The following is a transcript of our podcast conversation with Jess Yuen. You can listen to the full episode on Spotify or Apple Podcasts.
Sarah
Hello, and welcome to Humans Beyond Resources, an HR podcast by Reverb where we cover topics from culture to compliance. Reverb believes that every decision a leader makes reverberates throughout the organization. From hiring your first employee to training your entire workforce. We believe in building healthy, inclusive cultures that engage your team. I’m your host, Sarah Wilkins. Welcome to our latest episode of Humans Beyond Resources. Today, Jess Yuen, advisor and executive coach and former Chief People officer at Gusto and Couchbase, is joining me to talk about how to achieve an impactful CEO and Chief People Officer relationship and what to do if it’s not working. Jess recently wrote an article on the topic, which I really enjoyed, and so we’ve asked her on just to break it down and talk more with us about it and share some examples that we think could be beneficial to you all. Thanks for joining, Jess. I’m really looking forward to this.
Jess
Thanks, Sarah. I’m excited to be here and excited to chat more about this topic.
Sarah
So first, I just would love for you to share a little bit more about you and your work with CEOs and CPOS and why you’re so interested in this topic.
Jess
Yeah, well, it is a topic close to my heart. Nowadays, I have my own business that is focused on executive coaching and advising leaders, largely in the VC backed company space. And so I’m working with a lot of CPOS and CEOs and seeing this relationship up close, my background might be a little bit atypical for the average people leader. And I studied electrical engineering in school and then spent the first decade of my career in business. And so I started at McKinsey and Management Consulting and then did product management at Yahoo and then worked as a chief of staff in my first startup. So I was serving the CEO there, and then I led international growth and strategy, and then I became an operator as a chief people officer, as you mentioned, at Gusto and Couchbase. And so I’ve been able to see this relationship both on the operating side as the Chief people officer and an executive on the leadership team observing it, and now as a coach to both of these roles and figuring out how to navigate this relationship. It’s a really tricky one.
Sarah
Yeah. And we don’t want to miss one of your other very important jobs, I think, as well, being near and dear to my heart as a working mom of one six year old, I would love for you to share your other important job.
Jess
Yeah, my other important job is hugging and loving and helping grow two small humans and two much larger humans one day. But I have a four year old and an almost six year old who’s very much looking forward to her birthday party. So I’ve been putting on a party planning hat recently, too.
Sarah
Yeah, the many hats of a working parent.
Jess
Absolutely.
Sarah
Thank you for sharing. So I kind of want to dive in now to the topic and ask you from your perspective and your experience, both your experience but also your experience coaching leaders in this space, what have you found to be the characteristics of a successful relationship?
Jess
Yeah, so there’s four characteristics that I think are really important and I’ll touch on here. And it’s about being closely aligned, being complementary, having a strategic thought partnership, and being candid and honest with each other and reflecting that back. And I’ll dive into each one. But first I think it’s important to sort of step back and understand just how tough each role is. And it’s interesting because oftentimes the CEO role is called the loneliest job in the C suite or in the entire company because you’re dealing with a lot of things and having to compartmentalize often of what you can share and when you can share it and who you can share it with. And you’re thinking about things that pretty much no one else in the organization is. And the next loneliest job is often awarded to the Chief people officer because there’s similarities in what you have to compartmentalize and thinking through things and dynamics that no one else in the organization is. So first off, they’re both in these super lonely roles and trying to navigate that can be challenging because the Chief people officer is here to the rest of the executive team. Yet at the same time, the advisor to the CEO often has a heavier weighted input into the performance of their peers. And so the immediate structure that you’re put into as a Chief people officer includes difficult dynamics that you’re navigating to balance those. And so I think the third thing that makes it a challenging role is that the scope of the Chief people officer role is often not extremely well understood by others, including the CEO. And so just having clarity about what is owned and isn’t owned and what each of those pieces means is oftentimes a source for some of the friction or challenge that comes in the relationship. And so that’s why with those four elements I mentioned of being closely aligned, complementary strategic thought