Emily Lincoln-Gordon - Being Effective in an Interim Leadership Role Without Dropping the Ball
Holding a C-suite role requires plenty of energy and effort. I know it did for me. I couldn’t imagine juggling two at the same time. To learn more about what this experience was like I spoke with Emily Lincoln-Gordon who held the COO and interim Chief Product officer (CPO) roles at the same time while at Attest.
We talked about:
What she enjoys about the chaos of scaling startups
What it takes to be an early stage COO
Handling organizational transitions
How she thinks about saying no
What was most challenging about holding multiple leadership roles at the same time
Gaining trust when leading people in a role where you don’t have experience
We met through Jessica Zwaan when I asked on LinkedIn for more COOs for the series.
Yeah, she did a classical COO-style recommendation. Instead of adding any context whatsoever, she just tagged my name and nothing else, which is the most efficient way of saying: speak to this person.
So COO-like. I have operational things to do. You can read. You’ll figure it out.
Exactly. “I don't have time for this. You two have the context.” (laughs)
That's a really good point. There’s something I love about COOs. We're so operational trying to get things done that you find those efficiencies wherever you can.
It's true, it's very natural, I think.
Yeah, yeah, there is a particular type of person who is a COO though if you’d told me earlier in my career that I’d become one I would have been like, “Me? No, no.”
I think I probably would have said the same. The thing that you hear about COO is that it always used to be that you have to be a Management Consultant, which sort of made my bones shiver a little bit at the time. The other thing that you always get told is that they don't like chaos, they really like order, and they really like things to be a certain way. They’re the kind of people who wrangle that stuff so they naturally really like process.
Whilst I do like a bit of process and I write my shopping list in the order in which I know the items appear in my supermarket (that is who I am), I also didn't think I'd enjoy the chaos or wrangling of chaos the way I do. Or that I’d repetitively go back to want to find more chaos. As soon as something is sort of in a good place, I immediately ask: “Okay, what's a mess? What else can I touch that's messy?” I never thought I'd be that person. I used to be a lawyer, so thought I liked things to be in a neat and tidy order; that I liked certainty. Turns out, I like the process of getting to that clarity, and don’t find joy in the end result as much as the journey to getting there. Type 2 fun.
Isn't that funny? I too love wrangling chaos. Earlier in my career I used to say that I bring clarity to chaos. I love scaling businesses because there's chaos. I like process, but I don't actually like too much process. When it gets too much, I'm like, “Okay, now I'm out.” But you're right, they’re pretty comfortable with chaos, even if they want to improve it. It doesn’t freak them out where they’re paralyzed.
We’re going to have a great conversation. But before that, can you introduce yourself?
Of course! My name is Emily Lincoln-Gordon. Professionally, I'm a recovering lawyer turned COO. I always like to say ‘professionally’ because what I do is not who I am. Given what this chat is about, I’ll talk a bit about that ‘doing’ aspect of myself..
I've spent the last 10 years building and managing teams in startups across a number of different industries and functions, first as a General Counsel (the most senior in-house lawyer in a business) and more recently as a COO. In recent years, I’ve become quite vocal and proactive about the experiences of professional women in tech, and what good looks like. I am an Exec Coach and Fractional COO now, and spend a fair bit of my time mentoring and coaching women at different stages of their careers from mid/senior to Exec on how to show up for themselves.
Before all of that, and what feels like a previous life, I studied Fine Art - I retrained as a lawyer a bit later on. I actually didn’t do my homework at all before deciding I would become a lawyer, so had no idea what it involved. This is worth the tangent, because it’s somewhat symbolic of how I see the world, how I make decisions and as a result, my entire professional career - and what I now coach women on: just decide you will do the thing, figure everything else out later.
After my Art degree, I enrolled on a 2-year condensed LLB Law Degree in the UK (you effectively do your final year during the two consecutive summers) and I thought - I’ll do these two years and I’ll be a lawyer - awesome. Absolutely not how it works. I only found out once I had started on the degree that after finishing, I’d have to do another year-long course called a Legal Practice Course (LPC) followed by a 2-year Training Contract with a law firm, which remain notoriously hard to get. The Head of Faculty told us on our first day of school that we’re all more likely to win the X-Factor than get one. It didn’t help that the law school I went to was in the bottom of University rankings, relatively unknown, and certainly not widely respected - but hey, the material is the same and I’m a case study in not letting that affect you.
Fortunately for me, I’ve always been a dangerous combination of single-minded, anti-authoritarian, yet unhelpfully unafraid of failure or change. So hearing her tell me something isn’t possible, I decided I would get a Training Contract, just to make a point (I wasn’t even sure at the time I wanted to do the training if I secured it). So I applied to one law firm, went through the process, and was given a Training Contract. I’ve made it sound easy there, and if I am honest, for me it was - but so many people don’t have that experience and it really can be tough out there. I have always felt there’s something to be said about betting on yourself, and genuinely believing it is possible.
I sat on my offer for a couple of weeks debating what to do, and eventually figured it wouldn’t hurt to just do it (as it turns out, it was in fact pretty painful). But I finished it, became a qualified lawyer and for a brief period afterwards was an International Commercial Arbitration & Litigation lawyer (what a mouthful) in private practice at a Silver Circle firm. God, I hated it.
I moved in-house really early on because I looked at the Partners as soon as I qualified and thought, “That is the cart to hell, I'm not getting on it.” So I left the firm at just over 1 year qualified, and went in-house because it was a compromise with myself: stop lawyering, or try in-house first. I got really lucky and found my way straight into startups.
I went into an ed-tech startup called FutureLearn that was a relatively safe bet because it was backed by the Open University. It was a pseudo-startup in that it operated like a startup and it treated itself like one but it didn't have the financial instability or pressure of a VC-backed org. This has drawbacks (mainly bureaucracy) but I didn't really know that at the time, so it didn't really matter to me. It was miles better than where I was before. Since then, I've worked in a number of different industries, ed-tech, developertech, martech, but I tend to gravitate towards the creative chaos that reigns in a Series A to B, maybe heading up to C stage company. Once you get to 250 heads/post-series C, I'm usually just less interested in what lies ahead, and so naturally less of a strong fit. I don’t find as much joy in a role where the primary function is maintenance, not building. I love that solving-the-original-problem energy and the type of people that are attracted to early stage companies. It’s like we all know and appreciate that slightly different form of madness that only exists at early stage companies. I really like those folks, so I keep returning to find more of them in new places.
