Inside the Family Office: The Chief of Staff Role with Donald J Cunningham

0:09Most Chief of Staff advice assumes you work somewhere with an org chart, a title you get promoted out of, a recruiter you call when things go sideways, or a glass door page where somebody already warned you about your boss. Now take all of that away. Welcome to the Chief of Staff podcast. I'm Scott Amenta and my guest today is Donald Cunningham, head of family office for a senior member of the Qatari royal family. He lives between London and New York, and he spent the last 12 years working for four different ultra-high net worth families after starting his career in capital markets and lower mid-market M &A.

0:41Donald got into this world by accident. He applied to an obscure Indeed posting at three in the morning and called himself a recovering investment banker in the cover letter. It worked. Seven years in that first family office followed, and he's been in this space ever since. Family offices are the least visible corner of the chief of staff world. There are no job postings, no glass door reviews, no org charts on LinkedIn, no off-site recaps. So when someone who's lived inside four of them agrees to talk openly about how the work actually functions, I take that conversation. We get into the tools Donald uses to manage a principle with effectively unlimited resources, why he'll tell someone their idea is bad three separate times before executing it anyway, and what career progression looks like in a world with no ladder to climb.

1:25Here's my conversation with Donald. Donald, thank you so much for joining us. Welcome to the Chief of Staff Podcast. Pleasure to be here, Scott. Thank you for having me. I really appreciate the time. And we had an awesome conversation the first time we met. So I'm hopeful that we'll repeat it here. But I learned a ton from you just about, you know, working in private family offices. I'm excited to get into your career and talk about your experiences in that domain. So I guess before we get into the meat of it, Tell us a little bit about yourself, where you're coming from, where you're calling in from today, and how did you find yourself in the position that you are today?

2:05Sure. So I'm in America presently, but normally based in London. I'm just visiting some family for the time. I've spent about half my career in the US, initially in capital markets, investment banking, and then lower mid-market mergers and acquisitions, advisory work, before moving into the family office space about 12 years ago. and I now serve the fourth family I've worked for, which is a principal who's a senior member of the Katara Royal Family and is based between London and New York, which are my two homes. So that suits very well. And it's been an interesting transition to family life, family office life from banking.

2:45It's quite a different environment, but well embedded at this stage. What was your path from banking to your first family office? Did that happen naturally? Was it something that you were looking for? it did not happen naturally. I think I decided that I didn't want to grow up to be like some of the people for whom I worked in my banking life. And I really had a crisis of confidence around what I was meant to do. And I spent a lot of time speaking with family and friends about what they thought would suit me well in terms of a career path. And the most common bits of advice where you'd be a great COO, chief of staff, right-hand man, person behind the person.

3:25And I had no idea how to translate that into a career. And I really just started searching for chief of staff roles. And I was bored one evening looking for a new career. And I happened upon a very obscure job advert, I think on Indeed. And it was a Thursday night. I remember I was sat in Manhattan in my apartment. It was maybe 2 or 3 in the morning. I just happened to be a bit restless that night. And I applied for this role and I thought, I'll never hear again. And that ended up being my first family office job of 7 years working for quite a notorious hedge fund founder in his large single family office in New York.

4:04I remember you mentioning that that role as it was posted was quite obscure. It wasn't exactly asking for a chief of staff. and it felt maybe because it was 2am, you were like this, whatever, I'll throw my hat in the ring. We both know that a lot of family offices don't publicly disclose or post those job listings on platforms like Indeed or LinkedIn. I guess having moved through multiple family offices now, did that feel like an outlier event for you that was right place, right time? I think everything in family office life could be construed as an outlier, Scott. And I say that because it's not a typical world.

4:44And it sort of operates on the fringes of most normal kind of institutions. And the characters within are driven by the personalities of the principles. And those can often be very eccentric type of personalities, but often very secretive and private people. And it's easy to misconstrue the notion that a focus on privacy, for example, is a desire to hide something. In many cases, it's just that the very best sort of principles tend to be highly discreet and don't want to make lots of fanfare about what they're doing, keep their family lives private. That was very much the case for the first principal for whom I worked, who is a man of great principle, intellect and brilliance, and really just never wanted to make any headlines.

5:30An incredibly humble and quiet sort of billionaire, if such a thing exists. And I think for most of the population, many people would find that hard to believe because there tend to be a small number of very loud billionaires. This was not one of them. And most of the best family office principals from whom I've worked fall very much into that category, tend to be very subtle. In this case, I do think it was an outlier. I don't know that having a set path in trying to walk your way into family offices is the easiest sort of route. So very much it was right place, right time. I threw my hat in the ring.

6:06I never expected to receive a callback related to that role. I remember describing myself as a recovering investment banker in my cover letter for that application, which happened to resonate well with the in-house recruiter. We had a whole in-house recruiting team within that family office. And he had also worked in banking. He had also gone to the same university. And we'd had a very similar experience. So I think that was very lucky as well. And just that he and I had a lot in common. And that was the initial sort of foray into our understanding and my ability to tell my story around the things I wanted to do.

6:43And I think that was a unification of my background in banking and some of the detail-orientated quantitative work mixed with a lot of my nonprofit board work. I had served for many, many years on various national committees, the National Executive Board of the Boy Scouts of America, where I had been national youth president when I was 18. And that involved a lot of fundraising, national event planning, some strategic planning for the organization. And I was trying to match those two things. So I had this sort of unpaid hobby supporting an organization I cared about, combined with this very quantity banking and transaction background.

7:25And I thought, how do I marry these things? It ended up being quite a good formula for a family office environment, although that was completely unknown to me at the time. And it just happened to work out in a positive way, I'd say. And it's really helpful context in terms of marrying those two skill sets. And obviously, one of them wasn't coming from a purely professional sense, but was something that you were passionate about and clearly good at. Having made your way through other family offices now, do you think those skill sets have still served you? Or are there other things that you've picked up along the way that for maybe someone getting into this world for the first time or thinking about where do I start my career path to end up in a place like Donald?