partnership and candid and honest mirror, those are the pieces that kind of fall out of the fact that you have this really interesting set of roles that are coming together to lead the organization both on the business side as well as being supported with cultural and organizational impact as well. So the first one about being closely aligned is not about them agreeing to everything, the CEO and CPO will not agree to everything. And that actually is a successful relationship when they are kind of helping to push each other. But it is really much about more about are we on the same page? And if we are not, which is fine, if we’re not, do we understand why? Do we understand what is the cause of these different perspectives or the misunderstanding. And so I often talk about approaching relationships with curiosity instead of the first thing being like, that’s a crazy idea, why are you bringing up this idea? Instead? It’s I haven’t thought about that before. Tell me more about what prompted that or what triggered that for you. So that’s an example of that close alignment. And getting closer is coming at it with curiosity to get closer. And many times it might be educating too, on both sides. One great example I had was there was an early stage founder I was working with, and his people team was recruiting and it was taking them three months on average to place somebody in role. And he comes to me and he’s like, I’m so frustrated with my recruiting team, I can’t believe how slow they are. What’s going on here? This is ridiculous. And then he kind of pauses and has the curious moment. It’s like, what have you seen as being normal or average here? And I was like, Well, I mean, first, before we get there, what’s your expectation? Three months of slow? What’s your expectation and where is that base? And he talks about, oh, one month, because when I was placing the last role myself, I was able to get somebody in within a month. So that’s my expectation, what this team should do. And I was like, wow, that’s really impressive. And oh, by the way, the industry average is three months, so your team’s actually doing a pretty good job right now by all industry average standards. And immediately I saw him slip to a 180 and it was kind of like, oh, that’s normal. And you could see him going from this mindset of being, I’m about to reprimand my team for being too slow to, oh, I don’t need to do anything. They’ve got it under control and they’re doing it the way they should be. And he came out of it in a totally different perspective. So that’s what I mean about close alignment.
Sarah
Yeah, I love how you pointed that curiosity out and approaching it with the curiosity, especially maybe when you aren’t aligned on something. I think, as you pointed out, you can get into something and maybe create a story in your head about what should be happening or what they’ve done or that. But approaching the relationship or any situation like that with curiosity allows you to go in with an open mind without creating that story. Right?
Jess
Absolutely. I think that’s exactly what we’re trying to get around with the curiosity is instead of jumping to conclusions, is let’s make sure we understand what assumptions that we’re making and see are they actually checking out. So I think that close alignment is so important. And the second element is around that complementary skill set. So it’s complementary sometimes this is complementary styles, complementary attitudes, complementary experiences, but it’s really do the interests and skills fit together. And one of the terms that I bring up in the article is around being a front end people leader, a back end people leader or full stack. And so in engineering, these are common terms with certain meanings. And my version of it in the people space is that front end leader is really one that’s outward facing do a lot more communication to the organization is the person who’s sort of the face of the culture and face of what we think of organizationally attached to that back end leader is one who’s really adept at making sure that the infrastructure needed for the organization and for the culture and people programs is really tip top and operationally rigorous and analytical and all of those wonderful pieces come together and Full Stack is somebody who can straddle both of those. And Augusto was a great example, like with the CEO, this was a CEO. Josh was very invested in culture. He wanted to be the face. And so I was playing more of a full stack, even some cases back end piece to support him. And we wanted that for the organization because it made sense from a business standpoint. And that’s what helped with our ability to work closely together is to understand those roles and where we fit together.
Sarah
Yeah, when I was reading that part of the article, I really liked you pointing that out because I think sometimes we think that the leader has to be full stack and front and back end. But in reality, deciding and aligning back to aligning with the CEO on what role they want to play and what role is best for you. And being together and working together will make that really successful.
