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Ep. 5 - Why your company needs a Chief of Staff - feat. Dora Nagy

from Scaleup Leaders: Stories from Experience

56m 35s

Ep. 5 - Why your company needs a Chief of Staff - feat. Dora Nagy

A chief of staff is a critical role for scale-up companies, serving as a trusted partner to founders and CEOs. Originating from military and political traditions, the role has evolved into a multifaceted position that supports strategic alignment, operational efficiency, and executive focus. The level of the chief of staff—ranging from a junior executive assistant to a near-COO-level strategist—depends on the company’s stage and needs. At its core, the role ensures that the founder’s vision is clear, actionable, and consistently aligned across teams. Key responsibilities include setting priorities, creating executable plans, monitoring performance, managing people, and leading special projects. A successful chief of staff acts as a unifying force, helping to bridge functional silos and foster cross-team dialogue. However, the role is only effective when built on a foundation of trust and clear expectations. Common pitfalls include hiring at the wrong level, underestimating the role’s strategic value, or treating it like a general assistant. Founders must actively engage in strategy conversations to define what truly matters, as without shared clarity, OKRs and dashboards become disconnected from real business goals. Ultimately, a strong chief of staff enables founders to scale efficiently by focusing on what drives results—while the rest of the organization operates with clarity, accountability, and alignment.

