
The Operations Room: A Podcast for COO’s · 2026-02-05 · 1h 7m
Key moments - from our scoring
Substance score
64 / 100
Five dimensions, 20 points each
This episode examines what actually constitutes a CEO's job through the lens of Keith Wellington, a London-based chairperson and investor in VC-backed businesses including Peak, C2, and Sensone. Rather than treating CEO responsibilities as an amorphous catch-all, Wellington frames the role around five discrete jobs: establishing clear market strategy, building the leadership team for your stage, creating a horizontal operating model for strategy execution, deliberate observation of business dynamics, and packaging observations into time-bounded CEO-led interventions. Brandon reflects on his transition from COO to CEO, noting that many decisions bubble up due to unclear delegation rather than actual necessity. He introduces the practical tool of a delegation of authority matrix - a simple table defining what decisions he can make independently, requiring CEO consultation, or needing joint sign-off. This prevents guessing and slows unnecessary escalation. The conversation also touches on Brandon's evolving AI strategy (shifting from 'AI-first' to 'AI-native' as a cultural imperative) and his upcoming two-day offsite featuring Charlie Cowan on Claude Desktop and specialized AI tracks for product, engineering, and design teams. Bethany notes that observation naturally happens but special projects require active triage and packaging into discrete initiatives with clear ownership, success criteria, and time bounds.
A delegation of authority matrix is a simple table created between CEO and COO that specifies which decisions the COO can make independently (e.g., contracts under $X, hiring up to level Y, vendor approvals), which require CEO consultation, and which need joint sign-off. It's then communicated to the operations team so they know when to escalate and prevents unnecessary bottlenecking.
Strategy (clear market focus), top team (building leadership for your stage), horizontal operating model (system for turning strategy into execution), observation (deliberate space to watch market, team, and process signals), and special projects/interventions (packaging observations into time-bounded initiatives with clear ownership and success criteria).
Decisions bubble up because the CEO hasn't been explicit about what they care about, don't care about, and whom they trust. Without that clarity, team members default to escalating, and the CEO becomes an unintentional bottleneck due to lack of delegation framework rather than necessity.
A CEO-led intervention should include scope (what the problem is), explicit ownership (who runs it, not necessarily the CEO), time bounds (when it starts and ends), and success criteria (what validates or kills the idea), allowing the CEO to activate priority observations without executing them personally.
AI-first treats AI as a project or initiative, while AI-native embeds AI thinking into culture, performance reviews, hiring decisions, and daily rhythm, forcing teams to think in terms of 3X-10X improvements rather than incremental optimization.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode contains solid frameworks (five CEO functions, on-vs-in-the-business) that are useful for operators, but much of the content is spent on personal anecdotes (face peels, gym closures, book recommendations) that dilute insight density. The core frameworks are sound but not densely packed with novel operational specifics - the ideas are sensible but somewhat familiar to seasoned operators.
there's five things that make up the CEO's job
observation is a methodical, conscious process of observing your team, observing your business, observing the ecosystem your business operates in
The five CEO functions framework and delegation-of-authority concept are sensible but not particularly original - they reflect established thinking about CEO roles and operating models (Lencioni is cited). The observation about founder CEOs hiring product visionaries and the inevitable conflict is somewhat counterintuitive, but the overall thesis follows conventional wisdom about scaling and delegation.
there's five things that make up the CEO's job: strategy, top team, horizontal operating model, observation, and special projects
a smart, capable founder, product visionary CEO's gonna think, well, I must replace like for like. I'm only going to relinquish this task to someone who is my equal
Keith Wellington is a chairperson and investor across multiple VC-backed businesses (Peak, C2, Senson, Abley) with deep operational experience as a COO/executive for ~10+ years. He has concrete, practitioner-level credibility and speaks from lived experience running operating models and working with CEOs. This is substantive guest caliber - a seasoned operator and board advisor rather than a pure theorist.
I'm a chairperson and investor in a variety of VC-backed businesses
I've done this now as a sort of a Ned chair type person for about 10 years now, and of course, prior to that, I was an executive working with CEOs and stuff for some decades
The episode lacks concrete examples, named metrics, or specific case studies to ground the frameworks. Keith references Mimecast briefly, mentions Lencioni's Advantage model, and discusses hypothetical scenarios (e.g., "Series B of £30-35M"), but provides few real data points, timelines, or dollar figures. The advice remains largely abstract and principle-based rather than grounded in specific, replicable examples.
let's say it's a Series B which means we're going to now be working towards finding go-to-market fit
we started using it when I was at Mimecast, just enough structure
The hosts ask reasonable follow-up questions and probe Keith on frameworks, but the conversation often feels polite rather than genuinely challenging. Brandon and Bethany mostly validate Keith's points or ask clarifying questions; there is limited push-back, disagreement, or tension. The dialogue is conversational but lacks the sharpness of a host genuinely stress-testing claims or digging into contradictions.
Is that fairly deductive process? No, that makes complete sense
Yeah, you know what's interesting? I because of our situation right now. I feel like cash is not our constraint
Computed from the transcript - who did the talking, and the words that came up most.
In this episode we discuss: What is the CEO’s job? We are joined by Keith Wallington, Chairperson and Investor in B2B SaaS businesses Love The Operations Room? Please support us by rating and reviewing it here . We chat about the following with Keith Wallington: What actually changes in an operating model as a company scales - and what shouldn’t change, even under pressure? How do you design an organisation that moves fast without creating chaos or decision fatigue? When does adding structure genuinely unlock performance, and when does it quietly slow teams down? How can operators tell the difference between a scaling problem and a leadership problem? What questions should COOs be asking before a Series B or major growth phase to avoid painful rework later? References Biography Focussed on Series A and Growth stage B2B SaaS businesses that deliver vital, core services to their customers.
Transcribed and scored by The B2B Podcast Index.
Hello and welcome to another episode of the Operations Room, a podcast for COOs. I am Brandon Mincing, joined by my lovely co-host Bethany Ayers. How are things going, Bethany? I have been getting face peels for easily 20 years, and I've never had really any reactions at all.
And then last time I had one a couple months ago and had a really bad reaction and I thought, oh, maybe I was just being a bit aggressive beforehand, like using too many products, whatever, it's fine. And then I just got one on Wednesday and I'd been super gentle with my skin since the last one. And so I thought it would be fine, but it's not been. My face hurts.
It feels like it's on fire. They're basically everything. Cheek, nose area below, so chin, jaw, neck. I don't even think she put stuff on my neck, but for whatever reason, my neck is really on fire.
Okay. So break it down for me. You've gone to this woman for 20 years. You haven't had a problem, but you've had this problem this last time.
So what's going on here? Is it, is your face somehow different or what's, what's the deal? Basically, I think if you speak to any woman of a certain age, everything is hormones. Everything is perimenopause.
I can only imagine that that's what this is, but it's really annoying, really painful, didn't sleep last night, grumpy. Okay, so being in a position where you can't sleep because of a face peel seems like the last thing that you need given your circumstance of, you know, your CEO position. My stressful life. Yeah, stressful life and now pain on top of it.
So, you know, I go to my French electricity gym. It closes after today, so this is the last session of the year. Supposed to go at half 12. I don't think I can.