Jess
Absolutely. So much of leadership is what are my expectations and have I communicated them? And then the other person can actually respond and interact with it. And so much of this is done implicitly. We sort of figure out how we’re working together, but we haven’t had a chance to sort of pull that out. And so having language around it like this full stack, front end, back end. I find many of my clients have technical backgrounds on the CEO side. And so this speaks to them a lot more easily than some of the other languages that I’ve tried in the past to explain it.
Sarah
Yeah, I think that’s great.
Jess
Yeah. The third element of an impactful relationship, I find, is being strategic. Thought partners here. Really, the question that I think about is, are we stretching each other? To think a few steps ahead and to think around the corners and the blind spots and the recent scp situation was really I saw many of my clients jumping into action in this way, where even though you’re thinking, oh, crazy, crisis mode, reactive, how can that be strategic? Many of them were going, okay, well there’s immediate implications like how do we run payroll and pay our individuals? Right? This second, but also thinking through the secondary and tertiary issues and consequences of if this, then that. And so they were looking at, okay, how do we make sure that we have additional bank accounts that we’d be able to leverage in the future? How are we thinking through customer implications of this? How are we thinking through updating different levels of communication across the board, not only on what’s happening
Jess
right now, but how we’re thinking about the midterm and the long term. And I saw in many cases leaders coming up and brainstorming together and thinking through how do we make sure that we are coming at this strategically and not just reacting to the immediate but really surveying the whole thing. And that’s exactly what you do in these situations is you’re trying to think through not just what’s obviously in front of you and what you obviously need to protect and go on the defense for or the offense, but also thinking through. Okay, beyond right now, how did we think through? And some of the greatest stories of wartime like the armies that didn’t anticipate winter coming and ran out of resources and didn’t equip their troops is exactly the type of thing that comes with being strategic, is thinking a little bit further out. And some of those additional ramifications.
Sarah
Yeah, and I like the recent example you shared right, of the Silicon Valley Bank and how people came together with that. And I think some people think maybe people leaders weren’t really affected or a part of that, but in reality there was the implication of payroll and then also how we’re communicating with our teams around what’s going to happen and that kind of thing. So it’s broader than the reactionary. I like how you pointed out and how it was a full kind of leadership team kind of working together on the strategy around that.
Jess
Yeah. And the last component around an impactful relationship, I think sort of dovetails on being closely aligned and having complementary skills and experiences and the strategic thought partner. But it’s rounding it out with being candid and honest with each other. And really the people leader is oftentimes serving as a mirror. And the reflection that I encourage here is around are the words we’re using as CEO oftentimes consistent with what our team is comprehending and experiencing? Right. So the intentions of the CEO are wonderful and they are building this painting, this wonderful picture of what the vision is they’re talking about potentially the cultural values or what we’re most excited about or how we’re getting through the next stretch. And the hope is that people are understanding what’s happening. But just like the classic game of telephone that we played as kids and you go around a circle, you sit next to each other and someone puts a message and whispers it into someone’s ear and then that person whispers it to somebody else and so on and so forth. And at the end of the line, you hear the message and you’re like, that’s pretty different than what we put in. It’s oftentimes like that in a company where the CEO is putting out this wonderful cohesive, coherent message, or so they think. And then what the people leader is hearing from others in the organization is different versions of the telephone communication and they come back and are reflecting it. And sometimes what’s interesting is the solution is not necessarily, hey, there could be two solutions. Really. One option is, oh, we need to recommunicate what we need to put out there. And I often will say seven times in seven ways, like you’re going to assume that it’s going to take different mediums and different repetitive versions of this message to really get through to all the different audiences in an organization. But sometimes there’s a moment with organizations where you go, how this message is being interpreted is totally different than what I anticipated and maybe we should change. Those are moments where you’ll see companies sort of if they’re doing a refresh on their values, that might be some of those things. Like, oh, we talk about humility all the time, do we? Are our leaders actually humble and have humility? Right now, half our exec team? Not really. In our whole surveys, we’re seeing people getting a little bit like it’s causing some tension because they’re hoping for humbleness and they’re not getting it. So you’ll look for data points and indicators and it’s our job as people leaders to bring that to the CEO and say, hey, I know you love this value and as your mirror, your reflection, I’m saying it’s not showing up in the behaviors and actions right now. So we have a choice. We can change what our value is to capture what we’re doing now, or we can talk about how this is an aspirational value and we still have work to do. So that’s the type of mirroring that I’m talking about. It’s not like the Miming mirroring where you’re following exactly what they’re telling you to do.
