התמלול המלא של Stubby Talks Transformation | Episode 4: Sola Osinoiki

customer you find out what the customer really wants, you can actually deliver what they want and it will be first the right time as much as possible because you're giving them exactly what they want rather than you're a great programmer and you've gone to program something. So I think that's where it started for me and I think I've just continued that whether it's in consulting, whether it's mentoring and coaching, know, keep keeping your eye on the people you're trying to impact and create opportunity for. Dave Stubberfield: Yeah, that's a really great point you make. think for me that kind of customer experience, that skill set sometimes comes quite naturally to people. It can be taught, but I think the behaviors and the ambitions of people, sort of technical skills can be taught and learned. Um, but I think those human skills sometimes is that the want to learn and grow and that develop that, that they were going to come onto it, I'm sure. But that kind of the ability to understand people and customers and what they want that helps you along the way, doesn't it? So just on that, when people hear the term leadership coaching, what do you think they most often misunderstand about? the depth of the work that goes into it. Olusola Osinoiki: I think a lot of people just think leadership coaching is show me what the next step is and I'll just take it. I think that's what a lot of people think, but actually... I'll segway and then come back to the question. The segway is I do this leadership development for a very large organisation in Nigeria and one of the classes I teach is emotional intelligence. And there is a quote in that class from David Goldman that says that to see people that perform at their highest performance level, I think it's 98 % of the time, it's not because of their technical ability or the technical know-how, it's because of their ability to be emotional. intelligence, their ability to understand people, to engage with people and actually that's where you see the high performance come to bear and I think part of what people confuse leadership coaching is more like you're just going to guide me to get my best results but actually leadership coaching from my point of view is how do we help you be a better leader, how do we help you become more aware of your surroundings, how do you become more emotionally intelligent, more aware of the people around you, more aware of the in inevitable consequences of one decision you make. So you might be gregarious or loud because that's how you are, but then that intimidates your team. And I think it's only in real good leadership executive coaching that you're made to put the mirror up and reflection and see how do I make people feel. And we know the stats, it says that people don't leave organizations, they leave managers. And so be that manager that people don't want to leave. Dave Stubberfield: Hmm. Olusola Osinoiki: the manager that when you leave people want to follow you. ⁓ I had a manager like that that when she left, ⁓ year later, I decided to leave and get free I went to work exactly where she was. people people, people find people inspiring. I think what we're trying to do in our practice is to help people become ⁓ more the job they do, but actually become somebody who inspires beyond your day job. ⁓ Dave Stubberfield: Yeah. Yeah. Olusola Osinoiki: That's a long answer. But yeah, that inspirational piece, that transformational piece, that giving back, that it's more than just a job. ⁓ Dave Stubberfield: Totally, totally. think for me as well, it's kind of moving away from just changing a job title. It's actually how changing how you lead. that it might be progression. It might be a sideways step, but there's always developments you can take in how you lead people. And you've just hit the nail on the head there. People follow people. If you've built up a connection with someone that is trusted and they leave, are likely to follow them ⁓ you are case in point with that. But at the same time, if you've got someone that Olusola Osinoiki: Yeah. Yeah. Yeah. Dave Stubberfield: doesn't give you that trust and doesn't give you that care, like you say, you're going to leave them rather than the organisation sometimes. And that's probably why you see a lot of people in bigger organizations shuffle in between that same big umbrella because there's different opportunities, different departments to get the person they want. So they're staying with the company that they sort of share the values with potentially, but there's just changing that manage. It's really, really interesting. Olusola Osinoiki: Thank you. Yeah. Yeah, and I have a personal, I know you want to go to the next question, but I have a personal story to connect to that. I joined Glassware Smith Client as an analyst programmer, but by the I left seven years later, I'd done five different roles because I love the organisation so much. And so the opportunity to kind of just navigate that, go from programming to business analysis, to project management, to program management. was like you love the company and you don't want to leave the company and the company is giving you these opportunities