Ep. 53: The Chief of Staff’s Real Job: Turning Strategy Into Action
About this episode:
Original Air Date: July 27, 2026If you hired a chief of staff to be your leadership team’s star athlete, don’t let them languish on the bench. At many organizations, chiefs of staff are meant to execute high-wire strategic work. But the job is often reduced to: glorified project management, executive cat-herding, and catering to the CEO’s whims. They compensate for bad work design through effort and influence, carrying big expectations with no real authority.
In this episode, Rodney and guest co-host, Sam Rothkopf, lay out the first move toward becoming an organization built to benefit from change: Recharter your chief of staff as the leadership team's work designer. They dig into the three jobs most chiefs of staff currently hold; why the role should serve teams, not single leaders; and the authority they need to put business strategy into motion and free up executives to do the work only they can do.
Mentioned in this episode:
“built to benefit from change ep”: AWWTR Ep. 52
“failure of the ways of working ep”: AWWTR Ep. 50
In this episode:
Rodney Evans
Samantha Rothkopf
Listen now:
Episode transcript:
Rodney Evans:
I hate all of these equally, by the way. I want to talk about alternatives to all of them because I think all of these things should not be jobs.
Sam Rothkopf:
Spoiler alert, we don't think this is the way it should be.
Rodney Evans:
Spoiler alert, not like this.
Hey everybody. This is At Work with The Ready, a podcast about work design and how organizations can make change work in their favor. I'm Rodney Evans and I'm here with my very special guest co-host, Sam Rothkopf. Hi, Sam.
Sam Rothkopf:
Hi, Rodney.
Rodney Evans:
Today we are talking not just about snack crackers as we have been for the last 10 minutes before we started recording, but also about the moves it takes to be built to benefit from change. But first we have to check in because how you do something is how you do everything. So, so important. Sam, did you bring us a check-in question?
Sam Rothkopf:
I had one, but now I have a different one based on our snack chat.
Rodney Evans:
Let's do it.
Sam Rothkopf:
So I'm going to go for it, which is what is your favorite either celebrity owned or celebrity endorsed food or beverage item?
Rodney Evans:
Ooh, that's a good one. You can go first because I have to think about it, I think.
Sam Rothkopf:
Okay. Give it a thought. And I also say that even if you think it's not endorsed by a celebrity, it probably is or owned by a celebrity -
Rodney Evans:
Yeah, 100%.
Sam Rothkopf:
Because we were talking about you just can't only make blockbuster movies anymore. You also have to be endorsing snack crackers in order to be successful. Yeah,
Rodney Evans:
You have to make Steve Aoki pizza cheesies or what are you even doing here?
Sam Rothkopf:
I guess those ones are not going to be your favorites, but I have to say that the Mirabel Rose, which I believe, and maybe I should have done more due diligence on this check-in question, is owned by was an Angelina Jolie/Brad Pitt collab before they broke up. But it's one of my favorite roses in a relatively reasonable price point. And I had it at my wedding and I didn't even know that it was from their vineyard, but it's absolutely delectable.
Rodney Evans:
I have a real answer and then I have a shameful answer. My real answer is that I love Casamigos tequila and Ed made us blackout margs on Friday the 4th. We call them that because we all got so drunk that we basically didn't recall the evening after having one cocktail served to us by my husband. I don't know what he put in there, but it was Casamigos and it was great.
My somewhat shameful answer that I will admit only to you and our listeners is I think that the Blake Lively hair products sold at Target are really good. And I want to hate them for a variety of reasons, but they're just really high quality. They were in a gift basket or something and I tried them and I was like, holy shit, these smell amazing. They work super well. They're Target priced and I can't get off the sauce. I can't quit the Blake Lively shampoo.
Sam Rothkopf:
Interesting. I mean, that really checks out. I mean, Blake Lively, that would be a whole other podcast episode, but she definitely has great hair. There's no questioning that.
Rodney Evans:
Who better to sell me shampoo than Blake Lively?
Sam Rothkopf:
Truly, truly.
Rodney Evans:
It's the dream. That was a great check-in, Sam.
Sam Rothkopf:
I do what I can.
Rodney Evans:
It's a strong start.
The chief of staff already exists, but does the wrong job
So what are we talking about today? Why don't you tell us, because the whole idea of this episode was yours and I think it's really smart and I'm very excited. And also I'm recovering from being feral for the last three weeks and only just today for you took a shower with actual soap. So why don't you walk us into this thing?
Sam Rothkopf:
Wow. Okay. Now I really have the context of how you're entering the room and I'll do my best to do some of the heavy lifting here, Rodney. So you can just -
Rodney Evans:
Like a real professional.
