In short
The episode argues that AI should not replace human “messy moments” at work—small, vulnerable interactions (asking for help, debating respectfully) that build connection, psychological safety, and team performance.
Guest background
Sean O’Shea is an AI fan and business owner. He spent a decade at Microsoft (2008–2018) across CEOs Steve Ballmer and Satya Nadella, then founded companies focused on why teams fail to become more than the sum of their parts.
Key claims
When teams choose chatbots over colleagues, they automate away connection-building moments. AI can reduce noise and answer questions, but it risks preventing people from seeking human help after rejection. Connection correlates with motivation, retention, and learning; psychological safety underpins vulnerability.
Notable examples
A workshop where two people had a respectful heated debate was later misinterpreted internally as unacceptable behavior. Microsoft’s “mid-year review” (knowledge-is-power interrogation) was removed under Nadella, changing behavior and culture; share price rose from about $30 to $540.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOUnderstanding Messy Moments in Teamwork
1:33 to 2:19
Sean O'Shea explains the importance of 'messy moments' in fostering team performance and connection.
“I'm a chartered occupational psychologist.”
Understanding Messy Moments in Teamwork
2:21 to 2:48
Sean O'Shea explains the importance of 'messy moments' in fostering team performance and connection.
“You prompt for 20 minutes, the output is polished, is confident and is completely flipping useless.”
The Gap Between Team Members
2:57 to 6:50
Sean discusses the relationship gap between team members and how it affects business performance.
“I'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?”
Vulnerability and Connection in Teams
6:50 to 11:04
Exploration of vulnerability, shared experiences, and empathy as key elements in strengthening team connections.
“But I think there's so much potential there in reducing that gap, not just for business performance.”
Balancing AI and Human Interaction
11:04 to 14:00
Discussion on the risks of relying too much on AI and the importance of maintaining human interactions in the workplace.
The Appeal of AI vs. Human Interaction
14:00 to 14:51
Explore the risks of relying on AI for workplace interactions instead of human connections.
Building Connections in the Workplace
14:51 to 19:26
Understand the importance of building connections and the role of vulnerability in fostering relationships at work.
“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.”
Creating 'Messy Moments' for Connection
19:26 to 23:58
Learn how to architect moments that foster spontaneous connections among team members.
Ego and Team Dynamics
23:58 to 28:00
Discover how a manager's ego can affect team interactions and the importance of shared experiences.
Creating Connections in Remote Teams
28:00 to 30:00
Learn how to foster connections in remote-first companies through intentional interactions.
“And so maybe we can be a bit braver in remembering that that might go a lot better than you think.”
Show all 19 chapters
The Role of AI in Business Dynamics
30:00 to 31:50
Discusses the dual impact of AI on business, enhancing productivity but reducing personal interactions.
“As a small business owner, AI is a really important part of what I do.”
Cultural Shifts at Microsoft Under New Leadership
31:50 to 33:50
Explores the cultural transformation at Microsoft during Satya Nadella's tenure compared to Steve Ballmer.
“I suppose that makes sense because we're all moving up one level from the actual grunt work.”
The Impact of a Growth Mindset on Performance
33:50 to 37:50
Examines how a growth mindset contributes to organizational culture and performance improvements.
“Barmer, the company was doing well commercially.”
Practical Steps for Implementing Change
37:50 to 42:00
Provides actionable tips for leaders on fostering high-performance teams, regardless of resources.
“Well, let's talk about more about the reasons you started these companies then.”
Implementing High Performance in Teams
42:04 to 45:32
Learn how to define high performance tailored to your team's specific needs.
“in their own organizations so 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.”
Six Pillars of Team Effectiveness
45:33 to 47:47
Discover the six essential pillars that support effective team dynamics.
“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.”
Measuring and Improving Team Dynamics
47:48 to 50:48
Explore how to measure time lost and improve team dynamics through experimentation.
“What I'm interested in is how you bring people together and make that environment effective to deliver business performance.”
The Origin of Locon and Its Purpose
50:49 to 51:48
Understand the origin of Locon and its mission to enhance team effectiveness.
“and everybody goes off and carries on with their day.”