to grow. I that's the key. Dave Stubberfield: Yeah, go on. Yeah. Olusola Osinoiki: That's how you people connected to connected to leaders that they're following. ⁓ Dave Stubberfield: Yeah, yeah, really great, great, great story that and I think that's that for me is can have that progression inside one one organisation and then leverage all of that learning somewhere else, Kanye and you can apply all of that learning. That's really, really key. Your sweet spot is helping leaders trying to break through a glass ceiling. So I guess what are the most common ceiling types that you see today? Olusola Osinoiki: So the most common feeling types are, you know. sexism, So females, so a lot of my clients are females who are trying to, they work really hard but they can't seem to break the

glass ceiling because they just don't know the language of the boardroom or the language of the C-suite, so teaching them that. Some of it is also racial and having been in those those situations myself where you're the only black guy in the room because you're that level of leadership that that's the color you see in the room, I always reflect back to say actually for me through my career when I was in the industry I didn't have a black person I could look up to. was always like so trying to fill that gap and trying to help people navigate that because sometimes what we know is helpful. It kind of gives you a bit more context but nevertheless I have got to where I've got to. So there's the sex elements, gender sorry, gender race and then expertise. know, so sometimes people don't realize that actually I have the expertise to be a great programmer but I don't actually have the expertise to be a great leader. A lot of people don't know the difference between being a leader and being a manager. So you have a lot of managers who are trying to become leaders and that's a misnomer. you know leadership is a gift or leadership is a what's the right word for it right? It's a style, it's Dave Stubberfield: Hmm. Olusola Osinoiki: it's an opportunity and managing is an opportunity and sometimes a leader can manage and lead but it's very hard for a manager just to lead right so you have to learn the art of leadership be a good leader and an art of managing to be a good manager so that's why you can take a programmer who's done really well and you make him a manager and he's so excited because he needs extra training to be a good manager because it's a different skill set to being a manager. The penny dropped for me when I was in where I was a manager and managing a lot of stuff and it made me a leader. So I was made a leader before I really understood what it was and I spectacularly failed. And it took me being mentored and coached ⁓ to the difference between being a manager and ⁓ doing job as opposed to leading and thinking company first ⁓ rather my department first or me first. Dave Stubberfield: Yeah. Yeah, yeah, really interesting. And it's sad that discrimination plays a massive part in this. But form of pushback does that take in real life? And how do you help people navigate that without them losing themselves? Olusola Osinoiki: So I think part of it comes from understanding the cultural nuances. ⁓ a the people You know, we are now in the right? We're now more aware of unconscious bias, right? So that's now, you know, 20 years ago, nobody would have used that word, right? So there's conscious bias and there's unconscious bias. So actually, sometimes I would naturally do something. I would naturally flinch when somebody comes into the room. ⁓ would naturally be worried when I'm in a dark room and somebody appears, right? So that unconscious, you're not intentionally doing it, but that unconscious bias comes from conditioning, comes from bias. background comes from things you're comfortable with. you know, this is not a podcast about race, but I just give you an example when I've entered into rooms and people think I'm the IT guy to fix the, well, I'm actually the owner of the meeting, right? So ⁓ just unconscious. It's not intentional. It's just what your mind kind of understands. So ⁓ think the tools that I try to encourage people is to understand the cultural nuances. And I think my first book recommendation today will be ⁓ go and read Erin Maher's map and really gives you an understanding that this is way beyond even color, right? What an American would do in a room and what a British person would do in a room even though they are both Caucasian, it's very very different just because of the cultural context and so there's it's ⁓ subtle than just color of skin or race. It's actually there's nuances to it and I think me going to work in Germany ⁓ opened my eyes to how ⁓ Dave Stubberfield: . . Olusola Osinoiki: culturally diverse Europe really is, right? So you enter a room and there's someone from France, there's someone from Germany, there's somebody from Portugal, and there's somebody from Spain. And the interactions and the expectations are already dynamically different, even though dealing with maybe potentially one color of skin. I think I and help people do is look beyond race and look to culture and understand cultural nuances, and then through that, find a way to put your best foot