289: Building Trust With Your Remote Team - with Kerry O'Brien

30 Minutes Read

It's one of the hottest topics of our day—no, not AI: leading remote and hybrid teams. Businesses that get this right have access to high-performing talent around the globe. And businesses that don't find themselves in a world of hurt. 

When it comes down to it, the key ingredient to building a great team that spends some or all of its time working remotely is trust.

In this week's episode of the Superabound Podcast we share an in-depth conversation with learning and development expert Kerry O'Brien that will help you lead your remote employees even more effectively. 

You will discover:

  • What are the 3 ingredients required to build trust, no matter where your team is working
  • How to communicate differently to prevent unneeded conflict in a remote team
  • How to grow quickly as a leader of remote employees so you can be as impactful as possible


Connect with Kerry on his LinkedIn here.

Listen to his podcast, How'd You Learn To at hyltpod.com.

If you want support creating more trust in your team—remote or otherwise—we have openings for new VIP one-to-one clients. Learn more and book a consultation here.

Listen to this week's episode on Apple Podcasts here

Listen to it on Spotify here

Watch the video here

Full Transcript

Steve Haase  0:01  
Welcome to the Superabound Podcast with master coaches Erin Aquin and Steve Haase where business owners like you learn tools that help you clarify vision, clear up static and overcome challenges. You are listening to episode number 289. Building trust with your remote team. It is the topic of the ages, folks. And we are diving deep with a good friend, an expert on the topic, and a collaborative thinking partner Kerry O'Brien, I can't wait to introduce you to Kerry. And what's going to happen on today's podcast is a conversation with him, myself and Erin. Going into remote working, building trust growing as a leader. It's a fantastic conversation. And what you will discover is, hopefully some things you're already doing some things that you can add to your toolbox to work better with your remote employees to build trust to build alignment with people that you might not be able to see very often, if at all in real life. So we hope you enjoy this. If you need help making your remote team work better together. This is something that we help leaders and teams do. We would love to talk with you you can learn more. And schedule a visionary meeting with us with your own future self is kind of how it works had to be super abound.com/consultation To learn more about the process, and book your no charge, no pressure visionary meeting today. Hope you enjoy. Hello, it's great to see you. I'm here with my good friend, Erin Aquin and Kerry O'Brien, Kerry and I met at the first day of school at Shopify, we were in the same onboarding class, when we started back in 2016, March of 2016. And we were eye to eye, which is always a special thing when you're six foot four, and you can talk eye to eye with another human being like this is amazing. So we fell in love instantly and had been buddies since 2016. And even then, Kerry just continued to grow and contribute as a leader, as a teacher and coach of leaders. And so that is why we are really excited to have you carry on the podcast today to talk about all things, leadership development coaching, we're going to dive deep into how to manage hybrid teams, remote teams, it's a brand new world out there. And Kerry has been deep in the realm of learning and doing when it comes to managing remote teams building trust and creating high performance results at your workplace. So welcome, Kerry can't wait to dive in.

Kerry O'Brien  2:54  
Awesome. Now Steve, you did miss a very important part of our meeting story that I think informs what we're talking about today, which was we met in the lobby of the building Shopify was in so Shopify was up on one of the higher floors. And what we didn't know at the time was there's two different sets of elevators. And so you know, you show up, you go to the first bank of elevators, it doesn't go to the floor you need and you don't know to go around the corner that the second bank, and so it was like you, me, our friend, Carla, and a couple others and we just started looking for other like unsure kind of confused people we call kind of found each other in a knot. And then one of us probably Karla, worked up the courage to go talk to someone who had a Shopify backpack and they were like, No, yeah, you go around the corner go up the elevators there. So it was like a really interesting case study in what do people do when they're in an unfamiliar place with unfamiliar people? And how do they solve this problem of getting to where they need to go? And thankfully, we pass the test because I'm not sure if we would have had a second day at Shopify, if we hadn't.

Steve Haase  3:54  
I think that's part of onboarding is can you find the elevator and you muster the courage to talk to a stranger?

Erin Aquin  4:00  
Sounds like a corporate escape room?

Kerry O'Brien  4:02  
A little bit? Yeah, that's what it was that sort of as thankfully we were surrounded by good people. Exactly.

Erin Aquin  4:07  
Okay, so I want to talk about all of the tears, literal tears that I have, I have seen with, with my clients with people in my network about navigating this hybrid work life that so many people are in whether it's working remotely, having some some members of their teams in office, some working another time zones, and just this this whole world that we are now in how, how how how do we help people make this new way of working? Really effective? And dare I say because what we do here is sometimes about how do we also make it fun and purse sample and keep it human.

