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Welcome to The Boardroom Path, the essential podcast for aspiring and newly appointed Non-Executive Directors navigating the journey from executive leadership to the boardroom. Hosted by Ralph Grayson, partner at Sainty Hird & Partners, each episode offers insightful conversations with industry leaders, seasoned board directors, and governance experts. Our guests share practical strategies, valuable perspectives, and actionable advice on how to effectively transition into board roles, maximise your impact, and build a rewarding NED career.
[00:00:03] Ralph Grayson: Welcome to The Boardroom Path by Sainty Hird & Partners. I'm your host, Ralph Grayson, a partner in the board practice. In this series, we'll offer practical steps and useful perspectives for aspiring and newly appointed NEDs. Throughout its 30 year history, Sainty Hird has recruited senior board members across the City, Industry, the Public Sector and NGOs.
We're now also evaluating those boards, as well as coaching and mentoring those seeking to transition from an executive career into the boardroom. So we'll be speaking to some leading figures in the board advisory and NED world. Specifically, we'll seek their counsel about how and where to spend time and energy to make an effective transition into the boardroom.
The goal is to equip recent and aspiring NEDs with tips, tactics and strategies to be most effective and build a successful career as a board director. In the process, we aim to help you to think more about who you are, how you operate and how you can make this work in the boardroom.
My guest today is Rupert Jones. Rupert is Former Standing Joint Force Commander in the Army, having served and led in many high stakes environments, including Iraq, Afghanistan, Syria, Bosnia, and Northern Ireland. He was the youngest Major General at the time and was decorated twice for overseas operations. Amongst other roles, Rupert now works as a leadership coach, boardroom advisor and advisor to startup founders and multiple investors.
Today we live in a confused leadership landscape with politicians who are often binary, confrontational, divisive and populist. Outside of politics, the trend seems to be towards monochrome and socially constrained leadership. So today's question is, do we have the leadership culture needed to thrive given today's geopolitical landscape? And how should boards think about leadership, both within the board itself as well as in its oversight of the CEO and executive team?
Rupert was always going to embark on a military career as his father served with the parachute regiment and tragically lost his life during the Fawklands War. Rupert was only 13 at the time of his father's death who posthumously received the Victoria Cross. Rupert, can we just touch on how that shaped your understanding of leadership?
[00:02:33] Rupert Jones: Yeah, I mean, I think, you know, we are, we're all a product of our upbringing, whatever that might be. Many people have been through something visceral in their life that shaped them. Losing my father at 13 was my visceral moment, if you like, and to a large degree, shapes who I am.
What did it tell me aboutleadership? I mean, I suppose of course, at the time nothing very much.You've just described the circumstances of my father's death. I was incredibly, and I am incredibly proud of him andI guess it has shaped what I aspire to be.
I hope that I could have done what he did. When you face the ultimate test, can you face it down? Can you do what needs to be done? And so I think it tells me something about commitment, about seeing things through, about overcoming obstacles. Not every obstacle is charging an enemy machine gun post. But obstacles are real and they need to be faced down, and you need to hold your nerve.
So I think there's something around kind of moral courage, physical courage, that it taught me. I think also, you know, I'm very, I've always been very proud talking to people who knew him. Because he was a kind of really interesting character and he cared about people, and people cared about him.
[00:03:42] Ralph Grayson: Rupert, can we first start with a bit more of your background and transition from military to commercial leadership and ultimately into coaching?
[00:03:51] Rupert Jones: Yeah, so, so I mean, the military is like all businesses, you know, there are people who, as you become more senior, stay pure to the business's output, and then there's others who go into what you might call supporting function. So in the case of the military, now, it might be into HR, might be into procurement, any number of vital functions.
I stayed true to the output of defense, which is overseas operations and so I spent a lot of my time overseas leading multinational teams in very extreme circumstances. So I suppose when I got out the military, I thought, okay, how do Iparcel that as everybody does when they're transitioning from one career to another?
They try and ask themselves what it is, my skills, what can I transfer? You know, what do I bring to the market, if you like? And I felt there's something that I brought around leadership, you know, the military focus on leadership very, very specifically, and so I just asked myself, okay, how do I bring that to the market? What is the value of it?
Leadership in most walks of life is slightly taken for granted. People don't commit enough effort to it and it struck me that there was, it is something the military do quite well. They don't claim to be perfect, get it wrong as much as they get it right,but they definitely educate people in leadership. They train people in leadership, they practice leadership a lot, and so, how can I parcel that and bring that into the commercial environment?
[00:05:08] Ralph Grayson: So let's strip that back a bit. I'd like to draw on a couple of analogies between the military and civilian worlds.
We both started at Sandhurst with a little red book called Serve Lead, and leadership is imbued from day one. Conversely, we almost set up our commercial leaders to fail by not developing that leadership. So I've spent decades recruiting and advising in around the world of investment banking and it's always struck me as a almost counterintuitive that we take the best sales person on an equity sales desk and presume that qualifies them to be a head of sales, but we take them off what they're good at, which is selling.
You've talked about the leadership muscle and how leadership needs training and developing. Perhaps you could just talk to us a bit about that and think about how the evolution of leadership fits in your mind.
[00:06:04] Rupert Jones: Yeah, there's terrifying statistics, I think it was the Economist that published some statistics that showed that 82% of managers, leaders in this country have received no leadership or management training, and to your point, they've promoted up their organization in whatever vertical they were in. They may been an investment banker. It doesn't matter what their vertical was. But that's what they were good at and that's what they got promoted for and then suddenly they found themselves in a managerial or indeed a leadership role, and they're a sort of cross enterprise leader, and that begins taking away from the thing that they were good at in the first place, and no one's giving them the tools to do so.