forward. And that starts with, you know, self leadership, knowing yourself, understanding yourself, self regulation, self control, how do you respond, know, responding rather than reacting. You you could be reactive because somebody doesn't like you or doesn't welcome you into the room or doesn't expect you to show any level of intelligence in a particular So you not reacting to that, but rather taking your time, ⁓ Dave Stubberfield: Hmm. Olusola Osinoiki: I don't know you've ever come across that rule, Mississippi 1, Mississippi 2, Mississippi 3, you have calm yourself down and then respond. ⁓ teaching people how to respond rather than reacting is one of the key tools. Because the only day, they it and probably changing with the word of, mean, don't know how, okay, we're 14 minutes in before I say the word AI, but we're the world of AI, Dave Stubberfield: Yeah, yeah. Yep. Hmm. Olusola Osinoiki: something that one to self mastery, That's the key because everything else is changing so fast. And so that's one thing you can control. You can't control how people react to you, but you can control your response. And that's why I try and train people and educate them. And then using my own life experiences, like, so how did I navigate that? How did I navigate to become a senior vice president ⁓ in a multinational and being the top 100? So sharing from my own experiences. So that's why what I Dave Stubberfield: Mm. Olusola Osinoiki: do is more coaching mentoring rather than purely just coaching. Dave

Stubberfield: Really interesting. And you've mentioned they're staying relevant with things like AI. Now you've kind of taken that self mastery to another level with AI, haven't you? Olusola Osinoiki: explain sorry ⁓ Dave Stubberfield: So you mentioned when we first spoke that you've kind of, you've gone through that AI sort of self-learning and you've kind of, you've got into that in more detail, I guess to help so you can help other people, right? Olusola Osinoiki: Yeah, yeah, yeah, yeah, yeah, yeah, yeah, yeah, yeah, yeah, Exactly. Yes, exactly. So I was just I just came back from Legos where I did a founders roundtable where we're talking about AI and the impact of AI and how AI particularly when I'm working with founders and I tell them that look nobody's you're not gonna get money because you come to me and say I've got AI inside because I'm assuming it's AI inside. I don't even remember back in the day when we we had Intel and then they say Intel inside like it was almost like we have to tell you but now we assume every computer has some form of Intel inside right so I think I think that's it so where which you Dave Stubberfield: Yeah, yeah. Olusola Osinoiki: You have to recognize that the world is evolving around you ⁓ you know rules are changing and having been a programmer before I kind of understand the technical side but actually realizing that actually there's what we call no code code right where you're actually not right you don't have to understand a simple line of code you just have to prompt ⁓ engine to do what it needs to do so yeah so self leadership again self mastery understanding what you need to understand understand what you need what you need to to become good at your job ⁓ not necessarily being the person doing the coding. And I learned that also from one of the organizations I worked with where almost seven years ago, they started doing AI training for every senior leader. So anybody that was a senior leader in the organisation, you had to go for like ⁓ a couple of weeks of AI training. So this was way before ChantGBT and they just saw it on Horizon that AI was coming and it was almost like this cultural of what does it mean to have AI in HR? ⁓ Dave Stubberfield: Yeah. Olusola Osinoiki: AI in finance, what does it mean to have AI in production? And just learning from seven years ago, and they've continued to do that. So now they have a huge AI department, et cetera. So yeah, so there is definitely that need for us to go out there and learn, and not just learn good things, but also the negative things also. So ⁓ was being chatted up the other day to come and do a talk about responsible AI and how we can be responsible around how we use AI. And you know, there's so much happening in the world. I mean, if we just switch to AI, like there's stories upon stories. Every day there's a new story, right? So, for you. Dave Stubberfield: Yeah, yeah, yeah, it's really interesting as well because I think AI, like you said, a positive and negative side of things, people can look at that going, I can use this to really double down on my position and make myself stronger. And some people look at that go, well, AI is going to take my job and I'm going to become obsolete. So how easy is that for you to navigate people through that? And I guess Olusola Osinoiki: Yeah. Yeah. Dave Stubberfield: The advice might be, do you reinvent yourself inside the same organisation or do you move to a different environment? Does that depend on the person as well? Olusola Osinoiki: I think a lot of it depends on the person, depends on the organisation. So part of what I do in my leadership coaching is I say to people, not in isolation of your organisation. So if you don't understand what your