Kerry O'Brien  5:02  
which I would argue Aryan is actually part of effectiveness like there is there is not a human workflow that is effective that doesn't recognize the humaneness of humanity that it was a load of the same word and different permutations. I think I want to go back and I want to, I want to make clear because you said this is a new way of working, I think there are those who might argue with you, it's like, well, we've been doing this since 2020. Not really, though not in the same way. Someone said, I wish I can't remember who it was. But someone said early on in the pandemic, when we were all remote, you have to remember, right now, we're not watching the highlights of what this new form of working can be. We're watching the blooper reel, like we're all dealing with the uncertainty of COVID. We're worried about vulnerable family members, those of us with children and are trying to like homeschool while we're working. And so it's really only in the last couple of years, that we've gotten to a point where we are actually optimized to work effectively in hybrid teams. Now. The The upside of COVID If there is one, which I would argue there isn't, but the upside of it is we did get a wealth of research knowledge and experience in what working hybrid could be like. And I think what working hybrid remote, virtual, whatever you want to call it is is telling us is the biggest thing we're lacking is trust. So what we're seeing in the research is that when people aren't working shoulder to shoulder, when they aren't having those little runnings, those can you help me with those? Hey, what do you think of at the desk, what we're losing is trust with each other. And when we break down trust in terms of how, you know, psychologists think about how the research thinks about it, it really comes down to three components. We trust people when they have integrity, when they do what they say they're going to do when they when they don't do things behind backs, or when they go back on their word or anything like that. So that's one thing. We trust people when they have ability. So when they are actually capable of doing the things they need to do, or if we want to be selfish, the things we need them to do, and benevolence when they mean well for us. So trust comes when the answer to these three questions is yes. When the answer is, will this person do what they say they're going to do? Can this person do what they need to do? And does this person mean? Well, for me? If those three questions are yes, then when we trust that person. So to be super reductive and simplistic. All we have to do as leaders is create spaces for our team to demonstrate trust and build trust with each other super easy. 

Steve Haase  7:35  
All over zoom. All over zoom. Yeah.

Kerry O'Brien  7:39  
Or dare I say teams? Yeah, let's

Steve Haase  7:42  
go there. Microsoft shop? Well, I think that's, that's an interesting thing. Because like, as humans, we are wired for the social interaction, right? We judge books by their covers, we say, Oh, I trust this person, because he's, you know, she has a trustworthy face. And then you kind of are let down down the road if you are, but like, we have these snap judgments of one another, that in person kind of speeds up the process of coalescing of giving someone the benefit of the doubt, right? If you don't hear from someone for a couple hours, but you see them over their work, and you're like, whatever, they're doing fine. But if you don't hear from someone for a couple hours, and you don't see them, your mind goes to some pretty negative places almost on instinct. So what story crafting? Yeah, right. So so like, what are the what are the new approaches that we need to kind of get over ourselves in a world where we can't see somebody? And we're so used to seeing people? 

Kerry O'Brien  8:46  
Well, there isn't yet and I love that you went directly to the like, what can I do for me? Like, what what am I responsible to self manage, and the caveat, when we talk about these kinds of things, Steve, as I always like to say, there are systemic pressures that contribute to burnout. There are systemic pressures that contribute to a lack of trust, we are not solely responsible as individuals for creating optimum conditions in our organizations on our teams, what we are responsible for, is managing ourselves to where we can be the most impactful version of ourselves within the constraints that that the system presents. So the first thing is recognizing that we are a narrative species like the one thing that separates us from a lot of different forms of life on the planet is we use stories to make sense of the world. And we also, this is a very North American perspective, but we also live in a generally a low threat society. So we don't have saber toothed Tigers hiding behind every tree or rock waiting to kill us. So our threat detection looks at other things because there aren't like big threats available to us. Those two things in combination means that we tend to make up story He's to fill in the gaps in order to protect ourselves from the worst possible outcome. And that usually means I am assuming the worst of this person. So if, for example, I send a message to one of my direct reports, or even a peer saying like, hey, that proposal is not where it needs to be. And I don't hear back for two hours. The spray I tell myself is like, John is mad, Wake is frustrated, they're talking to my lead. They're, you know, all these things, when like, I've actually had this happen to where I've like, what am they responded to me? And then I go look at their, their calendar, and they're off this morning. Do you know what I mean? And it's like, usually, the actual story is so much more benign than what we make in our head. So the first thing we can do is like, recognize me tell those stories. And then choose not. Here's where I always I always trip up because I don't want to be like, just assume best intent of everybody. Because every human means the best for you can't even see it. I'm like, cocking my head and smiling brightly at this, like, we know that humans can be awful. We know that sometimes humans can have ill intent towards a so I'm not saying just like, leave yourself open to get hurt by people. But look at it rationally and say like, what do I actually know about this situation? What are the facts that I can put before myself? Based on those facts? Taking emotion out of it for a minute? What is the more likely scenario? Yes, Blake is usually very responsive to me. But maybe they have maybe their heads down working on something maybe they have an appointment. Maybe their their internet is out like there could be 1000 different explanations. That is not Blake is annoyed. And they're talking to my lead about what a jerk I am. Yeah, so the first step to go ahead. Well,