Somebody probably taught them how to do investments. Somebody probably taught them how to do whatever their vertical was in theirdigital individual. They've got digital skills, they learned, they were taught, but somehow leadership's different. You know, they can just transitionand I would argue that's not the case and that we set individuals up for failure. I'm glad to say that many businesses do understand the value of leadership and coaching and helping people, develop as leaders. I view it as a skill, an art, that needs to be developed.
So the Royal Military Academy Sandhurt the British Army's Officer Academy, which is widely regarded to be the best Officer Academy in the world. They solely teach leadership. When you pass out from Sandhurst, all you've demonstrated is that you can be a leader in the British Army. All the skills you're taught are really a vehicle to teach leadership.
Once you leave Sandhurst, you then go and learn the technical skills if you're going to be an engineer or tank man or whatever it might be. So it's one of the very few organizations that really focuses on this thing called leadership. You're educated in it, you're trained in it, and then once you join the military properly, you are constantly learning from other people about leadership is what I call leadership petri dish. Everywhere you look, there's leadership going on.
The other analogy I like to use is you look at the best sportsmen and the best musicians, of course, they've got some talent, they've got some determination, but they're only as good as they are because they're constantly learning and being coached. Look at Roger Federer. He has a tennis coach till the day he retires because he knows he's not the finished tennis player. There is no such thing, and so he needs to be given new techniques all the time to stay on the top of his game. The same with musicians, and yet we somehow think that leadership is different, that it's just kind of innate and you don't need to be taught it. You don't need to learn the theory, that you don't need to be mentored in it. At the head of this you talked about the threats we face and the challenges we face in Western leadership at the moment, and I think for our leaders to thrive in an exceptionally competitive landscape, economic landscape. Then layer onto that, the geopolitical threats that we face. We need leaders who are the very best they can be, and I think to do that, you need some help. You need some support to learn about the kind of arsenal of tools you need to be a really effective leader.
[00:09:11] Ralph Grayson: So how should a board think about that in its broadest talent sense? So you and I went through something called the regular commissions board. People recognized potential in us before we could, join the factory, the leadership factory of Sandhurst, and you touched on sportsmen, or musicians.
So how does a board think about from the graduate trainee through to the CEO? It's notable in my mind that more and more HR people are joining boards. Some people are, recognizing,the value added that a senior talent HR person can bring to that process. But if you were a new board member,what would you first do in that first magic a hundred days to look at what is the talent I've got in my executive team?
What's the culture of this organization? How does talent fit into what I'm trying to solve for as a board member?
[00:10:02] Rupert Jones: I come from the position that all endeavors stand or fall on the quality of leadership and the quality of people. Show me an underperforming business. Look at the board, and the first thing I'd look for is what is the board dynamic? What is the trust deficit at play? Sure, if the product they're selling for just doesn't have any market, then fine.
But if it does and it's still not working, I'd look at the board dynamic. Do people trust each other? Are they aligned? You mentioned HR executives getting themselves onto the board more and I would agree with you. I think that has to be a good thing, and I think it takes us away a little bit from the culture that existed for a long time of CFOs becoming the chief executive. Which the CFOs may be suited being a chief executive, but it's not necessarily a natural path because that tells you it's all about the P&L.
I would look beyond the figures, I'd look at the trust, I'd look at the people dynamic. So what do I think boards should be doing as they're looking at talent management? It is about diversity, and diversity as a word gets used in multiple settings. For me, it's about diversity of thought. It's diversity of background, it's diversity of outlook. I'm making this up, but if you're an oil and gas, I don't think you want a board wholly made up of oil and gas experts. You want people whocome in and ask the, if you're like the stupid question, cause they don't know about oil and gas, and nine times out of 10, it's not the stupid question, it's the question that everybody who is too close to the problem is missing.
So I definitely think it's about kind of diversity ofbackgroundthat really adds value to an organization.
[00:11:45] Ralph Grayson: Before we leave the military theme, you spent your formative years as a soldier, as a young platoon commander, me as a young troop leader, and the first thing we all learned was that battle hardened old bloke in the corner called the Troop Sergeant, or Color Sergeant. It may be a bit of a stretch, but there can't be any better demonstration of true diversity, socioeconomic background, everything between the cliched Cavalry Troop Leader,and his Troop Sergeant.
How,do you think that analogyholds water?
[00:12:17] Rupert Jones: When I first arrived at my platoon in, in Germany, I walked in very proud of myself. I'd commissioned out of Sandhurt. I was the new Platoon Commander, and I walked into the office and I met by Sergeant Jim Hendy, who had a bit of a reputation.
He was the,proper old sage of the Sergeants in the battalion, and he said, Hello Sir. We've met before you were aged about five. I was in front of your father, on a disciplinary charge, and you were sat in the background in his shorts, taking notes. And I thought, okay, I know how this relationship's going to work.
You know, he's just kind of put me firmly in my place. I've known you since you were a little boy, but I do think that's important, you know, that idea of,you know, in that military example, why do we have this idea of a young pretender, a young officer, and then a whiz and old sergeant? I mean, it's a stereotypical, they're no longer whiz or old.
But you get the point. Is because it creates a team. They're bringing different skills and they both have a value, and when they're in harmony, the officer and the sergeant, it's very, very potent. And I think the same principle applies.