8:07What would you say would be the most important? I think the most important thing is to really ask probing questions of people in the space and to try and understand how they got to their roles. It's never a linear path. So for someone like me coming from a banking background, it's very formulaic. So there are a handful, at least at the time when I was doing this back in the noughties, you had a handful of good recruiters that you knew because your friends had worked with them and you knew the ones to avoid. And if things were not working out in the current role, you spoke to that recruiter and you'd get a job at a competing bank in a similar type of product group, etc.

8:49In my case, I had a bit of a funny path because I went from working in capital markets, lived through the recession of 2008 and 2009, and spent some time in a recession hideout role, which was at a research firm, and then went back into banking. But in M &A, It's a very strange transition. Most people wouldn't go from debt capital markets and structured finance into lower mid-market M &A. And that was just because of a friendship that I had and someone who happened to be at a firm that was hiring, building out an M &A practice. But I had a lot to learn doing that. And so that's not linear either, but it's probably a bit more linear than either a corporate chief of staff role or just getting into family offices anyway, even if it's within the investment path.

9:35So if you're a CIO at a private equity group and you decide you want to pivot, you think that family office is sort of the holy grail and moving in that direction. I don't think that's linear either. So to get to the crux of your question, I think it's very slow. It's very deliberate. It's very intentional, but it takes a lot more time. And building out a network and sort of asking probing questions of people in the space and building a small network there is probably the best bet for trying to understand it. But I would also caution people who are interested in family offices broadly or a chief of staff role within a family office that it doesn't mimic other roles in corporate or even political environments.

10:17It's very, very different. And so part of that probing or line of questioning should be shaped by an understanding of how different it might be from those environments and whether that's a good fit. Because this life is not for everyone. It's very unstructured. It can be very opaque. The resources can be quite limited despite the scale of wealth. And it's very different from working in an institution. So one needs to ask oneself if that's for them or not. And it's important, just as important to know the things that are sort of unfavorable in these environments as are favorable. And that's part of our goal today is to shed a little bit of light on kind of what some of the situations look like.

10:56How do you describe generally, like when someone asks, what is the kind of work that you do? And do you frame that in a chief of staff light? Or do you frame that in some other context or metaphor that said party might be more responsive to? I think it also depends on the context of the person who's asking. So if I'm speaking to someone who has an institutional background, and I use the phrase chief of staff, many people understand what that means within a corporate environment. And that role can also be quite different along the value scale as well, can't it? It could be a glorified high-level EA plus to the CEO, strategic, project-driven, right-hand person who are the eyes and ears for an executive and making links across departments or product groups, etc.

11:53I think this role within a family office is more akin to that right hand to an executive, although it's probably a bit more varied and usually has a leadership role as well in terms of managing the team. So I think some people will understand that phrase. Within the family office space, my role de facto is really as head of family office. That's well understood within the space. For those outside of the space, I might say something to the effect of, I serve as the principal or chief advisor to an ultra high net worth individual. People usually don't know that that role exists. And I'll say, well, think of a random billionaire.

12:34Now imagine what is... Okay. So if someone will think of an obvious person, Jeff Bezos, for example, and I'll say, you understand what the business of that person is. And they will know Amazon, they will know sort of functionally how that works. And I will say, okay, so put the business aside. And now think of what it takes to run the life of that person alongside the business and how complicated that might well be with multiple homes, investment interests, boards, seats, an all variety of complicated family, financial succession and other issues, tax behind them and managing their finances. And I think people, if you frame it that way, start to think about their own situations and then amplify that in terms of how complicated it could easily get with a significant amount of wealth.

13:28And they say, okay, I don't understand what that means, but I could see the scale of it. And then my explanation is to say, well, I sort of oversee and tend to all of that in some form, variety or another. And that sort of helps to frame it. But it's funny because I was at an event in London for the Merchant Tailors, which is effectively a charity that supports young people and apprentices within the tailoring community. So think of kind of Savile Row cutters and tailors and coat makers. and a dear friend of mine is a head cutter at a firm and he invited me to this lovely event with me and his wife and their team.

14:07And one of their team I had met a few times and she's a young apprentice doing this role. And she was sort of joking. My friend said, you know, you may have to explain to our apprentice what it is you do, but she sort of pulled me aside yesterday. I still, I really don't understand what it is that Donald does. So we kind of had a chat and I realized oftentimes in those contexts that it's a very weird sort of thing and outside of the normal scope of what most people do, even at a high level of sort of professional existence within financial services. So it really depends on the context. Yeah. I mean, even the corporate chief of staff now over the last, let's call it 5, 10 years, has become a little bit more well-established.

14:49Geographically, there's some differences because some parts of Europe may be still catching up to the UK and the US in terms of adoption. But the role has become a relatively accepted form of strategic operator living alongside a CEO. But because it's in a corporate environment where lots of roles, like product management, as an example, have been made up along the years to fill gaps in organizational structure that you know, needed it for various reasons. Chief of staff has been like, I think, easier to digest and understand, even if it has lots of ambiguity still, and, you know, can range in definitions depending on principle or company.

15:30I think because family offices generally are not as active in sharing the way that their organizational structure works. Like they're much more opaque organizations, right? There's not, they're not actively posting on LinkedIn about, you know, Here's the best thing that we're doing for our team. Here's what the team offsite look like. Here's who we're hiring for. Even the job descriptions tend to be done in network, in more closed environments, more word of mouth than publicly posted. And that opaqueness, I'm curious from your perspective, if it's been a good thing for you operating and learning how to be a better head of family office, chief of staff, or Or if at various parts of your career, that's been a challenging part of the space as well.

16:17I think it's both, Scott. I think initially the shift is a bit strange because, and I say this not in any flippant way, but any kind of first-year analysts coming from a bulge bracket, say banking environment or working in the city in London, will have had, even if it's not a dedicated resource, will have had maybe a shared resource who's an assistant who will tend to administer tasks like dealing with expenses or sending out a DHL parcel or this kind of thing. Family offices just don't have that. You're lucky to have an office manager. So everyone does a bit of everything. And another thing that's a bit funny, I would say, but this is important for people to understand.

