Mastering Multi-Company Leadership: Sean Delaney's Secrets to Authentic and Effective CEO Perform...

Now, the question you might be asking yourself is, could you run 2 companies? You've got one humming along nicely and you're thinking, oh well, Elon Musk can run more than one company. Richard Branson runs more than one company. So can I. Well, my guest today is a CEO of several companies at the same time, and he's probably doing a much better job, to be honest, in terms of shareholder value than, than a couple of those people I've mentioned before. His name is Sean Delaney, and he's running a company out of New Jersey called What If. Sean, welcome to the show.

Thank you so much, Jim. I am excited to be here.

Well, I'm excited to have you here, and thank you because, you know, I know that you had a personal loss, and it's a, it's a sign of who you are that you've come on the show anyway. We could talk about making commitments and the importance of that integrity to the role of being a CEO when we come on to that. We're going to talk about fear and what that means for CEOs and how you are taking yourself from one business to the next and adding value to each of those companies without necessarily trying to change the culture of each of those companies and letting other people play a role in the growth as well. So, we've got a few things to touch on.

Yeah.

We're also going to then talk about clarity and you've got a gift at the end. for everybody. So want everyone to stay around and get the gift on— it's a free download you're going to offer on, on clarity, right?

It's a juicy one too. Yeah.

I would expect nothing less from you, Sean. So Sean, how do you do it? Tell us the companies you're involved with, and then tell us, you know, how do you break the maxim? Because when I ran 2 companies in Singapore, my accountant said very wisely, better to have one company run well than 2 companies run badly. And I proved him right, actually, that I was able to— I ran 2 companies badly. Um, you're, you're breaking them all. So, Sean, tell us the companies you're involved with and what do you have to do to run 2 companies or more successfully?

Yeah, uh, it's a great question. So, the 2 companies that we're going to talk about are— we have What If, which is a consultancy for entrepreneurs, and how to, how to go scale further, faster, funner, purposefully written poorly.

Yes.

And then the other one is BevGraph Packaging. So look at that one fun name. What if we're challenging convention? And the other one, BevGraph Packaging International, which is a company making the world's first biodegradable, recyclable, but biodegradable food packaging to take plastics out of the ocean. What? So divergent. How can I wear both those hats is essentially what the question is.

Yeah. And the second one sounds like a sort of a CIA cover business, doesn't it really?

With a name like that, sort of registered in Panama.

Yeah. So, Sean, how are you doing? And I've got, for anyone that wants to look at the YouTube channel, I've got the What If, and that's W-H-A, and then it's an upside-down question mark, That must give people all sorts of trouble when it comes to typing.

It does. Well, this is how we say what if in New Jersey. It's what if with a D, right? That's how you say it. But the D is for disruption because we like to disrupt people's thinking on the 10 fundamental disciplines that every business needs to deal with. But it's also a question mark because, yes, we turn questions upside down. Questions are how we learn. Questions are having the— if I asked you today, Jim, if I were a genie and I could give you, uh, absolute total recall on everything you've ever learned, heard, thought, or understood, but you could learn nothing more from today going forward, or if I could totally wipe your memory, I'll let, I'll let you remember who you took to the prom and who you married and the names of your children. But we're going to set you to zero, but I'm going to give you the power to always be able to ask the best question to find the information you need. You would take that 100%, the second one, all day, every day, right?

Yeah. Well, I think fatherhood made me lose a lot of my earlier memories anyway. Anyone that's been up in the middle of the night trying to look after young children will know that they kind of erase parts of your memory. But you're right. So asking the right questions. Is a key skill as an entrepreneur, right? What does the market need? What do my team need? What do I do better?

100%. And to do that, that puts you in— if you know that your chief responsibility or one of your chief responsibilities running anything is to ask good questions, then that puts you in a state of, I don't know everything and I am connecting with people and I am open to new ways of thinking, new paradigms, new thought, it immediately puts you in a better place than anybody who comes in thinking they have all the answers or thinking that as a CEO, they have to have all the answers because that is not true. And that's part of what sets people up to die in the grind, to feel like I always have to be something I'm not. I always have to put on a front. I have to have all these answers. I have to, have to, have to, have to. And that's just not true.