As of right now, I left my last role (an Interim/Fractional one) at the end of 2023, and I'm now building a fractional operations and finance business (The Ops People) with two amazing women I’ve worked with for a while. We work with early-ish stage companies in need of operational and finance capabilities, but not as full-time hires. It’s for companies who want to build something high-quality/mature regardless of their size, and in such a way that attracts really good talent, right from the start, because it doesn't have to feel like a scrappy startup. That's always the issue, right? That doesn't have to be true. You can do things in a way that's sort of proper-ish enough that it represents you and it represents a mature business, but you maybe don't have someone in-house who can do that or it's not worth investing in a COO, People person, or your co-founder isn't naturally that type of company and team builder. So we come in, do some of that foundational stuff, and set them up to be self-sustaining or help them hire someone less senior to maintain and evolve those foundations. A little goes a really long way when done well from the start. We’re all ex-operators so understand how to design but also get this stuff done in a way that works, and sticks.
I don't think it's necessarily true that everybody in a position of power is someone who wants power. I think sometimes a position of responsibility is one you find yourself in without design, but you choose to accept that responsibility, and you do the best you can to serve those that entrusted you with it. The best leaders I know are aware of the power they hold, and find it a bit scary to hold it. So you're constantly thinking, should I be holding this? Those high-integrity, low ego people that question their own power all the time are the best people I've ever worked with.
You have an interesting path. So how did you get into leadership? What was that first leadership role? What was it like?
A whoopsy daisy, I think. I mean, let's define “leadership” because I'm a lawyer, and I like to define things rather than assume a shared understanding. When you say my ‘first leadership role’, I'm hearing my first formal one where someone gave me a title and assessed me as someone who should lead and manage other people rather than, you know, the ways in which you do it in a sort of more informal way earlier on in your career?
Yes, I mean titled. It’s not that you can’t lead without a title because you definitely can but I use titled roles because the mechanisms and pressure are different.
Exactly. It's different, for sure. All of a sudden, you're accountable for it, right? I say I whoopsie daisied into it because when I went in-house from private practice, I was the sole counsel and the first UK qualified lawyer into the business. That’s unusual because there was no one there to supervise me, formally. My manager was great - she had qualified in the US many years ago and had not been practicing for quite a long time. She was a Business Development tornado, and so I was almost self-governing and unsupervised from the get-go - scary.
In hindsight I do wonder: who thought that was a good idea? By some miracle, that was okay though. It worked, but I was trying to figure things out as I went along: “I haven’t done that before, but let me work that out.” I relied so heavily on my (new) network of in-house lawyers, the people who were far more qualified than me working in startups already (in a network called the Disruptive GC Network (DGCN)). There are a few that I’m forever grateful to because without them realising, they actually taught me how to do the job of being a really great business advisor, not just how to know and spout the law…
So I always feel I need to be honest that I fell into leadership by being de facto responsible for all things legal for this company. Then all of a sudden the company started growing quickly, and the needs started growing, and we were doing quite well - so I needed more lawyers to support the workload. I had to hire somebody and all of a sudden I was the Head of Legal and had to figure out how to do my day job, but also how to help these other lawyers do their jobs and be happy at work, which was a really strange process because it's not something I looked for, nor had any formal training on - it was sort of something that happened quite organically over time, and I so enjoyed seeing these folks succeed (I appointed my first hire as my successor just before I resigned), which I suppose is the start of all that followed.
So it wasn't something that you had as a career goal.
It's a really fun question that one, isn't it? Because I have to be honest with people when they ask me about that - the forward planning aspect of my journey.. I don't have any career goals. I didn’t when I studied my first degree in art, nor when I went back to school for law. I still don’t. It's not that I'm unambitious - I am very ambitious. It's just that I don't have a specific title, or milestone or something else I need to be or become at any point to feel fulfilled professionally, and I don’t have a plan.
It’s served me really well to be totally open minded about where the things I love / dislike doing lead me in terms of my career. For example, I'm extremely biased toward action, I give 100% of myself to whatever I am doing so need to enjoy it, and I am not good with imposed authority or snobs - I don’t like being told what to do, instead of having a discussion based on reason, merit, logic and I can’t stand when people rely on the argument that it’s ‘the way things are done’, ‘the way things have always been done’, or people are disrespectful in how they view other people or express their views (basically, I don’t work well with jerks) - all are like kryptonite to me. So in terms of career choices, what I’ve always done is optimise toward or away from those big things I know about myself and what I enjoy/dislike day to day, and I honestly do not consider what title or role it will lead to, save for the fact it needs to make sense as time progresses and needs to do me/professional women justice. I care about the work I’ll be doing, the environment I’ll be doing it in and perhaps most of all, who I’ll be doing all of that with and how it positively impacts women who come up the ranks after me. My career goal has always been, and will always be, to love coming to work and never have the Sunday scaries.
Yep, me too. Same.
Maybe I should have known it would end here (being a COO), but it wasn't something I sought out actively as a goal with forethought. I’m actually always suspicious of the people who say they ‘really want to lead people’. Why is that? Why do they want that? Is that about perceived power, or what is that about? Everyone always says their ambition to manage or lead is because they want to help and support people and grow them, etc. I'm like, cool, “Why though? Why is that? What about that is it you enjoy?”
So I don't necessarily think it's negative when people don't have a five-year plan or something like that, because I didn't/don’t and I've done quite well for it, in that I’ve enjoyed my career and my day to day up to this point immensely. I think if you're seeking out really specific experiences, which is what I've done by looking for environments and people that are optimised toward the things I love and away from the things I don’t, it tends to end up okay for most people in terms of role and career. Just be sensible about showing up for yourself while you do that.