Sam Rothkopf:
—You can just sit on back and enjoy the ride here. I appreciate that. So ultimately in last week's episode, we talked a lot about the change in our thinking as an organization over the last 10 years and sort of how we have come out
On the other side of the last decade of consulting and ways of working consulting and developed a new thesis around building teams and organizations that are equipped and ready to benefit from change and not just bear it. And it was a bit of a philosophical rumspringa of a conversation, which I found really fun, but also wasn't super tactical in terms of, okay, being built to benefit from change sounds like a great concept, but what does that actually mean in terms of what I'm supposed to do in my organization with my team? And so we're going to talk a little bit today about something that's very tangible that we've seen as a really interesting first step as a step that's manageable, exciting, and can really start creating not just a new culture, but a new way of working that doesn't require an entire structural change or millions of dollars of investment, but can actually start really making a difference.
So we've got a few different examples of what are the moves we're calling them. What are the moves that you can begin to implement to create an organization that's built to benefit from change? And today we're going to talk about one that I think is really exciting, which is the future of the chief of staff role, what it's done in the past, what it needs to do in the future, and how it can really be a catalyst to helping move your organization in the right direction.
Rodney Evans:
Yeah, I'm very excited about this. And for the OGs, it's like we have long resisted the urge to "put a role on it" because of the failings of the head of transformation or the head of the PMO, these sort of ancillary kind of positions that get spun up to hold the body of work that's actually about the organization. Conversely, what we have learned and you've heard about on this show in the failure of the ways working ep and in our first ep together is if an organization doesn't already have a container for this shit, it's very, very difficult to make one. And I think that we were, I'm going to call it idealistic, not naive, but let's be honest, it's both. When we were like, "Oh, we'll just teach people stuff and then they'll be like that forever. And it doesn't really have to be someone's job. And it shouldn't be someone's job because it should be the team's job." Okay, that experiment failed.
The great thing about the chief of staff is it is an existing member of a leadership team that is doing the wrong job mostly. So it's easier to alchemize something that already exists but is borked, than to try to create a new category of executive and jam it into an ELT. So I love this concept because of all of those reasons and I am excited to hear what you think about it.
Glorified admin, project manager, and influencer
Sam Rothkopf:
Yeah. I though maybe we could start by spending a little bit of time talking about what we're seeing in the current chief of staff role because we work with a lot of chiefs of staff. I would say-
Rodney Evans:
Yes.
Sam Rothkopf:
—a pretty high percentage of the teams that we work with either have a chief of staff or they are our direct client. So we've seen so many versions of this person, this role at different altitudes too. I think it's also one of those roles that really changes depending on the sector. When I'm working in tech, there are like 500 chiefs of staff. It's crazy. Every ELT member has one and even layers below. And so the role in that configuration is really different from when I see a chief of staff at a nonprofit that has 50 people.
However, the role does and I think should exist kind of agnostic of your size of organization. We have a chief of staff and we're a small ragtag crew, but I would say that our chief of staff is critically important to our ability to function as an organization. So yeah, what have you seen, Rodney, in terms of what the chief of staff, who that person is and what they do today?
Rodney Evans:
Yeah. And then I'm going to ask you a follow-up about tech because I think that's interesting. I generally see the chief of staff as being a combination of three things. One is glorified admin. So even where an executive has an EA that holds the calendar, the chief of staff is often doing a lot of the cat herding, especially around things like assembling the board deck or getting ready for the big town hall. They often are in this intermediary coordination role with all of the executives that an EA is generally not going to do where they're like, "Yeah, no Chief Revenue Officer for real though, I need your numbers into the thing today for the CEO to stand up and talk about this." So it requires more judgment and more influence than an admin, but is also very, very operational in nature.
Two is glorified project manager. So I see a lot of chiefs of staff who basically are watching the Gantt charts and kind of being like "Tick-tock, deliverables, we have a milestone, blah, blah, blah. Where is this thing?" And especially around big initiatives where it's like we're going to do an acquisition or we're going to do a big restructuring or we're going to do an AI transformation. I often feel like the chief of staff is the holder of the project plan. I hate all of these equally, by the way. I want to talk about alternatives to all of them because I think all of these things should not be jobs.
Sam Rothkopf:
Spoiler alert, we don't think this is the way it should be.
Rodney Evans:
Spoiler alert, not like this. And then number three is sort of influencer. So I see a lot of chiefs of staff, and I'm curious because you've worked as an executive closely with the chief of staff more than I have. I often see chiefs of staff doing this weird combo of influencer/therapist/untrained coach to the rest of the executive team to be a translation layer between the CEO and the ELT to triage conflict between ELT peers. I see them as sort of being this lubricant within this system to just make things go. The reason I hate all three of these things is because all of them require an individual where a system should do the work. And I'm like, the big change I'm going to harp on today, so strap in everybody. I haven't talked to people in days so I am feral everybody.