17:04And this is where the low ego quality has to come in. And in many cases, a family office staff or team might be situated adjacent to or even within principal's home, potentially. So I've worked in environment. My first family office, for example, we owned about 12 % of a high rise in the Upper West Side. The family lived on sort of two adjoined penthouse floors. And then we had an entire staff floor. And then we had some other various apartments around the building where we would host meetings and things. But our staff floor was very proximal and accessible such that I would, on an almost daily basis, probably enter the family's personal living spaces with a key that I had that all of us had and access those spaces.

17:47That's very strange. And what it also means is even though perhaps at the time my role was director of operations, and I did a number of things, I ran a small team and we were sort of a project-driven problem-solving kind of team, maybe a toilet overflows, right? And the family are not going to be dealing with that. So if you just happen to be in the space at the time, it doesn't matter if you're the CIO, the head of family office, the chief of staff, or the housekeeper, like someone's got a... Someone's rolling up their sleeves. That's right. And that's not for everyone. So if you're coming from a private equity environment, and then you end up walking around, having meetings at someone's dining room table, and something like this happens, and you've got the dog sat alongside of you, barking at you whilst you're trying to have a meeting, or...

18:34All these funny things play out. It's very personal at the same time. And you often just have to roll up your sleeves. And I think the New York family office, my first role, they were very good for testing for that. And I remember in my interviewing process, I think that the person who would be my direct sort of boss in that role, I could tell he was a little bit nervous. You know, he was concerned initially until we got speaking a bit further. He wanted to make sure I wasn't sort of precious having come from the environment from whence I had come. Is this a guy who would be willing to roll up his sleeves and deal with it?

19:12And I think I told a story about a plumbing incident that had happened where I was the only person who could jump in and just happened to solve it. But that's important for these roles. But your question is about structure. So the opaque nature is probably unlikely to change. And that creates barriers to entry which are intentional for the industry. within the looseness of the structure for me is an opportunity and a challenge. And there's a lot of talk within research publication. Everyone's jumping on the family office bandwagon from the big four accountancies to all the wealth managers and all the banks.

19:51And everyone wants a piece of this because there's money to be made. And some of that's disingenuous. I think some of it is genuine. But what you will see commonly in those publications is this notion that family offices are becoming more institutionalized and more structured and invoking governance. And I think that's right. And I think that directional shift is appropriate at this time. But I think there's a bit of a balance there. There's something in between structurally that works because what makes family offices brilliant is they're quite nimble. They're not aircraft carriers like a big bank that are very difficult to turn or change course.

20:30If you're changing tack on a massive boat, you've got a lot of switches to flick and a lot of considerations to make around the wind speed and the intensity of the wind and the direction it's coming from. And you just imagine the bureaucracy that is akin to that in a large organization. Family offices are nimble. They can move quickly. They can pivot just like a small sailboat. So that's a great advantage. So if you become too institutionalized and there's too much structure, I think you've got a risk. You have a risk of overcomplicating and creating too much bureaucracy. So I think there's something there nicely in the middle of that, this balance.

21:11And there's a great opportunity whilst also staying nimble and quick to act where you can make fast decisions, react quickly, but also be more on the front foot rather than the back foot in terms of being proactive. And that suits principles very well. You're thinking about risk and what's coming down the tracks at any given point. and you can start to put out fires before they arise rather than firefighting. It's a bad place to be in any organization, of course, whether that's an institution or a small family office. One question that I just saw on our chief of staff community Slack was about, and this comes from a woman who's working in a corporate entity as a chief of staff to a CEO, and her role is increasingly becoming more focused on the kind of personal aspects of his life, akin to some of the examples that you just shared, where she was hired to be chief of staff to the organization, running strategy and operations and really being kind of the glue between teams and the executive team.

22:12And I'm curious in the way that you've approached your career in family offices or the way that the role for yourself has been structured and that's changed over time, is there a line that's drawn between what the family needs personally and what the family business needs from an investment and strategy and operations perspective? And how do you straddle that? Or is that an ever-moving goalpost? I think it's ever-moving. What might be different in the example that you've raised is this person is started out within the operating business or the operating company. There's a model for this, which we call an embedded family office, where perhaps a senior executive or founder will utilize some of the corporate resources in more of a blended, say, EA, PA role, for example.

23:04And that person starts to take on more responsibility within the personal affairs of the executive or the founder or whatever position that person might be as their wealth accumulates. In my case, across all four families, it's always personal. It's always a moving goalpost. It's oftentimes very little distinction between whatever the source of wealth is or the operating business or the portfolio, as it were, and the personal life of the principal and there's a swing throughout the day between those two objectives sometimes those objectives compete with one another and one's got to balance that similar to competing family interests um of the many challenges i would say of my first family office role one of the greatest was when the principal and his wife might disagree or mediation was required between them It's a very strange thing to think that as a professional hire, you might be asked, even in an informal capacity, to sort of manage a, not a dispute, a dispute is absolutely the wrong word, but a difference of opinion around priorities, let's say, between a husband and wife.

24:20At the end of the day, they're just people, right? So this is a billionaire, a self-made billionaire and his wife, who in her own right was accomplished in a number of different fields, including as a writer. But managing that, I mean, it's not part of the job spec. And there's a bullet pulling that says, you know, occasionally you'll be asked to kind of intermediate between family members. These are just the realities that creep up. And so if I'm the person on your Slack channel, I've got a couple of questions. Am I being asked to do these things because I'm so trusted that I'm being brought more into the inner circle?

24:58Or is there a question of my confidence on the commercial and professional side? And this person thinks I'm better suited to more of a support role. And I think that person will know if they ask that for themselves that question, what the answer is. And if they don't know now, I think they could think about it and observe. In many cases, I think whilst it can feel like a downgrade to have someone shift you away, say, from the operating business to tend to some personal matters, it might well be an indication of trust. It might well be a nudge to say, gosh, I really don't trust a lot of people in my life.

25:37This person is on a great job in my operating business. and it's the only person that I, even though this is a small little thing over here for my family or my children, it matters a great deal to me and I appreciate the level of detail and care that must go into it and I only trust that person to do it. And my guess, not knowing anything about this situation, is that happens a lot and it's probably a very positive not. I think it does happen a lot. I think it very often happens when founders, founders that may be coming from less material wealth have some sort of major exit. It's obviously happening a lot in California right now.