Sarah
Yeah, just being able to be candid and call out things maybe that you see differently or that are coming across differently to the people versus what the leaders or the leader thinks.
Jess
Exactly. And it’s so hard for the CEO to get that type of candidness, especially as the organization grows. And so it becomes that much more important that the people leader feels comfortable and can surface those things in an effective manner. And I think that’s the trickiest part because sometimes it’s tough. I heard a people leader go into a new organization recently and the culture wasn’t what it wasn’t that close to what it was on paper. And the way she phrased it was amazing. It was like it’s really hard to tell someone their baby is ugly. And for a founder CEO in particular, that can be a really tough message to deliver.
Sarah
So it’s important that all those aspects are there in the relationship. So you can as a people leader, do that, right, having a strong relationship. Which brings me to there’s elements that make it a not so good relationship and what are some red flags that you would see in the relationship. And maybe we’ll get to also what to do if it’s not working. And once we see those red flags.
Jess
Yeah, so I’d say this is one of the most important things is to understand. If I see some of these red flags, it doesn’t mean like, oh my gosh, everything’s hopeless. Like there’s still things to turn around. So we absolutely should talk about what to do if you’re seeing any of these flags. But the first one is around what I call being out of sight and out of mind. And this is where the CEO might be canceling or postponing one on ones with the Chief people officer. And for me, this Chief people officer is in charge of the well being at your organization, the well being of your organizational health, the connection between your business strategy and the productivity and engagement of your workforce, among so many other things. And I think it’s becoming more and more obvious as we’ve been through the pandemic and we’ve been through social justice and all these really incredible crises that have tested us. But if you’re not giving time to your people leader, if a CEO is not able to give time to your people leader, or you’re a people leader and your CEO keeps canceling or postponing, there could be a oh my gosh, they trust each other so much that they don’t need the time and they’ll be fine. But if you’re continuously seeing this happening and you’re not seeing that we’re closely aligned, we’re not becoming strategic thought partners for each other, we’re not reflecting back as candid and honest mirrors, then you start to go, something’s up here. I’m not sure if I need to be asking for more time at this point. And so I would be thinking about what are the blockers around it? And it doesn’t have to be, we have to have real time interactions. Maybe it’s async. But if you’re sending if they say, oh, great. And I’ve seen this happen where they’re like, oh, no time for one on ones in real time, but send me messages via Slack. Let’s do this async and so the people leader are sending messages via Slack, and then the CEO is not responding because they have so many Slack messages they never get to it. And so rather than being like, I can’t believe you’re ignoring me. What’s going on? Why are you deprioritizing me? Instead, it could be an empathetic response around I realize you’ve got so many things on your plate. One, help me understand, how are you prioritizing? But two, for things that feel like really big priorities for me or blockers, we’ve tried a few things what’s the next thing we can try? And so coming at it from, let’s get into problem solving mode and how do we stay on the same side of the table?
Sarah
Yeah, and I hear curiosity as well, right? Like, we’ve tried these things. What would work for you? Let’s problem solve this and let’s be curious about going into it, that they’re just ignoring me or they don’t want to make the time for me. But taking the curious approach back to that, I think, is absolutely.