Oh, because of the face. Because of the face. Right. Okay.
It's upsetting your day now as well. So you can't sleep. You can't do your stuff during the day. What is going on here?
What do these women do to you? But the thing is, is what did I do to myself? It's not her. It's really damaged my skin.
It's healed, but this is not what's supposed to happen for a face peel. You're not supposed to destroy the outer barrier of your skin. Well, thank God as a man or a male I don't have to do face feels or be in a position where somehow that's the expectation. Yeah, well, I used to get them because it was really good for all of my spots and it just like really healed any kind of acne that I had.
And then I carried on doing it now, you know, my hormones have calmed down over the years until now where they're going crazy the other way. And so I don't even know if I need them anymore. I think I'm now doing them for anti-aging, but questionable as to whether or not it makes a difference. Speaking of anti-aging, I just caught up with my former VP of Operations at Trent for lunch yesterday and it was wonderful to catch up.
She's actually written a book, which is phenomenal. So apparently she's shopping around with, what do they call them, agents, I guess, for trying to sell the book onwards type thing. It's a very talented woman. When I first hired her, she had come out of, I think it was BCG Consulting, and very talented individual came in as the head of ops and graduated over the course the four year period.
And now she effectively runs that place, I think, with Jeff, the founder. So I'm just telling her, by the way, my company is growing and we're looking for people. So if you know of any good head of ops coming from a consulting background similar to you four years ago, please recommend them. So if there's anybody listening to this podcast that is coming from the consulting background that would love to be a head of Ops, hit me up on LinkedIn.
I think that's basically what our audience is. So I should be getting quite a few after this. Be inundated. Yeah.
Well, that's great news. Did you write fiction on fiction? I think it was fiction. Yeah, sorry.
What am I talking about here? You know her. I do, which is why I was, like, particularly interested, you know? I was like, oh, cool.
I totally forgot about this. You were mentoring her for a short time period. Yeah, yeah. So I believe it's fiction.
She went to New York City for the summer and spent three months, I think, taking a course and writing the book at the same time. What else is happening? So I was inspired by you, Bethany, with your company offsite and bringing Charlie Cowan in to talk about ChatGPT Enterprise and upskilling the company. And you had Ryan Fuller also come in, who also is a guest on our podcast to kind of do all the upskill on the technical side of things for the developers.
So I've taken your idea and I've run with it, and it's now gotten out of control. So we've got a hundred people in the company, we've gotten the team from the U.S. Flying over, so roughly 25 people.
So we got a two day event. Day one, as usual, is strategy alignment, et cetera, et cetera. Day two, I've dedicated to AI up-skilling and taking six challenges of the business, six execution challenges, and saying to them, look, let's up-scale in the morning using AI tools. And let's take our kind of newfound skills and get together cross-functionally, self-select into the six challenges, and do those in the afternoon.
And we can showcase some of our results in the afternoon, or at the end of the day, rather. To show what we've come up with in terms of artifacts or demos or what have you. So, the interesting bit now is that I've got a three-track program for the morning. Track number one is Charlie Cowan on the ChatGBT Enterprise side of things.
I'm very excited for that. Track number two, we've got another individual that has a deep technology background, but in fact he's a CEO of a company, but very practical, hands-on. He's going to run our product engineering track and he's focused on cursor in Cloud Code. And we had our VP of AI and our tech lead sit with him for half an hour to kind of just vet him, just make sure he had the chops necessary to pull off this session.
And he's done this session several times in the past. And obviously he knows Charlie through their consulting AI network thing, whatever it is. So he's individual number two, and then individual three for track three is more of that product focus, lightweight prototyping for the designer, for the product team. Our CEO of our company actually wants to take this track.
So this is lovable, replete, and that third person coming in to do that. So we've booked off 9 o'clock in the morning to 12 at noon for the three hour block, take lunch, and come back and work on the challenges cross-functionally. Do people get to choose which stream they go in or are they assigned their stream? Yeah, we're going to allow them to self-select, so the week prior to the event.
During the morning. For that too actually. So the note that we'll send out the week prior will have two self-selections. One will be which challenge do you want to work on and which track do you to select into.
That sounds really cool. We'll have to hear how it goes after you've run it. We're getting Charlie back in as well for training in Q1. Not quite sure which date, because we have a big customer commit that is yet to land, and so we're waiting.
We have to be a little bit flexible in January to know when we can do our offsite versus when we're all going to be focused on customer work. So are you doing another offsite, is that what you just said? Yeah, well, I think we're going to do it on-site, but we'll do two days. And that will be Charlie training on Claude Desktop.
So Claude desktop now has all of the skills, and skills really are the way of making easy agents or more repeatable. We can start to move into the world of automations for just all of us, rather than having to use NAN or anything complicated. So we're going to do a special deep dive into skills. And so much has happened between when we talked to Charlie on Tuesday and now it's Friday around skills and Anthropic and what they're releasing that I can't wait to see what's going to happen by the time we get to the training in January.
It could be a completely transformational new technology. So we are doing that for the team on day one and then day two we'll be building stuff and also. Doing a certain amount of slowing down to speed up, particularly on the engineering side. I think we just need to build a lot of guardrails, for lack of a better word, so that the code written is automatically good code no matter what.
So all of those instructions, a bit boring, time consuming, but if that's just what we do for a day, it'll make a huge difference. I kind of feel like the half day for the training, half day for the challenges is way too short. Like you get a little taster of things, and I kind feel like to your offsite, that seems like the clear evolution of what needs to happen here, which is a full day dedicated to the training part and a full date dedicated to the so-called challenger making whatever you want to make.
Yeah, just because basically what you need to do is give the teams time to actually do stuff because there is in the same way as when you're a new manager or a manager and you have a new team member and you to slow down, teach them stuff and there's this feeling of like, I'll just do it myself, I can do it faster. And you know, you have to get past that. It's the same thing with AI. And so it's hard for the teams.
To accept not hitting their deadlines because they have to train AI, even though once they do, it'll be five times faster. So it's an opportunity to give the teams permission to slow down. No, it makes a massive difference. I remember this is not to do with AI, but it's a similar idea.
We hired an individual, this is many, many years ago. They came in at somewhat of a senior level. As they came in, there was, as always, tremendous pressure on this person to deliver it instantly. So within the first, I don't know, week and a half of their onboarding, it was even onboarding almost immediately, that person was stressed out, felt they had a massive to-do list, and almost ignored the onboarding in a sense and we're just.
Trying to like, I don't know, I guess like talk to people, pull together their action set almost out of the gates basically. And I had to sit down with that person and say to them, stop what you're doing. You know, you don't need to be in a stressful situation right now. You really shouldn't be, you can't be because what you have to do is pull back, do the onboarding, think thoughtfully and observationally around what's happening and take the time to do that.
Because if you don't you're going to catch yourself out, where you're gonna spin your wheels working on stuff that may or may not be the most important thing, and you may or might not be doing a good job of it because you don't know enough about the company and the product and what we're dealing with to really do things that are useful basically. So just stop where you are doing, put your list down and take some time to think about what's going on here. It's basically the same thing.