Sam Rothkopf:
She's ready.
Rodney Evans:
I want them to be building systems, not being there in the absence of systems to make things work. I don't know. How does that square with or diverge from what you generally see? And again, I feel like you have way more reps of this than I do, so please do correct me.
A recipe for burnout
Sam Rothkopf:
Maybe reps of being on the team and seeing how the chiefs of staff are actually operating. I think first of all, chiefs of staff are also just always super smart driven people who can get shit done. That's pretty much the profile is like, I just graduated from Wharton. I'm like -
Rodney Evans:
Type A.
Sam Rothkopf:
—Type A. I will bang some heads together and make sure that the thing that you, CEO, CMO, whoever it is that you're working for, the things that you care about are being prioritized. And oftentimes they're not things that anybody else holds. They're the stuff that's important to an organization but isn't actually in the job description of any of the other ELT members.
Rodney Evans:
Totally.
Sam Rothkopf:
But they end up either being like, to me, there's two kinds. There's either the like, "Oh God, Sam's coming down the hallway, everybody lock your doors" kind. She's going to come and be like, "Tick-tock, where's my deliverable?" Or there's the super therapist kind who's almost, I would say an agent of the CEO who's going and doing all of the gossip rumor mill, "This person doesn't like this person's hair color, this is never going to work" kind of thing. I don't think either of those are right, but those are the two archetypes. And I do think that what's hard about it is that it always feels like if you're on the executive team, when you're talking to the chief of staff, that person is really just a conduit to the CEO. So it isn't as if they're there to actually help you be successful. They're there to make sure that you're doing exactly what that person wants you to be doing and almost being a secret agent of that person.
So I think that the chief of staff role is also a very difficult role and it burns people out really fast because you're not on any team. You're kind of there to make someone else bigger, not to have your own authority, autonomy and constitution in the work. So I think that executives who have chiefs of staff love them because they feel like they're able to use a big stick on the things that they want to get accomplished. But in reality, it doesn't help. It doesn't help that much with team dynamics. It doesn't actually help you get things done or create systems faster. And it makes it so that you feel as a leader that you are giving away authority, but in reality you're just delegating tasks, but still all of the decisions come all the way up to you.
Rodney Evans:
And not just tasks, you're delegating the dirty work.
Sam Rothkopf:
Yeah.
Rodney Evans:
You're just like, what if I outsourced the emotional labor and the accountability holding to someone else who is, let's be honest, often a woman, often a hard charging woman if we're looking at the archetype. And so that I as CEO can float above the muck of saying to my direct reports, you two have got to stop arguing and go work it out yourselves or this thing has got to be here on... It's a very convenient thing to have a hench person doing your bidding and then to be able to basically, as you're saying, keep them in a toothless role with very high expectations and very difficult dynamics to navigate because every ELT has difficult dynamics no matter how wonderful the humans are because it's a fucking hard job and that's life. And so you're putting someone in sort of generally someone who is very smart and very ambitious into this role that in my opinion is hard in all the wrong ways.
Sam Rothkopf:
And invisible in so many ways too.
Rodney Evans:
Yes. Also that. This is one of the things that I was thinking about in preparing for this episode is that we're going to talk about what should go into this role. But I was thinking about the fact that in the best case, and I would say this is true with Mia in many ways, maybe a little bit less because we're a small company and some of the examples that I'm thinking of are bigger companies. But I feel like one of the nuances you're pointing to is in the best case, they're kind of invisible. If they're doing the system building right,
It doesn't require them. They're not sort of hand jamming the dynamics and the deck building and the coordination and the work because they have created operating rhythms and working agreements and role clarity and workflows and AI enablement to do the shit. And then their job is to keep tinkering with all of that stuff to optimize it. But I use Mia as an example because I think she's a great chief of staff. Mia is someone who's very skilled at, for example, designing and facilitating an operating rhythm. One of the reasons I know she's good at it is because you barely know she's there. It just sort of works and the group gets what the group needs and the job of the meeting or the moment or whatever gets done. And it doesn't feel like it's Mia's. It doesn't feel like Mia is driving us through it or having to really exert a lot of effort because she's so good at designing the thing to do the job that it doesn't feel like it's her even though she is the one who put us all into the maze.
Sam Rothkopf:
Yeah, absolutely.
Chiefs of staff are everywhere in tech, with almost no power
Rodney Evans:
So I am curious because for people who don't know, because we haven't talked about Sam's background really, Sam is straight up San Francisco tech lineage way more than I am. To be totally honest with you, I've had a few experiences working with clients in the Valley and I fucking hated it. And I ran as quickly as I could from that whole area and have basically not pursued business in and around San Francisco in eight years.