organisation does, how do you know whether you can navigate within an organisation? So a lot of people just come to their job, do their job, and get on with it. But actually, I got one of the best advices I got from one of my former line managers. we were just in the final interview. She'd made an offer. And I just said, OK, I'm going to give you the best thing you can read to prepare you for the job. And I was like, what's that? And she sent me the annual report of the company. She said, go read it. I mean, when I say go read it, I don't mean flick. I mean, read it. Understand we make money. Understand what our challenges are. Understand the company. Because when you understand the company, you can be a great leader in the organisation. And I think that's what people miss. People miss that, what is the bigger picture? What is the big picture? What is happening in this organisation? Where are we going directionally? ⁓ can I see how AI can come into this? So if you're reading the annual reports and the company is saying, we're going to lead with AI, that gives you Dave Stubberfield: Yeah. Mm. Olusola Osinoiki: energy to go to your line manager or go to your team or go to your organisation and say, hey, know, it's a company statement. OK, it might not be real right now where we are in the work we do, right, as we're pushing the file, manual files right now. But the idea and the direction is that we're going AI. So I think that's my first point is like understand your company and the company dynamics, understand your boss. I talk about one of my books, I talk about the idea of understanding what makes your boss tick. because if you don't understand what makes them tick, it hasn't influenced on you. So if your boss is like, you know what, I'm close to retirement. I'm not looking for any fancy AI or something. I just keep doing the job and keep it quiet. tells you that you have a feeling, Because they're not interested in pushing things forward. They're just interested in marking time till they get their retirement check. So understanding those dynamics will help you decide either you stay in that team. You might love the organisation, understand the organisation, but the team you're in is now going to be

limited because they're not looking to move forward in that. And that can happen in an organisation that is really, really good and dynamic, but you could have a team leader Dave Stubberfield: . Mm. Olusola Osinoiki: that could limit your personal growth. So understanding those nuances, understanding the company, understanding your team, understanding your manager, and then maybe the last bit, which is what we probably repeated a few times, self mastery. So understanding yourself. What do you want out of life? Like do you have the energy right now, or you just had a baby, and you're like, well, you know, I don't want to rock the boat. I just want to kind of, you know, just keep things stable for now. So those things are really important. So hopefully that answers your question. Dave Stubberfield: Yeah. Yeah. Yeah, no, it does. I think it's led me to another question. And I think it's you can, you can love the company, right, but still disagree with decisions and the culture isn't perfect, but you're kind of there to help transform it and take it on that journey, right? Olusola Osinoiki: That's how to give it, Okay. ⁓ Yeah, yeah. So, and that's the challenge, right? We've talked about leadership, but then the dimensions of leadership. So you could be coming and just lead, because the grass is green and everybody's OK. But you could also come in and be a leader. And it's more around transformation. So you're leading into a change. And I've been in those positions before where you come in and it's like, hey, you're inheriting a mess. Now organize it. So that's transformation. And there's habits that people have. There's that people have. Dave Stubberfield: Mm. Olusola Osinoiki: and there's this has always been done and if you do any other way we're not gonna hit payroll and then you have to take that command and say no we're gonna do it a different way and we're not gonna miss payroll and so now the gauge is not whether what you're doing is right or wrong the gauge is let's see if you miss payroll right so you see so I think that helps and brings that dynamic so transformational leadership is a little bit harder right and again you have to know whether you can do it so some people are asked to do transformational leadership and then they realize they can't do it. There's a young man in America right now who's been transforming organizations. He's just been going from one, currently that red lobster I think, and he's just, you know, he's very young but he's just transforming organizations, their turnover. And he was saying in an interview that, you know, it takes depth of character and a lot of self-belief and then trust in the team that we can build the line. Dave Stubberfield: Yeah. Yeah, totally. I think from my point of view as well, when I kind of go in transforming cultures, processes, customer experiences, you can sometimes see that not that leadership is the problem, but there are challenges, should we say, where leadership are kind of saying, you guys go and do it. It's