So we'll probably just get Charlie in every quarter. Everything's moving so quickly. Also, one of our OKRs in the past quarter was to become an AI first company, but now I was at an event and I got very inspired and I'm like, fuck being AI first, we're small enough. We need to become AI native.
And so it's not an OKR in this quarter. It's now just like. In our culture, in our performance reviews, in the rhythm of the company, how do we become AI native? How do we not hire people?
How do speed things up? 60%, 70% increase in optimization isn't acceptable. How do 3X, 4X, 10X what we're doing? So the vision is 50 people, 100 million.
So how do stay that slim and that lean and how do outperform everybody else? And that's what we have to get people's brains open to. Yeah, you know what's interesting? I because of our situation right now.
I feel like cash is not our constraint So therefore the natural thing to do is to add people and you get requests obviously to add People do all sorts of things that we're trying to accomplish I think in your situation having this forcing function where you can't just lay out The next hire net new hire and you have to do things in a different way to get a bigger outcome You're forced into a position where this AI shift becomes more not possible, but like you're forced down that road, whereas I'm not forced down that road.
So the question is how best in my situation to kind of get the company in a position where I know I guess we're doing both. We're doing the net new hires, I need to get done, but we're very much rethinking and reinventing how we're going things in a way that makes sense. So part of it for me is a forcing function with cache, but part of that is, so there's three elements. One is a forging function with cash.
One, which I think is genuinely the deeper drive is I'm curious to see if we can do it and I want to learn and I to. And then the third is it's so nice to work with a small team and the speed and the nimbleness of a small time. We're actually a smaller team than when I started and it's amazing how much faster we are. Yeah, they're really such an overhead.
I think what you have, because you have more of the pizza table effect happening where you have a small group. You don't need to have all these crazy communications and repackaging of things, which is beautiful. And to your point, once you get to this, I don't know what the number is exactly, but 45, 50 people from that point, it just gets amplified in terms of you become like an orchestrator. Like the little operation stopping us from what we do for living in some respects but how do we orchestrate large functional groups to work together and then nimbus way possible given the fact that we're no longer twenty people.
Yeah, and it's really nice to be small, but we have a lot of hangover processes from when the company was bigger. And so part of what we're also doing is just tearing down process, tearing down the processes that don't serve us and that ironically we also are missing key ones. So it's kind of like getting rid of the stuff that doesn't serve and adding the things it does. That's part of we're working on at the moment.
So we've got a great topic today, which is what is the CEO's job? We have an amazing guest for this, which is Keith Wellington. He is the chairperson, or is a chairperson and investor in a variety of VC-backed businesses, which come to mind peak. C2, Senson, Abley, and the list goes on and on based in London here.
So with Keith, he talked about a variety things. The first thing that I wanted to ask you was this question of the CEO bottleneck problem. Where they really have to be the approver and their blessing needs to be given for almost everything or a large portion of decision-making. How do you deal with that bottleneck as a COO?
And now that you're a CO, maybe you have some new thoughts on this, I don't know. I think as a CEO from a COO, I'm probably a little bit less controlling. There's definitely things where I'm happy to not make decisions, but yeah, I also now understand a bit more why CEOs care about everything from the lighting in the office to the fundraising deck and everything in between. Actually, maybe maybe a different question.
Now that you're a CEO, just reflecting on the challenges that you've had in the past related to this bottleneck thing, like what, how does that inform how you now think about delegation, I guess. I think one of the things that's interesting for me is how few decisions people want to make. A lot of stuff seems to bubble up to me to get approvals. I realize that's because I hadn't been clear on what I do and don't care about and where I do, and don't trust people.
It's back to this really clear delegation. I don't need to read every blog post before is out as long as the blog posts. Hit this level of quality, this is good, this is bad, I'm fine, like, just post them. So it's been a little bit the other way of like realizing I am a bottleneck and it's because of lack of clarity.
And it's like made me reflect on what do I care about and want to see and have sight of either approval or decision-making and what I don't care about. And then ultimately it comes down to whether or not I trust the person who's doing that work. To do a good job and how quickly they learn and are making good decisions. But it does require a level of reflection that again, it's maybe the theme of the day is slowing down to speed up.
If you don't actually sit and figure out and reflect on how you're being a bottleneck, you can't fix it. Yeah, so this takes a certain amount of self-awareness to really understand what is it that you're actually interested in or concerned about and to your point, having enough trustworthy relationships in place where you're fully happy to delegate A, B, and C, and it depends on the importance level of it as well and kind of this idea of giving flexibility, not just to the individual to make different decisions, but also to make mistakes at some level because that's going to happen too and being comfortable with that personally.
One thing that I have done repeatedly over time with myself specifically as a CEO working with a CEO, and I've done this three times over, is create these so-called delegations of authority. And it sounds formal, but really what it is, is literally a table that says between myself and the CEO, what can Brandon decide? And it's very practical things that do in fact, slow the business down. So we think about signing employment agreements, signing vendor contracts, you know, up to a certain level, threshold wise, expenditure-wise what can Brandon approve.
Type of thing without having to consult with the CEO, all that kind of practical consideration stuff to help the business move faster, being clear on what I can and can't do instead of guessing or me thinking I can do something when in fact I can't and I get slapped down for it. Nobody wants that, right? So this delegation of authority can be fairly straightforward in terms of Here's 15 things we've decided between the two of us and we've signed off that I can actually make decisions on.
I've taken the delegation of authority and then I communicate that to the broader operations team so they clearly understand as well when they should be referring things to me and when they should be refering things back into the CEO or things I need both of us to sign off on. Or what they can decide themselves as well, or like how far down does the decision framework go? Yeah, so actually this is a good point. It goes no farther than me right now.
Right, so now it's time for you to do that reflection. Yeah, it is a good point because I kind of it's almost like as always in life you deal with like the first problem The first problem is always at the top So now it needs to sit with me in terms of perhaps doing the same thing with my heads of Yeah, what are you being a bottleneck for? But that sounds like a really helpful template to share with our listeners. Oh, yes.
A template. It should go into our template pack or whatever we're doing on our... Yeah, exactly. The second thing that he'd spoken about was the five jobs of a CEO.
And I found this list of his five immensely illuminating and quite interesting. So I'll just quickly read through this just to refresh your memories. Number one, strategy. Ensure there's a clear focus strategy in the market that you're focused on.
That makes obvious sense. We know that number two, the top team. Building and evolving the best possible leadership team for the stage that you're at. That makes sense.
Number three, the horizontal operating model. So there's a clear system for turning strategy into execution. And as I'm reading through this list, other people do these jobs obviously, but it's for the CEO to be kind of accountable and responsible to ensure all this stuff happens. Number three usually that is the CEO, but that needs to fall into the responsibility overall bucket of the CEO ultimately.
Number four, observation. This one I loved. So number four, the number four job of a CEO is purely observation, creating deliberate space to observe the business, the team, and the market dynamics. And then number five, special projects and or interventions, as they call them.
And the interventions was quite interesting. It was kind of like, if there's randomized thoughts coming from the CEO or from others in the company that the CEO likes. What do you do with those things? So this is specific bucket of how do you triage those ideas, select what actually is useful utility wise, and then package that into an actual so-called intervention with a series of specific deliberate activities, which we can kind of get into in a second.
