Episode 104 · 6 June 2024 · 45:23
The Lonely Leader - 3 biggest challenges of leading a growing organisation
The Lonely Leader - 3 biggest challenges of leading a growing organisation
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The lonely leader — and why coaches matter
interview#leadership#coaching#loneliness
Managers as human shields (a theory from the 1960s)
interview#management#history#theory
What employees are really looking for
The psychology of group dynamics
The 3rd characteristic: obsession with onboarding
The true cost of replacing an employee
interview#cost-of-turnover#hiring#onboarding
Final word from Jonathan and outro
interview#podcast#outro#resources
Show notes
The Lonely Leader — 3 Biggest Challenges of Leading a Growing Organisation
Guest: Jonathan Bennett — executive coach, trusted advisor, and author of seven books, working with founders and CEOs across North America.
Growth is exciting. Scaling is brutal. And at the top, it can be profoundly lonely.
Jonathan joins Al and Leanne to unpack the three biggest challenges facing leaders of growing organisations — from the isolation that creeps in when you're the one everyone looks to, to the "Valley of Death" that swallows companies at the 10–12 employee mark, to the selfless path of building psychological safety without becoming an "umbrella manager" who shields their team from everything.
This is a masterclass in what nobody tells you about leadership — and how to survive it.
Key Talking Points
The Lonely Leader Jonathan opens up about the onset of loneliness for leaders — and the unique challenge of sharing information with employees, investors, and personal contacts when you're carrying the weight of the whole organisation. His advice: get a coach or trusted advisor who isn't in your ecosystem.
The Valley of Death Growth isn't linear, and it isn't kind. Jonathan explains the significant hurdles organisations face — particularly around the stage of 10–12 employees — and why professionalising management structures and implementing systems is non-negotiable for sustainable growth.
The Selfless Path Creating a psychologically safe workplace takes more than a mission statement. Jonathan digs into proper onboarding, long-term integration of new employees, and the delicate balance between being a supportive manager and becoming an "umbrella manager" who shields their team from growth, challenge, and accountability.
Top 3 Takeaways
Leadership is lonely by design — build a support system outside it. Your employees, investors, and even friends have competing interests. A coach or trusted advisor gives you a safe space to think out loud.
The 10–12 employee mark is where businesses die. The "Valley of Death" hits when informal structures break down. Professionalising management early is the difference between scaling and stalling.
Don't be an umbrella manager. Shielding your team from everything might feel supportive, but it robs them of growth. Real psychological safety means letting people face challenges — with you alongside, not in front.
Next Week's Episode
Geoff Roberts, co-owner of Outseta, discusses his unique business model where everyone earns $210,000 a year and can work wherever they want.
Join the Conversation
We value your insights and questions! Email us at hi@truthliesandwork.com or leave a comment on our YouTube channel to share your thoughts and queries.
Connect With Us
Get in touch, book a call, or find Al and Leanne on LinkedIn — all in one place: truthliesandwork.com/connect
Mental health support: findahelpline.com — UK: Samaritans 116 123 · Mind 0300 123 3393 — US: 988 — Australia: Lifeline 13 11 14
Truth, Lies & Work is part of the HubSpot Podcast Network.
Full transcript
Expand full transcript
Al ElliottThe dirty little secret is that most businesses think they know their customers. They have the data, the records, the history, but it's scattered across 3 teams and 4 systems. And in our case, it's about 216,000 spreadsheets, which means nobody can actually use it.
Leanne ElliottWhat you should be doing is using HubSpot, because why? HubSpot connects it all— every interaction, every support ticket, every conversation— into one platform every team Can work from. So when sales talks to a customer, marketing already knows the full story. And when you know more, you grow more.
Jonathan BennettNice.
Al ElliottCheck out hubspot.com, the agentic customer platform for growing businesses.
Leanne ElliottHello and welcome to Truth, Lies and Work, the award-winning psychology podcast Brought to you by the HubSpot Podcast Network, the audio destination for business professionals. My name is Leanne. I'm a business psychologist.
Al ElliottMy name is Al. I'm a business owner.
Leanne ElliottAnd we are here to help you simplify the science of work.
Al ElliottYes, this is the Thursday episode where we have an interview with an expert. Now, what an expert we've got for you today. You are going to love this guy. If you've not caught up with our Tuesday episodes recently, then they're just, they're just a bit more loosey-goosey, as we always say. They're a bit more of a news roundup. We have a new Summer Book Club, which has just been introduced literally a minute before Leanne said it. I think she thought of it. And, uh, we've also got the world-famous Weekly Workplace Surgery where I put your questions to Leanne.
Leanne ElliottSo what are we talking about today, Al?
Al ElliottBeing a leader is hard, we know that, but being a leader and growing an organisation is even harder. Today's guest has done exactly this.
Leanne ElliottYes, today we are joined by Jonathan Bennett, an executive coach, trusted advisor, and author of 7 books. Jonathan has extensive experience working with founders and CEOs across North America, with experience in urban, rural, remote, and First Nations communities. Jonathan's expertise is in social purpose, business strategy, governance, branding, change, and communications. Prior to coaching, Jonathan founded Laridae, a management consulting and training firm that helps nonprofit and public sector organizations Laridae has now served more than 200 clients. As its first CEO, Jonathan grew Laridae from a startup to a leading firm in its space and a proud B Corp. Jonathan is also a chartered director and currently serves on 2 privately held corporate boards. He describes himself as a feminist. He's an activist across social justice issues, First Nations reconciliation in Canada, autism and neurodiversity, and perhaps one of the world's biggest cricket fans. Jonathan knows that leadership can be lonely, and today his mission is to help purpose-driven leaders to go from overwhelmed and stuck to thriving.
