Introduction
Ceci [00:00]
Hello and welcome to Top of the Ops, the podcast where we have real conversations about what happens behind the scenes of startups. I'm Cecilia, ex-VC at Talis Capital and now FD at PortalOne.
Bea [00:10]
And I'm Bea, ex-VC at Lakestar, now Chief of Staff at Praktika.
Ceci [00:14]
Today we're going to talk about all the ways this role goes wrong. Some of it is the CEO, some of it is the company, some of it is bad timing. And let's admit, some of it is the Chief of Staff's own fault. So let's be honest about it. We have eight failure modes, real ones, ready for you.
1. You Can't Let Go of Execution
Ceci [00:31]
Number one. How does a Chief of Staff role fail?
Bea [00:34]
This one hits home for me, it was a hard topic. You cannot let go of execution. You prioritise small tasks, and you get so deep into the doing that you forget to step back and look at the big picture and the strategic side. At the beginning it's genuinely hard, because you're doing both strategy and execution, you're a one-person team, you have to do everything. You can try to segment the week, execution mode some days and strategy on others, but it is so, so hard.
Ceci [01:15]
I think it's inherent to the personalities who go for a Chief of Staff role. You want to feel busy, work hard, and fix things. Sometimes the thing you're fixing is strategic, the product, the financial model for the next raise. Sometimes it's just low-hanging fruit. Speaking from experience, I see something wrong and I want to do something about it. And sometimes, as you said, it's really helpful to take a step back and see where you stand.
Bea [01:47]
How do you understand whether you're the person who has to fix it, or whether you should let somebody else fix it?
Ceci [01:54]
I don't have the golden nugget, but the way I look at it is this: as a Chief of Staff you have high context on how the organisation works. So you should more or less know not just who should be doing what at any given time, but how the organisation needs to evolve to handle new tasks as they arise. Sometimes you just look at a task: can I do it? Yes. Does anyone else need to do it? No. It needs to get done, so go and do it. But sometimes you need to think strategically about whether you're the best person, and whether something in the organisation needs to change so that going forward there's a right person for it. My example was our booking tracking. At the start we had no system, so I came in, saw the gap, built it, figured out how to track it, reported month after month. It got to the point where the system worked and everything reconciled. Then I had to look at it and say, I don't think I'm the best person to maintain this. It should move under another function, because it's maintenance now rather than building.
Bea [03:18]
You're right. I actually think having a coaching mentality in the company is good, because, as you said, you have the most context and someone in a narrow function doesn't. I always found it useful to jump on a call with an IC or a manager in a function and make them understand the full context. At that point they usually reach the same conclusion themselves, fix it, and allocate time for it. If you'd forced your way in, they'd probably have reacted defensively, or not done it at all.
Ceci [03:53]
A pushback on that. Don't people hire a Chief of Staff just to get shit done?
Bea [03:59]
Some of it. But take an example. I can help in marketing, I understand it, I can prove an MVP in marketing, but I'm probably not the person who scales it. So the Chief of Staff can do an MVP of certain things, then hire someone or let another function take it. That's how we did our B2B segment. I opened the B2B landing page, proved we could convert inbound, and then we'll hire a person to run it, because I'm not a salesperson.
Ceci [04:32]
Going back to "can't let go of execution", how do you reclaim your strategy time when you realise it's been drifting too far into execution?
Bea [04:46]
You need to audit yourself and your work. Figure out why you drifted so far into execution, then treat fixing your own work as another process to be fixed, with the same lens. Most Chiefs of Staff don't have many direct reports, so it's hard from a hierarchical point of view to just go and allocate work to people X, Y and Z, because they have other managers. But you have to see yourself as the glue that can do that, because you can see how the company could perform at its best. So it's a combination of auditing your own work and thinking strategically about how the company performs better overall, and then you reclaim your strategic time. Does that make sense?
Ceci [05:31]
Yes. To wrap it up: of course the Chief of Staff is hired to get things done. But at the same time you have to reclaim your strategic, critical mindset, because otherwise you won't be able to advise the CEO on different problems.