But with those five, what do you make of those five? What do like there? I find it very helpful as a first-time CEO. I refer back to it quite often and feel like I've been focusing almost in the order.
So figuring out strategy, figuring out top team, and we're already talking about some of that operating model. I naturally do a lot of observation, so that one I think almost is by default. And then special projects. I basically think right now I don't need a special project, although I don t know if you would argue that the becoming AI native is a special project or is that the operating model is a little bit of both.
But it is, and they all feed into each other. So your observations then change your top team and change your strategy and create the special projects Okay, so you love it. So wholesale, those five, you think those the golden five as well. Yeah, well, I mean, I think there's the one that's missing for startup world, and that people always talk about is ultimately the CEO's job, which is make sure that the company has enough money.
And so I'd actually add a sixth song. All right, so I love that. And then in this observation bucket, so just a bit of a deep dive into this one. So he was saying, and this kind of dovetails into what you just said, but he was saying for observations, you're looking at market signals, you are looking at customer patterns, you looking at team capability signals, you're looking at process breakdowns internally within the company.
And as you're look at those things, obviously you can't act on everything. So the question then becomes, out of all those things that you're observing, how do you then start to activate yourself and what the most important things are? So what he was saying was, and he called this CEO-led interventions, where working with a CEO as an example, you would try to scope a specific intervention in terms of what it is, the explicit ownership of it, the time-bounded nature of it and some kind of success criteria.
So kind of typical things, I suppose. But I guess the idea is, you've got a bunch of observations and what is most important that can be serviced out. And then applying a bit of like kind of like a project to it, I suppose, that's being led by somebody that's not necessarily the CEO themselves. And there's clear accountability for doing something useful in terms of either validating it, killing it off, resolving it effectively.
Uh, is there a question or are you just summarizing? Yeah, sorry, I was partially summarizing or personally asking the question, like, do you like that? Because I've never really thought about it this way, like as an actual, I've never thought about observation as a thing, and I've never really though about the packaging as a discrete project thing either. But as I say it out loud, that makes tremendous sense.
I'm just curious what you think. Yeah, I think I have done, I've also done it as a COO before, like when I was, I think I was the official titles chief customer officer, but at peak, I had marketing sales, customer success and delivery all reporting to me. So I was responsible for the full customer life cycle. And I actually created a slide that had all of the customer life cycle on it and every month or quarter, I would share the slide with my team.
With basically just a worry scale. It wasn't more scientific than what's the most burning thing. And I would rate from most worried to least worried. And the thing that was most worrying would be what we focused on to fix.
And then when that went away from being the number one, we would go to the next and it would move around. And so sometimes it would be over months or sometimes it will be something that you resolve in a week or two. And so it's just very much looking at that customer lifecycle and figuring out what's the most pressing issue. And I think I'm doing that without it being a visual, again, anatomic.
So as a CEO, there's unlimited things to worry about and unlimited issues. And there's also unlimited opportunity and nothing is ever fast enough. And I won it all yesterday. And those are not, it can be completely overwhelming.
And so stripping it out and figuring out. What is the most important issue to think about and everything else can just wait, I have found very liberating. Fabulous, so why don't we park it here and get on to our conversation with Keith Wellington. What is it that we're supposed to be doing as CEOs?
And what is it that we should be reminding our CEOs that their jobs are? So I'm going to focus this quite specifically on the types of CEO that I find myself working with, and they are generally founders or sometimes non-founder CEOs of disruptive tech plays. And those types of CEOs often display quite a specific type of analogy trait. But inevitably, if we just simplify it, You know, day one, they're kind of doing everything, aren't they?
Or they're doing everything that their co-founder isn't. And then as the business gradually develops and adds more people, there are more people doing stuff such that the business can scale through people doing stuff in parallel and are not all being done by the CEO. Inevitably, therefore, the CEO's role is almost to constantly assess what the business needs and hence what the business needs from the CEO and that role does need to change. And we see some classic patterns that develop in the in the evolving journey of a startup, where CEOs can get the balance wrong, the balance being how much are they in the business versus on the business.
And if a CEO remains in the businesses, in other words, owning a process or being a part of a decision chain, if they're in too much of that longer than they should be, They become a pinch point for the business, they become a bottleneck. The business. And so it's quite a difficult balancing act for CEOs to constantly think about where they need to be elevating themselves above the business versus where they might need to stay in the business and I find that generally CEOs either inherently do this subconsciously without even knowing that they're doing it or more commonly doesn't happen at all and they do become pinch points.
I should counter this because I'm going to talk a little bit now about some of the frameworks I used to talk to CEOs about this, but I'm just going to quickly add some balance here. We also see the opposite where CEOs detach themselves too quickly, become too elevated above the business. So the balance really is important. A lot of people don't enjoy the CEO that's constantly under their feet and trying to everything and interrogating everything or still kind of being a part owner of everything.
But on the other hand, the equally dangerous CEO is the one that loses context on what's going on in the business is no longer close to their team and really understanding what's working and what's not and who might need more support or where the business might need to evolve its processes. So it's really important that CEOs also appreciate that this isn't a suggestion that you should step away and kind of, you know, waft about 30,000 feet above your business and hope that everything goes well.
So there's this kind of balance that needs to be managed. There's two approaches that I use quite a lot when I'm talking to CEOs about this stuff and helping them see it all through. And also I should add that, you know, this podcast generally focuses on the COO and the COO will crop up in this because the CO and that type of role becomes more and more important to the CEO as the business evolves. And I'll probably kind of naturally get to that.
So there's two things that I work on. The one is this concept called balance on the business versus in the business. And it's a really, really useful way of constantly assessing where should I be getting out of the way here versus where should I be staying in. The second framework, and I'll circle back between them, the second framework is, I don't know how academically correct this is.
This is my own view after having done this now. As a sort of a Ned chair type person for about 10 years now. And of course, prior to that, I was an executive working with CEOs and stuff for some decades. But I think there's five things that make up the CEO's job.
This certainly works for me when I'm talking to CEOs and it seems to help us audit the CEO and how they're doing and where the business needs them more or less. And those five things are as follows. First, And by the way, it doesn't mean that the CEO has to do each of these things themselves. They have to make sure that these things are done.
Initially, the CEO does them all. And that might be where the COO comes into play, I'm guessing. So item one is we need the best possible strategy we could possibly have in the largest market in the largest town. I mean, it kind of goes without saying, but without that, everything else is just a waste of time and money.
We need to have a great strategy, clear focus around that strategy, well, well-documented strategy that can be understood. Again, that shouldn't be built by the CEO alone, but it needs to exist. And generally, it's the job of the CEO to make it exists. Two.
We need to ensure that we've got the best possible top team we can recruit within the geography the business operates in. That could be global, if it's a fully remote business that can recruit globally or in some specific geography needs an exceptional team. By the way, the businesses that I work with, I tend to focus on businesses that are, hopefully have potential to be unicorns. So we really are looking for the best people on the planet to build these businesses.