Jess
And coming back to what are the assumptions I’m making? And how can I sort of reframe it or shift it so that it can come from a more problem solving space as opposed to a judgment space, which I think many of us have grown up in a judgment space. And so it’s very natural to be judging that they’re ignoring me. Natural conclusion, they don’t care about me or they’re deprioritizing me. And I think that is a muscle that many leaders are building as they’re in these roles. The second sort of flag that I would look out for are what I call swoop and poop interactions. And when I wrote the article, this was like the favorite phrase that came out, and I stole this. I can’t take credit for it. But when I was at Gusto, our marketing leader at Jealous Rosa had come up with this to describe what our CEO would periodically do. And it’s ironic because she’s now a CEO herself, so she understands it well. But swoop and poop interactions are when the CEO might ask the people leader to make a decision. It might be, how are we running performance reviews? Or what’s the communication agenda for an upcoming riff? Or whatever it might be. But then at the 11th hour has a change of heart, change of mind, and swoops in with a strong different opinion and then says, I know we said X, now we’re doing Y, and there’s a ton of rework to do. And so I think this is one that many of us have felt, which is this sort of last minute, like, it’s fine if you want to change your mind, but could you give me a little bit more time? Or give our team a bit more time so we’re not pulling an all night or having to work through the weekend. And so the thing that I really encourage, if you are somebody who’s experiencing a lot of swoop and poops or someone giving a lot of swoop and poops, is how can we schedule those swoops? So there’s periodic input on what’s happening and the ability to change minds, but at least there’s time to sort of seed the idea earlier, let it percolate, and hopefully those conclusions or change of minds will come out earlier in the process. And then I would say with the poops is be very particular about your poops. Right. Sometimes they are necessary and we might need to really left turn hard in a project, but we don’t want to do it every single time. And recognizing the amount of effort versus impact that’s involved in, if I poop on this, yes, I get people to do things my way, but is it worth the trade off and is it going to be that much different otherwise? So be particular about your Poops and schedule. Your swoops is what I’d encourage. And then the third flag is around left out or left behind communications. And so if you as a CEO are finding that you’re communicating with the rest of your team, but you’re telling your CPO later, or the inverse, you’re a CPO and you’re kind of finding out things. For example, if your CEO decided to shift from a hybrid to a fully remote environment, and they inform the CFO and the COO because they see direct implications, but then they sort of casually mentioned, oh, we’ve been talking about this, and we decided and, oh, people leader, by the way, can you just execute that kind of left behind? Communication is something that I worry about, and it’s not just for people related decisions. If there’s a major strategy shift, at what point are you bringing in the people leader and is it early enough? I used to be more focused on running. When I first started my business, I did people strategy. And so I’d go into an organization and essentially come up with their strategic plan for near term, midterm and long term. And I would always start the conversation with what’s your business strategy? Because you can’t have a people strategy without a business strategy. And so many times, one, either they couldn’t really articulate it or two, they were kind of like looking at me perplexed, like, why do you need to know that? And so that part of it is it comes back to educating the other of if I know this sooner, here’s all the things that I can then plan for and support and help to pivot faster because I’m brought into the loop. But I think traditional HR and the old school way of looking at it was HR was there more reactive and to take orders. And so we are still in this transition period with leaders who’ve been in the field for longer around helping to educate them on the value that HR can bring sooner if we are able to. And so part of it is us asking for it as people leaders, but also part of it is making sure that our CEOs are aware of it.
Sarah
Yeah, absolutely. I love that you pointed that out.