2. You Become a Glorified Executive Assistant
Ceci [05:46]
There's a sub-sector of "you can't let go of execution", which is you become a glorified executive assistant. Do you have anything to say about this pitfall?
Bea [05:59]
I've actually been called an EA by someone on my team before, we were having an argument about something. But I've definitely done tasks that would be in an EA job description. One, we didn't have an EA. Two, I've done my CEO's external calendar since I started. I've organised games for our retreats, fun presentations, Christmas parties for our London offices, those kinds of tasks. I was very aware of why I was doing it, but you have to take the company's perspective first, rather than your own ego, and we weren't in a position to hire someone for it. A lot of those tasks take me five minutes and four brain cells. It's one thing to lose strategic time to low-level execution that takes a lot of time. It's another to do those filler, five-minutes-here, five-minutes-there tasks. I was always very clear with my CEO about it. He knew it wasn't my core and that I was just doing it because someone needed to. But it does take a toll on how you're perceived internally and externally. It's weird from a perception point of view: you're the same person who's in a board meeting preparing the board deck, and also the person arranging a meeting from the CEO's email. It's a broad spectrum that a lot of people struggle to wrap their heads around. How about you?
Ceci [07:38]
We did an episode with Gaby, go and listen if you want to learn more. She says Chiefs of Staff tend to be women because they tend to have low ego, and this is the peak of low ego. You're qualified to articulate a board meeting, but so low-ego that you'll also arrange the CEO's calendar. Not many people can do it. I think I'd struggle. It really requires low ego. We both come from VC, where someone used to schedule my meetings, and now I'm the one scheduling the meeting. The irony wasn't lost on me. But the need of the company should always come above your ego. You just have to be clear, especially with your principal, that this isn't where you want to go, and keep a list of tasks you're ready to delegate the moment you can hire. In this day and age Calendly exists, and the traditional EA role is shrinking in its original scope.
3. You Fail to Build Credibility With the Broader Team
Ceci [08:56]
We talked about how you can fail because of the tasks you choose to do, and I mentioned perception. Something that's less talked about but just as important is your relationship with the broader team, and failure that comes from a lack of credibility within it. What do you think? Has that ever happened to you?
Bea [09:21]
It did, a couple of times. The role is hard because you have to influence without necessarily having direct reports. One thing that helped a lot: as soon as I joined, I did individual one-on-ones with the main people on the team. And as people joined, I was the one onboarding them, so I always interacted with them, built trust and rapport, especially as we're remote. But it did happen that I helped on a couple of product projects when the team was nimble and needed help. I remember scoping a Christmas project with the development team, and these guys were so confused, like, who is this woman, she's never done product in her life and she's telling us what to do. We collaborated well, but I could tell they were confused because they had no context on what my authority was, and they still didn't really understand what a Chief of Staff did. It was challenging, but it only lasted a couple of weeks. Did it ever happen to you?
Ceci [10:36]
At the beginning especially, I was the one putting myself out of certain lanes, out of my own lack of self-esteem, imposter syndrome really. I knew which areas I could be helpful in and which I shouldn't touch, but I restricted myself a lot. As I gained confidence that changed. I agree it's all about the one-on-one relationships you build, but it's also about how you contribute. I'm not an expert in how a marketing campaign should work, I'm not the biggest expert on closing a B2B deal with company XYZ, but there are things I can contribute. So knowing how to challenge people, where you can add value, and making them understand your role, is really important. I was always the kind of person who would either figure things out and help solve their problems, or challenge them because the CEO was busy. So I was either the fixer or the annoying person. Knowing where you stand with all of them is super valuable.
Bea [11:53]
Did anybody ever tell you, quite bluntly, to stay in your lane?
Ceci [11:59]
Maybe once, and I didn't agree with it, it was a lane I could have walked in. But mostly I told myself to stay in a lane. How about you, were you ever told to stay in your lane?
Bea [12:14]
No, I don't think so. I could sometimes feel the scepticism from the other side, but that's partly on the executive team to present the Chief of Staff properly: look, the Chief of Staff is a tactical task force, listen to what they say.