We're not looking at to create a little sort of. Lifestyle business, we're looking at fundamentally changing an important part of how the business, how the world does a thing in enterprise software, particularly in my case. So number two, we need an exceptional top team, leadership team, depending on the size of the business. That could be the first team or it could be that C suite or whatever is appropriate to the business of the state.
Three, we need to ensure that there is a really appropriate functioning horizontal operating model in place. Now, if one, two and three are in place, so we've got a great strategy, we've got a good team and that great team and all the other people in the business are being effective in executing on achieving the strategy because we've got this great operating model, this horizontal operating model that's working and by operating model I mean a clear framework for how we set strategy, how we turn that into goals, how those goals cascade down through the business, how, we communicate with the business how we review and iterate strategy how various parts of the organization meet And to what end?
The full... Horizontal operating model of the business. If one, two, and three are done and are working fairly well, our CEO, depending on the stage of business, our CEOs should have the opportunity to somewhat extract themselves from being a part of daily business as usual. And that should give them, and I'm not saying that they should, you know, not have a day job and should waft around, but it should give them enough space to do.
Numbers four and five, and numbers four and five are four is observe, observation. And people often think, what are you talking about? That sounds like a luxury. That sounds a waste of time.
But if you look at, say, military models, you've got things like OODA loops of observe, orientate, decide, act. Observation is fundamental. You have to understand the environment you're in to be useful in directing your team. And so observation is a methodical, conscious process of.
Observing your team, observing your business, observing the ecosystem your business operates in, looking at the horizon and you're looking for opportunities, challenges, maybe internal processes that are reaching the point where they're no longer fit for purpose, you're consciously observing the world around you. That is the thing you put in your calendar and you do that and good things happen. Observation leads to number five. Because through these observations, you can have identified a couple of things that actually do need your attention.
Maybe it's an opportunity, maybe it's the need to go and work on a strategic alliance, because you've noticed, you and your team have noticed a significant overlap in customer base. This point four of observation, as I say, might lead to an insight that you should work on a strategic alliance because there's an opportunity to, I don't know, get inside somebody else's distribution in some symbiotic way. Or it might be that there's an executive team member that's, as much as they might have been an amazing contributor to date, might no longer be stage appropriate and they might need to be a change to the executive team.
Tough and unpleasant as it is, you know, these things need work. Now, number four leads to number five, which is... Call them special projects or call them interventions, but this is where the CEO says, okay, there's a thing that might require a team or it might require just me, but I'm now going to step in and take on a special project, which might be one of the examples I just gave. Well, why is this important?
Well, if you think about CEOs, the CEOs that I've worked for and now work with, they have a lot of ideas. And on a daily basis or at very least a weekly basis, those ideas are brought to the fore and they can create quite a lot of confusion and disruption and they can disrupt the team from executing on the plan. Now, sometimes that's important because the idea is like, you know, OMG, we're about to run a ground here, but a lot of the time it's actually almost a subconscious process of a CDO that's just playing out their personality, which is an idea generator, which is why the business was started in the first place.
And that can be very chaotic and I've lived in this world in many ways and arguably even though I've not been a ceo I suspect I am like this too so I'm very self-aware by going through Four and five by methodically observing and telling the team that this is part of your job Like part of my job is to do this observation work and actually it should be everybody part of everybody's job to to a greater or lesser Degree depending on their role in the business and how much discretionary time they have doing this observation Work you tell people will lead to me occasionally Engaging myself in strategic projects or special projects now the team know that there will be places where the CEO is going to engage might go ferreting deep down into the organization, working with people that are, you know, multiple layers away from the CEO who might otherwise be picked up by the fact that the CEO has turned up.
So this process of like methodical observation and moving to clearly defined space projects helps the team a lot. Because what it does is it actually quietens down and orders. The degree to which the CEO sort of, you know, engages in the business. And it seems a little less random and it seems like everybody understands the structure for how this happens and why this happens.
And it's kind of more acceptable. So that's one of the frameworks I use, which is the five functions of a CEO. And what I'll often do with CEOs is actually run this almost like an audit, quarterly or every six months, sometimes every year. We're actually going to say, right, let's talk through the five functions and see how we're doing.
So we'll talk about how we are doing with strategy. Do we need to do any work with strategy? Do we have the right strategy? Or is there work that needs to be done?
We'll work through each of the team members. So how are we feeling about the members of the teams? How they're doing relative to plan, what do we need to do to make them more successful, you know, etc. And we'll pick up specific actions.
Each one of these steps in the audit will pick up specific actions that gives the CEO a space to think about the CEO role, to think about what they should be doing as a CEO without them just kind of staring at the wall and thinking, I don't know, am I a good CEO or a bad CEO? And then we'll go to number three, how are we doing on the operating model? Is it working? Is a jelling?
Do we feel like there's a cadence and a process. For this business that's working, or do we need to evolve stuff? It isn't all stuff that the CEO is going to do by themselves. This is just the two of us sort of auditing these areas so that we can then go away and work with the right people to evolve them where appropriate.
We'll work on these matters that have arisen. And then we'll actually walk through observation, like how are we doing with observation? What are you finding? Where are you looking?
Does that feel like something we should stand up in the next strategy session with the executive team, or should we work on that same? So we work on that and we work on working on the business versus in the business. And by doing those two things, we're assessing how's the CEO doing in the context of running the ship in terms of the five functions, but also what does your day look like? What does your week look like, what does you month look like.
So in terms establishing the balance of on versus in, the approach is let's look at what you're doing. So let's at your calendar. Let's look your to-do list. Let's put them all in a long list.
And let's establish which of those things you should be doing and which you shouldn't. And of the things you shouldn, who should, does that person exist in the business? Have they been empowered? Have they being disempowered?
Are you trying to do somebody else's job? Are they wondering why you're trying to their job? And then equally, there might be things that you shouldn do, and there's no one there to do it, which brings up questions around org structure, hiring. Is that timing correct for that thing?
So it's. It's a good way to really help the CEO get some order into their calendar, which can sometimes be very chaotic. And some of this is just a realization, which is, I'm just trying to do too much here, in which case you say, okay, we need to remove some stuff from your list. Maybe they shouldn't be done at all.
Maybe we should be passing that to somebody else. So they're kind of simple, but very useful exercises. And yes, I tried to touch briefly on the COO thing. You get some CEOs, particularly non-founder CEOs, that are good methodical executors.
And they tend to be that because they tend to have been brought into the business because the business needed a new CEO that could be a more methodical operator. And sometimes it's founding CEOs themselves that raise their hands at some point and say, look, I'm just not sure if I'm the right person to be a CEO, but just to reverse on this and offer a different angle on it, generally founder CEOs are product, visionary, disruptive thinkers. And generally in my experience, those people are not good operators.
People bring me opportunities to be a chair of a board, and they talk to me about the CEO, and this is normally venture capital funds that come to me. I say to them, start talking to me about a founder CEO that's an effective operator and it's a red flag, because it means that they're probably not product visionaries. And amongst other things, very often, the CEO does need to be that representative of the vision of the concept that this business was formed around. And so generally they need to be balanced with an operator and that's not to say that non-founding CEOs that are brought in, amongst other reasons, because they can operate well, like you, Beth, if I may, I suspect, you know.