26:14And suddenly have a whole new set of assets and wealth to manage and protect and need those additional resources around them. And if a chief of staff has been successful in the corporate environment for them, they tend to be first in line to start bridging that gap into that personal space as well. I don't know about this particular situation, but I've certainly heard those stories coming to light. And so I think there is a world where more corporate chiefs of staff may end up feeling like more family office chiefs of staff, even if not quite the same. But in terms of responsibilities, there may be more overlap.

26:53Well, and maybe it's an opportunity. Maybe if you are supporting an executive and they've had a major event, or you foresee, you catch wind of the fact that a liquidity event is coming and you're well positioned, it wouldn't be a surprise for that person to be brought along with that exiting, say, founder in this case. And it might be an opportunity for that person to have a discussion and say, I'd love to be involved in this. Have you considered setting up, I would call it a private office as a way to frame it potentially to help manage some of your affairs? And I think I could add value in these areas.

27:29I think we might need to seek outside help in these other areas. So an institutional corporate chief of staff is probably not well suited to being a portfolio manager necessarily or an asset allocator. So obviously, the support of potentially an outside CIO would be of use. But that person will know the personality of the founder and might well be involved in the hiring process and setting up the framework to build that out. It doesn't require an investment professional to have a lot of the key tools and understanding what's right. Because the personality bit of this is really everything. I know of countless examples, and there's one that comes to mind, top of mind, because it was a process in which I was involved with a very successful set of founders in, let's say, a tech-related sector who have accumulated unbelievable wealth in a very short period of time and have built out a family office.

28:27I think initially it was a bit embedded within the operating business and a couple of trusted people played a role. And now they've got to define family office. The mistake that I foresee as an outsider, but having seen a few family offices now and having done this for over a decade, there's the revolving door problem. I know of people coming and going, they built up, they hired quickly. But then I hear rumors that it didn't work out. People lasted 3 months, 4 months, 6 months, and they're out the door. And what that says to me is that the hiring process is not being conducted in the way that it should be.

29:03Or there's a level of hubris and confirmation bias there that suggests, because I've been so successful, because I've got this number attached to my worth, I know better than everyone else. And I would caution any principal or anyone advising them for that matter, who's maybe come from the operating side, to say, let's take a beat, let's pause, let's think about very cautiously about the things that we do know very well and the things especially that we don't know. And the things that we don't know can be very informing of how to go about those processes. It's an opportunity to pause and listen to outside advisors who have seen countless examples of what works and what doesn't.

29:45For most principals, the family office that they have is the only one they'll ever see. Most of them don't like to attend events with, unless it's absolutely within their peer group. They don't like to, they're not going to go to conferences generally and do these kinds of things. So they don't really see other examples of it. And yet at the same time, foolishly, they will have a sense for exactly how it's meant to be. Or perhaps their spouses get involved and they think they have a sense and they start to meddle in that. And that level of meddling, whilst appropriate, it's their office, it's their lives, their prerogative, of course, always.

30:20But it's an opportunity to pause and maybe ask some critical questions and sort of think about what is it we don't know and who are the best people to advise us on that. Let's take an opportunity to listen to those people and get their perspective. Recruiters are a great example of this because a lot of... In my experience, a lot of family office principals have dismissed recruiters as not the best in industry and people that are scrapping for fees and this sort of thing. And that's true. There are some like that, but many are very, very good. And many have seen so many iterations of this work and not work.

30:58And they've got a really good intuitive sense. And if they have access to the principal and really can understand how the organization works, a great recruiter, is a great partner to have and use time and again when we understand the culture and the personality, the principles. So it's absolutely incorrect to dismiss those kinds of people, those outside advisors who've seen many examples of what works and what doesn't. You hit on a couple of interesting points here, all related to what I think is probably the most common thread between chief of staff roles, whether in corporate, private sector, public sector or in this case, family office.

31:33And that is working with a principal, right? That the chief of staff role is very much tied to this principal. And that person may have a large ego, big personality, in some cases may be difficult to work with, in some cases may be a pleasure to work with and very receptive to feedback and responses that don't quite fit his or her narrative or agenda. I think that's rarely the case, but I've certainly heard of those examples. I'm curious, you know, from your perspective, and you talked a little bit about, you know, when that number is now attached to how they think about their ability to be successful in this world, right?

32:16And like, and how people might define their success. And I'm sure that makes a difference in how they show up in a room and, you know, have a stronger belief of what they say, you know, not just it should be responded to with a yes, but is absolutely right. How do you manage those personalities? How do you think about, you know, redirecting or, you know, making sure that organizationally, you know, you're following kind of like the plan or agenda that was set and not letting, you know, one person kind of see something sparkly and want to go after that, even if it's the wrong thing to do? The answer in short is very delicately, Scott.

32:57I think delicacy and delicate handling. I mean, the metaphor is sort of great dexterity. It starts with the interviewing process because, and I had to learn this the hard way, when I remember how excited I was going into the rounds and endless rounds of interviews i had from my first role in new york and when you start to realize you know when you're in the office of the well-known hedge fund you have a suspicion it's as things go on that it's probably for that founder you know they framed it in a way at the time that you know it might be an executive of the fund or something but it learns very quickly okay it's this it's this person and the gravitas of that it just you start to develop this notion that like any job interview, I've got this, I want this.

33:49And you're yearning for it because it's associated with something that's so significant or in your mind is so significant. And you start to position yourself in a way that's like, do anything I can to get this role and really put my best foot forward and do my homework and go well-prepared into these interviews. Most of the time in the office interviews, you can't really prepare for. There's nothing to really prepare other than to think about how you tell your story in a concise way. But what I've learned over time, having worked for some great principles and some really challenging ones, for better or worse, is to ask the right questions in that process and to not just think, gosh, I would be so lucky to work in this organization.

34:35Without saying it in any arrogant way, but especially someone with some experience, there's a balance there. And the flip side of the coin is this organization would also be lucky to have me. And how do I ensure that the fit here is right? So my objective here is not just to get the job, it's to assess whether I can work capably for this person on a long-term horizon and perform well for them over time. So how does one test for that? It's very difficult. And I think asking questions, the right sort of... The very personality-driven questions are the same sort of questions that an interviewer would ask an interviewee to assess fit, but the other way around.