Key Takeaways from Sean O'Shea
51:49 to 52:17
Sean shares three key insights that challenge common assumptions about team performance.
“It's really limited by how well they actually know each other.”
Transcript
Automatic transcript. May contain errors.0:00Here'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?
0:09Sean O'Shea:Our guest today, Sean O 'Shea, is a huge AI fan. He 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. So his warning is this. Every time someone in your team chooses a chatbot over a colleague, a tiny connection that could have existed between two humans doesn't. And it's happening hundreds of times a day in every company completely invisibly. The worry for me is that the advent of AI means that you are reducing the messy moments to almost a non-existent state. If you're presented with this AI agent who's never going to judge you, who's never tired, you're not interrupting them, and that knows probably the answer you're looking for, you are never going to choose a human interaction moment.
0:53You're always going to choose the AI agent. And we're already seeing the impact of that in how teams talk and operate with each other.
1:01Sean O'Shea:Sean 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. So if you manage a team or you're on one, this conversation is going to change how you see every interaction you have starting tomorrow morning. Hello, this is Truth, Eyes, and Work, the award-winning podcast where behavioral 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.
1:37My 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 two very different CEOs before starting two companies dedicated to one obsession. Why do talented teams so rarely become more than the sum of their parts?
1:54Sean O'Shea: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. He thinks he knows why, and he's got the data to prove it. So 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$540. Don't go anywhere. Does your experience with AI sound a little like this? You prompt for 20 minutes, the output is polished, is confident and is completely flipping useless. Well, that's what happens when AI doesn't know anything about your business.
2:32Sean O'Shea:But you know what does know something about your business? HubSpot. HubSpot's AI. It works with your actual customer data. every interaction, every signal your team has generated over time. So instead of prompting and hoping, you ask once and ship it. Check out HubSpot.com, the agentic customer platform for growing businesses.
2:57I'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.
3:32and 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 i've got a note down here that you used a term space between us is that what you're talking about here in terms of teams yeah so the way that we measure this we've got two 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 three years now.
4:02But the other company we've just launched is called Locon and that really measures this team environment and the effectiveness of this team environment in delivering business performance. And one of the six 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.
4:36But 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 the room, if you can picture it, leader in the room of that team as well. And during the workshop, we have one of those moments where two people in that team started having a little bit of a conversation, a heated conversation.
5:09And it was really good. It was respectful. These two 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.
5:46So they call it the boss's boss, if you like. And 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 familiar with that because the connections between people are getting wider and we'll probably explore why a bit later on.
6:52But 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 wider. So I just want to make sure I understand this. So in this example, then there were two 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 that you that you want in companies but then they they probably got some kind of rollicking later on for doing that i understood exactly how that worked how that went down yeah and it's a small anecdote but it's really consistent in what we see and the messy moments as a term i like because i'm a real fan of those messy moments between humans that i think us so important in how we build relationships.
7:46Imagine now if you were to join a company, a new company, and I'm in your team. And when you first join that company, you're very consciously incompetent, hopefully. 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 that 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.
8:20Can 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 six weeks then into your rollout 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 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 going to think about me is he going to judge me is he busy am I interrupting him but when we talk about that gap between people what you're 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 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 that gap between people those messy human moments are really important you know I get asked a lot about how do you 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 there are three ingredients and i think vulnerability is really one of those those critical ones what are the what are the two ingredients then you think so 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 two people going to present at a big event like an internal all hands or something like that and those two people have to go and do that that's a bonding experience for those two so shared experience 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 this sounds like you need a company is going to need a term that I've heard the ann 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 no no and that's psychological safety is one of the other six 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 and the connection they have with one another those two things are quite strongly correlated when you look at the 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 two 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 i want to play what leon and i call devil's avocado for a second so we've got a team here um let's say i'm on the team and i i want to i want to 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 what how should i feel how should i how should i act next this is what i think at a macro level companies are trying to sort out with 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.
13:11I think that naturally leads to a lot of noise, questions, statements, answers, etc. 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 people. And often it's the same people that are getting a lot of those questions, the high performers, the senior people, etc. 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.