I mean, there is a point at which every CEO, just because of what the CEO's job needs to be, will need someone that runs alongside them as their custodian of the operating model. And often that is, it could be a COO, which is somewhat a T-shaped role, which you can get to in a moment. It could be chief of staff. It could be a sort of an operations person.
And sometimes it's even just like a kind of a assistant that picks up all the stuff that the CEO needs someone else to methodically focus on, but they need to be operators. And so. Generally, I find that most effectively, number three in the five functions of a CEO, which is the operating model, shouldn't be owned by the CEO. The CEO should make sure it exists.
They should make that it is there, that it's transparent to everybody, and that there's an open discussion around how well it works and whether it should evolve. But it should be operated. It should be on a daily basis managed by somebody else. And that's very often a COO or a chief staff or a VP Ops or something.
The COO and Chief of Staff roles are very fluid. I mean, sometimes they are really horizontal-only owners of an operating model and don't have any functional responsibility for any teams, and sometimes they have vast functional responsibility. You see some COOs that pretty have, and it's sometimes the entire executive team reporting to them, and the CEO has one reporter, which is the COO, in the extreme. I've been on that continuum in my various C-level roles, sort of COO-ish roles, generally somewhere only between half and zero percent of the functions of a business.
One of the responsibilities you haven't listed is not running out of money. Yep, there's another one which is running the board. Yes. So is that in a different framework or are those just in addition?
Those are six and seven. And I think they all sit inside strategy because a strategy includes a financial model, a budget to run a strategy. So I might be using, there might be a lot packed into some of those items. I mean, arguably even running a board you could put inside a horizontal operating model because some would say that a key function of a CEO is to ensure they have an effective board, which I suppose is right.
But generally I would suggest not trying to do that yourself. At some point once you want to outsource it to a chairperson to some degree. But I would say, yeah, I would say that not running out of money sits initially in a budget. So this strategy with this financial plan gets us there without running out of money.
But equally, your operating model needs to be checking in on that process, right? That whole pro that whole cadence of setting strategy, setting goals, review. Doing iterating. The CEO, especially in those early days, is the fundraiser.
So when it comes to actual fundraising, it is the CEO that needs to go out there or express that vision, communicate that, get people excited by that. And hopefully they're paired with somebody useful to talk through some of the specifics around the financials and perhaps the pipeline and so on. But what's your view on that just in terms of the fundraising process, the responsibility of the CEO? Thank you so much for watching, and I'll see you in the next video.
Whether a founding or a non-founding CEO, I think current and new investors all imprint on that CEO. So the CEO has to be at the front of the fundraising exercise, certainly for the early to mid-stages of a business's life. Because as much as it's not all on the CEO, the CEO is at the top of the org chart and people want to hear it from the CEO. They want to know that the CEO can lead this business effectively.
So inevitably, they are the ones that are front and center in the fundraising process. But equally, investors need to know that there's depth, right, so you actually want to make sure that they can understand that there is this great executive team and that it's not all down to this, you know, one. One person as a CEO. As businesses get bigger, and I don't know what I mean by bigger, but certainly recently I've seen businesses raising C-RUNs where the CEO wasn't actually the primary actor.
It was CFO And sometimes it'll be like a chief growth officer or something that actually was running the fundraising process with the CEO popping in and saying hello to new investors. Quite interesting. But generally, I would say CEO is the lead. But obviously, the CFO is typically the primary partner if there is a strong CFO.
But there's generally eight partners. It's either going to be a CFO or a COO that are really fundamentally running the funding process together, the raising. And then this idea of a Series A moving on to a Series B, and your Series B is let's say 30 million pounds, 35 million pounds. So it's a decent size Series B.
And this question that comes up, which is, I have been a Series CCO. I think I've done a reasonable job of that. We're locked and loaded for the next fundraise and that's the expected amount. How does my job change?
What should I expect in this next round? So if I was to evolve as a CEO properly, what should I be thinking about here? When we go back to your. Framework is a particular aspects your framework that are more front and center when you move from a to b size if we go right.
We raised, if you think about how funds typically, and we think about the typical reasons for each of the funds in the earlier stages of tech startups, you raise a seed to validate problem solution. You raise an A when you've kind of got product market fit, right? So you sort of, that seed A phase is validating problem solution fit and then validating product market. When you raise product market, I mean, this is somewhat traditional definition now because things have moved around a little bit.
And then you go on to raising your B when you think you found go-to-market fit. You then use your B to find a scalable, repeatable go- to-market motion that gets you to a point where you can raise the C, and the C is apparently where this huge chunk of cash arrives into this highly predictable machine. And, you know, we just basically rinse repeat on a three times scaled model and everybody's a winner. The point is...
That at each stage of the, at each raise, you're proposing that the business will be, what the business would be optimizing for in that next period. So let's say it's 18 months of money or 24 months of the question is, what's the business optimizing for? What are we trying to learn in this new period? And hence, what are we going to use the funds for?
And starting with that question, you can equally think about, okay, so what's CEO going to need to do. If the answer to what are we optimizing for in this next process is, let's say it's a B, which means we're going to now be working towards finding go-to-market fit and subsequently go-do-market repeatability such we're gonna be able to raise a C around, what's that gonna take? Well, let's look at our team now. Let's say hypothetically you've got a CEO and then you've got a, I mean, this is somewhat extreme, but just to make the point, let say you've like two reps that report directly to a CEO because it's quite a commercial CEO.
And then the discussion needs to be, okay, but is that structure, is that level of sales leadership, both in terms of the amount of time the CEO can spend on that function as the leader or indeed the CEO's real experience in scaling a sales organization, is that sufficient to get us to a C-RUN? The answer might well be no, in which case the CEO should stop doing that. And what the CEO would do very soon, like rapidly after raising, is recruit an appropriate sales leader for that stage of the business's life.
So the CEO must hire a great sales leader working with people that can help them do that and then not do that anymore. So the CEOs job will no longer be directly running sales. And you can go through all the other functions in the business based on what are we raising this round for, hence what does the business need, what does business need to look like. Which naturally tells you what the CEO should and shouldn't do.
Does that make sense? Is that a fairly deductive process? No, that makes complete sense. Go ahead.
I'll just overlay that with, and as we go, the CEO should be doing less functional BAU stuff. They should own less daily cut and thrust for the business. Why? Because we don't want to fall into this trap where there's a CEO that becomes a pinch point in the business because they're accidentally still owning too much stuff and the business is now waiting for the CEO to make decisions.
And we've created a lag in the ability to evolve and execute, particularly challenging when you've started hiring great, more senior leaders who really don't need to, don't to constantly have to go back to a CEO for permission. They want empowerment. Which can only work as a strategy, going back to the five functions of a CEO. Clear strategy, clear operating model means you can empower your executive team to go off and act somewhat independently because we've fairly assured that they know what the plan is and we've gone through a process of hiring and observing them that suggests we can trust them so they can execute more in parallel.
And then I guess the operating model also includes what good looks like, the values, the expectations. Cause I feel like a lot of times CEOs become the bottleneck, but they want to sign off on absolutely everything because they don't trust that others have the same eye that they do. I guess I'm thinking like marketing ways or the, you know, the right colors, the rights slogan. Etc.