Steve Haase  11:54  
I like that you bring the likelihood into it. It's something I realized the other day with my children I, I termed it probabilistic parenting. I was like, hey, better had his clothes on. I was like, what are the actual probabilities that he has his clothes on right now? It's like 20%, why would I get all bent out of shape that he's got his clothes on when there's like a almost zero chance that he's actually got his clothes on. So when you're thinking about your colleagues, and your drumming up the story about how they're out to get you and you know, bad things are about to happen. Taking a moment to say, what are the probabilities that this person is actually conspiring right now versus doing something else? Or even in the middle of the thing that I asked him about? Yeah,

Kerry O'Brien  12:36  
exactly. And, and hear me, it's not it doesn't mean that they're not for all I know, Blake might actually be doing that thing. It's like that old Nirvana song, right? Just because you're paranoid doesn't mean they're not after you. But the point is, like, what, what am I going to do about that? If I operate, assuming Blake is doing that, and they're not, I'm now like, low trust with Blake, I'm guarded, bad things are gonna happen. That's the risk of thinking that way, the reward of thinking the other way of like going about my day, putting that to the side, waiting for feedback, and being able to be productive in the meantime, is much higher than the potential risk of missing, like doing that thing, because there's nothing I can do about it anyway. So that's the second step once you've actually like, figured it out. Okay, what's the story I'm telling? What is what is the probability of this actually happening? Now? What is the risk reward of just going about my day, probably the reward is going to be higher, and that will play out when it plays out.

Erin Aquin  13:38  
I love that you're talking about this from the the end of the one making the story. But I also think that as a one of the leadership skills we talk about all the time is the art of over communication, because we know that when we can only see from like the shoulders up, we can't read body language. Facial expressions really matter. The tone of emails, when you can't hear the voice of someone and you if you just assume that people actually might read this in their most negative narrative, the worst possible voice, it will also inform how you communicate, and I love a little bit of over communication, because it just helps to eliminate some of those ways in which Why would I call like people thought leap to the worst case scenario to the worst possible outcome. And if I as the leader can help people, not do that with just a little reassurance like this proposal is not where it needs to be. What are three things we can do like in a kind of in a coaching manner? What are three things we can do to improve this section specifically, and I give them a problem to solve rather than let their brain go to the Doom scenario? Are you? Yeah,

Steve Haase  15:00  
yeah, even getting ahead of that, because we've talked about like, what you can expect from me kind of the leadership manual, or how best to interface with me as your boss with me as your peer. If they know that your feedback will come with some questions, it's always in the spirit of helping them do better. And they see that consistently, than getting that email still might trigger the oh my god, I'm in trouble, you know, zone of their brain. But there will be at least a rational foundation of this is how Erin works. She told me to expect this, she has my best interests at heart, and let's let's collaborate, you know, at least there's a path for that.

Kerry O'Brien  15:41  
Yeah, I really like that. And the common thread I see through what you're describing, is being deliberate. That I think is the biggest mental load for leaders right now is how deliberate they have to be, versus how natural everything felt, when we were in person. So when we talk about communication, or B, I mean, it's not that you didn't have to be deliberate when you were in person, like, we all know that that person who just wasn't a good communicator, in person or whatever. But it's everything is so much more deliberate. Now, when we try when we go back to like talking about those three elements of trust, those three elements of trust, were all readily available, when we were working shoulder to shoulder, we can watch people do their work, we could see them do nice things for us, we could we could see them do the things they said they were going to do. And now, leaders have to be so much more deliberate about creating those spaces, leaders have to be so much more deliberate about communication, the time you spend thinking about process, just like interpersonal process, it's so much more now than it was when we were in person.