So for a chief executive, a founder asking themselves, okay, what are my skills? And if I've understood what my skills are, my experiences are, more importantly, what am I not? Where are the gaps in my personality set? Where have I got blind spots? And then bringing in people the equivalent of the sergeant who can bring those different skills to bear. See the things you can't see, bring energy to things that, that bore you. Cover your blind spots, I think is really potent.
[00:13:44] Ralph Grayson: Self-awareness and leadership often go together, in my view. How should leaders think about where their personality gaps might be, where their skill gaps might be, and as a coach how do you help them look in the mirror?
[00:14:00] Rupert Jones: Yeah, most people I coach, will tell you that they're self-aware, and I think most of us think to some degree or other, we are self-aware and others will have a view on that as to whether we're self-awareas we think we are. But I think it's always helpful to get somebody to, as you suggest, hold the mirror up and help us to really be aware.
And I think the coaching journey can help with that, undoubtedly. I think processes like a Hogan assessment can help with that enormously because there's so many data points behind something like Hogan that I think gives you a very good insight into the sort of person you are and your motivations.
And I then think, you know, working with a, an individual to ask them, you know, what sort leader do they think they want to be? What sort of leader do they think they are? How do they want to be perceived? How are they perceived? I think, you know, really helps in a kind of safe environment, allows people to kind of break that down and get under the skin of somebody just saying they're self-aware.
Okay, let's really understand what that means. What are your strengths? What are your weaknesses? How are you seen? Hold that mirror up in a very deliberate way. But in a collaborative way with the individual and help them begin to see how they're actually seen, not how they want to be seen.
[00:15:18] Ralph Grayson: I think that contrast between how you think you are perceived and how others actually perceive you is worth a bit more thought. In particular, I think it's important in terms of how you not only lead as an individual, but lead as part of a team, and every good C-suite has a center forward and has a fallback.
We follow that analogy that leaving the executive suite and joining the boardroom. Two very different skill sets. One is managing, leading in a follow me way. The boardroom, much more influence without control to be a good board member. What's your experience of that? What are your perspectives on that?
Both drawing on the military as well as your time as a coach?
[00:16:08] Rupert Jones: Military leaders go through that journey. So when you first joined the military, it is very much a kind of follow me style of leadership. You command, in my case, 30 odd soldiers and you know them all intimately. and it is a very much a leading by example style. As you go up the organization, you can't know everybody, you know, you're commanding thousands of people and therefore your style of leadership has to change. It's much more about setting the tone, the working through your subordinates, creating a culture, creating a narrative and that is undoubtedly a very different style of leadership. And it becomes much more about what I call influence leadership. People like to think of the military, you just tell somebody what to do. When you're asking somebody to lay their life down or potentially put their life at risk, they tend not to do it just cause they're told to. They do it for other motivations. Such as they trust you and they believe in you and they're inspired by you.
But when you get in senior levels and you're working in a multinational setting, the idea that a contingent from France or Germany or Canada or America, just going to do what you say cause you tell them to is a pipe dream. It's a coalition, it's an alliance, and you have to shape them and influence them and conjole them and slowly bring them around to your way of thinking. So it becomes a very different sort of leadership.
And I think that maps to your analogy in, into the boardroom. Where an early stage founder, for example, is the master of everything he or she surveys, you know, it's their baby, and slowly as. as the company grows, they have to delegate and then at some point as you say, you get to the stage where it's a really big company and you're up into the boardroom and it's a very, very different sort of allegiant that's needed.
It is much on that influence, you know, and you could push on the tiller, but nothing much happens. Why is the organization not moving? When a press on the tiller, where's the resistance? Is it a lack of resources? Is it institutional intransigence? Is it bureaucracy? What is stopping my guidance, my direction from turning into action?
[00:18:10] Ralph Grayson: And forms of language becomes important then. A friend of mine who's a special forces officer who remained nameless and the story may be apocryphal 'cause you were probably on the ground at the time. But they, he tells a famous story about, the Americans coming to the rescuewith some helicopters.
But choosing to go to an American, situation first before the British, because the British went all hell was breaking lease over the radio, famously said, yeah, it's getting a little bit sticky here. And that got totally lost in translation by the Americans who just didn't think, you know, that was kind of number four out of five of their priorities.
Whereas for Brit and culture, something being a bit sticky, that's probably one with stars on it. Right? So, how do people who live in the commercial world, how should a board member think about that if it's, a multinational business? So separate nationalities on a board, how does that fit together in a leadership context?
[00:18:58] Rupert Jones: Yeah, it's really interesting, isn't it? Because I think language does matter and you know, we don't want to be in a boardroom where it's all very directive, you know, thou shal do this. I think you can say, thou shalt do this, but in much softer language. I think it'd be a good idea if, you know, there's any number way of framing things, it kind of adds up to the same thing if I'm being understood properly. But not if people are kind of conceptually on, on a different language.
For me, the way you get around that is by letting people to know you. You know, there's a school of thought that says the leader should be, you know, a layer apart, and that is, of course, true to some degree. The loneliness of being the leader, the CEO, is undoubtedly valid. But I'm a believer in letting people in a little bit, helping people to understand your motivations. What makes you tick? How do you work? How do you make decisions? What are your foibles? Cause if you let people in, then they come in on the joke with you almost. And when you are giving guidance in a certain way, they understand where you're coming from, they understand, okay, Rupert's really serious now. Understanding the person is really, really important, and I say, I think leaders have a role in helping their people to understand who they are by just letting people in a little bit.