And I think that's so— yeah. And very liberating, actually, the thought that as the CEO, your job isn't to know all the answers, but maybe to ask the best questions, right? And is that part of your secret to moving from one company to the next and adding value at the same time to multiple places?

Yes. Early in my career, I had the benefit of having a boss and mentor who was, he was an ex-Navy SEAL. He was a nuclear engineer. He was multidisciplinary and just brilliant off the charts. And he hired me into MetLife. I didn't know anything about insurance, but what he liked was I was a recovering lawyer. I was an ex-standup comedian. I made a name for myself in the realm of HR. I knew a whole bunch of different, and I understood process management, whole bunch of things. I love tools like this. I love things that— I love the Swiss Army knife of people. And he knew that I leaned into that. So they brought me in to fix one of their divisions. I said, but I don't know anything about disability insurance. And he said, yeah, you know who does? An entire department of people over here know everything there is to know about it, and they can't get it right. What you know is how to distill things down to the essence of what they are. These are my words now, not his, in reflection. You know how to find the root of what it is and you know how to talk to people and you know how to get to the answer, irregardless of egos and what should be and what you're being told. Just get down to what it is and fix it. So I did that. And then he said, okay, you, you've done that. We're expanding your purview. Now you're going to go and be— we were internal consultants fixing big intractable problems. Now I'm going to expand your purview and you're going to go help dental. And I said, but I don't know the first thing about dental insurance. He said, well, what the hell do you know about disability? I said, nothing. He said, yeah, get over there. What you know is what they don't. How to unscrew up what they've screwed up just because they've been there forever and they're buying into whatever they're being told about the state of the world. That's just not true. And then by the time they said, now we're expanding you to life insurance, I said, well, I don't know. Okay, I know. I get it. I get it. Just bring what I know. And I'll figure that out. And then I realized that as I started then going out on my own as a consultant, working with other big companies, Nike, Uber, J&J, I found out that shoes or pills or advice or restauranting or manufacturing, it doesn't matter because all business is still down to what it is, is people. in a value exchange. I'm giving value to you. You're giving value to me. It might be commercialized through a proxy of money for the value, but that's all it is. And if we're giving more value to people than we're taking, and we're open and honest and being integrous with who we are in the world, magic happens. Harmony happens. No one wants a disharmonious system, a workplace. Right now, if we think about business as a machine, then we get into the cogs and the wheels and we lose the essence of what it is. And people show up not as themselves because they are towing some kind of corporate image that they need to follow. And things just feel disharmonious. And that's where the grind comes. Oh, I got to go to work. Or, oh, I created this machine and now it's killing me. Well, as an entrepreneur, you built something beautiful with a mission in the world. Why is it hard? That's just the way it— business is. No, it isn't. No, it is not. You're not lining all of the things that we all know as humans as true in the world in your business because you're chasing something. You're chasing an image of, well, they don't act like that at Nike. Yeah, but Nike's been around forever and it's a machine. It's a monolith. It's not in many ways true to the world. It's become its own thing, its own culture, its own world. And either you fit in or not. But if you can't be truly who you are, then maybe that model is not right for you. I'm not casting aspersions at Nike or any other big business. I'm just saying we all know that there's some institutionalized nonsense that happens there. There's waste. There's grind, there's friction, and it's just accepted because those are big businesses. It doesn't have to be that way.

Okay. So, as you go into a company and you have this idea that there needs to be alignment between who you believe you are and how you show up, right? And Sean is kindly on the show. He had a bereavement in the family even just yesterday. but he's still showing up today. And yes, you know, that's the measure of, you know, who you are. And obviously your family have given you, uh, the space as well, which says a lot about how your relationship works there.

Thank you.

When you, when you go into a company— or you're welcome— when you go into, um, a company as a CEO of a business, how do you deal with the expectation that the co-founders might have, or the other members of the team, that you're not there all the time? Because my experience of being a CEO is people You know, they kind of expect you to be like a— sometimes a bit like a parent figure.

Yeah.

And being sort of a stepdad is not— doesn't always go down so well, does it? So how do you reconcile that expectation for permanence with the requirement for being temporary?