Erin Aquin  16:53  
Absolutely, you also don't get a flavor for how people are as humans, like if you have somebody who in meetings is always looking down and taking notes. And then you see them at lunch. And they're always kind of looking down and being in their book, you get a sense of like, oh, this is a person who's like, likes to just kind of be in their work. And they're kind of in their own bubble, that on Zoom can really hurt trust. You know, we even even with our, some of our coaches, when we train them, we like tell them like this is how you position your cameras, you're always looking at the person you're talking to, do not take notes over here, if you have a second screen, and you're over here talking, it is such an interpersonal disconnect. And even if you're communicating everything so beautifully, there's not a personal connection that that person can feel from you. And I offer

Kerry O'Brien  17:48  
a little pro tip that I love for that. Yes, if you if you're a Mac user, and you have a window open, there's the little green, but you can probably hear me sliding my my mouse to make sure I do this properly. There's a little green button at the top of every window that you can use to maximize the window. But there's also an option to tile a window to the left of screen. So if you're taking notes, outside of zoom teams, whatever it is, you can tile zoom to one side of your main screen, your notes, whether it's in Docs, or the Notes app or whatever to the right, you can actually choose how much real estate on your screen each of those take. And then you can have one main screen so your eyes can flick from zoom to the camera to the notes all within one you won't move your head at all. It is really really helped my presence and engagement in in virtual meetings. People

Erin Aquin  18:35  
feel it, I mean that that is everything. Thank you for that tip. It's

Steve Haase  18:40  
it's just so interesting, though, because we are analog beings adapting to a digital world.

Erin Aquin  18:49  
Did Madonna write a song about that? We are living

Steve Haase  18:54  
in a world. We are analog beings totally. But like this idea that in order to connect with someone, you have to look into a little black.of a camera is so unnatural. It speaks to your point Kerry about the deliberateness that's required for leaders to have the impact that they want to have, which might have been more natural in a in person world. Which kind of segues into the next point that I want to dive into here, which is leadership training and development. You know, your your area of of expertise is how do we develop the humans at work so they can be more more effective, productive, fulfilled all that good stuff? Yeah, what what strikes me is the common thing that we see with leaders is they're often promoted from being an individual contributor to being a leader. And most of the time they are not told that that is a completely different job. And so the requirements to actually do develop those skills and become effective leaders is is enormous. But oftentimes they're not really given the support to do so. So I'm curious what you've seen that helps people make the biggest leaps in that new career that

Erin Aquin  20:16  
they had no training for?

Kerry O'Brien  20:20  
Well, and to pile on a little bit to what you're saying there, Steve, oftentimes to when you move from that individual answer, I'll speak like I've worked mostly in in software, I started my career in investments. So your mileage may vary, but what I've seen is that when you get promoted into that very first leadership role, you know, you're leading individual contributors for the first time, there's either an unspoken or very spoken expectation that you are also going to be doing individual contributor work. You know what I mean? Like, you need somebody who, who can lead the team, but also isn't afraid to get down in the weeds or isn't afraid to get their hands dirty is usually the way yeah, yes. Yes. The player coach, the myth of the player, coach, greatest player coach of all time, by the way, Bill Russell, Boston Celtics one I want to, he won 11 titles, but I think three or four of those he won as a player coach, which is just wild to think of, anyway, I was gonna

Steve Haase  21:12  
say, I was gonna say, Mike Ditka just because I'm from Chicago. Oh, yeah,

Kerry O'Brien  21:17  
of course. You have to. Yeah. Jordan would. Imagine if Jordan was also coaching the Bulls like, that would have been amazing. Anyway. He kind of was like, I don't think it would have worked.

Erin Aquin  21:27  
Here. There's no I have no sports.

Kerry O'Brien  21:31  
Yay. Are we going to turn this into  is the Superabound sports podcast to turn into? Anyways, all about to be in

Erin Aquin  21:40  
business player coach? Yeah, you call it a myth?

Kerry O'Brien  21:43  
Well, I say it's a myth, because you can't do them at the same time you'd like one or the other. Right? And so for example, there's, there's a project I'm on right now, where I am digging into some individual contributor work. And I'm not showing up as a lead for for my, for the people who are on that with me, because now I'm a co contributor, so I can't interact the same way. I think that so yeah, so those are the difficulties of being promoted into leadership. And then add on to that, too, humans don't like to feel like they're bad at something. So Steve, you have a really interesting story of like, digging back into piano, right? And like learning how to play again. And And was it again, or for the first time? Oh, no, it

Steve Haase  22:29  
was again, yeah, I took a 20 between high school and my 40s. So

Kerry O'Brien  22:33  
what did it feel like that first time you sat down and tried to play after 30 years

Steve Haase  22:38  
very janky. Very awkward, like, like I had, like, I had nothing. I knew there was stuff under there, but it was yes. Covered in crust.