[00:20:19] Ralph Grayson: Of course it's a well-known,cliche that the best boards add most value outside of the boardroom rather than necessarily inside it.
You and I were at a breakfast this morning with some founders and investors, and I think one of the most interesting discussions was how founders make their advisors or their board members invested. Not in a financial sense, but in terms of getting under the skin and really adding value rather than the cliche that came up of, quite often, particularly with early stage boards, they're there to be Christmas decorations.
They look pretty and they're bright, and that helps obviously, potentially attract investors. But it doesn't add value in terms of scaling up the company and helping the founder team think about how they lead a business. Do you want to just explore that a bit?
[00:21:07] Rupert Jones: Yes. I mean, I think, of course it depends what you want and maybe you do just want a Christmas tree decoration. There's not necessarily anything wrong with that, but if you want your advisors to genuinely contribute, then my experience of it is that the more you draw them into the process, the more they can offer. If you have them sitting on the outside, on the periphery, never really knowing what's going on, and you only engage with them occasionally. They'll find it really hard to bring their experience to bear. They'll offer the old bond mode, but it doesn't, that it doesn't add up to very much.
If you really bring them into the conversation,then I think they offermuch more. Somebody who I respect very much, gave me analogy when I was first getting out of the military. He said, any advisory role I do, I don't want to be on the touch line coaching from the touch line. I want to be on the pitch.
And I think that's kind of quite a helpful visual. Get your advisors on the pitch. Sure, they're not right in the scrum, but they're on the pitch. They know what's going on. They're involved as much as they feel able to offer and I think if you do that, you get much more out of them.
[00:22:11] Ralph Grayson: Interesting, cause a lot of the,the textbooks on board behavior will say, noses in, fingers out. How does a CEO think about leading his or her board in that respect to get the best out of them? But not inviting that board dysfunctionality of being too much executive?
[00:22:27] Rupert Jones: Yeah. I don't think there's any kind of magic answer is there, but I do, I'm a great believer that as youget more senior and you know, the organization you're responsible gets, gets larger. You can no longer know every, every element of it. You can't know everybody's job. You can't know every person. You can't know all the functions. And as you kind of get drawn away, how do you remain in touch? How do you understand? How do advisors understand the business well enough? And I think it is that it is about dipping your toe in an area of the business, asking some searching questions, and then using your judgment. Does that feel sound? When I ask the questions, I didn't necessarily understand the answers because it's kind of quite technical and It's not my field. Butdoes it feel solid? If it feels solid, you know, you're bringing in advisors who are pretty experienced, hopefully trust your judgment and they back away that bit of the business feels good. I can probably look elsewhere and then again, dip your finger somewhere else. And when you get questions, it just doesn't feel right. You know, your spider senses are suggesting there's something wrong here. They're not over the top of the detail. The culture just doesn't smell quite right. I can't quite put my finger in it cause I'm not right in the middle of it. Then there probably is something amiss, and that's one I think you need to, you know, begin to double down and pursue it and find out, what is amiss? How do I address that? How do I correct it? Is it a problem of resource? Is it a problem of culture? Is it, is that a people problem?
[00:23:54] Ralph Grayson: Which brings us to the most emotive part I find with all scale up businesses, is how you work with a founder to help them be self-aware enough to recognize now I need a chair, or now I'm no longer the CEO. I'm best deployed elsewhere for the benefit of the company rather than the benefit of myself.
How do you help individuals think that through?
[00:24:21] Rupert Jones: Yeah, I think it's really hard, isn't it? You know, some founders are genuinely self-aware enough to, you know, maybe cause they've been multiple time founders. They know their journey. They know what their skill set is. They know when their skills begin to run their course and they're kind of ready to make that transition.
But of course, many are not in that position and they're a first time founder and they've done incredibly well. But they are an entrepreneur. They're not the kind of long-term stable leader, and I think that's hard for an individual cause it's their baby. You know, they've given birth to it. It was their widget, it was their idea. They were there on day one with their co-founder when it was just an idea in a pub. So it's very, very hard to let go and I don't think many people can let go without a little bit of support, and I think that is where having good advisors around you, mentors, coaches who can challenge you, ask you those questions, help you get to the right answer. You can't be told.
[00:25:16] Ralph Grayson: Yeah, I think it was fascinating at breakfast this morning, we had one founder who was on his seventh startup and was just, you could just tell he'd seen every scenario and he knew what to do from experience, where we had another very young founder on his first startup, who I think showed incredible maturity in terms of his self-awareness of, here are these huge goals and was already thinking, how do I get the best out of a board?
Any perspectives onhow you could coach board members to think about how they help a founder, particularly an immature founder. I mean that in a good sense in terms of how long they've been in the seat rather than necessarily how many years they've been on the planet.
[00:26:01] Rupert Jones: Yeah, I mean, I think it is hard, isn't it? Because as you say,the founder you're talking about was hugely impressive. But a great many founders, particularly young founders, you know, they're bringing all sorts of incredible skills to, to their business. They're visionary, they're entrepreneurs, you know, they might be, you know, they might be quite unusual characters.
But they're brilliant, and thank God for it. It's why the startup scene is so healthy in this country. But it doesn't necessarily mean they are ready-made leaders. It doesn't necessarily mean that they're self-aware. For every, every founder you come across, like we did this morning, you'll find two or three who are probably not like that, who do need a little bit more help.