That's my core belief and I say it a lot – people tend to be really good at the things that they really enjoy. If you find yourself in the right environments, or you leave the ones that don't serve or value you, like private practice for me, then you will invest more of yourself for your own sheer enjoyment. In turn, people will appreciate and elevate you for doing those things well. And then give you more of those things to do. I don't like the word lucky. I've been fortunate to see those opportunities and be there to take them, but I also know none of that works out without just working really bloody hard, too. I was never thinking, I need to get to “Head of” and I didn’t think, “OK, now I need to get to GC”... I need to do this, I need to do that… It's just not what drives me.
I want to be clear though: I have definitely asked/fought for a specific title or promotion, because I’ve felt I deserved the recognition, reward and permission that comes with it and as women, we often have to ask or it won’t happen, but that’s usually been a type 2 promotion: where I’d been doing the role for some time without the recognition, and was asking for it to be rectified retrospectively, not where I had it on my career ladder as something to tick off. It’s not the way my brain is wired.
I’m nodding along because same – I’m very driven but I’ve never had a career plan. I mean, now I have some shape or outline of where I want to take my career but I’ve never had goals or five-year plans. Like you, I just followed my interests, where I could have an impact, doing things with people I enjoyed. I never expected to find myself the COO of a developer tools company.
Right? Exactly. That's kind of how I felt about it. I was like, what do you mean I now do this? Are you sure? Are you sure I should be doing this? Oh wait, I think I might be good at it, actually.
I ask because there’s this belief that everyone wants to get into leadership for power. I don’t necessarily think that’s true. Some do, but lots of people don’t. I interviewed Lilly Chen who describes herself as an accidental CEO. She even tried to give the role away and no one else on the team would take it so she had to keep it.
Yeah, I do think those are the best people to work with. The people who are there because of their skills, experience or whatever it is that lends itself to that moment in time. The ones always looking to share or abdicate power to others they trust are people with high degrees of integrity, and I love working with those types of people. I totally agree with you.
I don't think it's necessarily true that everybody in a position of power is someone who wants power. I think sometimes a position of responsibility is one you find yourself in without design, but you choose to accept that responsibility, and you do the best you can to serve those that entrusted you with it. The best leaders I know are aware of the power they hold, and find it a bit scary to hold it. So you're constantly thinking, should I be holding this? Those high-integrity, low ego people that question their own power all the time are the best people I've ever worked with.
On the flip side, of course, are the people who just wanted the title. Once they're there, they're just trying to figure out how they can make the very most of the fact they worked hard to get it, which is not necessarily a healthy motivation.
100%. I’m getting us off track because I’m so excited about this conversation. Most of the COOs I’ve met never really wanted the title or the power. Most of them think a lot about what needs to be done from the org and business perspectives.
I agree. The COO role is exceptionally demanding. It requires a deep internal drive to tackle an extensive to-do list efficiently. Vanity has no place here; it's about delivering what the organization needs. Those who excel in this role naturally empower others and tend to prioritise that organisational-enablement stuff over personal agendas. I do think you have to love the day to day of this role. I know someone who returned to their previous role as General Counsel after realising they didn’t enjoy the COO position they had moved into - and I have so much respect for them. It is a decision that is driven by low ego and high integrity, ultimately doing what is best for the business too, and I don’t know many folks that would make it.
Right, it’s also hard because if we’re doing our job right you don’t notice us. But if you’re not, everyone is unhappy. So you’re operating in the background making sure things run smoothly and there’s a different sort of pressure that comes with that.
Absolutely. It’s that famous Futurama quote: “If you do too much, people get dependent on you. If you do nothing, they lose hope. When you do things right, people won’t be sure you’ve done anything at all.” Such an apt summary of many operational roles, including the COO role.
It reinforces what we said earlier: the satisfaction in your work needs to stem from the work itself, not from others' perception of your responsibility for it, or you’ll be pretty unsatisfied in this job.
As a COO, you need to be very internally motivated because noone’s going to thank you. Folks might praise you occasionally for something specific, but mostly you’re not going to be visible or receive recognition because you’re not shipping anything, you’re not racking up revenue numbers on a leaderboard - you’re not doing anything visible most of the time. So if you don’t get joy from the sheer act of doing, or you need a lot of praise and validation, then you might struggle in this role.
If you do end up in a role like that, do all you can to make yourself redundant in that role from day one. Find efficiency gains, whether by process or through enabling people around you. Focus on replacing yourself (in the interim role). The CEO might be praising you and things might be going okay, but I assure you that someone qualified who chose that career path will do a far, far better job than you (or I).
You went from General Counsel to COO. What was that transition like for you?
You would be shocked wouldn't you, if I said: “Really deliberate, very strategic”. Well, it wasn't. It was quite organic. I'd been with the business for a while. I joined when there were 35 people. I came in as their first lawyer and sole counsel and worked closely with the Founder and Co-Founder. It was the three of us running and building the team and business for quite a long time.
Then we expanded to the States. Hiring for a General Manager for our New York office, folks were confused in interviews with me, and performed poorly. They were showing up to interview with the GC, prepared to talk contracts etc. and instead I was asking them questions like, “What's your management style? What motivates you? How do you handle these types of situations with people?”. The questions were much more about how they’d run a business themselves, because that's essentially what they were going to be doing – running an extension of the business for us in another timezone.
My title as GC was setting those people up to fail; they were unprepared and performed poorly every time. The three of us sat down as a leadership team to unpick this a bit, and ended up changing my title to GC&VP Operations, to more accurately recognize the job I had been doing there for some time, and remove that confusion. It was driven by external factors, and it made sense to change it to stop folks from failing through interviews for no good reason.
So I became that for a while. I really believe in that type of title change because it’s a signaling thing - so that people know what you actually do in an org, which is the only function that I believe titles should serve: clarity for everyone on what to come to you for, and what to expect from you. So I held that title for about a year, and rapidly began picking up more and more of the operational parts of the business, while simultaneously the first legal counsel hire I’d made 18 months before was absolutely excelling in her role and rapidly becoming more of a GC than I was at that point.