not our problem. And you almost want leaders to go hands up. Olusola Osinoiki: Yeah. Dave Stubberfield: we'll show our vulnerabilities, we need to get better and we need you guys to help us along that way. And that's what I love is when leaders are very open and honest about that saying that, yeah, we haven't got everything right. And yeah, okay, some of it is to blame on us, but at the same time, we want to bring you on that journey with us rather than cause more harm maybe. And I think that's where I love what I do because it's what you love what you do as well. It's people-based. If you're having a direct impact on people, that's what gives me a buzz out of what I do. Olusola Osinoiki: Yeah, and I'll tell you a quick story because as you said that, came to my mind. So I won't name them, but there was a client that we had and they were having problems with bringing transformational change within the organisation. And it was mainly because the call center was designed in such a way that it was siloed. So America deals with America, Europe deals with Europe, Africa deals with Africa. was never a And so the leader at the top was like, why is this not working? So they threw me out to India, went to Hyderabad to the call center. and just entered the room and I started talking to people and was like, oh, I only work with America. So what about when you have free time? Oh, no, no, I'm not allowed to work with Europe. But you have free time, you could work with Europe. And then actually the backlog that they were getting was just because people were so siloed. And all we did was change the culture to say, you're actually a global team, yes, you have different shifts, but when you're on duty, you cover everything and guess what? Backlogs went down. So there again, that's transformational leadership, which because of the way they were Dave Stubberfield: Okay. Okay. Olusola Osinoiki: set up, they were not going to succeed at the objective that they wanted, but they didn't realize that the problem was their setup. And so sometimes it's not like they're bad leaders. It's like, we want this to happen. It's not happening. Why is it not happening? And then they bring you in and say, OK, well, you have full cablans to go and find out why it's not happening. They discover that actually it's a simple course of cross-training Americans to handle European calls and Europeans to handle African calls. And then guess what? The problem goes away. And that sometimes leaves an outside eye looking in. Dave Stubberfield: Yeah. Totally agree. And I think that's why I love what I do. You are the fresh eyes to a situation and you kind of look at something and go, why is, why are you doing it like that? And there's the general answer is we've always done it that way. And it's that it's how do you change that perspective and that mindset sometimes, which leads me onto my next question. So a lot of organizations now are trying to scale kind of

rapid growth. What's the biggest mistake they might make? Those organizations might make. Olusola Osinoiki: Thank you guys. Yeah. Yeah. Dave Stubberfield: when trying to scale people operations quickly. Olusola Osinoiki: mean this is a good one where we can both give our points of view but from my point of view I think what I've discovered that people make a mistake about is the fact that they forget that scaling a business is equal to scaling your people. And so we spend a lot of time thinking about what are the new markets we're going into. And I can use a very good example, and I can say this on air, when I worked at Deliveroo, where if you go and read it, you can Google it. And in 2017, Deloitte said, Deliveroo grew by 100,000%. So when you're growing as an organisation at 100,000%, and you're churning your entire workforce, like we had 100 % nutrition one year, how do you manage? Dave Stubberfield: Wow. Olusola Osinoiki: like crazy gross with attrition. And I think that's where I learned the whole idea around your people are your most valuable assets. It's their ability to want to grow with you, right? It's their ability for you to tell a 22 year old who's your head of technology, well she was 23, head of technology, okay. Here's what we're ramping up. Dave Stubberfield: Hmm. Olusola Osinoiki: which you know she doesn't really have the experience but she has the heart, has the passion, she has the willingness, has the grit, she has the resilience and so then you come in and give her the support that she needs to deliver on that outcome, which we did. I think that's what you learn is that some people have the heart, have the willingness but they don't have the training. Some people have the training but they don't have the heart and so recognizing that human beings will do and respond to this growth you're talking about in different ways. Some people just walk away. That's not what I find out for. So we have a lot of people in delivery room, when the books are getting bigger, they were like, that's not what I find out for. I signed up for a small organisation. Everybody knows everybody. Now we're getting too big. Now we have multiple locations. Like, that's not what I find out for. So some people just say, that's not what I find out for. And they want to go back and find another smaller company that they can help grow. And actually, when you work in the startup space, you realize that there are some people that they just love baby companies, like where we're all just bootstrapping and Dave Stubberfield: Yep. Olusola Osinoiki: it's scrappy and they do really well in those environments. Once you start scaling up and you start having structure, they're like, I'm out of here, go find another small company. And that's actually people's jobs. So I think it's really understanding the times that you're in as an organisation. Like when we're talking about scaling, what are we scaling? But scale anything, you need the people to scale with it. And so I