So how do boards help with that, whether that's, say, fully formed board or are kind of remote advisory board or a mentoring board? I think it is about questioning. They're kind of brilliant at what they do and they're masters of all they survey and they're not necessarily going to be told. Nor should they be because they've driven through any number of obstacles to get the business to where it is. And they've, yeah, driving on hard, they're very single-minded, task focused. So I think it's how you help that individual get to the answer themselves. and of course, you know, that is in a way, is what coaching's all about.
You know, the great cry is get the coachee to do the work. Well, the coachee can only do the work if you ask the right questions, if you probe in the right way. If you drop in the right little bit of gentle advice and slowly in theory, that will help a founder get to the answer themselves and they'll get to the answer themselves when they're ready. But you can help them with that.
[00:27:42] Ralph Grayson: I spent a lot of time with aspiring NEDs, thinking about where in the food chain they best fit in, and what I mean by that is the size of the company. Is it public? Is it private? Is it scale up? Is it regulated? It's not regulated. I've been a,an investor in a number of FinTechs and a lot of FinTech founders, in particular, are technologically brilliant. But they're obsessed with code. And then try and get them to think about, okay, you are going to hire a head of sales, so let's just think what the job spec looks like. And all of a sudden they're, oh no, I've got to run down the corridor and write some code and avoid the leadership bit.
How do you make people self-aware? That's incredibly tough, right?
[00:28:29] Rupert Jones: Yeah. and you know, some people will never get there, you know? Is anybody uncoachable? No. But there may be limits to how much you can help some people. So it's about, helping that individual, this code loving founder, okay, what is it you want to do? Why are you trying to take their company? Well, it's kind of, it's going to be this code company. It's going to do X, Y, and Z. Okay? But you know it's going to fail. If you keep doing what you're going to do, it's going to fail. How do we stop that happening? So it's about asking the questions to help the individual to go, okay, the thing I really, really love is code. Am I best placed to lead the company or am I, best placed on the, as a CTO or whatever it might be? How can I bring my skillset, my passion to bear most effectively? So the thing that I love so much, which is this bit of software that I've created, can really come to market and thrive.
It has to be a conversation. I don't think you can just kind of sit down with somebody one day, hold up a mirror and go, Tadda. This takes time. These are long conversations.
[00:29:33] Ralph Grayson: Yeah, I think you've gone right to the core of it, and most founders think success is about product-market fit, fundraising, and then hiring, putting it off as long as they can. But success is as much about leaders scaling themselves as they scale their business.
[00:29:50] Rupert Jones: Yeah, undoubtedly. You know, and it's so difficult, isn't it? The one thing they're definitely short of is time. And so, you know, as the company scales, the demands on their time only get greater because then they now hire people and put in process and culture, and they now need a new office. All these things close in on them in terms of time. Takes them away from the thing that, that they were passionate about in the first place.
It also takes away two other vital things. The first one is the ability to think and to really analyze where their company is and where the company's going. Strategize if you like. But it also means they don't have the time for themselves to invest in themselves, and I mean, invest in themselves in the broader sense. So keep themselves healthy, in whatever guise that might be sleeping properly, eating well, doing fitness. We all know fit body, fit mind. Nurturing relationships are important to you. All of those contribute to how well or otherwise you perform in work. You're one of the same person, and it also reduces your ability to grow because you haven't got the time. I would do a course. I would do some coaching. I wouldlearn this management skill if only I had the time, but I don't cause I'm too busy doing, and I guess the question then becomes, can you afford not to do these things? And I think it slightly goes back to our analogy that, you know, people promote upper vertical cause they were good at it. I think often founders, they find comfort in the thing that they used to do.
So in your case, you know, writing code and it's a hiding place. It's a hiding place from doing the things that really need to be done. The hard, the tough decisions. Doing the things that are going to make the company really scale and grow. But they probably don't feel as comfortable doing, you know, making good recruiting decisions, for example.
And there's one thing I'd, you know, encourage founders. You got to make time and it's time to do some different things to the things you used to be doing.
[00:31:52] Ralph Grayson: And I think that brings us to certain key inflection points in any scale up journey. One VC I talked to recently talks about all the sevens, 7, 17, 70. He said that's either in terms of headcount of employees or turnover or number of stores you might have, but those are the key moments particularly. In that year four to 10 is when a lot of founders fail to make that transition from founder to CEO.
How should people think about those inflection points? How can they get the best out of their board, their advisor, their coach, to think about how do you scale yourself, I guess is the question.
[00:32:31] Rupert Jones: I think my thoughts on that would be, well, firstly, try and soften the transitions. You know, I think you said seven to 17, you know, in between those 8, 9, 10, you know, so try and soften those transitions. Okay, what point do we begin to scale to the next stage? Do that in a very conscious way.
As you know, if you scale too slow, you miss opportunities,and you don't thrive. Scale too fast, you get ahead of your skis. and that in itself can be a problem. So I think there's something about, softening the scale, doing it iteratively. But I also think it's about doing it really consciously, and that is where boards come in.
It is where advisors come in, you know, having on your board a, a serial founder who's been around the block a few times, seen this moment before, knows that the pitfalls so that you can plan for it and not go into it eyes half shut, and there's a company I work with who've scaling very rapidly and an awful lot of the things they seem to encounter feel like a surprise. But in reality, none of them surprises, you know, they're all predictable. They're to do with unique office culture, and, you know, as you scale, it's about the demands on the founder's time, recruiting the right people, which is very, very time consuming to get the right people, to keep the right culture, to keep the business growing.