So it goes back to a combination of operating model and the right top team. Do you have a team that you can trust? Yeah. And also that CEO needs to observe themselves.
Who am I? What are my issues? The control freak isn't going to fail as a CEO if they're self-aware. Why am I a control freak?
How can I get over this? Do I have a disproportionately low level of trust in other people's ability to get stuff done properly? Okay. How do I work on that?
Because the logic is simple that you're going to build a much smaller business or you're going to take much longer to get to success if you do it all yourself. So, but you see that a lot, you see fairly high levels of control, so, yeah, there needs to be a very conscious observation of themselves as CEO. Cause you see high levels of control and then you also see CEOs referencing Steve Jobs or well mostly Steve Jobs. I'm not sure who else was like, look, he was really controlling.
Everybody was afraid of him and he built Apple. But he must have trusted people, right? Cause he didn't build it himself. He didn't do everything himself.
You know, certainly the British design guy, I can't remember his name now. I mean, he, Steve wasn't telling him what the design should be. I don't think. So going back to, this isn't actually a COO problem, necessarily, or a COA CEO problem, but it's more a product CEO possible problem, which is founder CEOs tend to be the product visionary, hiring a good product person that will work with a CEO, that's a hard one to get right.
Yeah, may I? Yep, that's my question. I know there was, but yeah, assume the question in that. Look, yes, you're quite right.
And I've seen this. So what happens is, the CEO is the product visionary. The CEO is chief product officer for years, right? They effectively run product.
And at some point, they or others convince them or they convince themselves that they just can't be doing that anymore. There's just too much other CEO stuff to be done for them to also be the daily custodian of the product vision, right down into the minutiae of where button should go. And so, they decide, right, it's time to replace myself as the leader of product. And inevitably, a smart, capable founder, product visionary CEO's gonna think, well, I must replace like for like.
I'm only going to relinquish this task to someone who is my equal. And off they go, and they spend years finding this unicorn, and then they find them, and they have a huge love in. It's a honeymoon. It's beautiful, they love each other.
And then, what happens is, the new person naturally starts to share their views because they're going to disagree, right? It's very unlikely they're gonna completely agree. And so this new, strategically highly capable product leader starts saying, well, actually, I think X, Y, Z, we should go in that direction. And they tend to really dislike each other now.
And one of them leaves, I don't know, the CEO. So the trick is, I think, to hire product people or the first product person or the early product people that are, yeah, they need to be smart, obviously, and they need to have their own view of the strategy, but they should really be hired for their ability to take vision from a CEO. By the way, I think the CEO, particularly Founder CEOs, Product Vision Founder CEO's, I think they should always be very, very close to product strategy.
I don't think they can step away. I mean, it's just too fundamental. And actually, I make that case for the non-Founding CEO as well, because that's what you sell. That's what people use.
It's fundamental. Everything else is a complete waste of time and money if the product strategy and the product is wrong. So you always want them very close. So you want to hire product people that are smart and able to deliberate with the CEO and debate, but fundamentally can take vision and turn it into product strategy, product roadmap, chunk it down into the appropriately sequenced, well validated you know, pieces of functionality, and then organize a high-functioning relationship with the engineering team so that the product and engineering functions are well integrated and can execute on a product strategy.
You want an operator in product, and if it's the first hire or the second hire, you don't just want them. You don't want somebody that's overseeing product. You want a doer, a product manager or a product owner, but that are operators that know how to orchestrate a product process. Product strategy, product roadmap, relationship with engineering and work well with engineering.
You don't necessarily want this intellectual strategic sparring partner this year. You want them to be able to debate with the CEO well enough to sort the wheat from the chaff because, let's face it, sometimes this idea machine, the CEO, is going to come up with half-baked ideas, and we don't want a product person that's saying, oh, wonderful idea, wonderful idea, let me build that. There needs to be a gate, and that gate also needs to include decent validation with other stakeholders, other members of the team, customers, etc.
I have seen this go wrong a number of times in the process that I just described where a CEO hires a perfect product visionary person as their first product hire or their CPO or something and it's a disaster. Well, that actually brings me to a question maybe for you, like in your relationship, Brandon, because Brandon's a COO whose background was originally product. Do you find yourself doing some of that operational work with founders, like product operational work, Brandon?
It's fascinating I find myself not really doing that so to be honest for the most part I think over the past decade or so when there's been problems in product for whatever reason I've taken over product from a line management perspective to sort things out effectively and that's happened once or twice but beyond that I've always taken a step back from product and primarily because I'm not super interested in product these days, quite specifically, I'm much more interested in the horizontal operating system, how the revenue machine predictability-wise is working or not working, just from a personal interest standpoint, those are the two buckets that I find more fascinating, to be honest, in strategy as well.
So the whole product side of things, I tend to leave alone unless there's an actual problem where I legitimately need to step into to help in some form. So just getting back to your two frameworks, we have working on the business, working in the business and we have your five layer and five bucket framework as well. How do you distinguish between the two in some sense? So if you're working on business, bucket number four, which is kind of looking at market dynamics outside of the company, that's a bit of working on-the-business per se.
And there's some element of strategy which is also working on in the business. So when you think about those two frameworks can maybe just that be a little more clear in terms of the on versus in and how that relates to the other framework. For each item in the framework, I mean, let me just be clear here, these are just kind of rough sort of tools that I use, they're not peer-reviewed, highly researched pieces of the theme. You know what I mean?
I'm not using this podcast to attempt to launch a business book with multiple frameworks by Keith Wellington. That is not what I'm doing. So if you think about, you know, setting strategy, hiring and overseeing the best possible team you can, having a great horizontal operating model, observing and special projects, each one of those things can be done in multiple ways. In some instances, the CEO should do them directly themselves.
In some instance, the CEOs should not be doing them, but should make sure there are people that do them. So that's where the two kind of interact. So on the business versus in the business, for example, horizontal operating model. My suggestion fairly early on in a business's life is let's make sure it exists and let's make sure that it's just enough for the business.
I love the phrase, we started using it when I was at Mimecast, just enough structure. In the very early days, let's just make sure there's a horizontal operating model that has just enough structures. CEO could probably do that themselves and there's couple of tools that I like to use that are pretty simple in that regard, one of them being Lencioni's Advantage model Which I'm a big fan of. But as you know, 18 months later, and you've got, I don't know, 15 more people and there's a bit more complexity, maybe it's time to get that chief of staff to run the horizontal operating model and make sure that goals are being tracked and teams are glued together, etc.
So does that give you an idea of how they work together? My key thing with Onverse N is, is the CEO actually doing the things on a daily basis that are most important for the CEO to do? Or have they actually got trapped in some busy work? Actually, they just shouldn't be doing that stuff.
Yes, they did it 12 months ago because there was no one else to do payroll, for example, but that's not what we should be doing today as a CEO when we have at least one person in finance. So I use the on-verse-in thing to make sure that CEOs are doing the things they should be at this stage of the business' life. And that will involve all five of those functions, but there'll be various levels of being the doer in each of those things, depending on where the business is at. And then a quick follow on, so the, the, in the business part of it, where they've done it 12 months ago and they did it their way and it was the right way and so on.