Kerry O'Brien  22:46  
And, you know, you're also a very accomplished trumpet player. So you were you're like, whenever you get that Jones to do something musically. It's hard to like, Oh, I'm gonna reach for this thing. I'm not I don't feel good playing versus this thing. I feel great playing right. It's the same thing. When you're leading one thing, Liz Wiseman talks a lot about this in her book multipliers. I love that book, highly, highly recommended for especially for new leaders. She talks about the paratrooper. So the the paratrooper leader who, whenever things are going wrong on the ground, immediately strapped on that parachute and jumps right down into the weeds to fix it. And a lot of times, the reason they they do that is because it feels good. So the first thing I think new leaders need to commit to is, this is going to feel bad, and it's going to feel bad for a while. That's what the learning feels like. That's what it feels like to like, you know, go into a one to one where you've got a disgruntled IC, and you don't know what to say, Yep. But next time, you'll have a better idea of what to say. So that's the first thing coming to it feeling bad. And then the second thing is because you know, this is not a craft. I mean, I was meant to say you don't go to school for it. But I have a master's in leadership. So I guess you kind of can go to school for it. But it's not a craft you're like trained on it's not a craft you're brought up into so you really have to show you have to figure out what the craft is for yourself. So finding a mentor, who has been doing it for a while, even if they're not leading the same craft, if we're gonna say leadership is its own craft. There are transferable principles, no matter if you're leading developers, salespeople, you know, customer success, people, whatever. There's transferable principles. So find a mentor leader who's been doing it for a while and CO process with them. That's another piece of advice. I always give new leaders and just do treat it like a craft, like figure out what the competencies are. And I'll give you the if I was to say like, there are two things that every single leader needs to do well, early on as quick as they can. Number one, like you said, clear communication. So you know, get on with Superabound and what they're doing around strategic decision making. Learn how to make strategic decisions. Learn why you don't make strategic decisions today. Hmm.

Erin Aquin  25:05  
So well said, Yeah. And you, you mentioned it, but I just want to highlight it in case people decided to kind of glaze over that part. Getting your own support, getting your own mentorship, your own coach, the people who are who aren't just sympathetic ears and people who love you and your life. Those are great. We want those people to need those, but they need those. But we need people who, who get what you're going through because leadership we had a session with with some of our trainees yesterday, we took them through this exercise where they've had to for five minutes talk about their unique skill sets, their expertise, their positive attributes, positive five whole minutes, and then when they Oh, hi, oh, others had to come in and coach them had to like speak back what they were hearing. And one of the one of the participants said, she's like, I feel so fired up about this, I just realized there are so many great things that I do, that I never give myself credit for. And furthermore, no one in her company gives her credit for she thinks she's of the mind that if as long as my boss isn't talking to me, I must be doing okay. And she leads a lot of people. So it's one of those. So having those people not only to brainstorm, but someone who could see behind the scenes, I, you know, this I was a tour manager for musicians for a number of years and being backstage seeing the whole show come together, knowing what it took to get on the road. And finally play to that audience. There's something special when you have those people in your life that have been with you for that journey and understand what it took to stand on stage and get the applause. Or the people to clap for you. If no one. Yeah.

Kerry O'Brien  27:06  
There are those shows too. Yeah, the value of them. I think we often think of mentorship as a like, it's a course correcting function. It's the bumpers in the in the bowling game. But it's also a celebration function like meant the best mentors in my life. I've always been like, Kerry, when you first came to me, you were like X, Y and Z. And now you are an ABC, like you have actually grown because we you know, we don't see it. Because growth is so incremental. And we're with ourselves every day. But they have that sort of 10,000 foot view to say like, No, you have grown you have developed, you have changed really well done. They also have the ability to say like, you know, better than that come on, like, like, what are we below the line here? I think we're below the line, let's pull you about the line,

Steve Haase  27:49  
the experience of of acknowledging where you're at, and where you've come from? Is it significant for growth, and to the point of like, what will bring a team together across space and time? That's one of them. Right? Like, if there's one thing that builds morale, it's not, you know, lunch on the company, or, you know, Friday drinks, it's winning, it's growing, it's doing meaningful work. And so as a leader, creating the space for someone to win, acknowledging when someone is growing, and making it possible for the team to do something together that they never could have on their own is going to create connections better than any icebreaker activity, although those are valued at a party, or pizza. Right. But yeah, so how did those two even weave together because there is a place for icebreakers and pizza parties, even though the ultimate goal of the leader is bringing the team together in order to win and creative great work.