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Hello, welcome to the scale up leader this week. This week we're talking about does your couple wide is your company? Why your company needs a chief of staff? Now obviously this is for scale up, scale up situations and scale up executives. When do you need a chief of staff? Why do you need a chief of staff and so on? And to help us in this conversation, I'd like to welcome my friend, Dora Nagi. I met Dora at Google many years ago and we rode to Paris together as well. Oh, it's from Paris to London. But I mean, we met at Google, right? We met at Google Transit. Yeah, hi Richard. Yeah, I think we know each other for over 10 years, which is kind of crazy and yeah, we met so many times you haven't. So thank you all the all the cycling, right? Like it's also met at Google. I was in London and then shortly after moved to New York and then the valley. And I'd be reconnected as you said, cycling from Paris to London, I think, two, three years ago. So I love good conversations. I think I'm out of, you know, spedding together with a team, you know, hiking or cycling, for sure, I had some experience with it. Yeah. Oh, actually, let me just press recording. I forgot to say that one thing that I said that I was going to do was press record. There we go. I remember recording that. Anyway, um, yes. So, uh, which is, so yeah, we went through during that period and I mean, since then you went from marketing at Google and then you did some strategy work at Google and then soft bank, chief of staff, um, and now to then chief of staff at Cairo and they could talk to you and so on. One of the questions that I had that I really think is interesting is what is a chief of staff? Um, and I asked this question because I, one of the reasons I was at Amazon and I'm a very couple of years and people had this, there's this role they're called technical advisor. And I asked you, what's a technical advisor? And they'd say, well, it's like a chief of staff and that didn't really help me much. But um, what is a chief of staff and why, why do you need one? Yeah. Yeah. You know, this is actually a really good question. And I think there's a lot of confusion about what is a chief of staff. And there's also different understanding, I think in Europe, where it's still relatively new compared to the US, where it's been around. So, uh, you know, originally it comes from military. So that was a right hand person who made sure that the camp is all organized and, you know, everybody is ready and, you know, what they're doing. Um, and then later on, you saw in the, um, politics, you know, politicians, you know, uh, the president, like the United States, they would have a chief of staff. Um, and, you know, it continued to be this sort of right hand person that is trusted within the circle, you know, they are, um, almost as powerful as their boss that I'm going to call principle, uh, for simplicity. And so after a while, a company started, uh, you know, having a chief of staff, so the big companies like Google, um, you know, Facebook, Twitter, you could see the role of popping up in the valley. And then others started, um, sort of hiring that person in the valley. And then now I think in Europe, um, you know, the simplest way I think about it is really a range from like one to 10, um, all, all those people could be called staff. But one is really someone who is more like a super super good executive assistant, um, who can really help their founder CEO principle, let's just call them principle, to really focus, get stuff done, be organized. And then the other end of the spectrum, you have 10, um, which is someone who is, um, really strong in strategy and operations. And so in some companies, it's almost equivalent to the COO. And sometimes you could see that person growing into a COO role, for example, if they are in the end. And you see everything in between, uh, which is quite hard when you hire. Like a level one CEO, a level one chief of staff who's like, uh, executive assistant plus, so are you saying? And then, uh, it's like, it's like a COO reminds us. Yeah. So when you see quite a lot in between, and that's why, you know, when someone hiring a chief of staff, it's quite useful to understand which one they actually need. Um, if they need one to begin with, right? Because then you can hire someone who's not the right person for the role or for the stage of the company. Um, so those are important things to just come this in a little bit more like, what do you actually need when you say, I need a chief of staff. So, you, so this really comes down to what level of, what level of equipment staff I need and then be right high for that chief of staff, you know, necessarily just saying, some chiefs of staff are more seated in others. It's just, it's very much a matter of like, what do I need? And then how do I find the person that fits that role, is that right? Yeah, exactly. And, you know, sometimes, you know, I find, um, I work with a lot of founders and they think, oh, I'm so overwhelmed. I just need help. Like, let me hire a chief of staff because my buddy has a chief of staff. And they're just going to come in and just do stuff. Um, but actually it's worse really thinking it's true because you might need someone super junior and sometimes, um, those people can also be called the founders associates, which is really just a junior person, maybe out of college, you know, eager to do lots of stuff, follow you around, learn from you, um, to be in the business and just learn and they help you around from. Um, but maybe you need someone who's a lot more senior and you need somebody who is almost like, um, you know, your trusted strategian of person, maybe you don't even have a COO, but you need that kind of background and experience, you might hire from management consulting. Um, and that person becomes part of that executive team that's helping you with strategic decisions as well. So, what is the difference, what's the difference between a COO and a chief of staff that like we hear a great chief of staff and a COO, what's the difference? Yeah, yeah, I think that's a great question. And I think, um, oftentimes you see, um, those roles being very similar. So it's really, uh, coming down to sort of how do you divide and conquer? But typically a COO would have direct reports and they have deliverables, um, and they have reports, a team that they manage, they often have maybe finance or, uh, operations or, you know, facilities or reviews like all those things report into them. A chief of staff is an individual contributor. They might have like a mini mini like a junior associate report to them or maybe the EA reports to them, but they typically an individual contributor and they choose the role to get to know the business. So they stay in the role for like a year, maybe a year and a half and they typically move on to a function. So they become maybe head of people or they become head of marketing, depending on your interest in the background of the person. So you don't really see a chief of staff sort of staying in a chief of staff role for years and to come in the same company. Right, so is it a good entry, entries to a company someone so it gets to know the whole company and then, you know, context for everything and have relationships and what we do once we're functional role valves and then you already have this background of a broad breadth, I guess. Yeah, yeah, exactly. And also sometimes you see someone internally raising their hand and say, Hey, I would love to do more and I don't really know yet where I want to be in the company, but I'd really love the company. I love the founders. I just want to do more. I can I take this role. Um, and sometimes, um, you know, when people ask me, who should I hire, I actually, um, suggest hiring someone into the role that you already work with because then, you know, how good they are, you know, their style, you know, if, um, you have that sort of trust and relationship. So it's a bit like, you know, when you're marrying someone, you kind of want to have dated. So bringing in a completely new person and now you are my, you know, most trusted, uh, airline company that could be a big difference. Um, but that's it greatly for someone to year to get into the role. If they good, and they want to learn and then stay in that role and then move out to, okay, maybe it's going to be head of operations. Yeah, I can't make that much sense. And what, I know you have this sort of framework for helping people understand what is the cheaper stuff. You have these five teams. Yeah. I don't know if that's yours or the, the institution of chiefs of staff or whatever, whoever it is. But I mean, what is this, what is exactly it doesn't keep itself to you? Like, how do we understand this? Is someone who hasn't really come across it all anymore? Yeah. Yeah. And you know, there are different versions of it. And I sort of created my own version. But there's, you know, a couple of core things that typically achieve for staff will do. And the five piece would be one priorities. So helping the founder, CEO, the principal to really nail them. What is the focus for the business for the company? What are the things that really matter? So whether your next milestone is a fundraise or you try to get to an IPO or you try to get to an exit. Like, what are those three five things? Maybe that really going to move the needle so that your business, your company is going to succeed. Then the second piece planning. So how are you going to get there? And that's where you bring in OCRs, which I think you and I agree on that it's not just filling the spreadsheet because anyone can do that. But how do you actually translate those priorities into plans that people can agree on? And they can have the right conversations and the right secrets. And so they come to your solid plan that's actually executable. Then you have the third piece which is performance. So