We were growing in headcount, too. Our Co-founder - who was originally the COO - had built and grown the engineering/technical teams from day one so he was sort of the de facto CTPO rather than what I would at that point have considered the COO just in terms of focus and responsibilities. I think it is actually quite common for the Co-founder to be called COO while actually running engineering or product in the early days. It had, however, grown confusing again for folks internally - people were no longer clear on what to come to each of us for, and what to expect from each of us in terms of remit and decision-making. When that lingers, orgs become inefficient and frustrated.
My view here (and it is personal) is that the right COO for an org is the person with the most complementary skills required by the CEO to run and grow the business in the best way possible during whatever time period you’re in. It had been the Co-founder for a very long time. But by that point, it quite organically had become me. So we had an oddly uncomfortable but (in my view) mature conversation about our respective roles in the organization and what would be the right thing for everyone who works there today, and will work there in the future. What role distribution serves clarity and permission and minimises confusion. That culminated in the Co-founder becoming the CTPO, and I moved into the COO role formally. I can't say that that was an entirely smooth process as human dynamics never are, but I'm so grateful to the two of them for how they handled it.
The organisation met the change announcement with “Were you not already COO?” so that was nice validation from my perspective that they welcomed me into the role and nobody in our teams was upset by it.
Did you bring it up or did you all recognize it together that a change was needed?
I brought it up.
There are a few reasons I brought it up, but a really big one was that about two and a half years prior (about six months into my own tenure),I had hired a couple of lawyers. One of them was an exceptional lawyer called Amy, who by this point had just become much better at the job (of GC) than me. I was still technically the GC and the VP of Operations, but Amy was running that show single-handedly, including managing the team itself. She loved it way more than I ever did, too. She's also the most humble person I've ever worked with and just happy getting on with her job - she never actually asked for a promotion or what her pathway was, which speaks volumes of her and I really didn’t want to take advantage of that, or let that be a reason she is overlooked. She already had all the freedom she needed to run the team, but at the same time, I thought, “You're the GC. Why aren't you asking me for that job and all the doors that open for you in your career?”
So I went to the Founder/CEO to chat about the internal confusion at the org that I described earlier, while also raising the issue of wanting to make Amy the GC – I wanted to move her into my job and I needed somewhere to go. In a way, these challenges came together symmetrically as push/pull reasons to make some sort of change and recognize what had already been happening in practice for some time, and I just needed to bring it to the Founder’s attention so we could begin resolving it formally.
Right, right. The title was just lagging behind.
About six to eight months behind, yeah.
Sometimes it's hard for us to recognize it or it takes a forcing function to get us to get those things in the right place.
I think so. I also think it comes back to the thing of me not being that fussed about titles for the sake of titling - it’s really about what they represent and what they permit. The GC title is pretty cool. It tells you where that lawyer sits in the organization, such that you know that they’re the most senior legal person, and they have ultimate responsibility to be able to decide on something. The permissions I had as a GC to do what the org needed were pretty wide ranging. I didn't need anything else and the COO title didn’t change what I was entitled to do at the org. I had access to everything already, even a seat on our Board as a Company Director. Practically speaking, the COO title meant I could get access to my COO peers because I was legitimately now one of them, and that has been hugely invaluable to my learning curve and sense of community. But I also believe women should show up for themselves, whether that’s your pay or your title being accurate to your position, and that was part of this.
As a COO, you need to be very internally motivated because noone’s going to thank you. Folks might praise you occasionally for something specific, but mostly you’re not going to be visible or receive recognition because you’re not shipping anything, you’re not racking up revenue numbers on a leaderboard - you’re not doing anything visible most of the time. So if you don’t get joy from the sheer act of doing, or you need a lot of praise and validation, then you might struggle in this role.
The other interesting thing is like then you were the interim Chief Product Officer (CPO) for a while.
Oh, God, yes, and I always say I absolutely shouldn't have been. Definitely not for as long as I was, but ideally not at all. We should not have been in that position. It was quite a strange and in some ways, unfortunate, series of situations. After moving into the role of CTPO, our Co-Founder decided to leave. We had an Interim VP Product with us at the time on a contract, who I thought I’d be able to work closely with (and honestly, rely on to run that Product/Eng department), but he took a perm role a few weeks later and only had two weeks’ notice. So very quickly what I had agreed to (a light touch supervision/support role as his line manager) morphed into being responsible for all of Product, Engineering, Design and UX Research. Petrifying, honestly.
The natural question to ask here is: was there nobody else more qualified to do the role? And I wish the answer had been yes - but it just wasn’t. We were in startup mode, not top heavy and had a pretty small Exec team, and very few middle managers/layers in the org. I'd already successfully held other interim roles for the business, and was a practiced generalist, so quite adept at picking things up and making them work for a time. We all agreed I was the natural choice for that VP to report into temporarily, while we hired a new CPO. Which of course.. isn’t how this worked out.
Had I known how long the tenure in that interim CPO role would be, how much we’d struggle to hire for that perm CPO, and actually just how much I would have to do in the role - how involved I became - while still holding all the responsibilities of my COO duties, building out our US presence and traveling to the US one week in every four - I wouldn’t have taken it on. Or I’d have pushed for some alternative resolution really swiftly. It took a lot out of me, because I hold myself to a really high standard, don’t like letting people down, and I don’t believe in coasting. It was suboptimal for everyone. I quickly found out just how different leading that part of the organisation is too, and had to adapt super fast.
Quite quickly I ended up in this position where we had all 5 Product Managers, a sizable Data team, a full Engineering team, and Design and UX Research functions all looking at me asking, “What are we going to do? Where are we going? What’s the plan”. I inherited these teams from an organisation that had never had any written full strategy in place; some plans yes, but not what I’d consider a proper strategy. The teams were succeeding in spite of the setup we’d given them, but they wanted something more mature now - it was a lot to wrap my head around.
This is why I say that had I known I would end up being responsible for not just those people, but the underlying product strategy and ways of working and executing - I just wouldn’t have done it. I was never the best pick for that, and although the team was so awesome and we made it work, I do think it didn’t do them justice to have me in that interim role for so long, with such a broad scope of impact.