We'll be back after a quick break.

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Well, so, wow, we could unpack that for hours, but I would say—

Yeah, these are all big questions. We don't have that long to answer. I have to get you here.

Yeah. So, the short answer is we do have an architecture. So, I know people are— we've talked about this, you and I, that people are like, well, people might be frameworked out. But for me, having an architecture that says, look, here's the 20% of these things that must exist that are important, and we're not going to do the 80% because it's nonsense and it doesn't feel right and it doesn't get us anywhere. And so the 20% of strategic planning, for example. Now, what is strategic planning? At its essence, it's just how do we navigate when I'm not here?

Yeah.

So how do we navigate when I'm not here? Because I is we is us. We're a team. And so I have to first make sure that everybody has core value alignment. And so if I know that you, Jim, and I have core value alignment down to our bones, and you also believe in the same mission that I believe in, and you've bought into the vision that we have that we've set together for the future, It's very hard for you to screw things up, whether I'm here or not. Because if we didn't have a process for it, we didn't have a procedure for it. This just happened. What do we do? Sean just lost his father-in-law. Do we cancel him being on the podcast or do we let him do it? Well, we let him do it. Why? Well, because we all believe that our mission doesn't change because life has. Because if who I'm going to show up as in the world is dependent on what's going on in my life, then I'm playing some kind of game. I'm playing a role. But if I am who I am and my mission is to do everything I can to help entrepreneurs at all time, everywhere, and my clients, people who listen to me, the people in my community believe that, and then I don't show up today, they say, Well, that's disharmonious. That's, that's, he's not showing up as who he is. He said he would do all things. Now, I didn't say I'd fake it. So I said to you before the show, hey, if I break down crying in the middle because you say something that reminds me of my father-in-law, hey, we're just gonna roll with it because I'm being honest, authentic. And if that happened, I bet people would say, not see me as weak or some nut job. They'd say, Wow, the guy just lost somebody very close to him. Oh, here he goes. No, I'm not gonna break down. But here's the guy who just lost somebody very close to him, and yet he's still here. Why? Well, he— I, I know why. Because he frequently says and does that he is going to do whatever he can to help entrepreneurs build their dream. Because 10 people today, in the hour that we're spending together today, 10 people could hear this, change their companies, and affect— how many people could they employ? Hundreds of lives. Wouldn't my father-in-law want that? I'm going to go and do that because it's who I am. And so, and so I think that's a big freedom that entrepreneurs should hear, that as the CEO, you don't have to be a thing that is manufactured and polished. Yes, there's certain things that you need to do and you need to Strive. If you say, well, I'm a person who doesn't care about people, okay, well, you can be authentic and you're not gonna have many people working for you, but okay. Because if you say that you care and you don't, you're gonna show up in ways that people see your inauthenticity and they're not gonna follow you. You show up authentically, people will walk on water for you.

Now we've, we've talked about the 2 entirely different kind of companies. And, you know, you've been very, you know, open and honest about what you've got going on in your emotional life and also the importance of authenticity through your behavior. Cultures in businesses are different because your co-founders—

Yes.

Will have maybe the same mission and values, but they probably got different education backgrounds, different, uh, uh, Personal circumstances, maybe financially in different places as well. Interpretations of events will be different according to culture and so on. How do you balance that, you know, Sean, when you are going into, in effect, like 2 homes, right? You've got 2 partners and they're— they may be both homes and they're both aimed towards serving the clients and taking care of the staff and looking after shareholders where there are But they will have different cultures.

Yes.

How do you enable the 2 co-founders to feel equally in charge of the culture so it can be sustained when you're gone and have different cultures?

Yeah, so, so the way that I can bounce between and have, and have clarity between all of it is, again, it's that the, the, the architecture that I'm talking about, the harmonious architecture, is touching on the 10 things that are true everywhere. And so, while they—

You better tell us what those 10 are. You better give us a quick rundown. But we've only got another 10 minutes, so we won't get all 10 in.