Kerry O'Brien  28:54  
Yeah, so like the the role of an icebreaker in my mind as a as a learning person is just like, it's it's literally to break the ice, it's to get people talking. So we talk about, you know, breaking the seal, which is getting people to talk for the first time, especially in a Zoom meeting, because people so often are like, Oh, I'm on mute, or Oh, am I the wrong mic or whatever it is. And so you want it's, it's, it sounds so overwrought, but like you want them to have a safe to fail opportunity to practice speaking in the environment before they have to do it for real. And so that's what the point of an icebreaker is virtually the point of a pizza and then in person, it's the same kind of idea. They get just a feel for how their voice sounds in the room. They get encouragement from other people, all that good stuff. The point of a pizza party is just to provide like a social experience. And unfortunately, it has evolved into a meme of like, how corporate overlords are like what is the cheapest way that we can express our non sincere appreciation for these people. I think what you're describing those Back to what we talked about a little bit with the benevolence, right, like we need as leaders to, again deliberately now find spaces, methods and ways to express that we mean well for employees, because it is so much easier for them to get in their head about, about what we think of them. And I don't like I do. Like, I'm not, I'm not a CEO, I'm a middle manager, I have a boss and they have a boss. And it is it is a constant thing on my mind of like, what did they mean when they said that? They actually, or maybe they. And so what I recommend, first of all, is, I think it's table stakes, but weekly one to ones, even if they're half an hour, like just you should be connecting with your people minimum once a week. I think one other places that that you can create benevolence and well meaning is by being clear about like what you want in terms of development, like, let's work through development together, let's find out where you want to go. Let's work to get you there. Like, theoretically, you are leading the craft, because you're experienced in the craft. So if you've got someone who's Junior that that wants to get to mid to senior than helping co process how to get them there will go a lot towards saying like, yeah, they actually mean well for me. And it will also give you a bit of a buffer in those moments when you're like, hey, you really missed the mark on this thing. They'll at least have kind of like what you've seen before that bedrock of like, okay, I know that they're giving me this feedback, not because they want me out the door. But because they actually want me to succeed.

Erin Aquin  31:44  
Okay, I have a question. I have a hard all right. Um, because this comes up a lot. There are some amazing companies, I think the company that you work for who invests in leadership, and training and coaching and has someone like you working hard to, to, you know, really take care of people in a way that helps them be humans and be successful. There are companies like that, who invest in in the coaching and the training, and then there, and then there are companies that that is just kind of a fringe thing it is they haven't looked at the research the way that you have. And sometimes what we see is, people will think, Well, it's my company's job to develop me as a leader, it's my company's job to pay for my coaching or hook me up with a mentorship. And I think in some cases, it's a real disservice. I mean, I kind of sometimes I agree, but I'm curious to hear your thoughts. I won't tell you my thoughts. I want to hear your thoughts. Your job isn't to to make that investment.

Kerry O'Brien  33:00  
In your opinion. So back in, I'm going to go to a brief story back in like 2000, probably actually 16 around the time I met you, Steve. I was a big gamification guy. I thought gamification was the route. So gamification For those not familiar is the practice of turning learning into like games competitive games to to like,

Erin Aquin  33:24  
very, didn't know that about you. I love that game. I like that too. Yeah, well,

