Episode 309 · 11 June 2026 · 53:37
Stop Asking the Chatbot (And Start Asking Your Colleague), with Sean O'Shea
Featuring Sean O'Shea
Stop Asking the Chatbot (And Start Asking Your Colleague), with Sean O'Shea
0:000:00
Tip: click any timestamp below to jump there and keep playing.
Enjoying the show? Subscribe for free
Chapters & timestamps
Click any timestamp to jump the player to that moment.
Cold Open: The AI Connection Warning
interview#ai#workplace#curiosity
Meet Sean O'Shea: Turning People Potential into Business Performance
What Is a Messy Moment and Why Teams Hide from Healthy Conflict
The 3 Critical Elements to Fast-Track Real Human Relationships
interview#relationships#connection#trust
The AI Paradox: A Small Business Champion Worried About Perfect Tech
interview#ai#small-business#technology
Designing Connection: Architecting Micro-Moments of Collaboration
The Train Experiment: We Are Terrible at Predicting Social Interactions
Lessons from Microsoft: Satya Nadella's Growth Mindset Revolution
interview#microsoft#growth-mindset#leadership
Quantifying Wasted Time: Data on Collaboration Losses
interview#data#collaboration#productivity
The Story of Locon: Six-Week Experimental Sprints for Team Agency
interview#experimentation#team-agency#sprints
Show notes
Stop Asking the Chatbot (And Start Asking Your Colleague) — with Sean O'Shea
Guest: Sean O'Shea — founder of Craft Your Culture and Locon, former 10-year Microsoft veteran who witnessed the leadership transitions of both Steve Ballmer and Satya Nadella.
When you don't know the answer at work, what's your first move? Do you fire a question at a chatbot, or do you pick up the phone and ask a human?
Sean joins Al and Leanne to explore the hidden cultural cost of digital convenience. He's a genuine AI champion who uses it daily — but he's worried. Every time someone chooses a chatbot over a colleague, a tiny connection between humans quietly dies. Sean calls these interactions "messy moments" — the vulnerable, slightly awkward exchanges that are actually the engine of psychological safety, team learning, and high performance.
They dig into the "relationship gap" Sean measures through his data-driven work at Locon, the three non-negotiable ingredients for accelerated trust, and how Satya Nadella's growth mindset revolution took Microsoft from $30 to over $540 a share.
Top 3 Takeaways
Your team's performance isn't limited by talent or tools — it's limited by how well people know each other. High performance isn't just an aggregate of individual brilliance. It's directly capped by the quality of relationships between your people. Loneliness and disconnection don't just hurt morale; they cost businesses billable hours.
AI is not the enemy — but it's a silent relationship killer. Every time someone on your team chooses a chatbot over a colleague, a tiny connection is lost. AI onboarding bots are fast, non-judgmental, and always available — but they bypass the vulnerable moments of asking a peer for help. Those moments are exactly where trust gets built.
Messy moments are not inefficiency — they are the work. The awkward, vulnerable, slightly uncomfortable human interactions are the true engine of psychological safety and team learning. Protect them, design for them, and stop filling calendars with packed agendas that leave no room for them.
More From Sean O'Shea
- Sean O'Shea LinkedIn: https://www.linkedin.com/in/soshea7/
Connect With Us
Get in touch, book a call, or find Al and Leanne on LinkedIn — all in one place: truthliesandwork.com/connect
Mental health support: findahelpline.com — UK: Samaritans 116 123 · Mind 0300 123 3393 — US: 988 — Australia: Lifeline 13 11 14
Truth, Lies & Work is part of the HubSpot Podcast Network.
Full transcript
Expand full transcript
Al ElliottHere's a question worth thinking about. When you don't know the answer to something at work right now in your current job, 2026, do you ask a colleague or do you ask a chatbot?
Leanne ElliottOur guest today, Sean O'Shea, is a huge AI fan, uses it every single day, says he genuinely couldn't run his business without it. And he has a warning that has nothing to do with AI taking your job.
Al ElliottSo his warning is this: every time someone in your team chooses a chatbot over a colleague, A tiny connection that could have existed between 2 humans doesn't, and it's happening hundreds of times a day in every company, completely invisibly.
Sean O'SheaThe worry for me is that the advent of AI means that you are reducing the messy moments to almost a nonexistent state. If you're presented with this AI agent who's never gonna judge you, who's never tired, you're not interrupting them, and that knows probably the answer you're looking for, you are never gonna choose a human interaction moment. You're always gonna choose the AI agent. And we're already seeing the impact of that in how teams talk and operate with each other.
Leanne ElliottSean calls these the messy moments, the small, vulnerable, slightly awkward human interactions that are the engine of team performance, culture, and connection. And we're automating them out of existence.
Al ElliottSo if you manage a team or you're on one, this conversation is gonna change how you see every interaction you have starting tomorrow morning.
Sean O'SheaHello, this is Truth, Lies and Work.
Leanne ElliottThe award-winning podcast where behavioural science meets workplace culture, brought to you by the HubSpot Podcast Network, the audio destination for business professionals. My name is Leanne. I'm a Chartered Occupational Psychologist.
Al ElliottMy name is Al. I'm a business owner, and we are here to help you simplify the science of work. Now, Sean O'Shea spent a decade at Microsoft across 2 very different CEOs before starting 2 companies dedicated to one obsession: why do talented teams so rarely become Sean has spent years watching brilliant people sit next to each other, be perfectly polite, and completely fail to unlock what they could achieve together.
Leanne ElliottHe thinks he knows why, and he's got the data to prove it.
Al ElliottSo after this short break, Sean's going to explain what a messy moment is, why your AI onboarding bot might be quietly killing your culture, and what one CEO did that took a company's share price from $30 to $550. The dirty little secret is that most businesses think they know their customers. They have the data, the records, the history, but it's scattered across 3 teams and 4 systems. And in our case, it's about 216,000 spreadsheets, which means nobody can actually use it.