you often find chief of staffs managing OCRs or whatever you have KPIs and make sure that the business and the individuals know how we are doing. Like RB behind, like what's the issue, like how the teams are performing. And they really are on top of those metrics and KPIs to make sure that they can keep the company honest and keep the company in track. And then the fourth one would be people. So oftentimes you see projects popping up such as, okay, what's our leveling framework and how do we create a progression plan in the company and how does it tie to performance management and raises and promotions and you have some sort of things that a head of people would typically do and you see sometimes chief of staff partnering with a head of people and then they work on these projects together. And then the fifth thing is which is sort of projects which we call the special projects whatever is on the mind of the principal so it might be I don't know organized and executive retreats or we want to acquire a company I need someone on point to manage that project. So the chief of staff would pick these typically strategic important projects for the company and they make sure that those are delivered and executed to that quality that the principal needs. Yeah okay so you're saying right how does like in some ways some of these things sound like what you said with people in particular you have a cheap people else or a head of HR or whatever but in some of these things like planning and performance sounds like a either a people thing or a individual manager thing or a CEO thing or a principal thing I guess. Why do they need a chief of staff to do this? What's the real need here? What's the thing that makes you think I need someone else to do this instead of me or instead of people people? Yeah so honestly the most true answer is that because this principal needs someone who gets what's in their head they get the quality they get the vision they get the the the spirit of what the principal wants and so they need this trusted person in the mix to ensure that the principal gets what they want at the end and also remember that chief of staff doesn't really have a skin in the game compared to the other department heads because others all have you know teams and their own you know agendas and interests and you know they they you know naturally try to sort of play you know the game so that they get what they want at the end. The chief of staff is almost like you know United Nations across everyone however their loyalty primary relies with the principal so they always going to have the principal's interests at heart and regardless of any internal politics or power games or who is right who is wrong etc so if it's a good strong chief of staff the principal can really benefit from having their person and you know as they say being the eyes and ears into the business. Yeah I mean one of the ways I think I thought about it when I learned about this role is partially just about having the bandwidth you have a high bandwidth with one-on-one with the principal and then because the principal is often busy doing other things that they involve especially the CEO at CEO that they're often involved with with the executive so I read up the board or with investors or with customers or something like that and they have to spend quite a lot of time on that external face and thought of the role but the and you know even if you're internal you'd have quite a lot of internal you know working with stakeholders that has to happen upwards and upwards and across management what you're going to call that and the because they're the chief of staff can have more time available to principal mind meld and then secondly they spend the time sort of explaining that or getting that getting the rest of the team aligned but sort of like a like a secondhand care of hands to do that management more than the upwards and upwards stuff if that is already would that be right is that a sensible understanding. Yeah absolutely and you know if you think about the evolution of a founder who becomes a CEO and even you know within that role they are manager first and then they become a leader you know that there's some evolution there so some you know people who start out you know be like four or five people you know when they find themselves doing everything and knowing everything and they realize after wise not sustainable so you can't be in the same place and operate in the same way when you have already 50 people let alone 100 people 150 so you actually need leverage and you need a scalable leverage and that person is the chief of staff and the really good chief of staffs to recognize what is your strength and make sure you spend most of your time on those things so you don't spend your time on other stuff that could be outsourced or you know someone else could manage it or the chief of staff can manage it and that sort of reality check that the chief of staff can give you around okay do you really need to be in this or you know is this really that important or just being you know pulling up the mirror okay we said these are the priorities why are you spending all your time I'm looking your week like I'm spending time doing all the other stuff like you're not focusing on the things that actually matter so in that sense absolutely right the person is the leverage but in a sort of smart way that's a constant sort of reality check around okay are you doing the things you are best at actually matter for this business there's quite a lot of coaching and all of that there yeah I mean I love you know coaching and I you know I did my sort of coaching certification as well so sometimes I show up as a mentor so okay I have been there done that let me help you let me give you the answer but sometimes I show up as a coach and I really help people have the most important conversations that they need to have with themselves so I'm there sort of a you know coaching and trying to nudge and hold up the mirror but you need someone who is open to it's right and wants to get feedback and wants to get better and grow yeah interesting you mentioned actually now in our previous conversation we spoke a little bit about this about I guess for this kind of two parts of this whole thing but we did this question time your you were the chief of staff to a COO and then later on of soft back and then chief of staff to CEO or of Clarence but in your what's it is there a difference between being chief of staff to different kinds of roles and then is there it does it you we also saw it's a bit about the principle like you know the quality of the principle makes the most difference to your success and how that works you just talk about that a little bit yeah yeah so I think there's a difference between being achieve yourself in a big established company like a Fortune 500 company where you have a lot of the processes you know done you know it's well-edged machine and you know you have strong leaders in the functions there being a chief of staff you know you're probably going to have someone who's a bit more senior a bit more experience because they're going to run a little cross-functional projects you know you compare this to a startup where maybe there's 50 people 40 people under that I don't really see chief of staff so I would say you have a founders associate that's perfectly enough and as you start scaling sort of series A series B bringing a chief of staff because you don't really have well-oiled processes and you know there are no best practices and you know the companies growing out this child sort of phase or teenager phase to want to become an adult and so you need a person to come in and then you know figure out okay how can this streamline things how can we bring efficiency how can we set up certain you know ways of operating and and even thinking like there's a lot of mindset shoot that needs to happen as the company is growing up so a chief of staff can help with that kind of mindset shift if for example let's not task manage micromanage everyone but start managing towards outcomes and you know let's bring in all cars and let's have a motor software and I like what's the key to the business so you kind of do different things and you need different backgrounds and different personality even because some people enjoy the sort of earlier stage growing out of the chaos and some people love the you know the machine and things running and it's efficient and I'm just coming in and like doing interesting projects on top of everything yeah so I guess that really also makes it to be your principal is right to be your you know small start up with people 200 people whatever it's you're gonna be chief of staff to see you know because it doesn't make sense to have more chiefs of staff I guess you know small stuff like I never seen multiple chief of staffs versus you know big companies I know Google and I think almost every VP has a chief of staff so that's a new thing in the last like five years because they just you know realize that you know it helps them make it tremendously to be more effective in their own teams but you know one thing that you mentioned is the the relationship between the principal and the chief of staff and that's actually often underestimated like how important that trusted relationship is and the principal needs to trust the chief of staff they need to support them back them up in a way that they may be not even due with their co-founder or like other execs and sort of vice versa so they really have to be a close you know very strong team you know supporting each other so without that support and trust the chief of staff is this empowered so nobody's gonna take it seriously they just think okay whatever I'm just gonna go to the CEO anyway so you know don't but you know get out of the way so you need to have that really strong you know explicit trust and connection that people can also in the company understand and