But give us the top list. Things like navigation, which is how are we strategically planning things? So, core values, mission, and vision. Got it. How do we operate? This is project management. Now that we know who we are and what we're trying to do in the world, how do we start to run the race? We've planned it, but how do we start to run? How do we move and how do we allocate our limited time, energy, resources in a very specific laser-like way? And, and we're gonna limit the number of projects we're gonna do that are based on the most important metrics that we have to move, right? Serenity. This is the essence of when people say, why time management?

Okay.

Time management. You don't really manage time any more than somebody guiding a kayak down a river manages the river. It flows independent of you. You cannot stop it. It is a limited thing and it moves. So how do you allocate that in a way that makes you more serene? So many people come to me, so many entrepreneurs, and they say, I'm killing myself, I need more time. And then we have to unpack that because there's 4 buckets that every issue that entrepreneurs fall into, and you can parse them there and then figure out what people are really getting at. But we can get into that if you want. So those are like the Top 3 of the harmonious, but it's change management. How do we do it? We call it modify. It's analyze. That's metrics. You need to have your right metrics, but metrics just are numbers. The essence of it is how do we analyze it so that we know what we're looking at and can make decisions based on it? There's people management. We have people dynamics. No one does anything alone. I break that up into 2 things. Because management and leadership are 2 different things. The essence of leadership is inspiration, because leadership implies me getting others to do something, whereas inspiration is how do I get myself out of bed and show up and be the leader? And then how do I get you to want to be your best and give your best to the mission? That's inspiration. That's better than leadership. And then instead of management, We call it HOME. That's the H in Harmonious, which is Humans Optimized in a Meaningful Environment. Meaning, how do I make sure that Jim can be the best Jim he can be, knowing the mission, vision, and core values? So, you know where we're going. I've given you all the tools. I've optimized you and making it a meaningful environment so that, you know, I'm not here to just pull a lever for a certain number of hours and get a paycheck. No, this place means something to me. I spent an enormous amount of time here with these coworkers. And how can I take my job And directly be able to tie it to the effect I'm having in the world for our mission. Because that's why I joined this place, right? Not for a paycheck, for the mission. That's just a smattering of the 10. Everybody has to deal with them and optimize them. And we disrupt on— because, you know, there's whole disciplines and volumes of books written on all those things, but they're overcomplicating something and not really getting it down to the essence of what it is.

Well, and Sean, um, I think also it's impressive you've got an anagram out of, uh, harmonious and you've managed to get a letter for each one of those. That in itself is brilliant. But also part of the takeaway there is that if you go into an organization as the co-CEO or fractional CEO or part-time, that really you are a, a coach helping to put in place the values and, uh, and giving people confidence that they can be authentic. But you're not there to do the work for them, right? And, and you're like the coach on the sidelines watching people play on the pitch. You're not out there trying to kick the ball for them. So that means that you can be the CEO of many companies if you see yourself as coach rather than as striker, right?

And I've given myself permission to be able to go into a room and say, Hey, finance people, what's the answer? And they said, well, you don't know? No, I don't know. If I knew, I didn't need you. I need you because you're brilliant at that. I don't want to be brilliant at that.

I could—

could I learn it? I could. I don't want to go to medical school. I went to law school so I didn't have to go to medical school. I could probably figure it out. Don't worry, doc, I'll figure it out. No, I'd rather go to a good doctor and trust that they're going to have the answer. And I know what questions to ask them. I know what the mission is. I know what the vision is, and he and I are aligned on my health goals. Tell me what the answer is. And that's it. You have to be able to trust. But because I have that framework, it doesn't matter the culture, because the culture is just the mix of the people and personalities combined with the mission. It's a flavoring. But we still need strategic planning. We still need project management. We still need to make sure that people are allocating their time correctly, on and on and on.

Yeah.

Those things exist everywhere. So I would laugh when people would say, well, sure, you work with Nike, but what can you tell us here at J&J? I'd say, well, wait a minute. Do you have people? Yeah. Trying to do something in the world? Yes. Yeah, no, I'm good. We'll figure it out. Right? Your process is going to be different. Well, things don't work that way around here. Yeah, but they do. If I get people in a room and I talk to them long enough, we're all going to be on the same page. Yeah, you do. down all the stuff that you're layering on here that's complicating things. You don't have to have that.

Good. We get down to the human condition, don't we?

Yes.