Leanne ElliottWhat you should be doing is using HubSpot, because why? HubSpot connects it all— every interaction, every support ticket, every conversation— into one place. Platform every team can work from. So when sales talks to a customer, marketing already knows the full story. And when you know more, you grow more.
Al ElliottNice. Check out hopspot.com, the agentic customer platform for growing businesses.
Sean O'SheaI'm Sean O'Shea, and I guess the thing that I'm wrestling with that certainly doesn't make me famous, but that I'm fascinated by is. How do you turn people potential into business performance? That's the problem statement that I kind of wrestle with. The thing that I find really interesting is that you've got this promise, right? You know, on one side of the paper, there's this promise of, you know, teamwork delivers this result where you can achieve more than the sum of your parts and this kind of utopian picture of what that can look like. But what I think is interesting is that that's very far from where we are in reality. And actually what we see is that team environments not only don't deliver that typically, but they actually don't enable people to live up to their own individual potential. So, there's quite a big gap there, and that's what we kind of play around with.
Al ElliottI've got a note down here that you used a term space between us. Is that what you are talking about here in terms of teams?
Sean O'SheaYeah. So, the way that we measure this, we've got 2 companies that, that we run to, to explore this. One is Craft Your Culture, which is around leadership development and the role of leaders. We've been doing that for about 3 years now. But the other company we've just launched is called Locom, and that really measures this team environment and the effectiveness of this team environment in delivering business performance. And one of the 6 things it measures is how connected people are. And the way I talk about this publicly is I talk about the space between us, and I'm not going around with a tape measure, like physically measuring the gap between people. What I'm interested in is the relationship gap between people. And our hypothesis is that that gap is really important for business performance, and closing that gap will deliver better results. But the trajectory is that that gap is bigger than it's ever been and getting bigger. And I think that's a massive opportunity for companies to think about. Let me give you an example actually of where we see this, just to kind of paint a picture for people. So a couple of weeks ago, we were running a workshop for a team tech company. And lovely bunch of people, kind of 12 people in a room, if you can picture it, leader in the room of, of that team as well. And during the workshop, we had one of those moments where 2 people in that team started having a little bit of a, a, a conversation, a heated conversation. And it was really good. It was respectful. These 2 people were giving their different perspectives on a point of view. They weren't reaching an agreement, and that was okay, but they were quite passionately but respectfully Sharing their opinions, which were different. And for us in the room, this is a massive win, right? You know, you've got these problems that exist everywhere, but actually being talked about, actually being dealt with. We are making progress. So, we're silently high-fiving each other in, you know, in the room. But what was fascinating was a couple of days afterwards, I got an email, not from the leader of that team that was in the room, but the leader of that person. So, they call it the boss's boss, if you like.
Al ElliottYeah.
Sean O'SheaAnd she emailed me saying, look, I've heard about what happened in the workshop. I'm just so sorry. That's not a behavior that we would normally expect from our people. And I'm really sorry. And I was so surprised at how that had been translated internally. And when I reflected back on the workshop, it was a very engaged group of people. But at the moment that that happened, everybody gets their phones out and kind of looks away a little bit. It's almost like an eclipse. You know, you can't look directly at it. type of behavior. And it just made me realize how unfamiliar we increasingly are with moments where we are voicing honest opinions and we're stepping into a bit of challenge and a bit of tension and healthy conflict. You know, if you're a fan of Kim Scott's work, I guess this is what radical candor would look like when she was writing that. But we're so unfamiliar with it now. And I think we're getting less and less Um, familiar with that because the connections between people are getting wider. And we'll probably explore why, um, a bit later, uh, a bit later on. But I think there's so much potential there in reducing that gap, not just for business performance. It's important for us as humans as well, and the quality of our life to have those connections, but we're just not very good at it. And I think the gap is getting, is getting wider.
Al ElliottSo I just wanna make sure I understand this. So in this example, mm-hmm. Then there were 2 people having a heated discussion, respectful, but they were taking opposing sides. They were disagreeing about something. And at the time you were like, this is great because this is one of those sort of messy moments that you want in companies. But then they probably got some kind of rollicking later on for doing that. Have I understood exactly how that went down?
Sean O'SheaYeah. And it's a small anecdote, but it's really consistent in what we see. And the messy moments, that's a term I like. Because I'm a real fan of those messy moments between humans that I think are so important in how we build relationships. You know, imagine, Al, if you were to join a company, a new company, and I'm in your team. And when you first join that company, you are very consciously incompetent. Hopefully, you know, you don't know what you don't, you don't know how to go into the next team meeting. You don't know where information is. You don't know how to deal with certain situations. There's huge amounts of things.
Al ElliottYeah.
Sean O'SheaThat you don't know. And what's lovely about that starting point are all those kind of messy interactions you have to have with people. So if I'm on your team, you might pick up the phone to me and say, Sean, I need some help with this. I don't know where this is. Can you help me here? X, Y, and Z. And they're lovely moments of vulnerability where you are choosing to be brave and vulnerable to say, actually, I don't know this. Can you help me? You know, imagine you were 6 weeks then into your role, Al, and And there was something that came up and you were like, I really should know this by now. That's, you know, there's one of those things where you think, oh, I've definitely been through this. I've definitely read this somewhere. I should know this and I don't. And then you still pick up the phone to me and say, Sean, you know, can you, can you give me a hand? And that's, that's such an important moment for me because that's where you are choosing to be vulnerable. You're choosing to be brave and voice that uncertainty. Yeah. And there's a lot of risks going on in your head at this moment. You know, there's this kind of social status thing. You know, what's Sean gonna think about me? Is he gonna judge me? Is he busy? Am I interrupting him? But when we talk about that gap between people, what you are doing is offering a way to reduce that gap between you and I. And for me as a recipient, you know, that might be a really nice thing then that I can solve your problem, I can help you, and I might feel really good. About that. So, I might feel warmer towards you as a result, but equally, I might then have a problem later on that then I need some help with, and I'm slightly more likely now to ask you for help in that scenario than I was if you hadn't have asked me in the first place. And it sounds so small, but those moments I think are really critical in reducing that gap between people, those messy Human moments are really important. You know, I get asked a lot about how do you reduce that connection between, that gap between people? How do you expedite relationships? Which is a funny thing to think about, right? How do you do it? We've got no time, no space. So how do you expedite the building of relationships? And I think there are 3 ingredients, and I think vulnerability is really one of those critical ones.
