reference checks. And I don't care how many people say, you know, it's unethical. When you run your own business and you're, you're hiring and you need the best of the best for some of these leadership roles, you are gonna 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, you know, there's a silent search going on and someone isn't going to make it 6 months down the road, and you're looking towards your network to find the right person. And I just thought, you know, 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, you know, 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, asked, could you— could I 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 and relationships and people, and they need a community where it's, 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 I thought I could actually create a society and bring in the right people. And 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.

That's really cool. I love it. Sounds very needed.

Yeah.

Yeah. That's super cool. And now, so this is the third chapter for you, I guess. You had corporate, you were inside startups, and now this.

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

100%. That's right. It was all for you, even the challenging bits.

Yeah, especially the challenging bit.

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.

Thanks for having me, Mark.

Pleasure. 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 Twitter @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.