Sam Rothkopf:
Okay. But please don't, if you're listening to this and you're in San Francisco, you can call me. I'm interested in you.
Rodney Evans:
Yeah, call Sam. She loves it. That's great. I think that's great. Loo, I grew up in an investment bank. We are horrible in a different way. I'm just more comfortable with that kind of horrible. Everyone's horrible. I'm accustomed to being punched in the face directly, not passive aggressively. Anyway, my point being when you say tech, chiefs of staff are all over and everyone has them, I have noticed this in the particularly SaaS companies that I'm around. Why is that? Like why is that and how did that come to be? Because I don't think it was always like that.
Sam Rothkopf:
Yeah. I think it's one of those things that has really proliferated in the last 10 years. It used to be, and I think part of it is in tech, it does end up being more of the glorified EA role and project manager, but people don't want to be executive assistants here if they've like, I've just graduated from Wharton. And so part of it was a little bit of just a rebrand of the thing that executives needed or thought they needed.
Rodney Evans:
They're like, what if we gave you $300,000 a year, but you're not an admin.
Sam Rothkopf:
Right.
Rodney Evans:
But also...you kind of are.
Sam Rothkopf:
Yeah. And they're kind of two-year stints that people do too. It almost feels like I think a lot of my friends who have been chiefs of staff are all brilliant, first of all. And it's like a tour of war kind of thing. You're going to go and you're going to be the chief of staff for the CFO at Dropbox, Slack, Asana, whoever you want. And then you will have built a really great network because you'll be meeting a lot of big players. You'll be in rooms that you probably wouldn't have been in before and you're going to burn out because of all of the reasons that we've already talked about. And so some people, I have some folks who have stayed with executives that they really love, and same with great EAs. And they've gone for them from place to place. And those are a duo, but that person is specifically designed for that human being.
But I think this chief of staff for every leader across the organization is very specific to tech also because of the amount of money that was just being spent on headcount as well. I think it was just one of those things that was also part of the bloat of some of the big tech world.
Rodney Evans:
I mean, it's interesting because I also have a hypothesis that in a lot of those organizations where the ways of working aren't great and there isn't a lot of investment into and thoughtful design. I mean, there isn't anywhere, but tech organizations I think are generally considered to be better run than legacy gigantic bureaucracies. But even so, I don't always see that there is a ton of thought put into ways of working. There are exceptions to that. I think places like Netflix are very thoughtful about ways of working in organizational design and very smart about programmatically how they do this, but a lot of places don't. A lot of places it's like a second thought or not a thought at all. And so I also wonder if because there is a lofty desire in tech around great cultures, great talent, high retention, having the best engineer, all of those things, and then in the other hand, not a real mature discipline around work design, the chief of staff is kind of a bandaid for that, which is like this is how an executive can get work done in a place that is probably a little bit more chaotic than it should be.
Sam Rothkopf:
I think that's right. I also think, first of all, tech companies don't think they need any outside help in general.
Rodney Evans:
Of course, of course.
Sam Rothkopf:
Because they're the best of the best in their minds. In different ways they know best. And I think oftentimes the companies are built really product first and software engineering has kind of ruled the roost. And so agile ways of working are really embedded into how they do things. And I think that I've seen this in a lot of different places when you try to take the way that you develop software product and mirror that into other parts of the organization, it's just not apples to apples.You can do lots of things in lots of agile ways. But I remember 10 years ago when everybody, and maybe it was even 15 years ago, when everybody was like, okay, now we're an agile marketing team. Now we're an agile insights team. And it was just like these are not the same.
Rodney Evans:
It was like "Agile for HR!" And I was like, "What?""
Sam Rothkopf:
Yes.
Rodney Evans:
"You're just saying words."
Sam Rothkopf:
Exactly. And so I think that this chief of staff role is also a way to make the connection between how products are made and how the rest of the business needs to get run. I don't think it necessarily did that in the best way, because now we have 500 chiefs of staff per tech company. But yeah, I think that's where it came from. And this is a little bit off the cuff, but that's my hypothesis.
The reframe: serving the team, not just one leader
Rodney Evans:
I love that. Okay. So we've covered a lot of ground on the current state of chiefs of staff in a variety of places. And you have a strong view that chiefs of staff should be the primary work designers for a leadership team and that they are one move to become built to benefit from change. Give us what's the dream state? What are chiefs of staff newly chartered to be doing?
Sam Rothkopf:
Yeah. I mean, I think the biggest single reframe is moving from being a chief of staff for a particular leader to being a chief of staff for a particular team. And yes, you still will need to report to someone most likely depending on the organization, but I think ordinarily you are just there to get more work done for one person. But if the chief of staff role should actually be helping to activate the strategy for a team so that that's actually the marker of what success looks like for them is their ability to help bring strategy to life. Because I think that right now who owns strategy in organizations is also all over the place.