Al ElliottWhat are the other 2 ingredients then, you think?
Sean O'SheaSo the second one is shared experience. I think one of the most powerful things you can do to get people together and bond people in the smallest amount of space-time possible is to put them in a way where they're experiencing something together that's emotionally significant. So, you know, imagine 2 people going to present at a big event like an internal all-hands or something like that. And those 2 people have to go and do that. That's a bonding experience. Um, for those 2. So shared experiences is a big one. And then empathy, which I think is the victim of the, the real victim of the world we live in right now and the mess and the chaos that exists in the workplace. I think empathy is the victim of that because people don't have the time and the attention to genuinely invest in understanding someone else's perspective and to really actively listen with the only intent to understand. I think that's the real The real victim at the moment.
Al ElliottThis sounds like you need— a company is going to need a term that I've heard Leanne use a lot, psychological safety. Because if you are being vulnerable and then you're shot down, you're not going to do that again, are you?
Sean O'SheaNo, no. And that psychological safety is one of the other 6 pillars that we measure on team effectiveness. It is the foundational pillar. And a lot of what you need comes from that Foundation. But there is a strong relationship between the level of psychological safety that people in a team feel and the relationships, then the connection they have with one another. Those 2 things are quite strongly correlated when you look at the data, but they're really important because, like, back to those moments of vulnerability, if you do react in a positive way, that reduces the gap and it increases the feeling of psychological safety. 2 really powerful components of— of team effectiveness. But as you say, if you react in a way that is detrimental to that, even unintentionally, then the gap between people widens, the level of psychological safety reduces.
Al ElliottI wanna play what Leanne and I call Devil's Avocado for a second. So we've got a team here. Let's say I'm on the team and I wanna go and ask someone a question. So I go and ask Sandra a question and she basically goes, look, Email me, I'm too busy. At that point, I wanted subconsciously to create one of these moments you talked about, but I've been rebuffed. I've been just— the door's been shut on me. As an employee, not necessarily as like the organizational level or the lead level, as an employee, is there anything I can do? How should I feel? How should I act next?
Sean O'SheaThis is what I think at a macro level companies are trying to sort out with artificial intelligence and with technology. And I'm very pro That, you know, there are, in a world of chaos and too much information, too many channels for information to flow, so much uncertainty, so much ambiguity, and so much pace. I think that naturally leads to a lot of noise, questions, statements, answers, et cetera, that are flying around an organization all the time. And so I don't think more messy moments is necessarily positive if it creates more noise. And I think the role of technology and AI can play a positive role here in reducing that. chaos and that noise and all those questions going to, to people. And often it's the same people that are getting a lot of those questions, the, the high performers, the senior people, et cetera. So reducing that noise to them is a really good thing. But as with any conversation with AI, it has to be balanced with human interaction. The worry for me is that the advent of AI means that you are reducing the messy moments to almost a nonexistent state. Because, and I will answer your devil's advocate question in a moment, but if you imagine that you got rebuffed and then the company released an AI bot, onboarding bot, let's say, and this role of the AI onboarding bot is to answer all of these questions in your flow of work. What a wonderful thing. What an amazing thing to have. But the danger of that then is that we never have the messy conversations because, as you just said, in that moment where you've been vulnerable and asked the question, You've chosen to be brave and take that risk, and you've been rebuffed. Then if you're presented with this AI agent who's never gonna judge you, who's never tired, you're not interrupting them, and that knows probably the answer you're looking for, you are never gonna choose a human interaction moment. You're always gonna choose the AI agent. And we're already seeing the impact of that in how teams talk and operate with each other. Like the example.
Al ElliottYeah.
Sean O'SheaI gave earlier. Now, back to your question, the devil's advocate question. My real hope is that you'd be brave enough to then go and find somebody else that you can go and ask for help and invest in creating those connections with each other. We know through the data that the more connected people feel with one another at work, the more likely they are to stay, the more likely they are to be motivated. You know, there's that famous question, About do you have a best friend at work, which kind of the US people love, the UK people feel a bit sick about. But that is a really important indicator of how people feel about the business they work in. And it's a really important signal to understand if you are interested in how you motivate people and how you deliver business performance from the potential in your people.
Al ElliottSo the way you were describing that, I was in my head thinking, okay, if I was to buy something online, then most major websites now have a chatbot. that I can go, does this fit with my current USB port or something? I think what we're saying though is that, that if I was to buy that, I don't have the same relationship with that company as if I've lifted the phone and went, hey, can you talk me through, will this actually work with my equipment? And someone goes, yeah, of course it will. Yeah, it's gonna be great. Blah, blah, blah. I remember an example of a German company. It's an audio company and they sell audio equipment. And I had probably about a 20-minute conversation with this company.
Leanne ElliottYeah.
Al ElliottThomann, I think they're called. And now I'm like, everything I buy comes through this company because they took that time. Is that what we're talking about? Here. Similar idea.
Sean O'SheaI think it's similar. I mean, it's more of a, of a, of a different problem statement that we're identifying here in, in how a company can think about the relationship they establish with their, their customers versus the power of 2 people having a connection at work that enables them to then have other more valuable conversations that go beyond the, I've got a problem. That's the value that we're really getting to. But your point is interesting because it reminds me of the Zappos story, you know, the shoe company in the US and how, you know, when they describe themselves, they're not a shoe company. They're not the— I think they were the first online shoe company in America, if I remember rightly. So, this is early internet days. But what they really understood was their value is in the customer support they gave because the first point of contact that a customer has with them directly is actually when they phone up and say, I need to return this. And so, everybody in their company, when they started at the company, They had to spend 2 weeks in that customer support center. It didn't matter if you were this new CFO, you do 2 weeks in customer support and you learn the importance of that interaction and that relationship. So I think it's similar principles, different, um, context.