respect the chief of staff but they are representing this the principal have that strong connection with the principal because that's the value that you then build the relationship and the trust with your with your staff is that right yeah exactly because if the staff doesn't respect the chief of staff they don't believe that the principal trust them and for them, then why would they even listen to the children? staff, they just completely skip them and then go to the principal directly and work with them. And this is a good way of jumping into that whole topic of the mistakes that companies make with Chief of Staff, or the mistakes Chief of Staff make, or mistakes, principal make, Chief of Staff, I mean do you have any examples of these kinds of mistakes that things that go wrong? Yeah I mean first of all, hiring the wrong person, I think that's quite a big one, so if you hire the wrong Chief of Staff, it's just not working, you didn't think about the level you need, you hire the two senior, or maybe a two junior, junior person, and also you yourself as a principal, you haven't really thought through how you want to use your Chief of Staff, or you don't want to have, you know, you don't want to spend time with them, right? Like you just think okay they just go off and do their own thing that's not gonna work, so you need to have a very clear picture on what kind of level I want, what kind of background and experience I want, do I want someone who is gonna amplify me, or do I want someone who will compliment me, for example, and you hire the right person, so if you don't have the right person, it's good to just, you know, I believe fire, you know, fast, and just get the right person in, or maybe just, you know, move them into another role in the company, it's always a better option, because that must be something that they can do, right? It's just that role for some reason, doesn't work out. I think that's, so that's for a principal that could be a mistake hired a wrong person. The other mistake is, I think, not empowering them, so now I'm giving that trust and time and attention, and just hoping that, you know, they will just go and thrive without all that, because that's just not what else. Have you seen the problem like we saw what's a little bit before about, you know, some people treating those sorts of stuff like any decorative system, which is, which is a really valid and useful function for all of it. Okay, having the system is fantastic, but if you're treating it, if you hire a sheep of stuff and then treat them like an assistant, is that a kind of error that happens? And how do you counter that? Yeah, I mean, I have seen that. I think in that case, the question is, you know, do you actually need a sheep of stuff, where you need a rock star EA, because you could get a really good, strong EA, who can do other projects in addition to their, you know, typical EA work. In each case, you don't really need a sheep of stuff, so why pay someone that you don't really need, if your EA can do it, or maybe you need to hire a better EA. It's much better configuration. I think for, you know, chief of staff, it's not very wise to do the EA job, because if, you know, people around them see them as, oh, it's basically an EA job, with a close by title, again, nobody's gonna take that person that's seriously at the chief of staff. And it makes it, general. Does it make sense to that for it? Say it again? Does it make sense for a principle to have first an EA and a sheep of stuff? Like, is that a good solution to that problem? Yeah, I mean, absolutely, but the rules have to be very, you know, different on this too, so understood what the EA does, and then the chief of staff actually does the chief of staff job. So there's a big difference between the two roles, if you play it well. And they can really help each other. So the, you know, chief of staff can rely on the EA, where, you know, they need to. So for anything around the principle, the EA can support a super helpful for the chief of staff, because then they can look on the high impact high value. One of the things we were talking about, we were one of the reasons why, I mean, I was keen to talk to you about this, actually, is that one of, we as a, as a, I hope I have exact teams with the AKRs and frequently enough, the person that I relate to with the chief of staff, that's one of the people who either works with me to help this happen along the next step of the talk and I hope you've been okay hours, and I coached the team on things and it's like that and then they hand over to the, to the chief of staff or the chief of staff is just my main point of contact, that's actually the chief of staff to bring me in. And in some situations, as you said, the chief of staff actually does the AI implementation, and then they don't need someone like me, which is fine. But I mean, like, I'm keen to understand, like, you know, what, what is it that you would do in those situations, like, do, do, do you work? How does it, how should someone external work with the chief of staff in these situations, when you're kind of on that slide over the left? Or, you know, does that make sense in the, to you? Yeah, totally. And, you know, I have done projects where I did have a strong chief of staff in the business I could work with. And that's usually one of my first questions, okay, do you actually have a chief of staff I can work with, or do you have a head of ops, or, okay, do you have a great EA if you don't have any of those? And because it really helps that you as a, you know, consult and bring a very specific skillset and experience into the business. And, you know, chief of staffs are fantastic, you know, generalists and they have a lot of knowledge on the rights, kind of thinking and attitude. But maybe they haven't had those experiences that I consult and can bring in. And so then you just work with them very closely. And whatever the project is, and it actually really helps to have a, have a chief of staff in the business, because the principle is probably not going to be as available, as a legal staff. But I think as a consultant, it definitely makes, you know, life much easier. And there's a chief of staff that that person can work with a consultant. And it's easier for the principle as well, because they don't have to sort of engage with the consultants, you know, that much time. Yeah, so I mean, I've had a couple of experiences where I've worked with the great chief of staff who has been in that massive amplifier to do the effect. And just made things happen without a while, not what, you know, from my point of view, what I do, I really do need to relate this topic directly to the CEO as well. But having the chief of staff to help make it happen has been a good job. Yeah. And you know, sometimes I coach chief of staffs as well, because they might not have had that experience, but they came to learn. So as long as they are sort of open-minded, they don't feel intimidated by, you know, my God, this, you know, person is coming in and you're going to make me stupid for whatever reason. You know, that's that's a really good partnership, because you can actually help them to be whether chief of staffs and you can, you know, help them understand some of the pitfalls and mistakes that, you know, you have done or seen before, so they're not going to make all those mistakes again. So it's new working as a coach for chief of staffs. So right. Yeah. So I work with founders, but sometimes chief of staff will ping me and it's like, okay, I'm new to the job. I've never done this before. Like, can you just help me? But like, you know, Sean's got the answer. You know, I don't want to figure it out. You know, next six months, nine months, etc. Just give me the answer. When should someone come to you instead of hiring a chief of staff? Like, if a founder comes to you, would they come? Would you be like, I know, you know, in this situation, you should hire someone permanently as a chief of staff, or yes, I'll, you know, I'm just encouraging for you for some time and then the outcome of that is that you'll probably hire a chief of staff. Yeah. Is that what you think? Is that how it works? Yeah. So sometimes, you know, I work with founders to do have a chief of staff, which is great, because I can work with them as well. And they can just implement everything that we're working on together. Sometimes they don't have one. And so, you know, they come, I work with them and the outcome is, yes, you need a chief of staff. And I can help you understand what kind of chief of staff you actually need. And maybe I can help you hire one if I have someone good in my network. And sometimes the outcome I have, you know, conversations where the outcome is that you don't actually need a chief of staff at this point, where you are with your business. Probably, you know, nine months, 12 months down the line. I think you will need one. But then there's, you know, enough time to actually think about what kind of chief of staff you need. And you don't hire someone now that maybe you regret 12 months later, because it's going to be a different profile that you would want to have about one time. Yeah, that makes sense. Okay. And we talked also about, okay, I mean, obviously I do, okay, out, that's why my whole business, and I work mostly with founders, first stage startup, so it's a help them founders and executives who are the first stage startup plan work during that. And you've done the same kinds of things. And so, I'd like to talk to you about your experiences, seeing, you know, when that's worked really well, when it's worked really badly, in terms of, like, how that relates to their sort of priorities and planning partners, priorities and planning a kind of like so closely related with account hours, you know, if you have those, the five things you mentioned, what would they do? I don't know, if priorities planning performance people in projects, and I'm quite