Ceci [12:29]
On that, how much of the responsibility lies on you as Chief of Staff, the CEO, or the broader executive team?
Bea [12:38]
The CEO has maybe half, and half is on you. The way you project your confidence and who you are at the company has an impact. So it's a mixture of both. It's largely in your power, and the CEO makes it better if they reinforce it.
Ceci [13:02]
Yes, the CEO reinforces it, but you don't want to walk around the team saying "the CEO told me to do this, just do what I say." I think that should be 50-50.
4. You Become a Yes-Person
Ceci [13:09]
Right, we've covered the first three. What's the fourth in your opinion?
Bea [13:13]
You just become a yes-man, or yes-woman, and never challenge or push back on the CEO. This one hits home too, because I'm probably not the most confrontational person. So I have to make an effort and look at my subconscious and understand whether I'm saying yes because I want to be a people-pleaser, or because I actually think yes. It takes a moment to pause and reflect.
Ceci [13:46]
This is one of the hardest things, but I was surprised how naturally I walked into it. I'm really not confrontational, I don't have arguments with anybody, I just run away. But in the first sync I had with my CEO, the first 30 minutes on the job, we jumped on a Zoom call and I told him: this is a safe space. We tell each other the truth, we tell each other everything, we argue, we say things that would cause problems if anybody else heard us, completely safe, go at it. And when the Zoom is over, everything goes away. We really took that to heart. I had some of the most heated debates with my CEO, because I'd always say, I'm playing devil's advocate, I'm going to be the annoying one, this isn't working because of this, that isn't working because of that. Because we had a trusted relationship, he knew I wasn't angry at him, it was the role I was playing. And we're still really good friends. You have access no one else has, and it's your responsibility to use that access to push the CEO to be better.
Bea [14:56]
If anybody listening is a Chief of Staff and their CEO doesn't want to be challenged, I'd say look around, because that is not a healthy dynamic. Everybody should be low-ego enough to be challenged on their thinking and to check whether they're going down the right path. And they should be open to debate. Some people just get defensive and spend the next ten minutes defending their opinion, when the point is just to reflect.
Ceci [15:27]
Does it ever happen that it feels like you're having a healthy debate with the leadership team or your CEO, and it just doesn't lead anywhere? If so, what should someone do?
Bea [15:39]
Be the annoying one. As you said, if something isn't discussed properly, go back to it and rediscuss it. There are topics I go back to over and over again. In my experience, even if I hit defensiveness at first, after a night's sleep everybody thinks about it and comes back saying, okay, now let's talk about it. So give it time. For founders there's a lot at stake, and they might feel defensive, but the important thing is that they think about it and stay open to changing their mind. Whether that's at the beginning, after a night's sleep, or after the third time you raise it. If the other person doesn't counter your argument, I'd keep bringing it back. And if someone is just not open to being challenged, find another company.
Ceci [16:40]
One sub-problem of this: we're loyal. But when does loyalty become a liability? Was there ever a point where you cared so much about the company that it stopped you seeing the obvious?
Bea [16:53]
I've thought a lot about loyalty as a liability. Caring too much can make you worse at the job, but I think there's a different dilemma here: who should your loyalty be tied to? Should you be loyal to the CEO or to the company? And what happens when those two start to diverge? Are you loyal to the person or to the mission? It's really difficult. From an ethics point of view, your role is to be loyal to the company, and then push the CEO to realign to the company if there's a misalignment. That's where I landed. Have you thought about it, where do you stand?
Ceci [17:42]
At the end of the day you're working for a company, towards a mission. If the CEO isn't aligned with that mission and isn't the right person to lead the company from that point forward, then, and we're not talking about specific examples, being in VC we've seen it over and over, sometimes a founder is great from pre-seed to Series C, and when the company gets larger they'd rather be at the zero-to-one stage. In that case I'd be loyal to the company, because the best thing for it is a different type of leadership. That should also be clear to the CEO. If the founder is conscious that they have no interest in leading a thousand-person organisation, they should leave space for someone else. Ultimately our role is to increase shareholder value. People have ownership in the company, not in the leadership of the company, and it's normal that this changes over time. There are rare examples where founders mature into leaders of larger organisations, but more often than not, I mean, more often than not startups fail. There are also cases where the startup grows and they simply change the leadership.