Al ElliottSo let's talk more about these messy moments. I just want everyone to understand what a messy moment, what is a messy moment and what isn't. So we've talked about asking questions, being vulnerable. You mentioned there was 3, vulnerability, shared experience. You also talked a little bit on And you said you could present an event together or something. And what about the empathy side of it? Is, is that part of a, of a messy moment?
Sean O'SheaI think empathy is, is just a, an ability to really intentionally try and understand something from someone else's point of view. So, a messy moment for me is more of a fast-paced, quick decision to ask somebody something or have an interaction with somebody on something. And I think that comes as A result of you deciding to be brave in that moment and, and, and look for a conversation with somebody. I think empathy is, has gotta be more deliberate and more intentional, and it's gotta be more of the fabric of how our team operates. But I think you get that empathy from people having a connection with one another. So it's a good connection builder, but I don't think it's something that you can naturally build through these kind of messy, quick conversations and moments. With 2 people. But to give you a picture of where this is important, I think, and how it builds over time, you know, we've talked about these conversations in the context of, I've got a problem, I need some help. That's like the early stages of building the relationship. Where it delivers real business value is then back to this scenario of you and I working together, uh, in a team. We've reduced that gap between us, let's say, by having these conversations and having these interactions. And being vulnerable, brave, et cetera, in those moments. Maybe we've displayed some empathy as well because we've started to talk a little bit more and I want to understand more about your role and how you do it, et cetera. And so we've started to really reduce that gap between us. The value then really comes then because I'll come out of a meeting and I'll think that went really well. I'm gonna go and phone Al and tell him what happened, or something in that meeting happened. And I remember Al telling me last week that he had something similar. How did he deal with that? Or, I remember Al sharing this thing with me that was interesting. I've now got another perspective having just had this discussion. I wanna go and talk to Al. Maybe we can work together and solve this. That's where you start to see the business performance come from, the connections being made with 2 people. That's how I kind of feel about that trajectory, if you like.
Leanne ElliottDid you know that the UK's number one management podcast, that's Us, by the way.
Al ElliottYeah, yeah.
Leanne ElliottAnd the UK's number one marketing podcast are both on the same podcast network.
Al ElliottWe actually have a lot in common. We both use behavioral science to help people do better at work.
Leanne ElliottAnd we both had to wrangle Rory Sutherland on an episode.
Al ElliottAnd 2 out of 3 of us are devilishly good looking. And you're not gonna say which. Fel, host of Nudge, UK's number one marketing podcast. It's brought to you— we need to do this in 3s—
Leanne Elliottthe HubSpot The audio destination for business professionals.
Al ElliottSeamless. Seamless. Tell us about your latest episode, Phil.
Sean O'SheaUh, we've just done an episode on fake fandom and how New York indie bands are paying agencies to create fake TikTok videos about how much they like their work. And we talk about the behavioral science behind fandom and how that encourages people to enjoy the music and all of that good stuff and do some big things about how this affects the world of politics. business and brands as well.
Leanne ElliottIt is. It's such, it's such a good show. Of course, you'll hear all the stuff you want to hear about how to grow your business by using behavioural science in your marketing. But there's also just some really interesting episodes that'll be right up your street. Personally, I enjoyed Can Balsamic Vinegar Make Beer Taste Better?
Sean O'SheaIt can.
Leanne ElliottAnd Are We All Just Status-Seeking Monkeys?
Sean O'SheaI am.
Al ElliottGo and listen to Lunch wherever you get your podcasts.
Leanne ElliottBut come back.
Al ElliottYeah, come back.
Sean O'SheaDefinitely come back because Nudge isn't as good as this. So come back. I'll cut that out.
Al ElliottKeep that in.
Sean O'SheaOkay.
Al ElliottSo I think, I think we're all on board with messy moments. I think we're all like, yep, this sounds like, this sounds great. So how do we actually architect them? I mean, for example, I did read a story about, I think it was Pixar, where they put all the mailboxes like in, in the foyer to try and create what they called accidental moments, I think they called it.
Sean O'SheaYeah.
Al ElliottThat sounds, I don't know, does that kind of thing still work?
Sean O'SheaYeah. And you can do big macro things or tiny micro things. You know, big macro things are, you know, Apple redesigning their headquarters. So it's that circular shape where all the things you need, like the toilets, like the coffee machine, are in the center. And so it forces everybody into the center, right? So there's the big macro things that you can do that are trying to create those moments. And we know companies are keen on this, right? Don't we? Because of all these return to office mandates that everybody's bored of. And they're so poorly executed in most cases. And people end up coming into the office trying to create these moments that companies recognize are critical to performance. And they just sat on Zoom calls next to each other, often in the same Zoom call, and it completely ruins the, the aim of what they're trying to do. And it actually creates resentment, uh, more than anything else. But I'm a big fan of the micro things that you can do. So if you're a leader, Yeah. Listening to this, you can have a really positive role in helping create those connections between your team. There's lots of things you can do. I think the first thing you can think about is when you get your team together, 'cause every team will have some form of team meeting. I think the default position for most leaders is, A, cram it full of stuff that you wanna tell 'em because the chances are in this chaotic world, they've had a million messages about company priorities and important things. And as a leader, you're probably sitting there thinking they've not maybe read many of those. So, this is my chance to make sure they're all on board. And so, you broadcast at them for a whole day. And the other mistake that I see being made a lot is I think leaders are often quite scared about gaps in agendas and having a team meeting and there being space in that. And so, they fill it and they bring in speakers and they bring in people to fill that and fill up the agenda. And often what you'll find if you ask people, of course, is that what did you enjoy the most about that meeting? It was the small gap in between where you grab a coffee with X person that you haven't seen in a while, and that's the bit that they really enjoyed. So as a manager, try and rethink how you design that experience of people coming together. If you're gonna have a team meeting, that is your primary opportunity for connection. And then just think, is there a thing that we can solve, a way that we can work together that encourages connection. You know, I've seen some really interesting ones. So for a sales team, for example, one of them decided to bring all their salespeople together in a typical monthly team meeting. And they said, right, you are all going to be competitors today. So pick our main competitor. You are all gonna work for our competitor. I'm gonna split you up into small groups. And you all now decide what is your strategy to beat us as the competitor and then present back. And it was a really interesting activity because everybody was, had a common denominator to think about. It didn't necessarily mean that some groups were able to do it and some groups weren't, but you forced that small interactive group work. You gave a problem that was interesting. They got their head out of the day-to-day, and it just meant that people learned more about each other. in a different way, and it created really strong connections as a result. So, that first thing I'd say is really think about how you design experiences that focus on connection first, but still in a business context. You're not sitting doing Lego. You are thinking about how you solve problems and become more effective as a team as a result. And then I'd say just experiment constantly. The better teams get at experimenting, the more effective they will be. And there's good research on this about, I think it's called team reflexivity, about teams that look back at what they're doing, how they're doing it, and then constantly think, can we do it better? And then iterate, change, experiment. So, think about how you can do things differently constantly and ask your team for feedback on how you do that. And the last point, if you're asking me for advice, I think the third point I'd say is get your ego out of the way.