Of pressure and so on. What about with the brand building for What If? Because, you know, on this show, I'm also interested in you as an entrepreneur.

Yes.

What you're doing. You've got a partner in Brandon who's actually also been on the show and fantastic.

He is fantastic.

He is fantastic. You're lucky. And I told him you're lucky as well. So, you're both lucky. But what about marketing? Is there, is there some sort of a piece of advice? Because with your background now for many, many years working in corporate and with entrepreneurs, a piece of advice that you give people on the, on the marketing side, Sean Delaney, that, that you, you find you need to go into every company and say, this is really one piece that's common to everybody?

Yeah, so Oh man, I was gonna say one thing and then I thought of there's five things, but I'll tell you.

I'll tell you.

I'll tell you.

Maybe I thought I'd just narrow you down into one thing with the time.

Yeah, you know you're trying, but I'm fighting. I'm fighting it. So the I understand. I'm difficult. So oh no, we've got that. Yeah. So I would say around marketing, a mistake that I made was trying to be all things to everyone. And then having clients that are not in alignment. I mean, if I'm trying to talk about, well, I don't want to say certain things about leadership in case that upsets certain people who think they are good leaders. I'll get them in first and then we'll work on that later. Well, if they're not ready to hear it and they're not the kind of person that is the kind of leader that we can change, it's going to be an uphill battle the whole time.

And I'm not—

I don't have the time to waste doing that. I want People who are ready to listen and to change and to understand. And so, yeah, is that gonna turn off a ton of people? Massively so. You want that. It's the same way when you're writing a job description. People say, well, I can't write it that way because I won't, I won't get as many applicants. Well, how many applicants do you want? 1,000? That sounds horrible.

Yeah.

I would rather 5, right? Ideally 1, and they're the perfect one. But let me get 5. So write it a different way. I had a good friend who Was, uh, was doing online dating and he was having all these horrible dates. And I said, well, let me look at your profile. And I looked at it. I said, who the hell is this? He's like, well, what do you mean? I go, who is this person? I don't know who this is. He goes, well, that's the person most attractive to all these ladies. I go, yeah. And you haven't had a good date since. Let me rewrite it for the piece of garbage you are. Saying it lovingly as, as one of my—

From a nice place, an authentic place. Yep.

I wrote it. I, I rewrote it for him. Now he is married. To the person that he found because it was in alignment. Did he turn off a lot of women? He turned off a lot of women. Oh, I love saying that about him. He turned off a lot of women, but he found the one because he was being authentic and clear. And then, so the second thing about, and I'll leave it there, about branding is that once you forget the message of the people that you are talking to, I mean, If you're not protecting your core, which is this is who we said we are and this is how we show up. Once you deviate from that, you can have— you can destroy a business. Just look at Bud Light and let's not get political as to whether they were right with what they did or wrong with it. Doesn't matter. What matters is they had a brand. They were talking to certain people who thought like that brand thought. And then they radically changed it and expected everyone to come with them. That's not how it works. Instead, they left. And so just think about who did we say we are, who are we being, and be that. And if truly things have changed so much that you need to, to, to move, then just move, do it. But, but know that the people who bought into your brand promise now feel violated and may walk. Yeah.

And I guess we had to, And I guess we had the same with the Apple, with the latest iPad advert, didn't we? Where they're actually crushing all the creative instruments rather than enhancing it, which is a classic example of what you're talking about, where it was inauthentic as an advert, right?

And you say, well, what just happened? I expected you to be this. I expect— you said you were. This is what I bought into. Yeah, the products. Yes, the products. I'm buying more than the product. Everyone is. We're always buying more than the product. We're buying that feeling because it's still a proxy. Nike's a proxy for for you, right? For a person, because it's value exchange between individuals. And so we expect the people on the other side of the phone doesn't matter what insurance company we call. We expect them to be compassionate, and if and if because the brand probably says that they are, and if they're not. We go, well, what is this? Oh, I hate big companies.

Yeah, right?

Because big companies lose the soul. They're people. And we need to show up authentically.

So, yeah.