5. Right Chief of Staff, Wrong Time
Bea [18:55]
Something that's actually pretty common, and we talked a lot about it with Gaby, is that a great Chief of Staff is hired but the timing is wrong. Way too early, or way too late when the company doesn't need it. Do you think the role is needed at pre-seed or seed, or is that already a yellow flag for its success?
Ceci [19:27]
Maybe a controversial opinion, I don't know. I don't think a Chief of Staff is needed at pre-seed and seed. At that stage you're probably still paying some invoices manually, you might not have good infrastructure for scale, you're trying to prove your MVP. Honestly, I don't think you need one. Even a founder's associate, what are they going to do, be a glorified EA? I don't think that's really a need. The flip side is you could build very good ownership from early on at a seed valuation, which is great. For the scope I wanted, Series B would have been a little too late, because by then you probably have a director of finance, an HR and talent person, some processes already, so the impact and scope get reduced. The sweet spot is Series A: you have some revenue, you're starting to scale, and you're working out the processes for scaling. It can make sense at Series B too, but you have to accept the scope will be smaller. Controversial, because you joined Seqera at Series B, so let's have a healthy debate.
Bea [20:47]
I joined before Series B, but I've always said my preference would have been to join a year and a half earlier, so I could be part of how the systems are set up. What happens sometimes after Series A is companies just hire a lot of people without thinking about efficient systems, and then you reach Series B with things not going well, and all you can do is go back and unpack a couple of years of work, which isn't pleasant. I've always wanted to be there as soon as the Series A money hits the bank, so you can actually shape how the company scales. That's the sweetest spot. But it depends on the company and how it's scaling. It can reach Series B really fast on sheer product and sales, with the maturity of a late-seed company, and that's a great spot too, you're joining a rocket ship with the resources to sort out the operational side. You just have to think about whether the scope of the role gets compromised, and how you grow into it.
Ceci [22:00]
Do you think companies sometimes need to hire on the leadership side and end up hiring Chiefs of Staff instead?
Bea [22:07]
Actually no. I wouldn't hire a C-level executive too early, because you need the execution part more than the high-level strategy. If you hire a CRO at seed stage, who do they manage? How many AEs do they have, one? That person isn't going to do a lot. You need doers. I always talk about vertical players, which is what I love, especially in those situations: people who have a layer of strategic thinking but can also jump down into execution as needed. They can do both.
Ceci [22:42]
And what do you think about a founder's associate or Chief of Staff at seed stage?
Bea [22:46]
Company-dependent. I was actually interviewing with a seed-stage company. It's a good trade-off, you get good equity and the chance to set up everything. But you may not end up working on things that are strategic or interesting enough, so you can put your own ceiling on it. It really depends on the company. It's not a hard no for me.
6. The CEO Keeps You Out of the Room
Ceci [23:10]
I'd like to move to the next topic, which is interesting and probably something we haven't experienced personally, but I've heard about it from others: the CEO keeps you out of the room. In what contexts is that actually fine, and in which is it not okay?
Bea [23:32]
It's a massive red flag for your relationship with the CEO. Matt Mochary, the number-one founder coach, who coached the founders of Stripe and many other companies, even brings the Chief of Staff into his coaching sessions with the CEO. They think you need to be almost mind-melded. The only contexts I'd accept are if someone reviews your salary, or anything too HR-related. Or you're on holiday, climbing a mountain, taking some time off, that's it. What do you think, are there any other excuses?
Ceci [24:09]
There has to be complete trust, I agree. I've done the Mochary method coaching and I was in the sessions with the CEO. There are certain conversations that might be specific to one employee and need to stay private, or dynamics between founders, or HR-specific things, and that's fine. I don't have to be in the room if it's to preserve someone else's privacy, though I'll probably find out eventually.