13:48The worry for me is that the advent of AI means that you are reducing the messy moments to almost a non-existent state. because, and I will answer your devil 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 ask 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 going to judge you who's never tired you're not interrupting them and that knows probably the answer you're looking for you are never going to choose a human interaction moment you're always going to 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 I gave earlier.
14:53Now 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.
15:26And it's a really important signal to understand if you're interested in how you motivate people and how you deliver business performance from the potential in your people. So the way you're describing that, I was in my head thinking, OK, if I was to buy something online, and 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 okay can you talk me through will this actually work with my equipment someone goes yeah of course it will yeah it's gonna be great but 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 um common 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 a similar idea i 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 two 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 zapos story you know the shoe company in in the u.s and how you know when they describe themselves they're not a shoe company they're not i think they were the first online shoe company in 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 two weeks in that customer support center didn't matter if you this new cfo you do two weeks in customer support and you learn the importance of that interaction and that relationship so i think it's a similar principles different um context so 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 three is vulnerability shared experience you also talked a little bit on and you said you could present an event together or something what about the empathy side of it is is that part of a of a messy moment i 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 look for a conversation with somebody.
18:09I think empathy has got to be more deliberate and more intentional and it's got to be more of the fabric of how a 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 two 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 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 etc in those moments maybe we've displayed some empathy as well because we started to talk a little bit more and I want to understand more about your role and how you do it etc 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 going to 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 want to 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 two people that's how i kind of feel about that trajectory if you like okay so i think i think we're all on board in messy moments i think we're 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 yeah that sound i don't know does that kind of thing still work yeah 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 um 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 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 more than anything else but i'm a big fan of the micro things that you can do so if you're a leader 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 because every team will have some form of team meeting.
21:19I think the default position for most leaders is a cram it full of stuff that you want to tell them 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.
21:59And 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 going to 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.
22:32So 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're all going to be competitors today so pick our main competitor you're all going to work for our competitor i'm going to 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 are able to do it and some groups weren't but you forced that small interactive group work you gave a problem that was interesting that got their head out of the day-to-day and it just meant that people learned more about each other in a 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 um effective as a team as a result and then i'd say just experiment constantly.
23:39The better teams get experimenting, the more effective they will be. 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 and 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 because I do see that managers like to be the main point of 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 got to 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 want to 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 there might be some people listening going this sounds great but i'm very introverted or perhaps i just don't like spending time with people will it still work for these kinds of people yeah 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 two people together and say you run the next team meeting that creates that shared experience with those two people but then they're architecting it on behalf of their team and so you're 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're 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 eppley sorry if I've got the name wrong.
26:27And he had this famous experiment on a train and he gave people three different directions. 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 felt 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 going to go well the group asked to be on their own forecast that 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 any way near as energised 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 um 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.
27:52It 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. So 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 remote first company. Yeah, I think it's really difficult, right? And, you know, I think if you're a startup area, that's probably where you are. You're going to be remote first for quite a long time.
28:27So 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 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 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.
29:07But 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're remote only you've got to be even more intentional about making that work you because the gap between people is going to stay quite big and the business will suffer as a result of that.
29:44You are more likely to be successful as a business if you intentionally reduce that gap. You already said before that you're 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? Yeah. And it's a really good question, right? 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 am 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 for 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?
30:56Well, it's because AI is further democratizing technology to another level. And there's always been this trajectory and journey of democratizing 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 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 or Google or an AWS and so when you've got that democratization of technology what is the competitive advantage?
31:38It'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. I 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. Yeah, 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 going to be the same in the next month or the next week or even the next day.
32:12Every 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're an employee of a company suddenly the environment is shifting incredibly quickly and so 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.
33:02all 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 that gap between people of which messy moments is just one element of how we think about reducing that gap you were at microsoft for quite a long time and i think you were under two different ceos can you tell us what your experience was like there in terms of the culture yeah i was there for for 10 years so between 2008 and 2018 and so that was really nicely sandwiched between five years of Steve Ballmer who was the second ever chief exec of Microsoft and then five 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 five years of Barmer, the company was doing well commercially.