But, oh, now I've got all these HR problems, cause people come with problems. It's the, you know, it's the nature of them and that's very, very time consuming. But all of those things are actually predictable. You can plan for them, you can name off for them, but I think it is very hard for founders to step away. To really go away, and, you know, with a whiteboard, whatever it might be, and use what word you like, strategize, blue sky think, whatever it might be, andget ahead of these things and predict what is predictable.
[00:34:24] Ralph Grayson: I think that's an interesting point, and the textbooks will tell you there's three types of leadership, there's vision, there's operational, and there's strategic, and the best leaders learn to switch between all three based on what the business needs. How do boards think about that leadership matrix and how do they encourage a CEO or a founder to think about the skill sets that they need around them as the business grows and evolves?
Yeah, I mean, I think, you know, it does in part come back to making sure you've got the right team around you. Encouraging them to have the right team at the right time. You know, what is the founder's blind spots? How do we,mitigate that? I think it's also then recognizing that leadership one day is not the same as leadership the next day. You need to lead differently at different times for how many people you're leading. Who are the people? Are we leading in good times, bad times? Are we in crisis? Are we in steady state? Have I got a highly motivated team? Have I got a team whose morale is low?
[00:35:29] Rupert Jones: You've got to lead differently at different times, and I will talk about, you know, having an arsenal of tools that you draw out at different times, and if you try and lead, you know, you lead in one way, in one set of circumstances, works beautifully. The next month you try and do the same thing and it won't work at all, cause circumstances have changed. So I think it's aboutencouraging your CEO, your founder to understand that people need leading in a different way at different times. The founders are all in, aren't they? You know, it's, it is their business. They're emotionally all in. It's probably their money. You know, it's their life. They are all in.
You may have a few other people around you who are all in with you, but as you grow a great many of the people, they're just employees. They're doing a job and they move very hard workers. But are they from a startup culture?But they're coming at from a very different perspective and recognizing that different people bring different energy levels. The leader will typically have more energy than anybody else. They'll go to bed thinking about it, they'll think about it in the shower, they'll think about it when they're going for a run. This kind of restless energy and how, you know, how they harness that and if you like, gear it down to their team because the team probably don't have limitless energy. It's a good job. they're on a nice salary. Maybe they've kind of got some equity in thegame, but they probably haven't got quite the same energy, restless energy that, that you've got. And how do you gear your passion to their level, I think is quite a trick.
[00:37:01] Ralph Grayson: I think that's great perspective, as I always say to aspiring board members or advisors in the scale up world. That fit works for you if you are prepared to take the telephone call from the founder on the Saturday night, in the middle of the dinner party or the Sunday night when the founder realizes he or she can't make payroll on a Monday morning. That needs a certain amount of emotional investment rather than, particularly with a PLC board, which is more governance driven process, more risk orientated.
So how would you advise aspiring NEDs, board members, board advisors to think about their fit with a founder and fit with the evolution and stage of the company?
[00:37:48] Rupert Jones: Yeah, I think that's such a good point. You know, I very naively want to go out in the military. I was thinking, okay, so I want some advisory board positions. I want to be a NED. I didn't really know what I was talking about. Inevitably, and you begin to kind of break it down, don't you, and to your point, you begin to understand that there's kind of quite, there's public companies that have, you know, pretty regulatory based boards, and I probably wasn't a fit for that. So I had to work out for myself, you know, where I could offer, offer something. So I think it is about prospective board members being self-aware, taking help with that, to analyze, okay, what is it that I bring that is unique or that I can offer?
And that then begins to tell you the sort of company that you might be suited to to support. And part of that is to your point, is around your kind of commitment level and your energy level. If you want to, you know, read a 200 page board pack and go in and, you know, offer your wisdom and regularly advice, that's fantastic.
That's a very different sort of board role to the sorts of ones we're talking about where founders need, they need visceral support. They need a shouldered cry on.They need support through, you know, some, sometimes some quite basic problems, but they've never encountered them before. And it's a problem for them. And they're ve they're vexed about it and they're conflicted about it, and they need to just talk to somebody about it. And that's quite, that's kind of, that's rather lovely. It's very hands-on, but it's a very different sort of board support to, you know, the much more compliance based, you know, gray beard type, board role that some people think of.
[00:39:22] Ralph Grayson: Well, I think it draws on something that came up at breakfast this morning with the chair of the incubator who said his advice to founders is you don't want a mentor or a board advisor who's just had one successful exit who says, this is the way to do it and it'll be fine. Actually, what you want is somebody who's got it wrong five times, because the best advice they can give is, well, if you go down this route, here are the problems you might find. You go down this route, these are the problems you might find. So it's not about a right or wrong telling the founder or telling the CEO how to run his or her business. It's about that broader perspective.
[00:39:58] Rupert Jones: And recognize that every circumstance is different. So I haven't come across this particular problem before, but I've seen something quite similar. We did this and it did or it didn't work, and just my judgment, my intuition, all intuition is ultimately is a, golf bag of experience, isn't it? It's not a magic thing. Intuition, you grow over time and some people are more intuitive than others. All that really means, I think, is that they kind of almost listen to what's in that golf bag more than people are perhaps arguably less, less intuitive.
So it's about drawing, as you say, bring having board members who've got that big fat golf bag of experiences of lessons, things that went well, things that didn't go so well that they can draw and just, okay, I haven't seen this quite like this before, but my intuition, golf bag of experience, tells me that you might do this.