Bea [24:40]
You make a good point. There's a difference between being in every room and being informed of every decision. I wasn't in every room, but I knew about everything happening in the rooms I should have known about, ideally before it happened, or just after. As long as that's in place, you don't have to literally be in every room.
Ceci [25:00]
If you had to advise someone who finds out a strategic decision has happened, it's relevant to them, and neither the CEO nor anyone else told them, how should they approach it?
Bea [25:13]
I'd give the benefit of the doubt to the CEO and leadership team. Maybe you're a recent hire, maybe they've never had a Chief of Staff before, maybe they don't know much about the role. Give them the benefit of the doubt, have a conversation: look, that strategic decision was taken, I wasn't aware of it, but I'd really love to be on top of everything so I can tune my work accordingly. Ask the question. Ask whether there's a specific reason you weren't included. And if they shut you down, that's a red flag, change company.
Ceci [25:51]
You also need to earn being in the room. You have to show your founder or the leadership team what you do with that earned knowledge. If after a while you're just there to listen and can't apply what you hear in a way that creates good outcomes for the company, then the problem is on you.
Bea [26:14]
I agree. It takes time to build trust, and it's completely fine if it takes a little time and is earned. But I think after maybe four to six months, you should have earned the trust to be in every room.
7. You're Treated as a Fixer, Not a Partner
Bea [26:29]
Number seven. It's connected to the execution point, but another red flag is if the CEO treats you as a fixer and not as a partner.
Ceci [26:42]
What do you think the difference is, and have you ever experienced it?
Bea [26:45]
It's a really fine line, because your job is to do both. The difference is, if you're just fixing problems as they happen, you're a firefighter, which is super helpful for the company, and a lot of your job should be that. But you should also be working to prevent fires in the long term, more like an environmentalist. If you spend more and more time fixing fires, you can showcase output and look great very quickly, but the fires keep happening and you burn yourself to the ground. It's all about balance, like so many things we've talked about. I did spend a lot of time fixing things, because it's important and often the most urgent, but you need to carve out time to ask, okay, this happened, why did it happen, how do we prevent it, how do we change the broader scheme of things? I'd say I was able to maintain that balance. What do you think, how do you sit between the two?
Ceci [27:58]
Similar to the strategy-versus-execution debate. Sure, go and fix it short term, that helps. But do a post-mortem afterwards with the CEO: okay, what's the underlying cause, what can we do about it, and then implement the more strategic changes. For a few months I went into fixer mode, but I didn't spend enough time understanding why I was fixing things. After a while we drew conclusions, made changes, and the fires stopped happening. It is, as you said, more of an environmental challenge of preventing fires.
Bea [28:42]
When should you push back to your CEO that maybe you're doing too much fixing and not enough strategy? When does it tip the scale?
Ceci [28:50]
Every boundary I put was usually on myself, not imposed externally. When I highlighted it externally, the response was, yeah, of course, don't worry, let's shift priorities, you should be more focused on strategy. People often get to that point a tad too late, and it's just a matter of communication. Of course there are crunch times. In a fundraise, or when you absolutely have to deliver certain metrics, in that case I'd just shut up, do my job and fix everything.
Bea [29:23]
Absolutely. Sometimes you just need to get on with it, do it, and think about it later.
8. Your Work Is Invisible
Bea [29:29]
We're getting to number eight, and this one is punchy, and quite demoralising: your work is invisible. You spend a lot of time fixing, executing, strategising, working with the leadership team, and then other people get credit for what you built. Has it ever happened to you? What's the downside, and how do you think about it?
Ceci [29:52]
In my experience, I have a less traditional Chief of Staff role, in the sense that I'm responsible for certain functions. If those functions work or don't work, it's my credit or my fault. There are broader things, company processes, that I probably didn't get credit for. Communication is very important here, you still have to communicate what you're doing and its impact, and it's down to you to highlight it. My partner showed me a clip of Obama saying you just have to work hard, and if you work hard and fix things, people will notice. I really disagree with that, sorry Obama, I love him, but I disagree. You are your own advocate. You have to communicate what you're doing and the impact it had, and people will notice. I don't think they'll notice by themselves.