opinionated about some of these things, especially as they relate to, okay, out and so on. But what's your experiences of like them, you know, when do we, how helpful, when did they work with you in the organization? What did you say, if not working, and how does that relate to your own company? Yeah, I mean, I have implemented, you know, OCRs, you know, back at Google, I was basically running the, you know, well, old machine, once it was sort of set up, and so in the business organization, getting everyone, you know, it was back in the day, I think, 16,000 people across the earth to align on, okay, what are we doing next quarter? But, you know, that's a big company, it's established, you know, you have high quality leaders, you know, what they're doing. So it's quite different, then, okay, there's a team of, I don't know, 45 feet in, they've never done anything like this, and okay, whether you start or what's right, what's wrong for them. And I think what oftentimes people miss is, you know, OCRs is a framework, but it's really just a framework to help, you know, having the right conversations, and if you're not having the right conversations, you know, at the exact moment. executive level, and then with the rest of the company, then it becomes this sort of like spreadsheet feeling tracking exercise. And I have seen, you know, I really feel for them, Chief of Staff's, pulling their hair. When they're doing dashboard after dashboard, cascading, more dashboard, everybody is exhausted. And then they like, we hate OKRs, these don't work. And the founder says, OK, here's the three things I want to do at the time. And so when it becomes this like massive cascading, everything goes to, you know, Monday.com, whatever, or any KPI, you know, tracker, or in general, you know, these are all fantastic tools, but designed for different purposes. And so when I see things getting really lost in, OK, what's the tool? What's the software? You know, it's the point around, OK, can we just sit down for an hour and talk about what is going to move the needle for this business? And that's a really good exercise I always do, with any like exec team, with the founders in the room or, you know, in a virtual room. And you can do this in your next like, you know, team meeting when you have it. So you just basically ask as the founders to me or principal, you just ask your executive team, OK? Get a piece of paper, you know, we are all on Zoom, whatever, nobody's cheating, everybody's looking at their piece of paper, you know, just write down the three things that actually matter for this business between now and, you know, next milestone and you insert whatever that is, whether it's fundraising or an exit or an IPO, whatever it is. And you just get everyone to write down the top three things. And then you're going to show it like at the same time. And you will see me like how different people think about what actually matters. Now, if you can agree with your closest circle of execs on what are the things that really matter for this business, there's no way you can implement any OCR, any system. Because the fundamental thing is OK. Can we agree on what matters for this business? Do we understand why those things matter for this business? Yeah. How realistic we think those things are between, you know, now and whatever the milestone is? Because once you have those conversations and agreements, then OK, bringing the OCRs and let's put it into a spreadsheet or whatever you want to put it in. I do, I mean, that's just interesting. So quite a lot of people I talk about are ours, are on that mindset of let's have the perfect and brightening things down system. And let's cascade everything and link them together. And then let's put it into a dashboard so we've got moving blinds and graphs and things like that. And especially when you become from the software side window, I think there are software that really work well. There are software platforms that really work well. And there tends to be focused on the conversation. How do we grab a conversation? As opposed to the data and the dashboard thing. A piece of software that's focused on the data and putting in there, especially technically minded people, which most people in startups, even if they're not, even if they're not software developers, people in startups tend to have a technical mind or tend to be having interest in this kind of technology. We tend to get obsessed with this stuff, where we've instrument things and we have dashboards and we get excited about them. But what's really going on here is that conversation. And that exercise you mentioned about, like, let's everyone write down what the most important thing is. And if the exact thing can't aground that, I just want to say it again, but it's the exact thing can't aground that. How fair are 50 or 100 or 1,000 other people going to grow up this? And how do I know if there's that kind of play out in your actual daily life that can work? I mean, everyone, what happens in that situation is if it's ambiguous at all, then everyone else is going to make their own decisions or also not make decisions, nothing will happen. Or else they'll make their own decisions. And then you've got across this organization, 15 different strategies and executing effects. And then of course, it's not going to work. And this is where I think that that whole, make sure you have the conversation. Are you actually having the conversation to make decisions? Are you aligning on fixes really important? And one thing I think, I was more you mentioned about having read and made the video, talk about people having disagreements. Like, it's not, I don't think it's necessary. I think it's only key if you're a forceful person. I mean, I think it's necessary that everyone agrees, right? I do think it's necessary that we agree on what we agree, right? So if what I mean by what I mean by this is that, if we do ask that question of what's important, and we have some different views, that can be really good, that can be really helpful. Then we have a discussion about it. And we figure out what we decide to do. And maybe one or two people or a few people still different, they still have a good opinion. But then Amazon have this principle disagreeing from it. Like, you come to a point where you have to say, okay, I disagree with this. However, the team, the CEO, the founder, the principal, whoever it is, we're going in this direction, we've decided as a group. I still disagree with this decision. But I'm going to commit to executing it as well as we can, and I'm going to commit to helping the rest of the organization to execute it as well. And I guess if someone officially at the executive level doesn't agree and commit, doesn't agree to commit, then the best thing is to get off the bus. I don't know where you're thinking about that. We all brought some that up, but it's just kind of like, there's no point in trying to, especially in the exact thing to is trying to go in a different direction. Yeah, then they can go off and start it on company, right? If they want to sort of do things their own way. But if you only have five functions of a team, I think it's a famous book by Patrick Lancioni, probably pronounce his name well. I think when I wrote it YouTube, I think at some point, it was like a must read. We all got it because it's like, OK, five levels. And I think what you mentioned, I think, levels three or four, where, OK, we are one team. So even if we disagree sometimes, we commit. And then we go out and make that happen, right? So it's an interesting one. Again, fundamental is that level is trust, and then you have all these other layers to it. Yeah. And that's that whole thing is that that's very different to it's my way or the highway, right? Because it's quite a, to me, these consequences are quite different. The my way or the highway is like, I've decided we're doing this. It doesn't matter what you think. That the disagreeing commit concept is what we do. We have a discussion. We have a conversation, as we talked about. A conversation about what to do. We discussed things. We take the input. We find the disagreement. We discuss through the agreement. We explore it. And then at some point in time, we start to make a decision. It's quite different to that sort of the authority and our, you know, just not a word to this, but I'm trying to get where it is. But that authority and this is what we're doing. Let me think it's very different to disagree immediately. Do you have that conversation? Yeah. I think you had a good post about this idea of being a serene leader, which I think again gets quite misunderstood. Because sometimes I find, you know, some found there was thing that, oh, I need to have more democracy. And I want to make sure everybody feels included. And everybody, you know, is heard, which is all beautiful and nice. But sometimes the wrong decisions are made because it's made as a democracy. And, you know, as a leader, you want to make sure everybody feels included and being part of the conversation. But ultimately, you need to make the decisions that drive to the results that you need to get to. So sometimes you need to have that sort of, you know, disagree-but-commit situation. And especially inexperienced founders, leaders, who maybe never let it in before. There's a lot of these, you know, popular ideas coming up, the serene leaders, et cetera, that, OK, beautiful ideas. But you have to get the result. You have to get to the next fundraise. You have to get to the next milestone. So how can you sort of balance those things? And, you know, good chief of staff can also observe these things. And they, you know, good chief of staff seem to have a very high EQ and be able to get the dynamics, the subtleties, the unsaid things. And we can help a founder in that journey to be more sort of self-aware and become a better person than the leader as well. And that's, you know, that's a positive leadership