I will also say, just generally, that no person in their right mind who should be in that type of interim role should actually want to take that role. It comes back to the empire-building thing. If I had looked at that situation and gone ‘yeah, yeah, lemme have a go’, I think you should be very concerned. It was a rock and hard place choice for the org, the teams, and for me, really.
So come January I’d been in the role for about 3 months and we're still hiring for a CPO. The reality was that we found it very difficult to hire somebody (good) because it’s a niche martech product selling to marketers and so not the sexiest industry or tool out there. Pair that with the CPO recruitment market being pretty hot at the time, it was super hard to find the combination of what the CEO was looking for and people who were happy to come to work with us. Fortunately, we decided to hire a CTO about 9 months later which was a faster process, and I was able to hand the Product & Engineering organisation over to him once he’d ramped, and refocus fully on my COO duties, while the search for the CPO continued.
I think the other thing you said already, is if you're doing your job well, people hardly know you're doing it at all. So you filled this gap in a way that was competent enough that it didn't make it feel like a burning fire.
Yeah, the reward for doing good work is typically… more work. People feel the urgency of the role-shaped-hole a lot less when you’re casually getting it all done, all without looking like a headless chicken. It’s a blessing and a curse to be able to pick things up and just get on with it for a while. As a result of doing what is effectively ‘good enough’, I ended up in this role for about 12 months, which is wild.
You’re right though, if something is super terrible you’ll move faster to fix it (so what a nice endorsement for me), but on the flipside, the reward for doing a competent job was that the recruitment process felt more relaxed than it perhaps could’ve been. And I wish I had put a bit more pressure on that being resolved - for my own sake but also the teams’, they deserved better.
As a general point on holding multiple responsibilities, it is really easy to forget what your job is in that interim position. It isn't to get good at the job, it is to safeguard the function and to be just good enough to do it whilst using the opportunity to learn more about what it takes to get the right hire in and then do that really quickly.
What was most challenging about holding multiple leadership roles at the same time?
I've thought a lot about this because I get this question a lot. People always want to know the answer to this because I think they're all evaluating if they should be trying to take on more responsibility or hold more hats, and the answer from me is always: No. You should not. If you can avoid it, you must, and just because you can, does not mean you should.
In early stage companies, we are often expected to do this human bandaid thing as COOs - step in and fill whatever gap needs filling - but how to do it without being labeled incompetent is ultimately a really difficult balance that I don’t think everyone is meant to find successfully. Whether someone in particular should or shouldn't, I am never best placed to judge, so instead I mentally break that question of whether to be the human bandaid down into three things.
The first is knowing yourself, knowing your limits and making a conscious effort to continuously keep asking: should I be doing this? And if you choose to, then spending more of your energy finding the permanent person than trying to learn to be it, or just simply being it (momentum).
I will say that not everyone is meant to be a generalist; some people are meant to be specialists and that’s great, too. But they shouldn’t do the bandaid jobs. Some people get hyper stressed or overwhelmed by having too much on or not knowing how to be quick at learning to do something outside their comfort zone - if you are one of those people, be honest about your natural constitution as a person, and don’t take it on. The teams will suffer if you do. Momentum is also a really hard thing to resist. In my case, I had led our Customer Success and Account Management function for around 18 months before this CPO situation arose, so in many ways I failed to stop and question the impact of momentum when agreeing to take on another role in addition to my existing remit - it felt like it was swapping one interim for another, so what's the harm? But that isn’t how these things work. You have to constantly be considering: should I be doing this? How will it serve the teams?
This brings me to the second thing, which is the time and energy commitment it takes to hold two of those roles. It's the practical capacity to actually execute in one or both jobs you’re performing. So to hold all of that responsibility is a lot, but to then figure out what needs to be done, and to then actually go and execute on that stuff - to all of the required degree of quality and skill that everyone expects or is required - is extremely hard to do well, and requires so much good personal process, discipline and just.. sheer energy/willpower. But you have to, to be credible to the team and competent in each of those roles, at the same time; this isn’t optional. Letting stuff slide or go because, you know, it’s not your ordinary role or you have more on than usual so you expect folks to cut you some slack is just not fair to the teams. You agreed to do something, so now you must do it. You have to follow through on what you say you will, no matter how much you have going on. This is not a game, and it isn’t fun. That is very very hard to do. And people ask you for stuff from every angle, and that’s their prerogative. If you can’t work out how to keep up that energy and find that time to give to the teams, you become someone whose word they can’t trust. That’s a really big downfall in both of those roles when no one trusts you and it will affect your permanent role when the interim one is over, and as COO to ‘lose the room’ can be terminal.
In terms of the practical limitations of holding two full C-suite roles at the same time, I think remaining cognitively and emotionally available enough to yourself to know when you're doing too much or you're not the right person to be involved in that decision or the right person to speak to about that thing is incredibly hard, and a constant effort. When you’re super busy it’s easier to just keep ‘doing’ rather than thinking and deciding or delegating, and the business suffers. So you have to make an extra effort to always consider whether you should involve - or devolve to - other people instead of doing it yourself, or what you should say ‘No’ to - learning to be in control of momentum and how to step away is a steep learning curve, and a constant effort we don’t talk about enough in any C-suite role, let alone multiple. I found this one hard.
Then the third and last point I’ll make briefly is one that I think people don’t think about as much. How do I best say this…there are some serious emotional and mental acrobatics involved in acting in the shoes of someone you aren’t, while becoming enough of it to be credible, and not losing your existing teams trust and goodwill in the process. So much goes into both keeping your existing team needs met sufficiently, while simultaneously helping new people who want or need to follow your lead to see you as someone they can trust to lead them - all while openly admitting that you don’t have a clue what you’re doing (yet), and you’re just trying to figure this out from scratch. That is a really complex set of human dynamics.
You’re saying to these new line reports and teams: follow me, but give me a minute to work out what we’re doing. But also: please don’t see me as not credible. You’re also asking your current teams to do more, so that you can give more to another team - that requires super strong relationships and a lot of trust, which I was lucky to have.