33:57But 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, etc. 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 looks 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.
34:34And so you imagine this room, I think they called it the tent, but you imagine this room, there'd be like a hundred 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.
35:08And 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 three-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 day 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.
35:42So 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 them away. Tell a good story, hold your nerve and just hope that the Eye of Sauron moves somewhere else and that you're safe and that your team is 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 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're 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 dollars 540 dollars 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 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.
37:48It's probably one of the reasons why I started these companies. Well, 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? 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.
38:20what 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 thought there's so much potential here to unpick and 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.
Read the full transcript
38:58But 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 their 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 so you mentioned there that Sachi came in And what sounded quite simple was you said, I want you to change the way that you think, change your mindset.
39:42And that filtered down. I want to dig deeper into that because I feel like that's not the only change that you would have seen under that new leadership. No, there was loads. Right. But I think 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, you know, an external consultant trying to use that story, you'd say, yeah, they just they just told everybody to use a growth mindset and then it was fixed. And of course, that's not the case.
40:14And in the in the way that I tried to explain it, it was the communication of intent to challenge your mindset. You know, it wasn't we're going to have a growth mindset. I remember feeling directly challenged to 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?
40:48And the test came back saying, 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 as groups and these these rituals these meetings the the change of those was a really important part because when you're talking about the environment and the culture and 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 um delivering for the company there's a leader listening who's like yep i'm on board with this but they maybe don't have the budget um or the resources to get locon on board right now can you give them sort of like a couple of tips on how they can start to to implement this in their own organizations so 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.
42:21So I think about two 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 um 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 two 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 want to talk to somebody the only other person that can resonate really well with what you're 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 want to 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 in our performance quotient is how well does the team learn with one another and back to the opening statement around this gap between people and the and the connection teams have with one another the those two things correlate really well so the stronger there is there's a connection between people in a team the more effective they learn from one another and those two 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 in looking at a 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 from our data is showing that there's about three 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 three hours is lost in that and one of the strongest um 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 two 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 you talked about your pillars then i think you've mentioned two so far but could you just talk us through you say there's six yeah there's six that's right and and all of our work is focused on certain types of companies that are fast moving highly ambitious want to grow so we we operate in those environments that's where our specialism is so these six pillars might not equate for other types of companies but the six pillars are firstly we've talked about psychological safety that's kind of foundational pillar.
45:59Now 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 that'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 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 sixth 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.
46:53No teams are working to a three-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 two pillars. If you get all of those six in a good place, you're 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 six 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 you're launching locum what problem is it solving that wasn't being solved before it's really it's really measuring this team effectiveness i think there's loads of different surveys you can do for teams and people and 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 to 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.
48:12What 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 six pillars and the variance, how people feel differently across those six 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 have been faster if you had other people that could have input in some way.
48:50And 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 i really believe in is that you only really have two resources as an individual to spend each day to 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 want to 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 the we call them the hypothesis so the things that we think are holding this team back the main things we'd usually pick two and we form those based on the data we pick two 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 three or four experiments and then we give them a framework to to to follow and then they have a six-week sprint to try their experiment and we kind of note them along the way over those six weeks and at the end of the six weeks we talk to them about right how did it go what did you learn what worked well, what didn't work well.
50:26And because you frame it as an experiment, all of the pressure on success or failure is 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 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. The 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 going to 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 fabulous is locon where where's the word locon come from so 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 these different ways i didn't like anything and i thought the thing that i love the most in this world are my kids and so locon is liam kian and noah my three children and the o is o'shea and my eldest son came up with it so that's what locon is that was sean o'shea lee three takeaways yeah number one
51:48Sean O'Shea:One, 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. Number two, 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. And number three, 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 you can find sean on linkedin just search for sean o'shea or head to craftyourculture.co.uk or locon.co.uk all the links are of course in the show notes this is truth lies and work we will see you next week
From the publisher
When you don’t know the answer to a problem at work, what is your immediate reflex? Do you search for a quick answer from an AI chatbot, or do you pick up the phone to ask a colleague?