[00:40:49] Ralph Grayson: Yeah, I think that's great advice.
Can we just come back to the idea of teamwork and cohesion as a business scales. How does a board think about that evolution from the founder team through to employees who aren't invested literally on the cap table? How do you keep that north star, that mission, that purpose? For the founder team it's obvious. It's what drove them to do it in the first place. But once you get to a certain size, it's more difficult to keep that cohesion. What's your experience of that?
[00:41:21] Rupert Jones: I think it's incredibly difficult. Cohesion and culture. So a company starts with one person, two people, a widget, an idea. They form a culture around themselves and then they become four or five people and there is a little culture around them. They might even codify that. They might even write down what their values are and what they believe in, and, you know, that's what gets them out of bed every day. You know, the kinda secret sauce if you like, that underpins their widget, and how do you keep that as you grow?
The first thing is you've got to have a really clear cohesion and culture in the first place. If you start growing without a really strong culture in the first place, don't be surprised if it just kind of fragments. Cause it didn't really have any substance in the first place. So I think you've got to be really clear what your culture is, and again, you know, whether that's just in the founder's head or whether it's codified, you can take your pick, but there's got to be something that is potent and it has a kind of brand and a shape to it and then you can rally around that as you grow.
And then I think the key is about bringing in people who support that culture. So we've talked about you need diversity of thought, you need diversity of experience, but it's also a culture fit. Am I bringing in this person as I know my chief commercial officer for sake of argument, and yes, they bring all the skills I need and they've got a kind of diversity of background that I need. But, are they going to fit into the culture that I'm trying to grow? Because in a startup, it doesn't take many hires at the right positions with the wrong approach to culture for your culture to begin to fragment.
And of course the culture is under challenge as you scale anyway, cause you're just getting a lot bigger. There's so many things happening. You were five people, you're now 15, now you're 50, and that could be in the space of a year. You know, how do you keep your culture when you're just moving so quickly, getting into offices, hiring people, trying to sort out the IT and the before you know it, you look over your shoulder and the kind of culture's got a bitfrayed cause you weren'tpaying attention.
So I think that is really vital. So I guess what I'm saying is have a clear culture in the first place and then recruit consciously to double down on that culture whilst also bringing in diversity of thought.
[00:43:40] Ralph Grayson: Drawing back on our shared military background, for me that's all about the pride in the cap badge, right? When we got the best out of our rifleman or our troopers. It was pride in the cat badge and pride in the person to the left and the right of you. In terms of the lowest common denominator or the highest common denominator, and that's true leadership. Trying to imbue that, when I've used that reference with people who've never had that sort of background, I get a few blinks and a few blank looks. But to me that's the heart of leadership.
[00:44:10] Rupert Jones: Yeah, absolutely, and I think some brands do manage it, don't they? You know, we can think of some really cool brands where people do continue to buy into it. What was the legendary, was it one of the US presidents visiting NASA, and he asked the janitor what they're doing, as they're sweeping the corridor and the guy says, I'm helping put a man on the moon.
That janitor, if that story's true, that janitor had bought into the mission. You know, that's what NASA are doing, and I'm a part of it, I may be sweeping the corridor, but I'm part of it.You can do it, but again, you've got to have a really strong brand in the first place and a very strong story and narrative. I'm going to put a man on the moon. That's the story and everybody can get on board with it. So how do you create the story that people can come along with?
[00:44:52] Ralph Grayson: Conversely, my experience is that when things go wrong and they're people problems, they're invariably communication problems within teams, with investors, between the executive team and the board, and it's usually because they don't give feedback effectively or inspire positively. So how do leaders and boards manage communication and particularly in the case of boards, how do you think they influence rather than manage?
[00:45:19] Rupert Jones: So show me the best leaders and I'll show you good communicators. You know, I can think of very, very few really outstanding leaders who aren't also outstanding communicators, telling a story, inspiring people. I think it's so important to good leadership. And so again, I think it is about. The leader, the founder, the CEO, having a story, having a vision, and articulating it with clarity and with consistency.
Politicians repeat their narrative over and over again for a reason. 'cause you've got to say things a lot of times before it really sinks in and leaders I think, need to do the same. You know, they need to kind of keep doubling down on these are my priorities. This is where I'm going. This is what we're all about, and it's slowly, it gets imbued if you only kind of set once well it's just words. I think communication is also about reinforcement.
I think one of the other challenges of communication, it goes back to the self-awareness, is I know what I told people really clear what I told people. But how did they receive it? Did they hear what you communicated or did they hear something else? Did they willfully, or accidentally, choose to hear something different? Did they distill it differently from the manner in which you delivered it? And I think that's a real problem, and I think particularly with founders who are in a hurry, their brain's spinning at such a rapid rate. So they give their direction, their guidance, their vision, whatever it might be and 10% of the people in the room are probably right there with them. Got it all over it. Away we go.
But actually you're communicating to the individuals who aren't quite on your wavelength. Who aren't keeping up at quite the same pace. So how do you communicate for everybody? So everybody leaves the room understanding what it is I want you to do. What my vision is, what the big idea is. How do you check that they've understood and they haven't left the room and gone off on a tangent away from what they think you told them to do. What they thought was the vision. They're not doing willfully, they've just misunderstood.