35:14And I like to ask principals things about their values and things they care about or what keeps them up at night or what happens when things go awry. And whether they answer the question or not, at a certain stage of career experience, you can gauge a person's reaction and see what makes them uncomfortable or their nonverbal cues to understand maybe where there are some sensitivity points. And then you've just got to introspect and say, is this right for me? Is this going to be a fit? And if you've got the intuition of the red flag sort of going off in those discussions, you would do well to heed them and not ignore them and not just think, I've got to get this role.

35:57This person's a very serious person. Make it be as serious as you like. and it looks very prestigious, perhaps, that you've worked for them for six months. But what happens when it doesn't work out after six months and you're seeking a new role again? That's a very unfavorable position. So don't be convinced that it's always ponies and rainbows and butterflies and it will all work out. It won't necessarily. I think your question, though, is more in the core of when you're in the role, how do you manage it? And I think just a few tricks in the toolkit that I've learned, mostly from other people, One is creating the sort of trade-off, posing the trade-off realization for a principle, which is to say, the answer is typically yes, right?

36:43Can we do this? With virtually unlimited financial resources, generally, you can do just about anything. Within, of course, legal and ethical bounds and doing things always above board, most the best family office professionals will always draw a line on that there i'm sure there are some principles out there in the world who will test and push those boundaries those are not the sort of people for whom i would work or that i'd recommend that anyone do but generally with those resources the answer is yes so then the question is yes yes and what's the trade-off yes we can do this but it will come at the expense of this other thing over here are you willing to engage in that expense.

37:26And what that means is being prepared to know on the spot what some of those trade-offs are. And it's just a massive matrix at any given time because all of these various aspects of their lives are interconnected. And it just comes with experience like anything else. After 12 years, I've seen different things. I've seen someone flick a switch over here, and it affects something on this side of their life over here. And it's those kinds of questions that one has to ask. So I think the trade-off realization is a really important tool. My friend who does a similar role to mine, a good friend of mine in London, who's now working for a related family member of my own principal, he taught me the rule of three, which is three no's when he thinks that there's a bad idea and a principal...

38:14I think, as you said it very well, a principal might be distracted by a shiny object over here. And we know that's a bad idea for any variety of reasons, the rule of three applies. And that is to say, I think this is a bad idea. I think this is a bad idea. I think this is a bad idea. Now, after three iterations, if the answer is still, I want to go and do this thing, or I want to buy this asset or whatever, the job is to execute on that wish. But it's important to have raised your objection and provided good reasons for it to give the principal an out. And also for your own accountability and cover to say, not an opportunity to say, I told you so, but an opportunity in future when things go awry to have been on record as saying, I advised against this because at the end of the day, that credibility factor is key throughout and is essential to trust.

39:08So if you are a person who can consistently over time tend to be a voice of reason and of sound judgment, that bodes very well, as it does in any organization, of course. And you're not always going to be right. But I think owning mistakes quickly and honestly is important. And also raising objections when the time is right, not just sort of cowering and saying yes, because that's the job. That will lead to a very bad outcome, not just for oneself, but also for the principal that will drive them into a worse scenario in almost every case. And the last thing I would say that the third tool that I think about among the most important is to think about the long-term objective.

39:47So in the early days of working with a principal, having things like a family charter, an investment policy, some level of governance and structure that informs a higher order set of principles, objectives, or understandings that focuses not just five years ahead, but maybe 20, 30 years, maybe outlives your time with the principal, maybe outlives the principal, him or herself. If you can refer to those set of standards, it's like the American constitution. It's a written document to which one can refer that guides the principles of how courts operate, the interplay between Congress and the executive in the courts, that's an easy reference point.

40:30And it doesn't need to be long, elaborate, or complicated. But if you can always drive a principle back to say, that's interesting, we can do that. I would just raise with you the fact that we do have a set of guiding principles and values here. And I think this might run counter to that in terms of your long-term objectives. Maybe this is not a good financial decision today. And then maybe they pause and they rethink it. Or maybe they say, we go ahead. And again, that's the job. But if you can point to the longer term view, I think it's always a good outcome. It reminds the principle that they themselves have a responsibility to think long term, not short term.

41:09And it reinforces your role in helping them to get there and serve their best interests, because that is the job at the end of the day. Those were three very helpful tools. And I'm sure a lot of our listeners are going to walk away trying to apply those immediately. I'm curious, like you've obviously built up this skillset as you've progressed in your career, looking back at, you know, your, your first time in family office to where you are today with the Qatari family, how has that progressed for you? As you think about your, you know, willingness to say no three times or, you know, reflect on the, on the organization's charter or, you know, help, help steer, you know, your, your managing principle in a different direction.

41:52And did that come naturally for you earlier on in your career when you were a young gun out of finance world? Or is it something that you've developed over time and really just comes down to confidence in your own skill set and willingness to know that you are right when you're right and you're wrong when you're wrong and the ability to voice that when it matters? I think there are a few factors. The answer is it's a bit of both. there were aspects of confidence that probably stemmed from two parts of my life. One was the fact, and it's as silly as it sounds, my work on boards and national committees with the Boy Scouts positioned me with a number of really serious executives and board chairpersons and founders and political leaders that as a teenager, as an 18-year-old, having access to such people, phone call away, always willing to help.

42:52That was a great source of confidence. I had a lot of support from that. And that was very unique. And most people will not have had that kind of access. But that was a source of confidence because those people would listen to me. They would give me good advice. They would guide me. In a more professional context, I would say in my lower mid-market M &A experience, the great bit of the job was I was still associate VP level in my banking career. So coming out of junior into mid-level, I was never a senior banker. My job wasn't to generate revenue, it was to execute. So I was doing all the grub work of making pitch decks and writing, offering memoranda and just building models and all that.