Jess
And then the last red flag I would look for is what I kind of call ruptured values. And so this is when there’s fundamental disagreement, our core issues and what we believe, what matters or what we are optimizing for. And I would say there’s a version of ruptured values where you start to see it crack a little bit and you’re like, we’re sort of not seeing things eye to eye. And I was just talking to a CEO yesterday who was telling me here, with leadership, we really believe in being strategic and proactive, and we’re trying to make sure that we’re seeing all the things that are going on. And it was related to the Silicon Valley bank situation. And he pointed out there was one executive on his team who kind of looked at all the implications within his area, but then also thought about all these other implications company wide. Another leader came to the table. Actually didn’t come to the table. It’s a fully remote organization, but they just said, hey, let me know if you need anything. I’m here if you need me. And it was just this really interesting difference of leadership values of when is it that we are looking for a proactive leader to jump in and sort of be the general in the midst of it? And when is it that leadership is more, hey, come to me if you need something, and understanding those elements? And so you start to see small cracks in it. But then a situation like Svb, as this client encountered that’s one, where you really start to see this might be a lot bigger of a ruptured value than what we think of in leadership than we might have originally thought. A few years ago, I talked to Beth Steinberg, who’s a wonderful people leader and has been at many, many companies, including Facebook and Sunrun, and she’s currently at Chime as their Chief people officer. And she had said, when your values are fundamentally disagreeing on things at a values level, there are just sometimes where you just have to choose to put your badge on the table and walk away. And so if you’re finding that we’ve been trying, we’ve been trying to align, we’ve been curious, we’ve done all these things, and yet we’re just at opposite ends of the spectrum, then that is sort of the last thing to do on that is maybe we need to part ways. And so I think to summarize the like, if it’s not working, what do I need to do? I think let’s dedicate time piece of it is really important and finding the rhythm with your CEO and what medium works for them and how to get a hold of them. And Javon Sue, who was formerly at Stitch Fix and currently at Citro as their people leader, he does a monthly dinner with his CEO where they sit down. So this is in addition to their regular interactions with the leadership team and one on ones and whatnot, but it’s a monthly dinner and they get all sorts of pieces done outside of their regular. I know some CPOS are really into. Like, I’m actually in a really good texting rhythm with my CEO and I can catch them. And that’s the thing that they’ll. Respond to, so figure out how do you get the time. And sometimes it’s a creative version of it. The second we’ve touched on a few times is that if it’s not working, get curious. Sometimes you’ll hear your CEO say crazy things or vice versa. And rather than jumping to judging of like, is ridiculous, why in the world would we do it? Just get curious and dive in. And then third is asking for what you need. So I think sometimes we have a lot of thoughts going through our head and we forget to rearticulate it back out to the other person. And in the CEO CPO relationship, there’s so many things going on, but I think distilling it down and reflecting and taking the time to say, okay, I have like 10 million thoughts, but what I really need from the other party is more time on the calendar. Or What I really need from the other party is I need to be able to get through three items before they jump in with theirs. Make sure that you can be direct about that. And I talk about this idea of having the left hand column. And when I was at Gusto on our leadership team, we often would say, what’s in your left hand column right now? And it’s sort of when you read old school books, right? Like in school, if you needed to take notes of what’s going on in this part of the story, or that was a crazy comment, or I don’t understand, that was what we were trying to pull out. And so think about how to unfilter just a little bit what’s going on in your head and getting that out to the other person. So I think those three things of dedicating time, getting curious and asking for what you need are really important to do if it’s not working. And then if you reach like DEFCOM level five, then it’s a put your badge on the table.
Sarah
Yeah, these are really helpful and you’ve shared so much. And I’m curious if there’s any final parting thought that you’d want to leave just to wrap up.
Jess
Yeah, I know we’ve covered a lot of ground. I think what I would plus one for this relationship between the CEO and CPO, but for really any relationship as well, is how can you come at challenges from the same side of the table and really engage with curiosity and empathy first before jumping to any assumptions or jumping to conclusions. Because oftentimes there’s some context that’s missing. And one thing that I always kind of think about is the game. My kids actually play this game where they’ll like to clap out a song and then have me guess. And I find it like the hardest game because they’ll just clap something random. And then I’m left being like they are looking at me expectantly. And I’m like and I think that’s the thing is they have a song playing in their head with all the instruments and the words, and it makes complete sense, and it’s so obvious. And the person on the other side is just like, I just heard some clapping. Can you help fill in some of the blanks for me? And so in thinking about these relationships, how can we help to add in that color and context and give it the vibrancy much more so than the clapping that’s coming out when we first try to communicate it?
Sarah
Yeah, that’s a great example. Everything has been so helpful. I know that people can take some information from this and apply it in their working situation, so I just so enjoyed the conversation. Thank you.
Jess
Thank you, Sarah. It was a pleasure.
Sarah
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