Rodney Evans:
What a hot potato that is at the moment.
Sam Rothkopf:
Right? And then how many months can we be developing OKRs for? And it's just so crazy the way that we're doing it.
Rodney Evans:
I think at least seven, is the answer to that question.
Sam Rothkopf:
At least seven. And then you're executing for three months, then you change them for the last three.
Rodney Evans:
That's right.
Sam Rothkopf:
But for an ELT, I think the chief of staff should own the operationalization of the strategy and that making sure that that is possible through work design and system development should be their marker and they should have authority and autonomy to actually make the decisions on how that gets done.
Rodney Evans:
Yeah, I think that's right. I think it's a combination of a lot of the things we've talked about on this show before where it's like it is designing and facilitating an operating rhythm. It is building and keeping metrics fresh. And I don't mean your shitty MBR finance download. I mean the living health of the business leading and lagging indicators that executives should be looking at on a regular cadence and making sense of. I think it is figuring out what the communication cadence is with the larger organization, not fiddling with drafts, but being like once a month we do a Loom. Once a quarter, we do an all-hands. This is how it goes. This is how it's a loop. I think in the best case scenario, they're creating routines for the ELT to rely on. And I want to come back to that in a second. So flag that one for me. And then also they're creating a feedback loop between the ELT and the rest of the organization. And it's not just cascading comms bullshit. It's like this is the living system for how we hear from the company and the company hears from us and those things sort of inform one another.
Building your “shelves”
I have a client who I love very much. I've talked about her on this show before. And the way that she describes this that I love is she thinks of this sort of battery of routines, including operating rhythms. And I mean mainly that is how she's talking about it. But role clarity and decision rights and the basic shit that we always say you need. She always says as an executive team, when you have those things, everybody has a set of shelves and there's a space on the shelf for every piece of work.
And so then first of all, there's no sort of overhead or extra work to figure out where to have the conversation. It's like on Mondays we look at these metrics and on the last Friday of the month, we retrospect against this strategy. And on that Tuesday, every six weeks, we do a sky meeting where we talk about market forces. And she's like, and then you don't have to think about when's the next time. And she's always like, we want to execute with calm and what that requires is shelves. And two is the way that I tie that to being built to benefit from change is then when something big emerges, you have the slack to get after it because all of the team's sort of cognitive overhead, all of the energy doesn't go into just surviving day-to-day. So there's room. It's like when you have predictable routines and when you have discipline as a team, then you don't have to think about that shit.
And then when you want to do something big, like you want to acquire something or you want to go public or you want to do a big transformation, it's not like, well shit, where are we going to get the time? We are so full up with just the day-to-day.
Sam Rothkopf:
Right. Or how are we even going to talk about this or put it through the diligence to even think about where it fits? I mean, I think you're totally right. It's being really prescriptive and sticking to the operating rhythm and where different discussions are happening and having them in public when you can. And that is what allows you to be able to benefit from the changes that's coming. Otherwise, everything feels like a chicken with your head cut off moment.
Rodney Evans:
Yes. And if you have the right rhythm held by a really dialed chief of staff, for example, when we have Sky meetings, Mia is bringing really interesting market signal and trends to look at. It's not just like, "Hey everybody, here's your sticky notes. Let's talk about what's happening." It is a really well-designed moment to be like, "What are the quiet signals we should be paying atention to? His is how I think we came up with the ambition that we're working on now is because there were these containers to do this kind of sensing. And I say that because part of being built to benefit from change is knowing what fucking change to benefit from. And if you don't ever get to look out and be talking to your team about where the puck is going, shout out Sam Spurlin, then how are you ever going to get after it?
So it's multi-threaded. It's like the day-to-day experience of most leadership teams is already overwhelmed and being consumed with the present business. And a great chief of staff in a well-designed operating rhythm has us in the loop of what's out there, what are we going to do about it? Do it. What's out there? What are we going to do about it? Do it. And it's not so chaotic like most ELTs that I'm around where they're just like, "Well, that's interesting, but where would we ever find the time?"
Sam Rothkopf:
Absolutely. It frees up real space to be thinking about the things you should be thinking about as an executive team instead of who's going to be at this meeting? When is the offsite? This person's talked to the executive last, so that's the way it's going to go. I mean, there's just so much unfortunate politicking that happens. And I actually think a lot of it is because this role doesn't exist in ELTs. And the amount of time that it frees up for the CEO in particular to not be having conversations about jockeying for resources or having ad hoc meetings and really thinking about work design. The CEO should not be thinking about work design.