Well, as you have done, Sean Delaney. Now, Sean, you know, about this sort of stage, I asked for a number one tip that you would give a fellow entrepreneur. Can you share something? that you now would sort of believe is your mantra? We've talked quite a lot about authenticity, for example, but is there anything else around that?

Yeah. If it's the number one tip, we kind of touched on it already. It is just to forever put your place in, don't be afraid to ask good questions. You're not going to seem foolish. In fact, frequently I will say, okay, I'm going to ask a lot of really dumb questions. Right? It was one of the first things I asked when I got— when I went into the room and they started describing disability insurance in all its forms and functions. And I said, hold on, let me back you up. Now, what's insurance? And they all laughed. But I said, no, I'm really asking you, what is it? And they were all like, well, don't we have bigger fish to fry? No, I want you to define it for me like I'm an idiot, because I am. And again, they all laughed and then they described it and it was Fascinating how people described it differently. And I said, okay, we're already seeing that we're maybe not all on the same page.

Yeah.

And then you get into it, and no one thought I was foolish. I built a career on being, well, he's going to come in and say, okay, so what are we talking about? What are we trying to do? Are we all on the same page? And just ask those questions, even if I thought I knew the answer, because in the mucking and grinding around through it, And me being the most vulnerable, vulnerable person in the room saying, never. I've seen how many executives have you seen nodding at a screen with a nonsense chart up there? And you know that they don't know how to decipher it. They don't know what the bars mean, but they don't want to— the emperor has no clothes. They don't want to ask the questions. And I'd be the one that would raise my hand and say, that chart looks cool. What is, what's the difference between red and blue? And then you'd see everyone else would start to ask good questions too, because I asked the dumbest one and now I gave space for more questions. And guess who was the most powerful person in that room, Jim? Me.

The person asking the question. So, I've got one last question for you because we're running out of time, I'm afraid, which is a book or a podcast you'd recommend. And then we're going to do the link to the giveaway. What's your book that you would recommend?

Well, if we're talking about disruptive marketing ideas, a book that really stuck with me is Made to Stick by Chip and Dan Heath.

Okay, wonderful. So, that's Chip and Dan. Sounds like a kind of an ice cream, doesn't it? But Chip and Dan Heath.

I'll have a Chip and Dan Heath crunch, please.

Yeah. So, that sounds like Heath bars, isn't it? We've got here at What If, we've got the business architecture. This is— what are you offering here for listeners, Shawn?

And so, there was a diagnostic I used to use for the Fortune 100 that takes 10 minutes to take. It's very simple. You answer a bunch of— you say yes or no to a bunch of diagnostic questions. And it gives you a window into where you are with the 10 fundamental disciplines and tells you what to do for each of them to move from where you are to where you want to be. Free. And there's a 3-video series, 3-video modules that come with that that explain what it is you're looking at, why it's powerful, and how to apply that into your business.

Shawn Delaney, thanks for explaining. So many things we've covered. Today, especially considering your personal circumstances. Sean Delaney, if you want to find out more, where do they go to get you?

So they can go to whatif.com. That's W-H-A-D, as we talk, I-F dot com. And we're there. There's links to my own, our own podcast called The Ether and our community and The Diagnostic and all things us.

Thank you for being all things us with me today. So ladies and gentlemen, we've been listening to Sean Delaney, the multiple, uh, sort of CEO, um, talking about how he can be CEO of more than one company and really about helping coach in other companies the authenticity and the leadership and the vulnerability. But the key point is to ask great questions and not be afraid of what other people think, because in asking the questions you're moving the whole conversation forward for everybody in the company. So if you've got any questions for me, please do put them in the chat. Also now with Buzzsprout, you can actually send an SMS on the player and it comes to me. So that's an innovation from the Buzzsprout people. So do send me a message. I'd love to hear from you. And in the meantime, until we meet again, please leave a review. Sean's got his finger pointed. Do you wanna say something?

Jim, I've done hundreds of podcasts. This is one of the best interviews I've ever done. So anybody listening, stick around with this man. He's doing wonderful things in the world.

Right, you're very kind. And by the way, I did not pay or ask Sean. There is no bribery taking place.

If you paid me, I wouldn't have done it.

And with that, we'll say thank you for listening. And until we meet again, just keep on communicating.