think the biggest mistake I see people make is forgetting that fight and doing everything else but the people preparation. Dave Stubberfield: Yeah. Yeah, no, I totally agree. And I think kind of echoing what you've just said there, that people are a company's greatest asset. I think I see a lot of times now in the customer experience space where organizations are like, right, we need to improve our customer experience. We need to be the best in the market. That's fantastic. But their people are sitting there going, well, can't we get the same treatment as the customers because we're not treated great. So how can we be on the same playing field? And that's really kind of the disappointment where, again, we're going back to the conversation earlier where people then go, is this job right for me? Should I leave? Should I go somewhere else to a company that I share their values with? And that's that for me is kind of the knock-on effect of that company that's scaling at growth versus those that want to have massive growth, but kind of are only looking in one direction. it's, they're kind of tunnel vision there doesn't align with everything else that the business needs to do in order to scale. So that's really, really interesting. Olusola Osinoiki: Exactly. And linked to that is this whole idea that I learnt again. I'm an avid learner, I'll tell you where I learnt it from. So I learnt it from Will Shu, CEO of Deliveroo. And one day, we were just talking to him and said, when you're dealing with people who are leaving the company, don't see them as employees who are leaving the company. See them as customers. who are leaving one organisation, but as they leave, you want to keep them as a customer. So don't see them as an employee that started with you on the 1st of February, now they've left you on the 2nd of February. They actually, as they walk out the door, you want to keep them as a customer. You want to make sure they don't delete that delivery app. You want to make sure that you're the, we are the app of choice, five years from now, seven years from now. And that stuck with me, that he didn't see his employees or his riders as just the function they did, he saw them all as potential. customers. And actually now, how many years ago did I leave the delivery room? Ten years ago, something like that, right? But my number one food app is still the delivery room. Because when I left the organisation, I didn't leave as an employee who leaving the organisation. I was ushered into, hey, lifelong customer. And I think that really helps me, even when I help my clients. I'd say, think about your employees as customer. Dave Stubberfield: Yeah. Olusola Osinoiki: they stop working for you, whatever you sell, if it's something that they could buy, it's direct to customer, you want them to walk out and say, okay, I'm leaving the company, it's not the right place for me, but I love the product, I'm gonna keep using the product. Dave Stubberfield: Yeah, totally. And I think that again, it's the advocacy you want customers to be advocates of the brand, the product, the service, whatever it might be. But you want your people to be doing the same as well. And I love that that that is still your number one app because that strikes a chord with everyone that there are going to be companies that people have worked for. They go never going to touch that again. And I'm never going to recommend it. I might not openly say it, but I'm not going to be openly saying Yeah, you should use it. Whereas those that kind of can't sing their praises enough going, I believe it's the best and here's the list of reasons why. people get so passionate about it. They could talk about it for absolutely ages, which I absolutely love. guess for me, going back to a previous point, you said you worked in Germany before Sola. How many countries have you worked in? Olusola Osinoiki: Yeah. Yes. Yes. 45. Yeah. Yeah. Dave Stubberfield: Not bad, not bad. So I guess why I'm going there is you have seen lots of different cultures, lots of different ways of working, into working like you said when you was in Germany. What do you think those experiences have given you that kind of shape how you help and coach people through their leadership challenges right now? Olusola Osinoiki: Yeah. So I think what it's given me, working in all these different environments, what it's given me is a perspective, right? It's a different perspective. It's a cultural perspective. It's like when I was working in India, we talk about call centers in India, but we