Al ElliottYeah.
Sean O'SheaBecause I do see that managers like to be The main point at which all the noise and the activity goes to them because they see that that's their value. Often, particularly first-time managers, they struggle with the boundaries and they think, I've gotta be online all the time and available all the time to my team, and I should be there for any problem or question or issue or good news, bad news, whatever. I should be the person they go to. And that's often at the expense then of those connections between people. You know, the best performing teams I've seen, are where the manager is not often in the loop on that. And people are phoning each other. They've had a bad day, they've had a problem, they've had a good idea, they've done something really well that's worked and they wanna share it. All of those things happen across the team without the manager needing to be involved. So that third point really is kind of get your ego out of the way a little bit and let your team have those conversations with each other.
Al ElliottThere might be some people listening going, this sounds great, but I'm very introverted, or perhaps Um, I just don't like spending time with people. Will it still work for these kinds of people?
Sean O'SheaYeah. I mean, you have to meet people where they are, I think, and be always conscious that different people and different personalities explore connections with others in different ways. And that's why I think the experimentation is, is really, really important. One of the things I've seen teams do really well is use those team meetings moments, back to that idea earlier. Where they get the team on a rotational basis to own that meeting and to think about that rather than the manager trying to solve it all themselves. And again, that creates a shared experience. If you put 2 people together and say, you run the next team meeting, that creates that shared experience with those 2 people, but then they're architecting it on behalf of their team. And so you are more likely then to create ways that are better fitting for the wider team. If you do that over and over again and you rotate that ownership of that team meeting, you can then Instead of trying to solve it as a manager on behalf of every different individual person, you are enabling the team to build up that muscle themselves. But also don't underestimate how bad we are at forecasting how we think connections with other people will go. What I mean by that is a fascinating piece of research by, I think his name is Nicholas Epley. Sorry if I've got the name wrong. And he had this famous experiment on a train.
Al ElliottYeah.
Sean O'SheaAnd he gave people 3 different directions. One group, one group had to talk to a stranger on a train. One group had to be in isolation and kind of stay in their own lane, if you like, and not talk to anybody. And the third group, I think, just do whatever you were going to do. But then he asked each group to forecast how they thought that would go. And so the group that had to talk to somebody, of course, forecasted this is going to be terrible. You know, I'm going to feel really awkward. The other person's going to hate it. They're going to reject. The conversation, it's not gonna go well. The group asked to be on their own, forecasted it'd be a really good positive experience. And then the reality after the experiment was that everybody who had to interact with a stranger felt like it was one of the best parts of their day. So not only did it go well, it was one of the best parts of their day. And the people that had to sit in isolation did not feel anywhere near as energized as they expected. And what was even more interesting was I think they'd extended this research then into waiting room context and they said, how many people do you think will respond well to you going and asking them or engaging with them when they're a stranger? And I think the number was around 40% was the forecast. And the reality was every single person interacted positively when they were engaged with by a stranger. It was 100%. And so I think the story from that is that we are really bad at forecasting how well we think an interaction is going to go with somebody we don't know. And so maybe we can be a bit braver in remembering that that might go a lot better than you think.
Al ElliottSo imagine you're going into a remote-first company. Your job is to create these messy moments. I feel like that's a huge challenge. I wouldn't even know where to start with that, with remote-first company.
Sean O'SheaYeah, I think it's really difficult, right? And You know, I think if you're, if you're startup area, that's probably where you are. You're gonna be remote first for quite a long time. So typically in the SME micro business, you might be remote first as a company. I think less so now the large corporates, from my experience, I'm seeing a general trajectory to try and bring people back more into an office environment. But if I think about how you can solve that, if you're a, an owner of a company, a small business, and you're looking to how to solve that, I do think you need an element of face-to-face. Um, in the mix to help you build those connections between people. You know, I've seen some really interesting companies that are remote only, so everybody works remotely, but what they do is they have a period of time in a year where they come together for a week and they are in the same place for a week. But all of those sessions that they have from the Monday to Friday across that week are all designed very intentionally to build the connections and the alignment between Everybody. And so, they maximize that time together across that year in that one week, and then they see the benefits of that through the rest of the year in the connections they have, then have to have remotely. So, there are ways that you can do it, but I think if you are remote only, you've gotta be even more intentional about making that work. You've, because the gap between people is going to stay quite big and the business will suffer. As a result of that, you are more likely to be successful as a business if you intentionally reduce that gap.
Al ElliottYou already said before that you are bullish on AI, but then AI, as I think you've said, is taking away these messy moments. So why do you love AI but also hate it for taking away messy moments?
Sean O'SheaYeah, and it's a really good question, right? I mean, as a small business owner, AI is a really important part of what I do. I already think I'm at a point now where AI is so central to what I do That I could not now not have the tools that I use, you know, from whether it's Claude, whether it's ChatGPT, whether it's Midjourney or Lovable, you know, these tools are now really central to me being able to do all the things that I want to do. So, I'm certainly a big fan of AI and the role that it can play. But I think as with any conversation that I see with artificial intelligence, there is a really critical role.