In this episode of Truth, Lies & Work, we dive deep into the hidden cultural cost of digital convenience. While artificial intelligence is incredible for cutting through administrative noise and streamlining corporate tasks, it is quietly automating away the most critical asset your business has: human connection.
Our guest today is Sean O'Shea, the brilliant mind behind Craft Your Culture and Locon. Sean spent a fascinating decade working at Microsoft, sandwiched perfectly between the leadership of Steve Ballmer and Satya Nadella. He witnessed firsthand how a radical shift in corporate mindset and the intentional removal of rigid, performance-stifling systems could skyrocket a company's share price from $30 to over $540.
Now, through his data-driven work at Locon, Sean is on a mission to measure the "relationship gap" between team members. He breaks down the phenomenon of "messy moments"—those vulnerable, slightly awkward, but entirely essential human interactions that act as the true engine for workplace psychological safety, team learning, and high performance.
If you are a business leader, founder, or manager trying to navigate remote-first challenges, return-to-office mandates, or AI integration, this conversation will completely change how you design your team interactions tomorrow morning.
Key Takeaways From the Episode
The Trap of the Frictionless Workplace: AI onboarding bots and agents are fast, non-judgmental, and always available. However, by relying on them exclusively, employees bypass the vulnerable moments of asking a peer for help—the exact moments where corporate trust is built.
The High Cost of the "Relationship Gap": High performance isn’t just an aggregate of individual talent. It is directly limited by how well your people actually know each other. Loneliness and disconnection don't just hurt morale; they actively cost businesses billable hours.
The 3 Pillars of Accelerated Trust: How do you build genuine, bulletproof workplace relationships when everyone is short on time? Sean reveals the three non-negotiable ingredients: vulnerability, shared emotionally significant experiences, and active, empathetic listening.
Overcoming the "Eye of Sauron" Management Style: Reflecting on his time under Steve Ballmer's mid-year review process, Sean highlights how defensive corporate cultures destroy innovation. True leadership requires getting your ego out of the way and letting your team collaborate without you always being in the loop.
The 6 Pillars of Team Effectiveness: Sean breaks down the core framework measured by Locon: psychological safety, accountability, connection, learning, clarity, and adaptability.
Episode Timestamps
00:00 – Cold Open: Are chatbots silently killing your team's natural human connection?
01:15 – Meet Sean O'Shea: The mission to turn people potential into business performance.
04:20 – What is a "messy moment" and why are modern teams hiding from healthy conflict?
07:30 – The 3 critical elements needed to fast-track real human relationships at work.
10:45 – The AI paradox: Why a small business champion is incredibly worried about the rise of perfect tech.
15:10 – Designing connection: How leaders can architect micro-moments of collaboration instead of boring, packed agendas.
23:15 – The Train Experiment: The fascinating behavioral science proving we are terrible at predicting social interactions.
30:30 – Lessons from Microsoft: The real story behind Satya Nadella's growth mindset revolution.
39:45 – Quantifying wasted time: The data showing how many hours your team loses each month by not collaborating.
45:10 – The story of Locon: Using six-week experimental sprints to give teams true agency over their culture.
Connect with Our Guest
To learn more about Sean's work, access his data diagnostics, or follow his daily insights on corporate culture, use the links below:
Craft Your Culture Website: www.craftyourculture.co.uk
Locon Website: www.locon.co.uk
Sean O'Shea LinkedIn: https://www.linkedin.com/in/soshea7/
About Truth, Lies & Work
Truth, Lies & Work is the award-winning podcast where behavioural science meets workplace culture. Hosted by Al Elliott and Leanne Elliott, a chartered occupational psychologist, we are here to help you simplify the science of work, boost employee engagement, and build high-performing teams.
Truth, Lies & Work is a proud part of the HubSpot Podcast Network, the ultimate audio destination for business professionals.
📬 Connect with Al & Leanne
– LinkedIn: https://www.linkedin.com/company/truthlieswork
– Al Elliott: https://www.linkedin.com/in/thisisalelliott
– Leanne Elliott: https://www.linkedin.com/in/meetleanne
– Email: hello@truthliesandwork.com
– Book a call: https://savvycal.com/meetleanne/chat
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