Kerry O'Brien  33:30  
I love I love gaming, but I'm actually turned around on gamification now. And the reason is, I read a book called drive by Daniel Pink. Yeah. And the whole thesis of dr is that there's external extrinsic motivation. And there's intrinsic motivation. extrinsic motivations are things we think of as like, we categorize the sticks and carrots, right. And so the things that like, we will either punish you if you don't do this thing, or we will reward you if you do these things. Intrinsic motivation is the drive that all humans have to improve their conditions. And so good learning can leverage extrinsic motivation, either punishment or reward, but it will have lower impact, lower effect, and you'll burn people out on it after a time. If you can access intrinsic motivation with learning, you have a much better chance of having one your learners engaged fully and then to them retain everything. So that's why the first principle of adult learning is figuring out the What's in it for me. Position Hey, I'm asking you to take time and effort to intake this knowledge, develop this bit, develop this skill, change this behavior. And the reason I'm asking you to do this is because the value will be x. The reason I bring this up is because I've seen kind of both awful sides of the pendulum in my time. I've seen like the fully fleshed out like totally Eat there for you Leadership Development Program. And I've also seen the like bare bones do it yourself. And there's there's, there's poor experience on both sides like anything else, you want to be somewhere in the middle, where you were providing the supports to help people along their journey become more impactful. But you're also not doing it for them. Research, for example, shows that programmatic mentorship generally doesn't have great uptake or impact. And the reason is, good mentorship happens. When a potential mentee does the work. I'm like circling my chest over my hand right now listeners that is that is the word for doing the internal work figuring yourself out. And then saying, Okay, I want to grow in this area, this area in that area, I am going to find a mentor who will help me do those things. And I'm going to invest in that relationship. Because frankly, you know, we often hear about like mentors, leaving relationships, like I'm too busy, I'm not getting value here, yada, yada, yada. Oftentimes, mentees are the ones who fall off because they should be the one who are driving the relationship. And they're not. All that to say is a really good leadership development program, accesses intrinsic motivation. It identifies it says, Hey, we want you to grow as a leader, because we believe that's going to impact the company's bottom line. There's a reason leadership development is a flagship of most learning and development organizations. And that's because it is the the highest downstream impact. When you have good leaders, you tend to have good, impactful teams. But it doesn't try and replace that intrinsic motivation. It doesn't say, we are going to do all this for you. It doesn't say we are going to figure out mentorship for you, it doesn't say we're going to figure out all these things. It's like, it's all here, you need to do it. And again, the caveat there, the biggest impediment for a lot of people, especially when they become a new leader is is workload compression, they have so much more work to do, and they don't know how to make time. And it becomes difficult for them to participate in leadership development. So with those new leaders coming alongside them a little bit more making sure that value prop is clear to say clear time for this, because it'll have this value for you. But they still need to do the work. So that answer your questionnaire

Erin Aquin  37:18  
Absol. I love that. I think that's great. Well,

Steve Haase  37:21  
the thing about time was a really interesting one, because so often, the very reason people have to not engage with coaching or personal development or leadership development is, I'm just so busy, I don't have time for this. Even though like it can be said and they can read and they can like see, this will help you with that whole time thing and prioritization and delegation, like the reason you don't have time is because you haven't done this training. But until someone has their own, come to the gods moment, you know, they come to the moment of like, Oh, my God, I am the one who needs to take control of this. All the training in the world is just going to, it's going to ring hollow until they actually buy into this as my path from my current state of being overwhelmed, frustrated, and not delegating to my future state of being an effective leader who has, you know, a enjoyable work life harmony.

Kerry O'Brien  38:23  
Yeah. And again, this is Steve, where the, where the systemic stuff comes in, like, we're, especially in the software world, there's always so much work to do, and so much high impact work to do. And I can't fault anyone for saying, Well, if I take this time, that project is not going to ship on time, I better go ship that project. So there is part of part of that in terms of like creating the right conditions for leadership development, is also systemically setting the right expectations for leaders. If you have a leader who you can look at and say reasonably, I don't see where they would fit in leadership development. And you are committed to like I want this person here long term, I want them contributing to the company long term, I think they have a lot of potential, then you as the person's lead or the organization have the responsibility to say we need to pull something back and signal to them. We want them to take the time again, they have to take the time there has to be that intrinsic motivation there. But we also have to create the conditions where they can take the time without having mission critical things fall.

Steve Haase  39:30  
So good. So if you're in that case, where you think there's a systemic issue, how do you put pressure on the system to make that space?

Kerry O'Brien  39:42  
That is a really hard thing to do. And I would be lying if I ever said I'd done it successfully. Systems are really hard to change. And, you know, I can't fault a Chief Revenue Officer for saying And yeah, leadership development is all well and good. But you know what also is well and good this company existing in two years. So we need to ship this thing now. It's there's no, there's no silver bullet here. I think that if you are a, someone responsible for the strategy of a business, and you do not think that your business is viable, when you make time for leadership development, I would argue with you that you are probably not optimizing for long term success, and you are kicking problems down the road, and it is up to you how far down you can get those problems before they become unsolvable. I would also point to all the research and there is so much you can find that says the number one thing people are looking for? Well, the number one thing people are looking for in this economy is money. The second thing they're looking for is developmental opportunities. And so if you want to get the best talent available to you, and hey, we are a virtual hybrid world, you now literally have an entire globe's worth of talent available to you. If you want to get that best talent, you want other talent saying on Glassdoor I had the ability to grow, I was given the space to develop, my manager cares about where I'm going. So that's, that's how I would respond to that. That's