So there's something about kind of checking back, reading back. Coming back to you, Ralph, in a week's time, right Ralph, how are you getting on? You know, what have you done with the guidance I gave? Just kind of read back to me, you know, where you're going with it. And I think the other thing I'd say is where I see leaders and subordinates, for want of a better term, get out of sync, is where there's not a constant dialogue. To me, the best leader led relationship is where there's a constant dialogue. I'm telling you the whole time what I'm thinking, you are constantly just updating me informally about what you're doing, where you're going, and I have an opportunity to kind of shape you without having to micromanage you. And I'm indirectly just tweaking you in a way that you are feeling is collaborative. You're not feeling emasculated, but you're going away knowing exactly where I am. You've got my trust, my confidence, but I just steered you a little bit, almost imperceptibly. So I think it's about a constant flow of dialogue.
[00:48:24] Ralph Grayson: Before we finish, I did just want to go back to your LinkedIn post, and the premise that we're living in a confused leadership environment, and the need for a readiness mindset against decision paralysis, which you touched on in your post, and the purpose of the post, I think, was to think about ambiguity, constant change, and a particular need for resilience. Just come back to that.
[00:48:50] Rupert Jones: It sounds a bit trite these days, doesn't it, to say we live in uncertain times? Shocks just kind of come around the corner the whole time. We are being challenged in a very real way. There are economic and strategic adversaries who want to challenge the Western way of things for a better term, and we better be ready for that.
And whether that is Russia or somebody else conducting cyber attacks into London and make a mistake, they're doing it. Through to Chinese companies buying up UK companies, maybe in entirely good faith, sometimes not. So it's recognizing the geopolitical environment in which your company is operating, and then it's making sure you are fit for that. Have you got your cyber resilience in place? Fine. That's just a kind of little process thing. But are you really resilient? Are you ready to challenge and face down the obstacles that are going to come your way?
And some of them might be predictable. They may be in your market and you predict them. Some are not predictable. Some are about global events, and you need to be ready for them. You know, from our old world, the military are very good at contingency planning at war gaming atheading off those strategic risks. There's a term the military use: What if this happens, then what? And you put in place a contingency, you prepare for it, you train it, and you de-risk that thing happening. So when it happens or something a bit like it happens, you ready for it and you can adapt, you can adjust, and indeed you can seize an opportunity from that risk rather than being cowed by it.
So I think, you know, resilience is about individual resilience,to make sure you are kind of match fit your, you can surge, you can sustain yourself. But it's about organization resilience. Are you really ready for the world we're living in? Because it is a different world now to the 1990s, for example, and leaders have to be prepared for different challenges.
[00:50:50] Ralph Grayson: I think that's really interesting.
I was at a EY board event, a few weeks ago, and the central premise was how did boards fail to see Trump's tariffs coming? We knew from his first term, that was what he was minded to do, but for whatever reason, didn't quite get round to it. So it should have been glaringly obvious that second time around he was going to come straight out of the traps with it.
But most boards missed it and didn't think about the implications for their supply chains, didn't think about the implications for their business models. Similarly, the queen firmly saying, how did nobody see the financial crisis coming? And I think what's fascinating, wearing my search hat, you see certain waves of searches coming and we, you know, we went through diversity of thought and diversity broadly on boards.
Then we went through an AI and a cyber risk, and now I'm seeing a tidal wave of we need people on the board who understand geopolitics, who understand how that impacts strategy, who understand how that impact operations, and I think that resilience in uncertain times, whether you are the founder, the CEO or the new NEDor established NED.
That has absolutely got to be the front of everybody's mind in terms of where they think that fit is going to be with whatever board they choose to sit on.
[00:52:06] Rupert Jones: I think that's absolutely right. You know, I think we talk about black swan events often events aren't that much of a Black Swan. So, you know how great a surprise was COVID really? Well, COVID itself was of course a surprise. But there is a reason why government had been planning for pandemics for a very long time is cause they knew that a pandemic would come along in some guise or other.
So they had contingency planned for it. Now you can have a, you can take a view as to how well they had contingency plan, but they had identified pandemics as a threat and they had contingencies for it. Boards must be doing the same. If they don't, I would argue they're failing their employees. They're failing their shareholders. If they're not going to a dark place in the head, looking at what the risks are out there, what are the future threats and some of those are well signposted, whether it's Trump's tariffs or anything else. We know they're coming. And the better prepared you are, come the day the race, you're on it, you're ready. You're not surprised. You put on your A game, and you live through the crisis and you come out stronger.
[00:53:10] Ralph Grayson: Rupert, we've got to draw a line in the sand. Fascinating conversation, if people want to follow up on any of these themes with you, or the light bulb moment has gone on, I now see the role of a coach and Rupert's that coach. They can connect with you through Sainty Hird. You are a member of our coaching team and well established there. How else do they reach out to you?
[00:53:29] Rupert Jones: Find me on LinkedIn. Send me a message,introduce yourself, say what you want to talk about, and I'll be delighted to talk.
[00:53:35] Ralph Grayson: Great. Well, wisdom indeed. Thank you for your time, Rupert.
[00:53:38] Rupert Jones: Thank you so much, Ralph.
[00:53:39] Ralph Grayson: I hope that you've enjoyed listening to this podcast and have found it helpful when thinking about how to approach your own path to the boardroom. If you would like to push this a little bit further, Sainty Hird runs a bespoke one to one programme designed specifically to this end. For more information, please visit our website, saintyhird.com, follow us on LinkedIn, and subscribe to the Boardroom Path to receive new episodes. Thank you for listening.