thing when I posted that. I got what I expected, which was some sort of controversy from some people who have a different opinion. But I mean, from my point of view, seven leadership is super important. I mean, it's a fantastic way of getting done. But it has to come secondary to results. And that whole concept of like, you've got to figure out, you know, someone's supposed to become it, it was now results, results first team always, right? And I kind of agree with this. It's one of those things where you're a risk of dying a little bit. Say that, but I mean, results first is really, we're trying to get the results. And the best way of getting the results is often to serve the team. And make sure the team is, you know, being looked after and people aren't feeling looked after or served, then they tend to engage very well in delivering the results. But if you just serve the team, you get nothing. And that's, that's, that's actually not even served the team in them. But yeah, it was, it's also sort of, this whole sort of concept is a self-honored station in Europe, I find. But it's because one of the things that I've noticed is different with, I don't know, I don't know whether you've worked a great deal with European and country companies as opposed to US and England. But I mean, certainly my experience at US and England countries is that not necessarily hierarchical, but they're more comfortable than at least the German, Germanic companies that I've worked with tend to have a very consensus and an audit in the Scandinavian countries. tend to have a very consensus-driven approach where we all have to agree before we go forward and until we agree we can do it. And that's sort of a natural thing that happens in some companies in a consensus thing. It can be, not just democratic, like some say, sometimes you have democratic roots, like, well, I'm not making a decision until we've done a majority, but this is very much like, until we have the sort of consensus. Yeah, and it's quite different. And you know, do you have a experience working with companies that have a different kind of culture where how do you balance the consensus culture [BLANK_AUDIO] I mean, very hangar, you know, a couple of years with, you know, it is so bank as Japanese company culture. And you go to Japan, you see very different ways of being and working, while still being, you know, in Silicon Valley, which is where I work with people in the valley who are used to that sort of Google culture. So you go from one that's very, let's challenge each other, let's just, you know, have a great debate, let's just question everything, let's just not accept. You know, how things been done today, to date, to another culture where you're really not supposed to challenge your superior. So you are disrespectful, if you do that, and there's a reason why, you know, things have been done in a certain way, and there is appreciation for that sort of tradition and that way of thinking. So I think I have seen sort of pretty much both extremes, like all has, you know, pros and cons, of course. But one of the advantages of a team of staff, I think, if this is, this also happens as a coach and gets over the next to our person, is you can go and ask that coach and get that disagreement from somewhere where the things, in that kind of culture, the CEO can't always get that. Yeah, it's always, you know, that's why, you know, oftentimes I feel like company is bringing the expensive consulting firms as well, because it's easier to, you know, point at them that, okay, they ask the question, they suggest to do something that someone internally challenging or disagreeing with, even maybe with a CEO or the other execs, right? Yeah, yeah. I would say, I'm not that expert, I don't think it depends on what you've done. Hey, we've had a comment from someone, this is not a question, it's a comment. Someone said, Jason says, "I need to move into other things in a day, but very much hope you made the recording available." Yes, it will be available. It will be available on LinkedIn and on YouTube. We've also probably used to cut out of this to sort of post it various times, but you'll be able to find that. Great topic and great discussion so far. So thanks, Jason, for the comment I've looked at, it's always interesting to see what people are doing and why they're interested in following this. Funny enough, on this system, I don't know, you're going off, I don't know, and you can see this door, but on my screen, I can see the number of viewers, but weirdly enough, the number of viewers in this application says zero. Every time I do this, I go somewhere else, I go afterwards and it says 23 or so, not that. So it's kind of weird. I know there are people there. If you're here and you'd like to make a comment, you'd like to ask a question, you can ask a question to me or to Dora. Just post a question on LinkedIn or YouTube and that way, if we can get to that, but although it is coming up to the end of the conversation, feel free to stick something there. And anyway, we will go back over it later on, and if there's anything that you've asked and sure will be able to find a way to send that message back and somehow I'll see the question, whatever it is. But anyway, just sort of we've sort of talked a lot about this whole but pro planning that. Yeah. And how's sheet of staff works with also stuff and how okay, how's work and all that sort of stuff. Do you have experiences of like, okay, how are the presentations that we're badly, that you're talking about, they will be we're sharing, I mean, I did it, but I mean, I'm good to do that. Yeah. I have seen, you know, when I see these monster spreadsheets and dashboards and, you know, sitting in meetings with the principal where they look quite surprised, like why, why are we even talking about these priorities? I have completed different priorities and see people have been working on those for weeks and there's a complete disconnect between what the principal is thinking in their heads and whereas that's what the truth is too. And actually, you know, one thing I see is very slippery slope, you know, founder CEO thinking, you know, my vision is so clear. It's so straightforward, it's so obvious, like everybody should know that and understand that and maybe they can even point to you in a case and maybe once a quarter or, you know, maybe once a year, they share that and there's a genuine belief that it's clear to everyone and I can compare this to like, you know, when you have kids, like you assume they know that you love them, but you don't just tell them you love them once a quarter, right? You sort of repeat and repeat and repeat and so when I see sort of CEO's founders not really having those conversations and internal homes and just, you know, talking about their vision and the strategy and how those are linked and therefore what does execution need to look like. When those conversations are unhappening, you know, OKRs, it's just a painful, completely kind of useless process because then it's just like KPIs and spreadsheets and dashboard. So those side recommendations, you know, if not clear on what is your priorities, what's your strategy and why and you don't have those regular conversations with your team, then all the other stuff becomes kind of irrelevant because it's so, you know, separate from what's actually in your heads, in fact, CEO. My experience is like, in terms of like how to solve that problem and how to make sure that doesn't happen. One of the things that I found is that OKRs are kind of like the, you know, that you have to have a strategy and a vision first and that the end of the game has come out of that the way. Like I wrote this book called, I agree strategy, bad strategy. I really like the way it approach, which is strategy is a diagnosis, what the current situation is. So we all agree on what current problems are, what the current driver, a guy in policy of what we're trying to do and we communicate what that is. And in fact, guiding policy happens to be a 45 page PowerPoint and it's probably not clear enough. It's probably not clear enough policy is to make it sort of like crisp and sort of like focused as a policy. But then the outcome of that is that you then have a series of coordinated actions like this straight here and sort of framework of actions that you're going to carry out. It's implement that. That's all part of the strategy. Once you have that clear, then writing your accounts is actually not going to be hard because what you're doing is you're figuring out what are the most important things to do first or what are the things that needs to do now to get this done. And what I do find is that when you have our team, the exact team that is struggling to write their own accounts, it's often because they don't really align or know what their strategy is. And not always. But I mean, often that's the case. We just don't know what the strategy is. And the other situation that could happen sometimes, especially when you take the OKR system to literally do it too much bottom up, is you get all of this input and a people set objectives in all of the company, but it doesn't create a strategy, it gets together in any sense or way, and it doesn't match with what it is in the CEO or the executive. Yeah. It's a very good one, because I see that happening where, again, it's a very natural way how people think. So you see functional leads who really focus on, OK, what is my team delivering? And they really focus on it and show it, and it's like, oh, we are so busy. And that's why I need to hire 10 more people and it's all the things we're doing. So people go into this mindset of my team versus what is the cross functional, what is the cross company, you know, focus. And so that's where you, as a principle, can balance that kind of thinking out with, OK, let's actually think as a team. I know you are all busy and doing amazing things and your, you know, your teams