Erin Aquin  41:30  
beautiful. We have a company that we work with. And about once a year, at least five or six of their newest managers will go through a course with us. And it's, it's really amazing, because then the development becomes cultural. And everybody's teams know where their lead is at that time. And they have that mentorship and support within their company, they have each other that they can bounce things off of that they can play with. And it becomes not just one person seeking out a mentor or a coach and hoping they can make systemic change. But actually a group of people who are saying, You know what we're going to bring up, we have a concept that we talked about static, we're going to do talk about collective static at our next meeting, on this project. And that team's doing it, and this team is doing it and that team is doing it. So it becomes something where those four or five people can roll out a whole shift in the mindset of how people work. So if I

Kerry O'Brien  42:38  
was to development, what I love about that Erin too, is like, the like the important when we talk about craft beer, we often talk about community as well, right? Like one important thing about growing in a craft is having a community of people practicing that same craft, which again, if we're gonna say leadership as a craft, we need that. So so the one thing I'd say all leadership, all really effective leadership development programs that I've seen have in common is a cohort model. You've got people going through it together. So I joined Cleal. Back in November, I've obviously been you know, I've been doing leadership development for a while I've been leading for a while, but I'm joining our with it's called base camp, which is our leadership development program. And I'm in a cohort and each cohort actually has triads. So you have a larger cohort of I think my cohort is like 25 to 30, I could be wrong. But then I have a triad of two other people who I do on the weeks we're not meeting I get together with them and talk through some of the content and one of us it like we come from very different organizations, one of us is a lot less experienced in leading than the other two, but you're getting to like discuss this craft and and the value for me too is again, someone who's been doing it for a while, who has a solid theory base, I get this person asking questions. And I'm like, That's a great question. I actually don't have a good like it prompts me to, like fill in holes in my game. So there's super value there. So yeah. Again, if you're a leader, and you're looking for like, what do I do next, find the people find the people practicing the craft and and whether that you can do that in your company, which is so great, because you share that context or like finding external places to do that. But find people practicing that craft, and talk about that craft together.

Steve Haase  44:18  
Amazing. Well, Kerry, thank you for taking the time to talk about the crafts with us. This has been a fascinating conversation. I hope it's been very helpful for all our listeners. If people want to connect further with you hear more of your wisdom, where should they go?

Erin Aquin  44:35  
And by the way, well,

Kerry O'Brien  44:36  
thank you. That's very kind. So for me personally, my LinkedIn is the best place to go. I don't have like a website or anything like that yet. So check out my LinkedIn. Connect with me message me I love talking about this kind of stuff. It's not so much my wisdom. But back in the fall, I co launched a podcast with a friend Lauren. The podcast was called How'd you learn to you can find it on Spotify Apple I don't think Google podcasts exist anymore. Maybe it's on YouTube. Or the website is hyltpod Hyltpod.com. And we talk to people who have achieved mastery in some really interesting and esoteric practices, and just talk about how they actually learned to do that thing and what were the processes and what were the bumps. So we had a professional magician, we had a breakdancer, we had a certified tea sommelier, really great listen if you want to understand how humans learn to do things, so I recommend you check that out as well.

Erin Aquin  45:32  
I know what I'm doing today. No, just kidding. I'm working.

Kerry O'Brien  45:39  
Maybe you can listen to podcasts and work depending on the work.

Steve Haase  45:44  
That sounds like the perfect project for a learning professional. Right. There's like, how, tell me tell me you're an l&d Geek without telling me you're in l&d geek? Well, that

Kerry O'Brien  45:55  
was actually where it came from. Because the choice was like, okay, because I wanted to do a pod. I knew I did want to try that. And it was like, Okay, do I want to do a professional one, but that's like, boring. Do I want to do like a personal one, but like, Great, I'm the 1 million music pod on Spotify. And so it was like, this idea was something okay, I could post this on LinkedIn, because my professional network will geek out over the learning learning. And then I could post it on my my Instagram because my, you know, my friends will be like, Oh, wow, that's really really cool that they learned how to do magics. So yeah, it was it was a perfect confluence for like me personally and professionally. Okay, thank

Steve Haase  46:28  
you again for sharing your time, your wisdom and your humor and generosity with us. We appreciate having you here.

Kerry O'Brien  46:36  
My absolute pleasure. Thank you for having me.

Erin Aquin  46:38  
Thank you.