Operationalizing strategy, for real
Rodney Evans:
I agree with you. And I also think that one thing I was thinking about yesterday, I was talking to two people that I adore. They're listening to this podcast. They know who they are at a client. And we were talking about doing strategy work. And I was saying how the thing that's tricky about strategy work is a) to your point, it's no one's job or it's the head of strategy's job, which is like we'll do another episode on that sometime and why that gets real dicey. But every executive for whom it is not their first rodeo has an opinion on what strategy work is and how you do it. And what I've seen a lot of times, especially in doing the ELT resets, which we're going to talk about on a different episode, is it can be very easy for an executive team, including the CEO, to spend a lot of time debating the premise of what goes into a strategy and what the strategy process should be.
And is it OKRs and is it a deck and is it a narrative? And is it a vision statement? And is it a five year? Is it an LRP? Everybody has an opinion on this. Mostly I would say arguing the premise is a waste of time because you're avoiding the conversation that's actually interesting, which is what the fuck are we going to do of all the possible things we could do? And I think that a chief of staff who has real skill and who is vested with the right authority kind of goes like, "That's not your job. None of you are going to get to do this exactly the way that you probably want it and we're just going to do it."
And that's not someone's job on the executive team unless it falls to the CEO. And to your point, it really shouldn't. I really love to see a chief of staff holding that container, particularly in strategy season, which spoiler should be quarterly, and having the rest of the team show up with the contents to be like, "I'm really convicted about this. I really think we should place this bet. I really think we should shut down our core business." I want executives to show up with opinions on the business rather than opinions on how we're going to make the sausage. And that will only work if it's somebody's job and somebody has the authority to be like, "This is how the sausage is going to get made. Everybody shut up."
Playing “favorites” with the important projects
Sam Rothkopf:
Yeah. And the other thing too that happens when it's not either the CEO or a chief of staff is that it feels like the CEO has picked someone that they think is smartest and best who's going to lead the strategy development, which is immediately going to make the development of that strategy almost impossible.
So it's just so, because I've seen that happen so many times. And as someone who got picked to do that many times, if I might say so myself-
Rodney Evans:
Yeah, flip that hair.
Sam Rothkopf:
It was always like, "Oh yeah, of course they picked Sam because Sam's their favorite. And then I'm going to poke all these holes in the plan no matter what." And I probably didn't lead it correctly, but if you pick a line of business or a particular function to do the strategy development, it's going to have a real bent in one direction or another. And it's going to be really easy for people to not bring their A game to the content because they're going to be so focused on who is in charge of the development of it. It's just a total nightmare.
Rodney Evans:
Well, and I'm curious your opinion on this because I have a take, but I don't know if it's right. I sort of think that if you're doing company level strategy, my take would be that every ELT member, every member of the C-suite has a role that is not their functional role, that is their role on the ELT to create org level strategy and that it would be hard to be in that role if you're leading it from a function. If you're the product lead but you're doing company level strategy, you're potentially missing revenue strategy that looks different and maybe is acquisitive or maybe looks like a sale or maybe looks like joint ventures or a bunch of other things. You're going to come to it from your perspective. And for what it's worth, I think product-led strategy is better than a lot of other led strategy. But I still feel like if it's the company level strategy, I don't really know how you get a functional person to effectively truly lead that.
Sam Rothkopf:
Yeah.
Rodney Evans:
Is that right? Or do you think I'm full of shit.
Sam Rothkopf:
No, I think you're right because it's really hard to wear both hats in that situation because you need to be bringing both the overall expertise and then the content for your function and it's just hard to do it.
Rodney Evans:
Totally.
Sam Rothkopf:
And it's not your job. So it's just another thing that gets put on top of everything else and/or it gets outsourced to a McKinsey and then a strategy comes back that is not executable. And then people call us and say, "How can I do this? "
Rodney Evans:
Yeah. That was part of my conversation yesterday where I was like, "Don't do that. " And the other thing is that just occurred to me is even the CEO is going to be biased because every CEO came from a function. And so it's like I've worked with the CEO that was the CFO and their strategy always has a very resource-heavy, a real financial bent to it. And I've worked with CEOs who were CROs and theirs is a very sales-led customer-led kind of strategy. And I've worked with product CEOs. And even when I was the CEO of The Ready, I am such a practitioner. And as you know, because this was the first six months of our relationship, you were much more commercially oriented and like, "Bro, you have to change the way that you talk to the market about this stuff." And I was kind of like, "Blah, blah, blah. I know what I'm doing. I'm fucking great at this."
And you were like, "True, and it doesn't really matter." And it's like every CEO is going to have their bias based on what they grew up in and what they're really great at. And so I think everyone on that team recognizing that biased strategy is probably not the best and letting this person hold the way that that gets done is probably wise. And I'm like, I'm spending a lot of time on strategy because I think that creating strategy and steering strategy is the most important thing an executive leadership team does. And it's done so poorly in so many places that I'm like, this just feels like easy wins for a chief of staff to make this 50% better the first time that they even try it.