For that CEO that continues to work with those people that are now taking over those different functions and responsibilities where effectively they're kind of checking their homework and they're catching them out, so to speak, where it's like, okay, You know now you're doing payroll. But by the way, I think you missed this account over here, and this over here is missing whatever number type thing, and the feedback may be legitimate where in fact something actually was missed.
How do you respond to that kind of CEO's thing to the look, you know, you may be catching things, you may check your work in a way where you feel like you're being helpful, where in effect it's not, and here's the reason why. Yeah. So, you know, there's this phrase that emerged over the last couple of years, which is trust and validate. So you recruit people, you make sure everybody's aligned to the same strategy, partially because they co-authored that strategy with you and it wasn't just foisted upon them.
And then everybody's clear on how we're going to operate. And then everybody goes off and does their jobs and they regularly review and interact with each other. So everybody's on the same page. And of course, the CEO is going and have chickens with people.
And they should be checking in with people and in those check-ins they might discover that a thing didn't work properly and then it's a kind of a coaching discussion which is so what's up with that you know what went wrong how do we avoid it again you know why did it go wrong how do we avoided again is there a change in a process is there skills issue you know etc etc but there's another factor here which is CEO needs to think about the balance of experience in the business so if we only hired people that were doing their jobs for the first time The business will evolve at the rate at which these people learn how to do their jobs, and the business will suffer all of the experiments that those people will run and many before them doing the same job to figure out the right approach to doing that thing.
Equally, if the CEO only recruited highly experienced multi-journey veterans, they might lose the, they might lack the plasticity and the creativity. That comes with people that are seeing something for the first time and don't know what the woods look like. They just know, I don't want to solve this problem like no one has solved this problem before. So there needs to be a balance.
And I raise this now, Brandon, because it touches on your point around a CEO identifying an error in payroll. My view is it's unlikely that CEOs are going to know how to do payroll better than the person who's doing payroll. If we have a situation where that is the case, we have problem. There's kind of common sense and smarts and logic, but really...
The research, I'm going to who did it and how long ago, but there is pretty strong research that says don't labor your business with unnecessary risk by recruiting too much first-timer. You need the balance and that is a massive, massive de-risking exercise and I've been a part of doing it. Subconsciously, we didn't know we were doing that and I'll say it's MIMECAST because the topic has been studied and it turned out that MIME weird because we didn't realize was actually one of the businesses that seems to have recruited more experienced people much earlier in its journey than the average.
And I think that played out very effectively, except in some places, which is a topic of another podcast. But, you know, Kelly, the business was a great success and continues to be. It's really important that CEOs think carefully about the balance of experience in the team. And it also plays back to the profile of the CEO.
So talking about the control freak CEO, as we did a few minutes ago, the control free CEO might be more predisposed to recruiting juniors because juniors are easier to, frankly, control. Also... It's possible that the control freak CEO can't recruit more experienced people because the more experienced I'm a full-blown adult now, so I'm not taking this role. It's really important that CEOs are very aware of themselves, so the kind of observational work that we do by going through these frameworks, and I'm also a big fan of personality profiling, should help a CEO understand who they are so that they know how to manage their own behavior so that can achieve those five functions most effectively.
I think there's another part that I'm starting to find as being a CEO, which is a very quickly perspective taking is a lot easier than it used to be as COO because there's just everything ends up with you and being able to see the full perspective, the mess up in payroll suddenly it's just not very important compared to... The person who just signed off 150,000 pounds on something random and how in the world were they able to sign it off? Like the three pounds in payroll is not an issue.
And I don't know if that coming in, look, I'm not a controlling CEO, but also maybe just like stepping into more complexity has made it very fast for me to see perspective. And do you see that in other CEOs, that being able to see what matters and what doesn't becomes much clearer. Um, no, I don't, yes, but not as a, not as a rule, but interestingly, I've worked with quite a few people. Well, I mean, most people, their first job wasn't CEO, right?
So actually we've all worked with people that have had lots of jobs before they became CEOs, but I have worked with quite a, few people in the last couple of years. That weren't the founding CEO, but are now CEO for various reasons, sometimes in the business that they co-founded and they all, well, the majority of them. Seem to go through the process that you describe which is wow my whole perspective has changed my sense of what's most important right now and how i wrap my hands around it is changed.
I don't think that discredits the others in the team or other roles i think as you say you have you have a great altitude and you have more information on a daily basis and frankly probably more of a sense of responsibility notice i was less responsible you know you're the CEO of the backstop to you. Yes, that will happen, but isn't it also because just having the job CEO makes your brain shift that way? I mean, you're just naturally thinking, okay, it's on me. As a COO or a CPO or CTO, you might well feel like you're one of the custodians for a business, but I suspect when the job title changes to CEO, it is quite a fundamental psychological shift.
There's that, and it's also just, even though as a CEO, you see the brets of the business, you just see that little bit more brets and just see all of the things going wrong all of the time. And you're like, oh, that's not really like, yeah, it's fine. That's your problem. This is the thing that's like the really big issue that I need to focus on.
It's that higher level of perspective, I think, is interesting change. Look, I think it's very person dependent. It's also the dynamic of the CEO versus the COO or the personality type of the CO versus the other people in the sort of key leadership team. You naturally play to what the business needs from you.
So for example, when I was COO, CXO at my cost, I mean, I'm quite a strategic person. I know from my previous work and my career that I'm a strategist. Peter Bala, the founding CEO of Mimecast, I would say, is an exceptional strategist. He's very good at a lot of stuff, but he's really strong in strategy in many facets.
When he and I were together, either physically or just both operating in the business, I didn't feel like the business needed to hear from Keith as another strategist, I mean, yes, I was running some strategy stuff and I think we made some good strategic decisions, but I was naturally more the operator. My brain almost a sort of invoked operator, Keith, when I was next to Peter, because, you know, he was clearly in strategy mode. And so you kind of wanted to, I wanted to balance him.
So, okay, well, like, that's the strategy. What do we do to put that in place? How do we execute on that? How we operate the business to bring that to bear?
And I think, I think a lot of us just naturally do that almost, almost subconsciously. So, Beth, you're going through the counter sort of flow, which is moving from COO to CEO, you thinking, okay. So I need to invoke more of that, that more sort of strategic, high-altitude horrors, you know, almost looking at the horizon and seeing the bigger picture where the operator is tending to look at from your feet out to... The middle distance.
The CEO almost maybe naturally is looking at the middle distance up to the horizon sometimes. Yeah, I think it's that. And so it's like, that's fine. So Keith, we are running out of time, unfortunately, but I have a final question for you, which is if our listeners can only take one thing away from today's episode, what is it?
I would say if I have to pick one, it's be very clear on what your business is optimizing for right now. What are you trying to figure out over the next 18 months? And design your strategy and your operating model and your team for that. Don't just sort of rinse repeat or think you just kind of need to keep evolving in the trajectory you're on.
Think very clearly around what are we trying to optimize for over the 18 months and design for that? Love it. So that is a wonderful core question that I will be contemplating post this podcast as I roll into our kind of series B round myself. So thank you, Keith Wellington, for joining us on the Operations Room.
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