As a general point on holding multiple responsibilities, it is really easy to forget what your job is in that interim position. It isn't to get good at the job, it is to safeguard the function and to be just good enough to do it whilst using the opportunity to learn more about what it takes to get the right hire in and then do that really quickly. It’s a challenging thing to keep your eye on because you're doing so much, and again the gravitational pull is always toward doing the do. I haven’t always gotten it right - I think I did a lot wrong along the way, and I learned a ton and the teams were very kind to me in that process, but I would think thrice before doing something like that again. I mean, when I left, I took six months off. There is a reason for that, right? … I was exhausted.
Yeah, after I left my COO role I took a long time off. I’ve never been burnt out in my career. We were also going through an acquisition which is like doing two jobs at the same time. Yeah, it’s madness.
Yeah, same. I've never experienced that before. I talk about this a lot when people ask me about supporting them as a Fractional leader with completing a big operational project, e.g. writing a company strategy and the success measures to get there, management training or helping them execute on a reduction in workforce, for example, and why it is so hard to get these things right without people like me helping. And it's because in most cases, you’re trying to plan and execute on that project alongside business as usual priorities, which probably already take up near 100% of your capacity. You are trying to cram things into time that doesn’t really exist, so something has to give and often that is focus, rigour, discipline -- and then things ‘don’t go right’. It isn’t about not having the competencies in-house, it’s about the intersection of competency+time+desire to do it in-house. It's always the combination of managing projects versus business as usual and trying to do both of them at 100% that is exhausting and leads to mixed results.That's what you were doing in your acquisition, right? You're still trying to do business as usual, but also this massive project that should really take up 100% of your capacity. How does that work?
Oh yeah. It was exhausting. People ask if I’d be a COO again. Maybe, but not through an acquisition, especially when you can’t talk about it with the team. Like, “You’re being weird, you’re busy and less available.”
Absolutely that, people think: She's just off again. Why is she not online? Why can't anyone reach her? She must just be very lazy. Perception is reality, and this is a really sticky one to navigate over prolonged periods and takes a lot out of you.
Exactly. So to go back to something you said. As CPO, you led Product, Engineering, Data Science Design and UX Research, right?
Yeah, for a period. It was a really unfortunate set of circumstances. Along with the VP Product contractor I spoke about earlier, we also had a Director of Data Science and he had been there almost as long as I had. When the Co-founder left, he took over the Engineering team and I took on Product, Design, UXR. That worked okay for a little bit, but he was pretty burned out and for his own reasons made a decision to leave a couple of months later. On a human level, I was very supportive of his decision and it was absolutely the right one for him, but it left us with nobody for those teams to report into but me - again. So that was a bizarre little tornado, where there’s no VP of Product or Director of Data Science; no senior technical leadership. We had no Head of Engineering (he’d left a few months prior to me coming into the picture), and the team had carried out a restructuring that saw us lose a couple of great Engineering Managers that might have been able to step up. Much of this happened before my tenure, and worked fine until those two dominoes fell, so I ended up having all of those teams reporting through me until we hired a CTO. I have to say, it was a lot and again, the teams were so awesome and patient with me while I learned how to best help them, but I wish it had been different - for them.
That’s how things go at scaling startups, right?
At early stage, absolutely, yes. Because there's no human redundancy, right? You rely on one person to do something. There really isn't just another person who can step into their shoes. You don't have that luxury at early stage. I will say though that this had been particularly poorly set up, and we learned a lot from it.
Right. It's the trick of it. I’m curious. How do you lead people in a role where you don’t have experience? I mean, COOs do that all the time but I think this is a unique situation.
Yeah. I think it is, and I think particularly difficult because the CTPO Co-founder that left was well-liked. I think, rightly or wrongly, people associated all this really quick change and multiple senior departures in that org with something negative or nefarious. I never felt people were holding me personally responsible, but it was a pretty intimidating time to walk into a room full of people where the vibe is basically: Hello, I am unqualified but please let me sit with you. I felt I was met with a bit of ‘bring back the other guy’ to start with, and I totally get it. I enjoyed working with him immensely as well. People experience change in the way they experience grief, and they had quite a lot of change in a short period of time.
Three leaders leaving is quite a lot in that part of the org, where nothing had changed for quite a long time. The Co-founder had been there since day dot. And so when I then walked in asking them to work with me, I think the biggest challenge I had was a couple of the senior technical folks thought I was a right dickhead, because they'd only ever been exposed to me at all hands and I always had to announce all the hard stuff, or answer anonymous questions with honesty - it is easy to form a view of someone based on those interactions alone. So they saw me as this person with less softness than the outgoing person - someone who wouldn't get them, wouldn't understand them, couldn’t fight their corner. They'd never really had much to do with me beyond that kind of company-level stuff up to then, so it’s natural to be skeptical. We did turn this around pretty quickly, but it really was a lot of effort and honestly, we don’t acknowledge enough how intimidating that process of proving yourself to teams can be.
The other folks that I was most concerned with were the Product Managers, who had worked most closely with the Co-founder. There were some quite robust personalities in that bunch, and they’re a really smart and emotionally intelligent group. The job to be done for me at the beginning wasn't to come in and get to work. I knew I was coming in like a hot potato that no one wanted to touch. Who even does she think she is - and that’s a really fair question. So the thing to do was to get them to understand that I wasn't there to change things or be prescriptive - but just to understand first, and help them do what they think is best, next. That was the job. It sounds cliché, but the job was for me to understand them and to give them the time and space to understand me, so that they could trust me to lead them in a domain where all of them had more experience than I did. Not hard, given I had… none.
In terms of how you build that understanding and trust to help people work with you from such a crap foundation, I think it may be different for everyone. I personally spent quite a lot of time meeting with everybody in the first couple of weeks and taking time to explain something along the lines of: “I have no idea what I'm doing. I want to be here doing this as much as you want me here, but we're here now and we're gonna work this out and I'm gonna give you everything I can so you can do your best work, but you’ll need to help me to do that. Where would you like to begin.”