Every CEO’s first hire
Sam Rothkopf:
Yeah. I also think that if you're being hired as the CEO of any size, your first hire should be an incredible work designer who's going to be your chief of staff.
Rodney Evans:
Hard agree. But like who's doing that?
Sam Rothkopf:
That was my first move and would be my first move if I went anywhere. I don't know who's doing that. I feel like right now what people have is their playbook of consultants that they'll go to, which can also work. I think there can be a fractional chief of staff that you bring in. That's a service that we offer. But you need someone whose job is to come and whip the team up and make sure that the strategy can be developed and operationalized. That's their whole job. Because right now it's always just a side gig of someone's job or you're paying someone for a deck, not for a full op model for the strategy.
Rodney Evans:
A system, exactly. And I would argue even if you hire someone fractionally like us, in the perfect world, I see that as a period of time to train an old-fashioned chief of staff to become a real work designer and then to hold this work. You ultimately should have this person in the seat even if you need some other intervention for them to do this role effectively. So I think that's really interesting. But where you came from, you didn't have this. Did you know that you needed this?
Sam Rothkopf:
It was not nearly as clear to me as it feels now having been here for going on a year, let's say. Because I think that also just the practice of work design and what it actually is was not clear to me before I came here. Also, I think there are elements of it that feel like as a leader, this should be your job. You should be running great meetings. You should be designing fabulous strategy. This is what it means to be a leader when in reality one of the main things that I've realized coming here is to be a great leader means that you're making time for the things that you uniquely are amazing at and being able to continue to do those things and enabling other people to have the authority and autonomy to do the other things. And I think it could depend on who you are as a leader and where you come from.
There are probably some CEOs who are work designers at heart and that is their secret sauce, but then they need to figure out how to delegate other things. So it depends a little bit, I'm sure, on who you've got around the table and the skill sets. But what I realized was no matter what level I was at, whether it was I've been a chief growth officer for $100 million business, I've been a head of brand for a smaller health tech company so much of my time was always spent on the team's operating system and relationships between people and management of people. And having a chief of staff, even we're a smaller business has freed up so much of my time to deal with the things that I uniquely can do. No matter what the size of business, I feel like it's a role that I think needs to exist, at least for me and for a lot of the leaders that I know.
Rodney Evans:
Yeah, I think it's exactly right. I think in this climate with things changing as quickly as they are, I really want to see CEOs spending their time customer-facing, investor-facing, market-facing, reading. The best CEOs that I work with and I'm working with two right now that I think are pretty top drawer among the hundreds that I've worked with in my career, they spend a lot of time reading and thinking and having ideas. And I think that's where they should be. And also that's why I'm there is so that they don't have to worry about the three-day offsite that's coming up. They know it's going to be fucking dialed. They know it's going to be what they want it to be. And they bring a lot of ideas that they've been incubating to that meeting and to that experience because they haven't been like, "So does anyone have any vegetarian requirements or what should we do as the fun event?" They haven't thought about the rest of it so they can just show up and be smart and have provocative ideas, which is what they get paid for.
So I love it.
Sam Rothkopf:
Yeah. And what you want all of their team to do.
Rodney Evans:
Yes. Yes, exactly.
The authority chiefs of staff actually need
Rodney Evans:
Okay. I have another question for you that I think is a juicy one and I want people to pay special attention because I think this is probably the most important part. Describe to me what the authority is that a chief of staff needs to have to do the role that you're describing.
Sam Rothkopf:
That is a really juicy part. I think that they need to have the authority around the design of the operating rhythm for the team. Everybody who listens to this podcast probably knows what that means, but what meetings are happening when, who's attending them, what decisions are being made, what kind of meeting is it? And the authority to tell people not to have other meetings to talk about those things too. There's an element of...I'll be in a one-on-one with Mia, which I have, and I try to have as few one-on-ones as I can so we're doing more in public, but I'll bring up a topic and she's like, "We should actually talk about it here." And the ability to speak-
Rodney Evans:
And she's pointing you back to an op rhythm.
Sam Rothkopf:
That's right.
Rodney Evans:
Yeah. She knows where the shelf is and she's like, "Nope, that goes over there."
Sam Rothkopf:
Yeah. Or I'll be like, "Oh, I really want to send this Slack message with urgency." And she's like, "You're just going to have to wait two days until that meeting. There's no reason there's no urgency around that. " And so I think the authority to be in charge of information flow and operating rhythm to me are probably two of the most important things. What would you add to it?