Al ElliottYeah.
Sean O'Sheafor humans to play within that. The most recent conversation I mentioned, Claude, the most recent conversation or interview I saw with the CEO of Anthropic was that he spends 40% of his time on culture. And if you think about that, why is the leader of one of the biggest, most disruptive businesses in this space spending 40% of their time on culture? Well, it's because AI is further democratizing technology to another level. And, and there's always been this trajectory and journey of democratization.
Al ElliottYeah.
Sean O'Sheademocratizing technology. I was at Microsoft for 10 years and I saw that happen. When I started at Microsoft, you could have a video call, but you'd need to use a Cisco system to be able to do that with somebody. And so not many companies could afford to do that. I can have a video call with whoever I want, with as many people as I want on them, and I own a very small business. And AI is a further example of democratizing that power of technology. I can have the same access to these tools as a Microsoft, a Google, Or an AWS. And so when you've got that democratization of technology, what is the competitive advantage? It's people. That's the only thing left that's a competitive advantage. And so how effectively your people work together is the thing that will determine how you outperform your competitors now.
Al ElliottI suppose that makes sense because we're all moving up one level from the actual grunt work. And so we're able to have Naturally much more opportunity to have these messy moments.
Sean O'SheaYeah, yeah, exactly. And if you've— we're not living in a world of certainty and we're not living in a world where we know the tasks and the roles that we do are gonna be the same in the next month or the next week or even the next day. Every company that I work with now is facing huge disruption because their competitors are doing things differently and their competitors might be different tomorrow than they were today. There might be a new one that launches. The customers they serve have different expectations around what they want, and they're changing quite quickly as well as the industry evolves. And equally, their own services and products are evolving and changing quickly in line with the technology changes itself. So, if you are an employee of a company, suddenly the environment is shifting incredibly quickly. And so, if you've got this continual change and this fast pace, you need people around you that can navigate you through that, whether it's through answers or help, whether it's through ideas and innovation, whether it's through support and how you cope emotionally with all of this going on. All of that relies on connection with people and the ability to be able to pick up the phone and talk to somebody in the moment that you need to. And that relies on reducing that gap between people, of which messy moments is just one element. of how we think about reducing that gap.
Al ElliottYou were at Microsoft for quite a long time, and I think you were under 2 different CEOs. Can you tell us what your experience was like there in terms of the culture?
Sean O'SheaYeah, I was there for, for 10 years. So between 2008 and 2018. And so that was really nicely sandwiched between 5 years of Steve Ballmer, who was the second ever chief exec of Microsoft, and then 5 years of Satya Nadella, who's the current chief exec of Microsoft. And it was really interesting to be in the middle of that because as I was in a sales business at the time, I was a sales leader. And under the 5 years of Ballmer, the company was doing well commercially. But if you look at the share price, it was $30 a share pretty much consistently for all of his tenure. And of course, he famously missed some of the big innovations like search, like phone, tablet, et cetera. But what their culture felt like at the time was very much knowledge is power. So, we had this really interesting process called mid-year review, and this was a big thing that happened every kind of January. That was the middle of the financial year. What this looked like was that the big leaders from the US would visit every region, and they would spend a few days in every region interrogating all the senior leaders of each region. And so, you imagine this room, I think they called it the tent, but you imagine this room There'd be like 100 people or so in this room, all very senior executives, half of them from the kind of, you know, the US side, and then the other representing the other leaders of the different regions represented on the other side. And it would be an interrogation. It would be, how well do you know your business? How much can you recall off the top of your head? And I would watch these senior leaders prepare for days and weeks and months on the buildup to this event. And then everybody was subjected to this. And what was fascinating was the ripple effect of that, because I was a sales manager at the time, and I remember the expectation for me was to do a mini version of that. You know, I would need to know that every Monday I'd have a 3-hour forecast meeting with my director, and I would be expected to know all of my business. I'd have like 150 deals or something like that, maybe 200 deals across all my people. And so I'd expected to know every single one. What was the update? What was going on? And they could ask about any single one. And my value in that room was to be able to recall instantly what was going on. So then I'd prepare all of that Monday morning before that and all of the Friday before that as well. So at least a day and a half a week to prepare for this meeting. And my whole aim was keep the eye of Sauron off me and my team. Keep 'em away. Tell a good story, hold your nerve, and just hope that the eye of Sauron moves somewhere else and that you are safe and that your team are safe. So if you amplify that and aggregate that across a company, how much time is being lost and wasted as a result of that? And so when Satya came in, the first thing he talked about was not this big culture change program or these new values or anything like that. He said, I want you to challenge your mindset. I want you to think, how can I go from a fixed to a growth mindset? And I vividly remember that rhetoric seeping through the organization. And that's fine. You know, good comms around culture, that's fine. Doesn't change behaviors. But what he did around that was then he removed that mid-year review pretty much straight away. That whole process was removed. And so for me, I wasn't part of the mid-year review process, but I was part of the process that led up to that. And so the, my meetings then started to change. The way that I was interrogated started to change. So the systems changed, but then the behavior changed because no longer was my value in those rooms on a Monday afternoon, how much can I recall instantly? It was a really different conversation. And so suddenly the feeling in the organization was really different. No people around me had changed, but the way we were behaving had changed. The mindset had changed. And I think it's incredible to watch what happened. I mean, the share price went from $30, I think, to its peak at $540 under his leadership, down to about $400 now. But that all came, I think, as a result of how he changed how people behaved and thought, how they felt. And so for me, that was one of the moments where I realized there's so much power in thinking about how you change the environment and How people behave and what the culture is like and how that leads to business performance. It's probably one of the reasons why I started these companies.
Al ElliottWell, let's talk about more about the reasons you started these companies then. What was it that you thought was missing in your potential clients and the people you work with?