are delivering and working very hard, but, you know, let's just put your team aside and your functional side. And let's think together, like for these companies, like our baby, like what are the most important things? Because they are truly the good OKRs, OKRs that become sort of, OK, what is the marketing person delivering? And then what is the legal team delivering? And what is the sales team delivering, you know, kind of is jointing? That's not the essence of tuning cross functional, OKRs. Exactly. So you get the whole company in the local hours that sort of cover, you know, the whole range of what we're trying to do as a company. And then that gets interpreted into the team, so why can't we talk about plan? What I use to recommend people to do is write down their plan wherever they can and some people agree to write their plans and some people less creative it. It's OK. So I mean, you know, you write down the plan in whatever mechanism it is, whether it's a dad chart or a one-pager or a series of user stories or whatever makes sense to you. And you write that down. But then you bring that back to the exact team and sort of say, well, this is the marketing plan. And people want to look at it, try and get everyone to understand what the marketing plan is. And how does that relate to the objectives that we set as a team for the company? Right. And what I want to do is I want to see the CTO understanding the marketing plan and ask you the dumb questions, but you know, questions about marketing, so I understand that some of those questions are going to be questions that like, you know, well, that CTO is not a marketer. So they don't have the staff. So it's marketing. And that's OK. At least you're educating about this. But then the act of doing this then means that now it's together as we sort of collaborating on a series of plans across the business that it can result in these OKRs. And now everyone has some sense of relationship with this. And what I want to see is likely to be, you know, the marketer looking at the product plan, and the finance person looking at the operational plan, and whatever else it is, like all these cross-functional conversations happen, focus is this plan going to help us achieve that company and get rid of these plans working together. And by having these different possibilities, you get a brain's trust in that team that's sort of cross-functional brain's trust that is able to sort of get those results. Yeah. And I mean, you know, the same thing you were like a principal could be to dive too much into those conversations and try to hand hold and spin speed. But the reality is, you know, if your key execs aren't able to have those conversations together, they aren't able to think it through together, like, you know, challenge each other, come to some answer, you know, plus maybe one or two questions to then discuss with the principal. If you really have to dive in and you have to micromanage, or you have to send your chief of staff to almost work it out for them, you know, I would question sort of whether you have the right people. at that executive level or maybe you need other people to come in and maybe more experience for more knowledge because you shouldn't need to sort of go diving too much and be part of those conversations. You want to be there at the end and they all come and then they all have had those conversations and pressure test more things and you know you're going to change a few things and maybe they have sort of stuff you haven't thought about which is the best thing then you know they are actually thinking right and if you have to really dive in or your chief of staff is basically designing the marketing plan for the next year and probably something is off there. One of the common themes that I have with my companies that I work with is that isn't this level of conversation that's happening if I'm using it. It's not just one person that's like all teams it's like they're a little bit too siloed they're a little bit too isolated maybe they feel insecure about their knowledge of cross-functional areas or whatever or maybe they just haven't been involved together. One of the things that I find is that through the UK programme that I usually work with the volume. We spend a little bit of time at OKRs and quite a lot of time on team data apps and how this works and it ends up being an excuse for coaching of getting these getting people to raise the level of their work. You know people talk about a lot of these sort of leadership and career books or management books talk about people at that level whatever whatever you are you need to be thinking the level above. And so if you're at that sea level in your functional leader your most of your mind thinking kind of needs to be at the sea level to be cross-functional. You're understanding you're written that that does not not happen especially as companies are growing up and people come from a smaller background they come from their function and they're they're solving their function. So you have to do some work to elevate their thinking to the company level and it has a great talk of doing that and for causing these conversations and even for prompting the conversation where the CTO investigates and understand the marketing plan and it faces up to some of those gaps in the knowledge about marketing. And then they start to do it and I found that to be a reading school that we really use the tools for making that happen. Yeah absolutely. And you know people are always meaning well and the first part and try hard but if they've never been exposed to that type of thinking or the way of talking the way of having those conversations it's very hard to sort of figure it out on their own. So like you coming in or like myself coming in or you know you bring in an exact from another company and then starts you know implementing those kind of rituals almost you know CTOs could be a great you know allowing that one then it helps because then people can get into that cage and get into that tree done. And so you know it's almost like the rituals around okay how we talk how we actually focus on the important things how we challenge each other. So as you know as companies grow and you know as a chief of staff you know comes in start sort of implementing OCRs you know a good one actually also starting this change management which is the mindset shape the okay how we work together how we operate like how we sort of grow up as a company. So and there's a lot of that sort of mindset and behavior shift that actually happens between sort of early stage two all the way through you know later stage IP or CTOs. Yeah. Hey Dora it's coming up to you to time we talked for almost an hour which has been wonderful I really enjoyed it I really enjoyed talking to you before we go if someone wanted to get in contact with you under what circumstances would that be a good idea and that will help us through these issues so like what is what what when I guess what are you doing? I feel like when I can talk about these things for a very very long time so we can do a part two at some point but yeah best thing to reach me on LinkedIn I think that's where anyone can find me and I'm mainly coaching founders some C suite sort of chief of staff in the sort of series B series C space. Last year I got a bit more involved with one startup but I'm transitioning out so now I'm just working with a handful of interesting companies which is what I read off so interesting ambitious individuals sort of creating something remarkable I think that's what really energizes me so yeah ping me on LinkedIn if you have any questions what if I can help you in any way. So there are a few people who are chief of staff so we've got the principles we might need a chief of staff but to have one or people who have one who needs some help from extra or person who's got experiences and contact you. Is that correct? Yeah exactly also I have a network of chief of staff so if you're looking to hire one you know I'm happy to sort of forward and you like jobs back or helping with the jobs like I said I have some good networks of chief of staff as well. And if someone wanted to be a chief of staff but isn't with you with the help of people who want to be chief of staff. Yeah I mean I find you know there are some really interesting really high potential individuals that I occasionally sort of coach and help them to get the right role and chief of staffs more you know like occasional coaching so my primary coach is our family or CEOs and senior executives. I don't I don't even coach sort of junior first-time managers I'd recommend a few people for anyone. Yeah it's interesting I to be honest I'm a bit the same in terms of like I'm looking with people who are first-time managers I think there's a huge amount of them but for them and I'd love to help them at the same time it just doesn't to be honest it's not a great business because it's really hard to make a business out of coaching junior people so I find that I have much more impact and I actually work as a business of a coach and I'm seeing people in the exact same way. Thanks for thanks for your time I miss what did I want to say I wanted to say oh I'd say thank you very much and if you've been watching this if you're watching this on their replay or if you were watching it now and you've got a question that wasn't answered just stick the comment in the question in the question in the comment wherever it is linked in YouTube whatever you're watching we I'm sure we'll be able to find a way of getting back to you on it but I'm a tuned in next week I'm going to have another interesting interview next week I'll get to the other set of Wednesday but I've got someone like that for you anyway thanks very much Dora hang on the line for me with me I'll end the broadcast now but hang on the line and we'll come to chat afterwards but thanks for watching everybody have a have a have a great weekend