Rodney Evans:
Well, I would add to the operating rhythm one I think you're spot on. Also, the authority to have the meeting because especially executive team meetings really get jerked around because it's like, "We're traveling. It's a board week. We blah, blah, blah, blah, blah." And that is the surest fire way to skip the meetings that feel unnecessary but actually are existential. And those meetings are always the meetings that are either about learning or about the future. Because the meetings that we prioritize are the meetings to take action in the present.
If you are just in the cycle of triaging the urgent, you will never get to what is coming and what is important and how to do it better next time. And I think that a chief of staff should have the decision right over whether a meeting gets canceled. And I think that they should have it even if the CEO wants it canceled. I think a good chief of staff says, "Sorry boss, we need to have this governance meeting. I know you're busy. You don't have to come. It can be a recording, whatever, but we need this. " And I especially think for CEOs, but I think for executive teams in general, when I feel like I know what's going on, it's very easy to be like, "We don't need to talk about this because I think we all know what's happening." And you need a chief of staff to go like, "Well, maybe that's true and maybe that's not. We're going to find out because we're going to use this 45-minute meeting and I'm not going to let you punt it because you have other shit to do today." If you don't give your chief of staff that decision right, you will never have a good routine.
Sam Rothkopf:
Because there's always going to be somebody that's like, "What if we didn't?" And you have to have the narc that's like, "What if we did? I'll see you in 10 minutes."
Yeah, that's true. I would say that having to be the narc is the one thing that might remain consistent in the chief of staff role from yesterday to today.
Rodney Evans:
I think that's right. I mean, I think it's like the coach that's like, "We're doing wind sprints. You're doing them. You don't get to not do them this Friday because you won the last game. Do your drills."
Sam Rothkopf:
Yeah.
Rodney Evans:
Do Your drills.
Sam Rothkopf:
Sports metaphor. I'm impressed.
Rodney Evans:
That's my second one today. I am an athlete.
Tooling, comms, and where the team does its work
There's something here you can help me figure it out that's a little bit about tech stack and comms. I don't think you necessarily want IT being the sole decision maker around tooling that is really about how employees experience your organization and get their work done because that's not their job, it's not employee experience. And now the way that we interact, that is a huge part of our interaction through technology. And so I do think, especially with AI tooling, I think the chief of staff should probably have some role in saying, is it Notion or is it Granola or is it Zoom transcription?
I think because obviously you don't want the proliferation of nine million tools. That's stupid and expensive. And especially in a digital first world, we are trying to create the virtual water cooler that people want to come to. And just like they have to design those op rhythm containers, it's like great chiefs of staff are also like, "We use this Slack channel for these things and we have this lack bot in this place and we use this notion page to feed this meeting." And I think they should have, I don't exactly know what the decision rate is, but it's like they should be able to make some call over where the team does its work.
Sam Rothkopf:
And how the ELT is communicating its work to the organization.
Rodney Evans:
Yes.
Sam Rothkopf:
Yeah.
Rodney Evans:
Yes.
Sam Rothkopf:
I'm with you. And I do think that's an interesting one because it can be a little bit of a slippery slope around are they now owning internal comms? And for me, I'm like, no, they are owning the communication of how the strategy is being operationalized to the business. And a big part of that is how that is getting disseminated through what tools and through what medium. But to me, the chief of staff isn't figuring out how we communicate a new HR policy.
Rodney Evans:
No, for sure no.
Sam Rothkopf:
But they are in charge of how do we make sure that everybody in the organization feels connected to the strategy, they know their part in it, and that they're gathering all of the feedback and information that they need to continue on in the operating rhythm of the strategy.
Rodney Evans:
I think that's exactly right. And I think you're doing a really good job pointing me back to the purpose of this role is the execution of strategy and building a system where that's possible. Building the system to execute the strategy and steering the strategy as things change is the job of the chief of staff. And they sort of shouldn't really be distracted by other shit.
Sam Rothkopf:
Right. And it's so easy. That's the other thing. It's just so easy for them to get pulled into other stuff. And it's also because the role of it's nobody's job to design and figure out how to execute the strategy. And it's the most important thing. It's just so interesting. It's the most important thing. And I don't know if I know anybody who would say "You know what's great, our strategy process and the OKRs we develop." And that's what I'm looking at every day. No one.
Rodney Evans:
No one. No one. Yeah. Yeah. It's a lot of planning and then a lot of hope. A lot of hope. This feels like a great place to wrap up our journey through chief of staff land.
Sam Rothkopf:
Awesome. Yeah. And I think we're going to take the next episode or two to talk about other moves that feel really tangible so that you can keep helping your organization be one that has built a benefit from change. So excited to have some more tangible examples that you can hopefully implement in the next couple of weeks.
Rodney Evans:
Nice. This show is edited and mixed by Taylor Marvin at Coupe Studios and produced by Jack Van Amburg. At Work With The Ready is created by The Ready, where we help organizations around the world change the way they work. Thank you for listening.