43:36What I got out of that job that I enjoyed the most was that I worked with the CEOs and CFOs of companies who relied upon me to help them run a process. They were great operators, but they didn't know how to sell a business. They didn't know what it was worth. They didn't know how to represent themselves across the table from a sophisticated financial sponsor who was looking to potentially acquire them at the lowest possible price. And that's where I got to come in. And so it was the times in the diligence phases and building the offering memorandum that I got to sit alongside these executives of these$100 million companies, small businesses, sort of bread and butter of American business, and learn from them and ask them questions and understand how they ran their companies that gave me some confidence as well.

44:25Because I was still young, but interfacing with these people that I perceived to be quite good at running a business. So I think those were sources of confidence. But on the other side, when you're sat for the first time across the table from someone who's worth, you know, eight to$10 billion and they expect you to have an answer, it's just very intimidating. It doesn't matter how confident you are. so it's just a mix of a bit of experience and sort of seeing different things coming down the tracks observing what others who've been in the organization ahead of you have done and kind of how they behave in front of the principal and how they interact what seems to work in terms of what's confidence inspiring i think today i don't i don't have any there's no cover it's just me so we have a small team i have a great team that support me and the principal who are quite independent and they do their roles very well and i'm lucky because i inherited i didn't hire these these chaps i i um i inherited them um and we've got some lovely household staff as well who support the principal they're all very self-sufficient and graded their jobs and that's that frees me up for time to do strategic things but i don't have someone between me and the principal on whom to fall back if I don't have an answer.

45:41What that forces me to do is to always do my homework, to think about all the angles and to come in with a plan, with an objective and with a recommendation. And at the same time, I usually have a set of options. So again, the rule of three here sort of applies. Typically, in most scenarios, there are three sort of sets of course or direction one could take. And I might say, look, you've got three to five options here. My recommendation is number two. And these are the reasons why. And in most cases, my principal and I, because our personality fit is so aligned, it just works. And he was probably already thinking the same thing before I got into the room.

46:23And so it just clicks. And that's a glorious thing, but it doesn't always go that way. So you've just got to be prepared coming into it, which is a good old Boy Scout adage to be prepared for those skills sort of permeate throughout. coming in and having done new diligence is really, really important in these scenarios. It is a mix of both confidence from experience, but also being humble in the moments and realizing this is a very serious person with a lot more experience than I have in life, building something that they've done something extraordinary. And I've got to be respectful of that. And I have to also think about what their objectives are and try and get in their head and what's their priority in this moment?

47:06And how can I think about how we do this in a way that serves their interests? And we meet somewhere in the middle and trying to understand what I think is best for them long-term and convincing them of that. And that can be tricky. That's always tricky in these scenarios. But it comes down to that fit. And the last thing I would say on that point is just what I've realized at this stage of my career is I've come across so many funny things within the family office space. just some very silly some very involved and complex most of them somewhere in between and nothing surprises me that's a source of confidence i could be i worked on a family related matters a family legal matter for related party in the last year that ended up involving five different jurisdictions in terms of five countries i don't know the laws of country x y Zed in Eastern Europe, right?

48:04Why I'm not expected to, that's not part of the job set. It doesn't matter. I know given my experience in this space, I've dealt with enough lawyers. I know the right questions to ask and I can get on the phone and sort of probe and think critically enough in that situation that I can distill the points and sort of set the direction and make a good recommendation. So I can go into those things with confidence just because the variety of the role has put me in so many different situations that I know I can handle it. And I know if I can't handle it, I've got the resources through my network or ex-colleagues or peers that I have to sort of pull a lever and raise my hand and say, I need some help.

48:45I need some advice. And I'd like to get your perspective on this. And I will find someone who's been there and who has a solution. So that's really important as well. It's all very helpful context. The underlying question that I was asking for that you answered is, how have you progressed in this role? And not all chiefs of staff positions are created equally. And there is a clear leveling framework, if you will, of people progressing and moving up the ladder into more senior ranks. And part of that comes with trust from the principal. Part of that comes with ownership and jurisdiction and the things that you're able to execute on inside the organization.

49:27And I'm sure you've got lots of interesting, funny stories of like variations of what that looks like from the different family offices that you've worked for. You know, whether they're putting you in charge of, you know, what might appear to be like relatively small projects or things that are like much bigger than anyone could possibly imagine, you know, even from like a financial scale. And, you know, I think that's what's so interesting about this role kind of behind the scenes is like, it's very difficult to read the tea leaves of what you're actually doing and what you, what you own and kind of where, where that line is drawn.

50:02I think that's right. And the point of career progression is a tricky one too. And I say that because if we're delineating between the corporate environment role and the family office role, there's not really a ladder that's right yeah it's quite horizontal it's a bit funny because you've got to reframe this idea that you're going to get a new title because you've served as an associate for two years or three years and now you become a vice president it doesn't work that way so what you can hope for in these roles is exposure variety and an opportunity to see a lot of the world through the lens of someone with a great deal of influence.

50:44And that additional responsibility and delegation is really the prize. So if you work with a good principal with whom you have a good rapport and you can build trust, there's more delegation. There's more opportunity for you to take on some of that decision-making authority to free up what's on their plate and give them space to think about higher order problems as it were. And the sky is really the limit. I mean, And there's generally, there's so much that could cover or touch these people's lives. It becomes very interesting. So I may wake up and be dealing with a family law matter in the morning to thinking about a budget exercise in the afternoon to this week, I'm working on a property acquisition in America and reviewing the legal docs associated therewith or negotiating on price or other issues.

51:34It's always very interesting and dynamic. And that's not the same as progressing in a corporate environment. In fact, I would say it's much more rewarding. But you've got to have the patience and the low ego to endure that and know that there's not a linear path to that career. If you were to give advice to someone that's just landing their first chief of staff role or something akin to that in a family office, what would you advise them to do, say, in their first 90 days or their first year? there are a couple of things I would say. One is to look for some easy early wins. And I remember saying to my current principal, is there anything, are there some things that have really been bothering you that you think maybe I could solve for you in the first 90 days?

52:24And just very plainly ask that, is there some low hanging fruit, you don't even need to frame it that way, but are there some things that are just sat out there that for whatever reason, due to circumstance have not been resolved for you that are just hanging over your head that you'd like me to sort and take that on. You've got to be careful to understand whether you can in the moment sort of promise that you might be able to do it in such short order. But usually there are a handful of things that someone's had lingering and you just love to have that cleared, sort of clear that deck. That's a great win in the first 90 days.