Sean O'SheaIt's just back to that word potential. What really, I think, frustrated me when I was in teams is that I sat around with a group of people and I'd look left and I'd look right, and I think there's so many talented people here. How do they do their job? How is that person going out and doing what they do? We're doing similar things, and yet I understand nothing about how they go and do it. What are the mistakes they're making? They come and talk and they share a little bit, but it's often the glossy things that have gone well. How can I understand all the actual nuts and bolts in the reality of what my colleagues are doing? And I just felt there's so much potential here to unpick.
Al ElliottYeah.
Sean O'SheaAnd to benefit from. There's so much value and none of it was ever being felt. And then when I started to become curious about this and start these companies, every team I was exploring was the same. No matter what the team function was, it was a group of individuals that reported to a manager and they were very kind and warm and friendly to one another. But so much of that potential to be more than the sum of your parts was never being reached. And I just thought there has to be a way to tap into this that goes beyond the traditional things, you know, the team bonding activities or the personality assessments, which I think is often what people, you know, leaders try and invest in to solve the problem. That doesn't solve the problem. It's a nice day, but nothing changes afterwards. And so I thought there has to be a way of doing this differently. And so that's why I really wanted to explore it. And I started the companies basically As a vehicle to explore my own curiosity. That's the purpose of them.
Al ElliottSo you mentioned there that Satya came in and what sounded quite simple was he said, I want you to change the way that you think, change your mindset. And that filtered down. I want to dig deeper into that because I feel like that's not the only change that you would've seen under that, uh, under that lead— new leadership.
Sean O'SheaNo, there was, there was loads, right? But I think the, the one they're famous for and the one that is publicized externally is this move to growth mindset and the work of Carol Dweck and how much that was talked about in the company. So, that's the publicized version of that. And if you were an external consultant trying to use that story, you'd say, yeah, they just told everybody to use a growth mindset and then it was fixed. And of course, that's not the case. And in the way that I've tried to explain it, it was the communication of intent to challenge your mindset. It wasn't, we're going to have a growth mindset. I remembered feeling directly challenged.
Al ElliottYeah.
Sean O'Sheato have a growth mindset. There was even a test actually, Al, where you had to answer some questions about, do you have a growth mindset? And I remember thinking, well, of course I have. I absolutely have a growth mindset. And it came back with one of my areas saying, no, you're demonstrating a fixed mindset here. And it was in the space of how I felt about somebody else's success. So a colleague of mine's success and how does that make me feel? And it was, and then the test came back saying, you have a, you're demonstrating a fixed mindset. And I felt very challenged by that, and I wanted to be different and improve in that space. So, part of it was around this communication and the way that he challenged us to be more growth mindset than fixed mindset and explaining what that meant. But really don't underestimate the other things that happened as well. So, those system changes, removing the mid-year review, the moving of and the changing of the processes and the way that we worked together.
Leanne ElliottYeah.
Sean O'Sheaas groups and these rituals, these meetings, the change of those was a really important part because when you're talking about the environment and the culture and how people work, you're talking about all these different signals. How does your leader behave? How do your team behave with you? How do we turn up in a team meeting? What posters are on the walls? What meetings am I going to? How do people behave in those meetings? These are all signals. And so, the more of those signals you can change, The more likely you are to influence behavior at scale. And so that's, I think, how it really delivered in the way that it ended up delivering for the company.
Al ElliottThere's a leader listening who's like, yep, I'm on board with this, but they maybe don't have the budget or the resources to get Locom on board right now. Can you give them sort of like a couple of tips on how they can start to implement this in their own organizations?
Sean O'SheaSo I think the first thing to think about is that Every team is different and every definition of high performance for a team will be different as a result. So I think about 2 axes when I think about what type of category team do we have here. One axis is how much dependence is there in the team on people working with each other to achieve their task. And the other axis is how much certainty is there in the role and the tasks that they're doing. So, if you've got, for example, we talked about a sales team earlier. So, a sales team might be a group of sellers that report to one manager. So, there's not a lot of dependence on them to be able to be really effective and to do their tasks. They've actually got their own customers, they're off doing their own thing. So, there's low dependence, but there is high uncertainty because of the environment they're operating. Most of my customers are tech. So there's a lot of uncertainty in how, what you're selling, how you're selling it, what customers want, all that kind of different stuff, what your competitors are doing. So if you've got low dependence and high ambiguity or uncertainty in the role that you're doing, that type of team, what they really value and what's really high performance for them are 2 main things. One is that they can support one another because if you're having a tough day or if something's going on and you wanna talk to somebody, The only other person that can resonate really well with what you are going through is another person in that team. So that kind of support is really, really important. And the second thing is sharing what you're learning because, you know, back to that example we talked about earlier where you've got people off doing their own thing and you really wanna understand how your colleagues are doing those things. The more you can learn between each other and the more effective you can create those learning moments, the higher the performance of that team will be. That's another pillar.
Al ElliottYeah.
Sean O'SheaAnd our performance quotient is how well does a team learn with one another? And back to the opening statement around this gap between people and the connection teams have with one another, those 2 things correlate really well. So the stronger there is a connection between people in a team, the more effective they learn from one another. And those 2 typically lead to— high performance. In fact, one of the things that we measure is how much time is wasted by teams, because one of the measurements we find in looking at team effectiveness is how much time is lost and how people feel frustrated at that time being lost. And so, we look at what's being lost in terms of time and where that time is going. And so, one of the interesting things from our data is showing that there's about 3 hours per person per month that is lost on people doing a task that they feel like could have been faster if somebody else could have helped them, or they could have talked to somebody else about that task. About 3 hours is lost in that. And one of the strongest questions that correlates to that is how well do they know other people in their team and how well do different personalities in that team work together? They're 2 of the strongest correlating questions to that. time being lost. So the more you can connect a team, the better you can bring diverse people together, the less time is lost by people when they're trying to perform tasks in situations of high ambiguity and fast pace.
Al ElliottYou talked about your pillars there, and I think you've mentioned 2 so far, but could you just talk us through, you say there was 6?