Podcast Summary

Key Points:

  1. A chief of staff is a trusted executive partner who helps founders and CEOs focus by managing priorities, planning, performance, people, and strategic projects.
  2. The role ranges from a high-level strategic advisor to a junior executive assistant, depending on the company’s stage and needs.
  3. A chief of staff acts as a “right-hand person” with deep access to the founder’s vision, ensuring alignment across teams and preventing internal misalignment.
  4. The chief of staff provides critical leverage by reducing a founder’s workload, enabling deeper focus on core strategic decisions and avoiding time spent on non-essential tasks.
  5. Success hinges on a strong, trusting relationship between the founder and chief of staff, with the latter acting as a neutral, objective, and loyal voice across the organization.
  6. Common mistakes include hiring the wrong level of candidate, underempowering the chief of staff, or treating the role like a standard executive assistant.
  7. The role is especially vital in growing startups to establish systems, shift from task management to outcome-based leadership, and foster cross-functional alignment.
  8. Founders must have clear conversations about priorities and strategy—without which OKRs and dashboards become irrelevant and counterproductive.

Summary:

A chief of staff is a critical role for scale-up companies, serving as a trusted partner to founders and CEOs. Originating from military and political traditions, the role has evolved into a multifaceted position that supports strategic alignment, operational efficiency, and executive focus. The level of the chief of staff—ranging from a junior executive assistant to a near-COO-level strategist—depends on the company’s stage and needs.

At its core, the role ensures that the founder’s vision is clear, actionable, and consistently aligned across teams. Key responsibilities include setting priorities, creating executable plans, monitoring performance, managing people, and leading special projects. A successful chief of staff acts as a unifying force, helping to bridge functional silos and foster cross-team dialogue.

However, the role is only effective when built on a foundation of trust and clear expectations. Common pitfalls include hiring at the wrong level, underestimating the role’s strategic value, or treating it like a general assistant. Founders must actively engage in strategy conversations to define what truly matters, as without shared clarity, OKRs and dashboards become disconnected from real business goals.

Ultimately, a strong chief of staff enables founders to scale efficiently by focusing on what drives results—while the rest of the organization operates with clarity, accountability, and alignment.

FAQs

A chief of staff is a trusted advisor who helps a founder or CEO focus on priorities, manage operations, and stay aligned with strategy. Unlike a COO, who typically manages a team and has direct reports, a chief of staff is an individual contributor who supports the leader by managing priorities, planning, performance, people, and special projects without a formal team.

Startups should hire a chief of staff when they grow beyond a small team—typically at Series A or B stage—so they can scale effectively. Early-stage founders may need only a strong executive assistant, but as the company grows, a chief of staff helps streamline processes, manage complexity, and ensure alignment across teams.

A chief of staff typically manages: 1) priorities (defining what matters most), 2) planning (translating goals into actionable plans), 3) performance (tracking KPIs and team results), 4) people (developing talent and progression plans), and 5) special projects (overseeing high-impact strategic initiatives).

Trust is essential because the chief of staff acts as the CEO’s eyes and ears, ensuring alignment and offering honest feedback. Without trust, team members may bypass the chief of staff and go directly to the CEO, undermining their value and effectiveness in decision-making and execution.

A common mistake is hiring someone at the wrong level—either too junior or too senior—without clearly defining the role’s scope. Founders also often fail to give the chief of staff the time and autonomy needed to build trust and deliver value, treating them like an assistant rather than a strategic partner.

OKRs can become misused when they are implemented without first aligning on clear priorities. Over-reliance on dashboards and spreadsheets without meaningful conversations leads to disconnection between leadership vision and team execution, resulting in confusion and inefficiency.

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