52:59It builds some credibility to say, this is someone who can execute. it's someone who's asked me a question with an objective to make my life easier. And it's someone who is thinking about this role in a productive way. FaceTime is important. I think just sitting down with the principal and getting to know them, what makes them tick, every opportunity that you can take to not just be on the phone with them, but be in their presence and sit with them and see how they go about their life is a really great way to do it. And that may be tricky because they may be traveling a lot. They may be on their private jet.

53:35They may be liking to spend the summer on some island or a boat somewhere. I'm not suggesting you should demand to go and accompany them on their holiday. But when we meet, for example, my principal travels a lot. When we meet and he's away from London or we're not overlapping somewhere in New York or whatever, we usually have a FaceTime call, not a normal phone call. We're speaking on the phone or WhatsAppping most of the day as it were. So we're in constant contact anyway. And we have a nice rhythm as a result of that. But otherwise, we still want to see each other, even if it's on video. And that just helps to build something.

54:11And it's helped with our personalities and my understanding of who he is as a person, his family and the dynamics and what keeps him up at night. And he, I think, cares likewise about those things for me. He asks about my family. He wants to know how things are going for me personally. And that's not a given. and he's a very special man and I'm very lucky. But either way, the same principle applies. If you have the face time and you can really utilize that tool, it's just a natural osmosis. It comes from having understanding between two human beings at the end of the day. That's a great advantage in the beginning.

54:46If you try and be avoidant and kind of because you're worried about being in a firing line and sometimes the intensity of someone like that, then the question is, you know, is this role right for you? that's probably number one but number two just force yourself to be uncomfortable and just just be in there and endure it and then over time it will get easier and you'll sort of understand that flow and it works but it just comes with time and and there's nothing like being in the same room as another person in terms of understanding this kind of role so i think those are those would be my top two bits and then just awareness sort of checking in with oneself and being aware of what resources you have, what you don't, and being adaptive to the situations and being willing to roll up the sleeve.

55:30These are all great tools. And those are not novel things. I think anyone in a role like this will understand that well. But it's important to remind yourself of just getting back to basics and thinking about those things. So that's helped me. And I think it's helped others in these kinds of roles as well. I think these are the most important aspects of nurturing a relationship and certainly doing it in person or at least having that virtual FaceTime helps you understand kind of emotional capacity and, you know, things that are actually on their mind versus what can be screened on just text or just a phone call.

56:03And yeah, I think for any chief of staff, family officer or not, it's one of the most important pieces certainly to do at the beginning. It definitely feels a lot more uncomfortable at the beginning. But if you don't lay that foundation, it never gets set properly and becomes much harder to do later on. It's better to find out early that the relationship is not going to be maybe what you thought it was and have an opportunity to either write its course or change direction for yourself, for your principal, than it is to avoid the situation and find out much later that this is not working out as you might have expected.

56:38That's exactly right. And that applies to anything, I think. But it's easy to be fooled in a family office environment by, let's say, the prestige of the principal being associated there with. It could be the most significant person of such mass wealth that you feel there's a badge of pride. That means nothing at the end of the day. If you can't get on with them and do the job because the fit works, there's nothing like having that. And sometimes it takes, by the way, multiple iterations to get that right. I've certainly experienced that in my career where I've been in situations I knew it wasn't right.

57:13And you're better at getting yourself out early and recognizing that rather than suppressing it. And as I said earlier, that interviewing process can be a two-way road where you do have an opportunity. If you've asked some thoughtful questions and see how people respond, it can be quite telling and you do well to heed those responses. So that's what's worked for me due to trial and error and making a lot of mistakes. But now I think in retrospect, those were great lessons to have learned. And it's all relative. So in my current position, which I'm very fortunate to have, I appreciate it all the more having had some bumps along the road and work for some very difficult people.

57:55I can appreciate this principal in the way that he operates to a much greater degree than I would have say, maybe 10 years ago, because I didn't have the vantage point of seeing the variety of principles, let's say, in terms of their behavior and the way they operate and the way they run their family offices. So those principles apply on both sides, of course. Donald, you led me right into a perfect bridge to one of my last questions here, which is this world runs on a lot of privacy. Some might even argue secrecy. You're not going to find reviews of difficult principles on a platform like Glassdoor or LinkedIn, in for that matter.

58:39And so, you know, my question for you is having lived in it and in a few different versions of it, do you foresee a version of this where there is kind of better public knowledge of kind of family office generally, but, but also like the inner workings of those family offices and, you know, does, does the chief of staff work get elevated because of that more public knowledge? Do we attract a, the next generation of strong operators who want to be chiefs of staff within the family office ecosystem. You did say earlier on in this episode that family offices are putting more structure around themselves, more governance.

59:16Does that play a role in having more public access domain, if you will? I would be very skeptical to think that the gates, let's say the high hedges on these little funny organizations will somehow get trimmed or clipped or lowered. If anything, they'll be let to grow. I think that's right. And I think there's good reason for it too. So it's not just for the sake of it. There's plenty of good reason. It's all shaped by the principles. I do think on the other side of this coin, you referenced earlier, just a number of young Silicon Valley types who've had liquidity events who are doing this. They probably take a very different format and approach and style that may well be more open than say you know a stodgy traditional principle of a certain generation who's conducted his or her affairs in a very specific way and that's just generational it changes with anything i think networks are important in these environments and really building a network of peers and mentors to ask those kinds of questions and help you frame the understanding of the space.

1:00:32I do dream of a glass door that somehow allows people to review principles and environments in a way that creates transparency. But I don't know how you do that without libel or people using it as a platform to air their grievances, which is not healthy either. Much like a review or a survey, people fill things out when they're unhappy rather than when they're happy. Not to mention breaking NDAs and things like this. Exactly. And that's very tricky. And it goes without saying, but unlike perhaps a corporate environment, these roles, because they thrive on discretion, if you're good at your role, you're very careful about...