I think it helped massively that I had already run parts of the commercial team as an interim leader, and those folks were friends with each other and willing to say nice things about me. I had also built and led five central teams (legal, talent, finance, operations, people) and all of them allegedly enjoyed working with me and said some encouraging things to their peers. A thing I know helped when those teams were talking, is that the teams I had worked with up to that point didn’t beat around the bush and said quite openly versions of:, “I know she's maybe a bit unconventional, but give her a minute because you won't regret that.”
Some of those new line reports later told me that what helped them to give me a chance was that they could see how much autonomy my existing teams were enjoying in their work, how much praise and credit I was giving quite openly, and how well they were doing organisationally. Looking back, I think that carried me quite far - that those people were so kind about how it was to work with me definitely helped. I think lots of them had coffees with people who were a bit more reluctant and said nice things about working with me. I didn't know they were doing that at the time, but I found out later and am still really grateful they did. So it is now my experience that a big factor to doing something interim like this successfully, is already being established in the organization, and someone people broadly don’t hate working with.
I don’t believe in "fake it till you make it." People are smart and they’re not buying a thing you’re saying. Show up and say, “I don't have a clue.” That's okay. People are quite good at reading other people. That's how we survive and build friendships and relationships. I think that they would have known if I had shown up with the wrong motivation to be there, or some faux confidence about my non-existent capabilities in those domains. I say that because I have worked with and interviewed many leaders who were empire builders. Super focused on finding opportunities to take over a team, hire more people, manage more people - I really dislike that. I think that people sniff that out, too. So because I was somewhat thrust into this interim role reluctantly, I think that people were a lot more forgiving than perhaps if I'd arrived with excitement or saying something ridiculous like “I'm gonna have fun doing this.” People are smart, and deserve to be taken seriously. Taking on management of someone is about as serious as it gets, professionally.
Right. Coming in like, “I don’t know what I’m doing.” takes courage and vulnerability. I think people then trust you more than when you say, “I got this.” with false bravery.
Yeah, for sure. I did not got this (laughs). I think that being honest with people like that allows you to remain credible and let’s them decide whether to trust you a bit, right? How or if they actually follow your lead eventually is a different question. Trust first, always.
I tried to make sure that I was really honest with people in 1:1s and group catch-ups about what to expect from me, and what I expect of them. I wanted folks to know I say what I mean, and I mean what I say, so not to worry about hidden agendas or whispers as we learn about each other.
I repeated myself many times because that’s what the CEO of the business had taught me - he was a McKinsey-ite who told me that people don’t hear something until they’ve heard it nine times. So I kept repeating myself: being clear what I am good at/bring to the table, how I can be useful to them, where I am learning this domain, what I need from them to be able to help, and how I would like us to interact.
I think it is important that for the things you say you are good at, people can see plenty of other examples around the org in your past work - corroboration, if you like. But I do think that combination of honesty, what we probably call ‘growth mindset’ and genuinely wanting to learn and be there to help them even if it made me look like an idiot at times, is what carried me through this pretty turbulent change. In the end, these amazing people were willing to work with me in that leadership role, and that was a brilliant outcome.
When I came into this role, I needed to learn, but I made sure they knew that the onus was on me to figure it out. I can ask lots of questions to learn, but I was never going to ask them to sit down and explain to me how it all works so I could learn. The minute someone thinks they’ve carried me, even for a mile, they’re not going to follow me. That’s not the job to be done – to carry me. The job is for me to carry and push you, but I need to get up to speed first, so I take us in the right direction. So I try really hard never to make these folks my teachers, while still learning from them.
I love the distinction you made between trust and following because they’re different. It’s a tricky balance between being vulnerable and open when you’re in an interim role and it’s not an optimal situation.
Right. It's not. I mean, we should all acknowledge that this is not good - this interim position stuff. We should all want this to end very quickly. The other thing there, though, is that I think people have a very allergic reaction to leaders, regardless of the domain, when they come in new and they ask you to teach them or carry them. When they ask you to hold all that effort for their benefit. Leadership is a privilege, and I do think teams know that, and feel that.
When I came into this role, I needed to learn, but I made sure they knew that the onus was on me to figure it out. I can ask lots of questions to learn, but I was never going to ask them to sit down and explain to me how it all works so I could learn. The minute someone thinks they’ve carried me, even for a mile, they’re not going to follow me. That’s not the job to be done – to carry me. The job is for me to carry and push you, but I need to get up to speed first, so I take us in the right direction. So I try really hard never to make these folks my teachers, while still learning from them.
One way to avoid leaning too much on your team members is to look externally for help on learning the domain. When I took the role on, I came armed with a plan for how to learn the domain. I had friends who connected me with other CPOs at other businesses, I spent my evenings and weekends (and flights to/from NYC) taking formal courses on Product Management, Product Leadership, Engineering Management etc. run by industry specific providers like Mind the Product, Reforge, and so on. I was trying to figure the basics out for myself, as much as I could. I think people respected that I was trying my best to meet them where they were, even if that was already impossible. You can't be mad at someone for trying, can you? You have to give me a minute, but you can't be mad that I'm trying.
I think you always feel like you need to be giving more than you are for the benefit of the teams you support. Even when you're doing one role, you want to do your very best at it and do people justice, and the difficult thing about interim leadership is that you know you can’t do that - for either role. And you have to get comfortable with that terrible discomfort.
What did you struggle with most balancing two leadership roles at the same time?
I think you always feel like you need to be giving more than you are for the benefit of the teams you support. Even when you're doing one role, you want to do your very best at it and do people justice, and the difficult thing about interim leadership is that you know you can’t do that - for either role. And you have to get comfortable with that terrible discomfort.
And I think the very difficult thing there is to know that you can't.
When it comes to execution I want to do all of the things on that list. I so genuinely believe there’s nothing I cannot do if I just try hard enough to get it done. So getting good at saying no to stuff was personally hard for me.
I had to think about how to be as clear as possible with people. How to externalize what's happening in my head on how I am prioritizing when I say no to something, and why. What I'm thinking about, and what it is I'm optimizing for in that moment, so that you can fully understand and it's not hard for you to hear ‘no’. I don’t want people to stop coming to me with things. I just want them to understand why it’s not now, not me or no, and for them to follow fully what went into that decision.