don't know what that means. But when you actually go to a call center and you walk around there, can you understand how they live? And it's like a 24-7 house. And actually, people are... I mean, it's changing now, but it feels like they're kind of trapped in the job. They just have to stay there, they live there, they eat there, so they can get the job done. It gives you a better understanding of people and the variety of people that, and that's I talk a lot about culture, and that's why I feel like Emma Meyer's book on culture map is such a great book, because without you traveling, you can already start feeling the differences and the nuances. I think that's the real thing where technology is technology. Even with AI now, so let me kind of segway that and pull it back together. So even with AI, you know that, yeah, you can deploy a system and you can have agents doing it for you, but ultimately, who's the customer? It's still a person, right? Who's the customer in Germany? Like what does the German want? What are the German like? And what does on time mean in Germany as opposed to Amsterdam? And just understanding those different nuances has really given me a really good perspective. Dave Stubberfield: Hmm. Olusola Osinoiki: on life and work. Dave Stubberfield: Brilliant. I love that. I think that's amazing. I think that for me, working in different environments, I think every organisation has got its own

culture. Every team has got its own culture. But when you see the big cultural differences, country to country, it gives you so much idea of how can help people. It gives you something different to frame as well. ⁓ Olusola Osinoiki: Yeah. Yeah. one more thing to add to that ⁓ you might get there in a second, but it's the family dynamics also So I'm you know, I've got three kids. I'm a grandfather also and so when you're when you're working with organizations I'm thinking am I if this organisation building products that my kids would use these organisation building products that my grandson would use Right and it just gives you that multi-generational layer that what would I buy? ⁓ would my kids buy and what potentially with my and how does the world change? And then actually in one person, that's me, you can think of, I don't know what I am, a boomer, whatever it is, and then you have millennials and Gen Z, and then have the Gen Alpha and Gen Beta. And that in itself also is another cultural kind of dynamic and map of different, you know, we talk about who is your ICP, who is your ideal customer profile, and actually sometimes we just profile. Dave Stubberfield: Yeah. Olusola Osinoiki: ourselves as an ideal customer and then we forget that there are other potential customers that are out there the customers that right now your products is not even they're not even born but you want to make sure that in 10 years time they're buying that product. Dave Stubberfield: Yeah, it's a really great point. And I think the personal side of things that helps shapes us who we are as leaders. But like you say, you come at it from a different angle. You could be looking at a product or service and you really kind of look at that as a parent or as a grandparent and rather than as a professional. And I think those life experiences really help give us some grounding sometimes in what we're looking at. And I really love that the Olusola Osinoiki: Yeah. Yeah. Dave Stubberfield: the business could be building products or services for people that might not be born yet. And you have to think like that sometimes. Far too often, I'm working with organizations and teams and I'm asking them, what does the customer want? And they go, well, we think they want this. And I'm going, hang on, you think, have you actually gone and asked the question, what do they want? They went, no. And you're like, we're missing a trick here guys. Rather than just assume, let's go and ask them. Let's go and see how happy they are with the product or service. What could be better? You might find that they, Olusola Osinoiki: Yeah. Dave Stubberfield: have a bit of moan and just get something off their chest. But then that's when you get to the real things that really matter to them. It would be great if we could get this working. Cool, okay, you now know what the customer wants. And I think all of these life lessons that come our way sometimes really shape we are in the workplace. Just move on to you as an angel investor, what do you look for in a business or a person before you invest? Olusola Osinoiki: Yeah. So. I think my what's called investors thesis is fully 100 % influenced by the organisation that I've worked for. So I used to work for a company called Naspers Prosus And I worked there, and that's the company that took me to Germany, I realised that didn't invest in products. They didn't invest in businesses. They invested in people. And so there was like a connection. Like, I like David. So whatever David is doing, let's find out what David is doing, and then support David. And ⁓ that led What McKinsey calls one of the biggest investments of all time where they invested in a company called Tencent in China About 20-30 million they invested about 15-20 years ago that investment is now worth 120-30 billion depending