Bea [30:51]
I've always operated under "who needs to know, knows, and who doesn't know, it's probably not relevant," which is wrong. So many times in my career I ended up underselling myself, then having to regain trust because people didn't know what I'd done. So don't take my advice. If the CEO doesn't know 10% of what I do, that's fine. But the CEO should be the person with the most context on your work, even if other people take credit in the company. You should also worry about optics within the company, because it serves you. If people think you're doing a lot of things, which you are, they're more likely to respect you and to do what you ask, which makes your job easier and faster. It's a virtuous cycle. I came in and did a complete 180, I started thinking, I don't care, the CEO knows, I don't care about anybody else, and at the end I realised, actually, it matters.
Ceci [32:00]
Absolutely. I keep a Notion tracker of all the tasks I do, and the completed ones get filtered out automatically, so they go into the void. Sometimes I deselect the to-dos and in-progress and select just the done, and I see the long list and think, wow, I'm great.
Bea [32:22]
Two things I used to do a lot, when I was a bit younger and underselling myself majorly. One is to keep a list of wins. As soon as you have a win or an impact, write it down somewhere, and at the end of the quarter you have all your achievements and can feel good about yourself. The second, which I should reinstate, is a boost folder. Every email that gives me praise, and I'm such a sucker for a little praise, I'd put in the boost folder. When I felt down or insecure I'd go in and read all the compliments people had given me, great work Bea, clap clap, and I'd be revitalised. I started doing it in banking, moved it to my VC days, but now it's mostly Slack so it's harder to do.
Ceci [33:16]
What helped me at my previous company, this one is different because finance is less broadly public, was sending out a weekly newsletter on what was achieved, with a bunch of random sarcastic things just to chat, and then the whole list. I remember starting the week thinking, my God, what am I actually going to write here that I worked on this week, and then having a long list, and you feel good, you achieved it.
Closing
Ceci [33:45]
Across all eight of these major pitfalls, I was so ready for us to blame everybody else, and we ended up blaming ourselves a lot.
Bea [34:00]
Typical women. How much do you think is self-blame and how much is the environment around you?
Ceci [34:07]
There's one thing to be said about the environment: the Chief of Staff role, especially in startups, is fairly new. There aren't many playbooks or mentors who've done this for twenty or thirty years that you can ask about how to act in certain scenarios or how to progress your career. So it's a role we're figuring out by ourselves, which is also why we wanted to do this podcast. The environment isn't the most conducive to completely reducing failure. The other part is that the people drawn to the role tend to be those who don't mind doing the dirty work or propping other people up. It's a personality thing. But you don't always want to be that person, you're still a C-level executive, a really important part of the company, and you should try to make the role the best it can be and change that within yourself.
Bea [35:09]
Last question, and I want the real answer. If you could go back to the start of your role and do one thing differently, one thing that would have changed how the role landed, what would it be?
Ceci [35:20]
I'd be a bit more inquisitive about challenging the CEO and the company, less of a yes-person, and step more into investigation mode. If I'd stepped into it a bit earlier, we'd maybe have found solutions to problems a little quicker. It's also true that people have to make their own mistakes, me included, to evolve. But that's probably the major one. And maybe carve out time for strategising more than executing, with clear times where I'm just on the big picture and less on the doing. Those are my main two. How about you?
Bea [36:05]
I'd focus earlier on the broader team, not just building trust with the CEO, and try to impact the whole executive team from the beginning, build trust and challenge them as well, not just the CEO. So quite similar to you. You just have more impact, and sometimes you stop yourself from questioning things you're actually entitled to question. And I think that's also our advice for everybody listening: if you're in a Chief of Staff role, don't be afraid to challenge your CEO, position yourself as a trusted partner, and be the challenger.
Ceci [36:45]
Be the challenger, be the annoying one.
Bea [36:47]
Thank you so much for listening. This has been Top of the Ops, real conversations about what happens behind the scenes. Find us on Spotify and YouTube. See you next time.