Sean O'SheaYeah, there's 6. That's right. And, and all of our work is focused on certain types of companies that are fast-moving, highly ambitious, wanna grow. So, we operate in those environments. That's where our specialism is. So, these 6 pillars might not equate for other types of companies. But the 6 pillars are, firstly, we've talked about psychological safety. That's the kind of foundational pillar. Now, we balance that against accountability because the mistake a lot of companies make is they go all in on psychological safety, which is great. But one of the byproducts of that sometimes is that leaders reduce that level of accountability because they think—
Al ElliottYeah.
Sean O'SheaThat's detracting from psychological safety, which is not the case. You need to balance accountability with psychological safety. So psychological safety, accountability, we've talked about connection. So that's the third pillar. And then the relationship with learning is the fourth. So those two pillars go hand in hand as well. And then the fifth one is clarity. So how well do teams understand what their priorities are and what they need to go and do? And then the 6th one is adaptability. And what we're really looking for here is how well and how effective is a team able to adjust to change? Because in the environments that we work in, the change is absolutely constant. No teams are working to a 3-year strategy anymore. Those strategies are changing in year. So, the balance between clarity and adaptability makes a lot of sense, and that's why they're the other 2. The other 2 pillars. If you get all of those 6 in a good place, you are far more likely to get a team that works and achieves more than the sum of its parts. But it's not just about getting all of those 6 high because it depends on what your type of team is, as I said earlier, on that axis of kind of level of interdependence and ambiguity or uncertainty in the role that they do. So think about where you are on there, and then different pillars will be more important depending on where you are.
Al ElliottYou're launching Locom. What problem is it solving that wasn't being solved before?
Sean O'SheaIt's really measuring this team effectiveness. I think there's loads of different surveys you can do for teams and people when you've got engagement surveys and all that kind of stuff, which is all fine. And we're not lacking in data and insight and sentiment around how people feel, but I think they get stuck on what do you do differently as a result? You know, I've had, I've been a manager that's had loads of engagement surveys and I've had the results and then I've been given the results and told, right, Off you go, go and do something about that. And I don't know what to go and do about that. I don't have the time, maybe the energy or the skills to go and know what to do about the results that I've been given. What I'm interested in is how you bring people together and make that environment effective to deliver business performance. And I think that needs a very precise type of measurement for that, where you measure what's going on across those 6 pillars and the variance, how people feel differently across those 6 pillars. The higher the scores, the smaller the variance, the more effective The environment. But the critical thing is also quantifying it, and we quantify it in time lost. So each pillar, we measure the time lost in those spaces. We talked about one of those earlier when we talked about this idea of how much time is lost in doing tasks that actually would've been faster if you'd had other people that could have input in some way. And so the ability to quantify the time helps us to identify the frustrations felt in the team. And if you can reduce that time being lost, then you are more likely to deliver performance. One of the things that I really believe in is that you only really have 2 resources as an individual to spend each day that determine how successful you'll be that day, and that is your time and your attention. And both of those are under attack every single day. And I think people really resent where their time and their attention is being dragged into spaces that don't enable them to be successful. And I wanna measure that and capture that. And then I wanted a process to do something effective against it. So when we run the diagnostic, we then bring the team together and we have our workshop, which we love doing. But as part of that workshop, we challenge— when we've unpacked all the, we call 'em the hypothesis. So the things that we think are holding this team back, the main things, we'd usually pick 2 and we form those based on the data. We pick 2, we unpack them, we talk about them, we discuss them, we Do all that kind of different stuff. But a third of the day, my favorite bit of the day, is then spent on enabling these teams to build experiments to change their own environment. And I love that because the things that they come up with and the experiments they create are amazing. We typically get in a team of 12 people, 3 or 4 experiments, and then we give them a framework to follow, and then they have a 6-week sprint. To try their experiment. And we kind of nudged 'em along the way over those 6 weeks. And at the end of the 6 weeks, we talked to them about, right, how did it go? What did you learn? What worked well? What didn't work well? And because you frame it as an experiment, all of the pressure on success or failure's gone because the intention is, what did you learn? Do we carry on doing it? Do we change it? But what did we learn? And that, that is the magic for me. So that's why we built Locom, was to find a better way to measure the effectiveness. To identify the things that need to be different, and then to actually change them. So you don't just have a nice workshop and everybody goes off and carries on with their day, that things actually change and a team feels a sense of agency and think, actually, we can change this for ourselves. We don't have to moan to people that aren't gonna do anything about this. We've got more agency than we think. We can change this for ourselves. And that, that is the magic for me. That's what I love about what we do.
Al ElliottFabulous. Is Locom— where, where's the word Locom come from?
Sean O'SheaSo I was given some advice when I was starting Locon that you shouldn't name the company after what it does because you won't stand out. And of course, at that point, I'm sitting there with Craft Your Culture. And so I thought long and hard about, well, do I get a Latin name for team effectiveness and all of these different ways? And I didn't like anything. And I thought the thing that I love the most in this world are my kids. And so Locon.
Al ElliottYeah.
Sean O'SheaIt's Liam, Cian, and Noah, my 3 children, and the O is O'Shea, and my eldest son came up with it. So that's what Lokon is.
Al ElliottThat was Sean O'Shea. Leigh, 3 takeaways.
Leanne ElliottYeah. Number 1, your team's performance isn't limited by their talent or their tools. It's really limited by how well they actually know each other. That gap is measurable, and it's costing you a lot more than you think.
Al ElliottNumber 2, AI is not the enemy. But every time someone in your team chooses a chatbot over a colleague, a connection that could have existed doesn't. That's a leadership problem, not a technology problem.
Leanne ElliottAnd number 3, messy moments are not inefficiency, they are the work. Protect them, design for them, and stop filling every agenda with things you could have sent in an email.
Al ElliottYou can find Sean on LinkedIn, just search for Sean O'Shea, or head to craftyourculture.com/Sean. Culture.co.uk or locon.co.uk. All the links are of course in the show notes.
Leanne ElliottThis is Truth, Lies and Work. We will see you next week.