on what's happening in the stock market Dave Stubberfield: Wow. Wow. Olusola Osinoiki: So 20 million to 130 billion and annually they get, this is all public knowledge, they get five billion in dividends every year from that investment. but they would say that the reason why that investment went through was because they just liked the guy. Didn't even understand the product. ⁓ imagine what WeChat could even look like at the time they were investing, ⁓ there was something about the chemistry between them and the David of that day that made them think, we like this guy and whatever he's investing in, whatever he's doing, we want to kind of support think that's the same thing for me that when it comes into the angel investing I realize that I actually connect with them as people first so sometimes there are people I'm coaching then they say ⁓ this is my side hustle this is I'm doing I have this company that I'm building so it becomes an easy thing I already know you I know what you're Dave Stubberfield: you you Olusola Osinoiki: do and me supporting you by investing is a positive thing. Sometimes they come to me out of the blue but then we connect and we talk and I realize hey this is your heart and I'm gonna give you just some money to kind of say hey I'm supporting that and then because of that then I realized that I'm in agritech, I'm in food tech, I'm in edutech, I'm in fintech but that's not because I sat down and said I want to be in fintech right it's more like I like what you're doing and what it like what is the area so I probably sometimes going to learn about the area because I like what ⁓ this area actually mean? I don't understand it, I like what they're doing. So there was a lady that I spent some time with, which was doing functional medicine. I didn't understand what it was, so actually go and study it. And then I realized, ⁓ wow, this is amazing. She had a personal story to go with it. So that's a way of saying I invest in people, which would be with what I've been saying all day. I invest in people rather than products. ⁓ And that has good side and its bad side. Dave Stubberfield: Yeah. Olusola Osinoiki:

that if you invest in people but you didn't really understand that person, you might get disappointed. Which just happened to me a couple of times, but not as many. So I would say 95 % of the time it's worked out, but there's always that 5 % where you think you know somebody but actually you get to discover them and you realise, okay, the reason why this is not gonna work is because you don't work, right? So yeah, so that's probably the most... Teases I use. Dave Stubberfield: Yeah, yeah. Olusola Osinoiki: Now with AI and now with everything else, right? So there's now new rules of investing people, but that person's got to leverage AI and you can't come to me with an idea. Ideas don't work anymore. Because if you give me your idea, I can create a product for you by the end of the day by using lovable or something else. Right? that's not right. You can't come to me with an empty sheet of paper. I have this amazing idea. It's going to be billions. Right? And I was like, okay, show me. Yeah. So that's informing. That's a new 2026. Dave Stubberfield: Yeah Yeah. Olusola Osinoiki: 5.20.26 new layer where it doesn't take you six months to build a product now. A couple of hours. Yeah. Dave Stubberfield: Yeah, yeah, it's so true. So true. this has been a great conversation. I'm going to finish with ⁓ final question before we go into some quick fire questions. ⁓ you could give one bit of advice to leaders that feel stuck ⁓ they need some help, what would that be of advice be? Olusola Osinoiki: Okay. Okay. Learn, relearn, learn again. Adam Grant that wrote a book about think again, right? Think about what you're thinking about. Observe the world around you. Don't ⁓ too siloed in your thinking. ⁓ that we live in a world that changes rapidly. I mean, we're recording this on a day where interesting things have happened over the weekend, right? I don't want to say exactly if we don't date the time we recorded this, but you know what saying? Like ⁓ one weekend, the world that you knew could change just because of some world event. And so if is true, right, then what is the best thing for you as a leader to do is have this ability to be continuously learning and growing and adapting to that change while holding your core, right, because it's your core of who you are that doesn't change but you're willing to learn about things around you. Hold your core and learn and learn again. Dave Stubberfield: Yeah. Yeah, absolutely. Brilliant. Love that. I've got some rapid fire questions for you now. So one that you won't compromise on. Olusola Osinoiki: All right. reading. Dave Stubberfield: One mistake that's taught you the most. Olusola Osinoiki: not being ready for the next level because you're so deep in the current level. Dave Stubberfield: Interesting. Yeah. And one thing that leaders don't talk about enough. Olusola Osinoiki: their fears Dave Stubberfield: Brilliant, Solo, it's been an unbelievable conversation. Thank you so much for coming on the podcast today. Brilliant. Cheers, Solo. Olusola Osinoiki: Thank you for your time. Thank you for having me. Yeah. Thank you.