I found that difficult because it's a lot of work mentally and emotionally to constantly explain yourself to people. You have to do the extra emotional labour not to just rely on your experience, instinct or heuristics - you have to be able to help people follow you fully from A to B to C, and if you‘ve never tried that day to day, you should - it is really really hard to do constantly.
I think the other thing is the sheer amount of time you have to give to something like a COO role and then to something else you have to learn, while doing. You’re doing a crash course in something new and you’re trying to make sure people actually want to work with you. It’s a lot of time, lots of 1:1s, lots of meetings…just lots of time. One of the impacts on me as a human was sleep. I really struggled to sleep during that time. The more sleep-deprived you are, the harder it is to exercise, the less you exercise, the more tired you get. My health just went down the toilet – mental, emotional, and physical. It was a tough period. The result of that is that I felt I couldn't get out of that hole. So by the time I left, I really didn't feel like I had much of a choice for myself but to go and rest.
I think about that a lot and often feel it is a shame because I think that maybe my trajectory would have been different had I not taken that interim role with the company. I loved working there. I loved the people there. But at some point, I just had to decide that I needed to sit down. I think that that's the hardest thing about doing multiple things - you don't and you can't account for how much time that's going to take and what the sort of intangible consequences that people don't see after working hours are. People don’t know that even when I was asleep, I was thinking about it. I may be out with friends - but I’m thinking about it. It’s so much pressure, and so much responsibility and I never wanted to let anyone down, and so it’s constantly with you.
If you really care and you're doing the thing for the right reasons, it probably never leaves you. That’s tough to do over a long period of time. I did that for a year which is just far too long. No one should want to do that. Again, going back to those who want to empire build. They’re the very people who shouldn’t be doing it. So you’re in this sort of catch-22, where the only people who should do it are the ones who don’t want to do it, and who it will exhaust. So the only real answer is for everyone in the exec team to focus on making that interim period as short and as supported as possible.
I had to think about how to be as clear as possible with people. How to externalize what's happening in my head on how I am prioritizing when I say no to something, and why. What I'm thinking about, and what it is I'm optimizing for in that moment, so that you can fully understand and it's not hard for you to hear ‘no’. I don’t want people to stop coming to me with things. I just want them to understand why it’s not now, not me or no, and for them to follow fully what went into that decision.
It's a great point. The COO role on its own…I was constantly thinking and rearranging pieces in my head. And then to do another interim role…I just can’t imagine it. I didn’t sleep much during my time either. I slept a lot afterward for months. I was just exhausted in a way I’d never been.
Same same. I became a one-task-a-day person for quite a while: I'm gonna do this one task today, and that’s it. And because I've diarized that or scheduled that, I'm gonna go to the post office and drop off a return. That is all I'm willing to schedule for myself. That happened for about three months, one task a day.
Yep for me too. I contemplated leaving the industry completely. I thought about doing travel-related business. My friend who has a startup that’s doing amazing was like, “What are you doing? You have to come back.” (laughs)
Hahaha! That thought process feels eerily familiar…
I’m glad I came back. What did you most enjoy about doing both of those roles at the same time?
I painted a really grim picture, but I actually had a really great time on the whole and that is purely down to the people I did it with. Both my existing teams who were such absolute legends at virtually running themselves and making my life easier, but also the new teams that gave me a chance to work with them.
Once people accepted me as one of their own and stopped being suspicious of me, it was like faith in humanity had been restored, and the support and proactivity I felt from the teams was incredible - I’ve never experienced anything like it. The people in middle management roles really showed up. Some of those are people I now consider close friends and I have so much respect for them because they showed up in that period of time, not for me, not for their own benefit but for their peers and their own line reports. These are people who probably want to end up in that role I was doing (CPO) eventually and I just sort of sauntered in and ‘took’ it. A lot of folks might be resentful, bitter or just rightfully pretty indignant at that setup, but not these beautiful humans. They were all there for a cause greater than themselves, even if we had a few bumps at the start -- when that team came together, something really magical happened and I am so grateful to have been a part of it. It’s still one of the best bunch of humans I’ve ever worked with, and many I’d work with again.
The central teams I had to step away from a bit to be able to do this interim role really stepped up and into their own light. They exemplified my favourite way of working: proceed until apprehended. Stuff just got done. I was being informed of things rather than treated like a bottleneck, the teams made sound, reasoned decisions and I wasn’t required for any of it. I always say the best thing you can do as a manager or leader is make yourself redundant - it’s a sign of a team that likes having you around, but doesn’t need you. This team did not need me, and I loved that for them.
The other thing for me personally was that until that point I had never worked that closely with engineering and product people. Learning about how completely differently a product manager needs to be approached and managed vs a lawyer was so enjoyable- to be humbled in that way. I have ten years of leadership experience, and have built lots of high-performing teams. Yet none of my bag of tricks was working. Not a single thing. So I had to think about how it would work, and build a new bag (of tricks). Learning from and alongside these new domains and people added an entirely new layer to my abilities as a manager and leader. That was humbling and so deeply enjoyable.
Jessica Zwaan who introduced us talks about building and running the People function as a Product team using the same principles of Product Management. Her mindset is so much about the product's way of thinking. Before this stint, I had not really spent much time thinking or understanding what product principles are or how you can apply them, and now it’s a huge part of how I think. I’m a much better COO for it.
What advice would you give to other senior leaders who are navigating an interim role at the same time?
Much of what I said above, probably. Be there for the right reasons. Be honest with yourself about your limits. Serve the team, rather than your ego. And if you think you’re someone who should be doing it, you probably aren't. So that's a fun catch-22 for you to navigate. :)
If you do end up in a role like that, do all you can to make yourself redundant in that role from day one. Find efficiency gains, whether by process or through enabling people around you. Focus on replacing yourself (in the interim role). The CEO might be praising you and things might be going okay, but I assure you that someone qualified who chose that career path will do a far, far better job than you (or I).
And of course, be honest with people, don't fake it till you make it. Nobody is buying what you're selling.