1:01:15I may well sit in a public space if I'm meeting someone and just have a look around because I I would be very concerned, let's say, if I'm having a private conversation about something, whether it involves my principle or not, as to who might be around and overhear it. And it breeds in some senses a level of paranoia, perhaps, and extra concern around privacy for good reason. But I do think sometimes it can go a bit too far. But again, it's shaped by principles. So if you're a self-made person who suddenly has a net worth of multiple billions, what do you worry about? You worry about someone taking that away.

1:01:53What would happen if this were lost? To a certain extent, it can become part of one's identity, which is a different mistake for a different episode, perhaps, and the psychology of that. But I think it behooves any executive supporting a family office principal to be thoughtful about that. There's also a question around regulation. So there's a lot of talk around how family offices might be more regulated in some form or another and create transparencies. This probably happens on a much smaller scale than has happened to financial institutions, say like hedge funds and the regulation of the hedge fund industry over time.

1:02:31It's probably more on the order of ultimate beneficiary disclosures. And we've seen that in the case of in the UK, we register limited to companies, for example, on a platform called Companies House. They've been a bit more rigid about having identity checks and things like that, whereas it was pretty loosey-doosey in the past. In New York State, for example, and in New York City, there's been regulation around property holdings, for example, where in the past, you could stack different entities, multi-member LLCs on top of another to go back so many layers to avoid who the ultimate beneficiary or beneficial owner was, I think it starts with that.

1:03:11And some of those disclosures are probably good, but just because someone wants to be private doesn't mean they're hiding something. And that's important to remember too. And regulators won't always understand that. But I think the regulatory environment will also influence some of this. And that will be, to a certain extent, beyond our control. There's not a lobby that advocates on behalf of ultra high net worth individuals. You could imagine the pitchforks and the flames at the gates if someone were to try and create one. We are fortunate to benefit largely outside of a heavy regulatory environment, which allows a certain level of privacy and a nimble approach to being able to operate.

1:03:48At the end of the day, it's someone's private capsule. And so if we try and over-regulate that, again, different discussion, but that poses a different question around an then to democracy as well. So I think it's important to have a calibrated approach. I do think principals have an obligation to do good with their wealth. And I think many have good intentions to do just that in their foundation work and otherwise. And those are often insights into their lives and their personalities and their priorities. And so those are good ways to understand them as well that are a bit more in the public domain.

1:04:23In any case, it makes sense that some of those external factors have kind of huge implications in the way that organizationally you're set up and what is publicly shared or public knowledge, you know, generally becomes, uh, kept private, but within kind of the organization's four walls, which is much different than how most, you know, corporate chiefs of staff think of themselves now as, you know, even kind of public faces of their companies in some ways. Yeah, I think that's right. In my case, it's a silly example, but I, for 18 months or as much as two years, I didn't have a LinkedIn profile, for example, because I just, I don't really need one.

1:05:04And usually it results in people soliciting because people go and search for family office and then they try to pitch you for a deal. There's a chap that I know from my work on the Boy Scout board who messaged me. I haven't seen him in 20 years and he was raising capital for funds and people get in their minds that someone has told them, you know, there's a great source of capital within family offices. That's a great place to try and raise capital. So you've just got all these people pitching and trying to solicit. And usually no one's done the homework to kind of understand because it's difficult to sort of find what the priorities are for a would-be family office investor.

1:05:41And just sort of, you know, throwing the proverbial crap on the wall and hoping that it sticks. And family offices are very, very skeptical of, sensitive to, and appalled by that sort of approach. And as a result, it kind of builds the walls up naturally. And the chiefs of staff and heads of family office and CIOs and CEOs in these roles, they end up being gatekeepers and sort of protectors of the principles to sort of keep that rubbish out. And there's a lot of it to go around. and we like to avoid that as all good family offices do. So some of that is also very much by design and serves the interests of the families and the principals.

1:06:25And it does appear that the best chiefs of staff in any context here do have to play that proactive gatekeeper and should be the one saying no more often than the principal has to say no because that is a protection of not just his or her time but also just general mindshare. I think that's right. And it's an old cliche adage, but for a principal who has unlimited financial resources, what is their greatest commodity? It always has to be time, right? And this role is to optimize their time. And if you can do that, and you can do it thoughtfully, you're doing your role very, very well. And you get to have an exponential influence as a result, because you're now associated with someone whose influence is so much greater than your own, and you become an accelerator to that person, you can be associated with any amount of good that they may be creating in the world through thoughtful investments, through foundation, charitable work, and through being a good employer who may have a small but mighty team that are bringing thoughtful professionals together to do good work.

1:07:36And I think that's a great thing. And I think that's one of the greatest things that a principal could do is to create jobs and invest wisely and put their capital to work in positive ways. And if you get to be associated with that, that's really the pleasure and the privilege of such a role. Donald, thank you so much for joining us today. We really appreciate you sharing these stories, shedding some light on an industry that doesn't get enough of it, and just being present. It's my pleasure. Thanks very much for having me. It was a real joy to be with you. Three things I'm holding on to from this episode.

1:08:12The first is the trade-off question. When your principal has effectively unlimited resources, the answer to can we do this is almost always yes. The useful follow-up is what it costs somewhere else in their life. And being able to answer that one on the spot is the whole job. The second is the rule of three. Say it's a bad idea, say it again, and say it a third time. Then go execute their decision because that's the work. The objection is at least on record and your credibility stays intact. Nobody spends the next year wondering whether anyone spoke up. The third is the one about the career ladder because frankly, there isn't one.

1:08:47You don't get moved from associate to vice president on a schedule in a family office. The reward for doing the job well shows up the surface area, more trust, more delegation, more of somebody's life running through you. I think the last piece travels well beyond family offices. Whether your principal is a founder, a CEO, or someone with houses in four countries, the mechanics are all the same. Protect one commodity they can't buy more of, earn the right to be in the room, and be willing to be the least popular voice in it when it matters. Donald, thanks so much for the time today and for the candor.

1:09:19That world doesn't get talked about honestly very often. If this was useful, send it to someone who's thinking about a move just like this one. And if you want to be around several thousand chiefs of staff who do this work for a living, come find us at chiefeststaff.network. We'll see you next week.