Al ElliottSo in this episode, we are going to be talking to Jonathan about the 3 main challenges of being a leader in a growing organization. Number one, it's the lonely leader effect. Number 2, The Valley of Death. And number 3, The Selfless Path. I interviewed Jonathan a few weeks ago, and we're going to join the interview now as we meet Jonathan, learn a bit more about him, and also learn why leaders can be lonely.
Jonathan BennettOkay. So, my name is Jonathan Bennett. What I do, I'm an executive coach and a trusted advisor. I serve founders and CEOs right across North America and beyond, primarily in small and mid-sized companies and nonprofit organizations. What am I famous for? Well, I don't know if I'm famous, but I'm known-ish for having written a bunch of novels and books of poetry as a sort of a parallel career, I guess. Here's the thing, kids. Poetry doesn't pay. And so I learned that the hard way, maybe, through my 20s and 30s. And in addition to wanting to fulfill my first love, which was writing books and telling stories, I developed a career that ended me up in senior management roles. And so, I've done both and I feel super privileged to be able to sort of sit here with some gray in the beard and be able to say I was able to kind of walk both paths.
Al ElliottWe've had 3 or 4 leaders, one from IBM, which I won't name, but we had 3 or 4 leaders who have kind of implied that it's lonely at the top, but we've never really delved deep. So can you tell us what is it about a lonely leader that, like, how would you know what they look like? What are they feeling? You know, what, how do they compare and what's going on in their heads? Just talk me through the whole thing.
Jonathan BennettIt happens. Gradually and then suddenly. So when you found a company or you buy a company and you're at the top, it's really exciting and you're super busy and all the things are happening. You're growing and you're hiring people and you're trying to get more products or services out to market. And, you know, it's a bit of a roller coaster. It's up and down. But over time, you realize that There's only so much that you can share with your employees because if you overshare, you'll scare the shit out of them. And there's only so much you can tell your investors because you have to make sure that they are getting a return and that they think you're great. And there's only so much that you can share with your spouse or your roommate because after a while, it just sounds like you're boring work stories to them. And they don't want to hear it anymore. And so where that leaves you is alone with your own thoughts. And sometimes folks have friends and/or other CEOs that are in similar positions to them, but there's only so often you can go to those wells. And so what then happens is that leaders find themselves kind of isolated and feeling kind of alone. And not always sure who they can talk to and how they might work through some of their problems. After all, they're supposed to know everything. They're the CEO, they're the founder, they're the boss, uh, and, and, and they can get themselves into a loop of thinking, uh, and it can be quite destructive. And so often eventually they'll find somebody like me to talk to that's a coach. Or a trusted advisor who can sit there and just hold the space. I've been there before. I know what that roller coaster looks like. I know how it feels. I know where it's going and where they've been. And so I can ask them hard questions. I can give them advice when they need it because I've probably seen— if I haven't experienced it myself, I've probably worked with somebody that has. And so they butt up against something and I can say, Well, it sounds like you don't have the answer inside you. Let me tell you 3 ways I've seen this dealt with before. And probably one of those 2 doors, or one of those 3 doors, I should say, will be the door that they're looking for. And it just helps the loneliness dissipate. It doesn't mean it's not there, and it doesn't mean that those things aren't true, but getting into a regular rhythm of talking with somebody that does the kind of work I do allows for somebody to go with you on that journey, somebody that knows the ins and the outs. It's not every conversation isn't starting from scratch. They build, you know, and so like any kind of relationship, they get richer as they go along.
Al ElliottWhen you start describing this lonely leader, I think you use the words, you can't talk to your investors, you can't talk to your staff, you're growing, you're increasingly isolated. This sounds like an inevitability for anyone who's building a business and growing a business. I mean, the Musk of the world, perhaps he's above in the stratosphere where everyone just says he's amazing, but there'll be a point to which surely every leader's going to reach this kind of thing.
Jonathan BennettYeah. I mean, and ages and stages, right? There can be phases that you go through as a leader that you feel particularly isolated or particularly alone. And there might be other, phases that are really energizing and that in fact you are able to be super transparent with the folks around you or you've got an off-sider or a business partner and that you're of like mind and it's easy to be able to share and needing or wanting a trusted advisor or a coach might seem like just one extra thing that you had to try to schedule and it's the last thing you need in your life. No problem. It is one of those journeys and the pressure associated. Like, keep in mind, like, if you own a small to mid-sized business, that shit's on you, all of it. All of those mouths are for you to feed. You have to feed the beast. You are the chief sales officer. You have to be thinking about what's after, what's next. You have to make sure that you look strong, that your company is growing, that you're a place that people would want to work, that you're a place that people would want to buy from. That pressure is heavy. It's a heavy pressure and it's not for everybody. And it can be for you for a while. And then you might go through a period in your life where other things are going on. Maybe your kids have got a thing, or maybe your relationship is going through a thing, or maybe you lose, you know, a loved one or a parent, and suddenly you're not at your best for 18 months. And it's not that you're not great at doing what you're doing, it's that you're going through a rough patch. And so, all those things can be true, and probably will be true at some point for most founders and most leaders.
Leanne ElliottThe idea of managers as human shields goes back to the 1960s. The theory goes that the best bosses protect their teams from organizational noise and let them focus on their work. That noise could be demanding colleagues in another department, or just those boring, silly tasks that take time away from more value-add activities. An extension of this is empathic concern. So that's asking, what can I do as a manager to make your job, my employee's job, easier? How can I remove the friction or the roadblocks to performance? And it's that empathic concern that is really good for business. There is a ton of research that shows empathic leadership boosts employee performance. And what's more, empathic leaders are better at predicting employee performance. So yes, great managers hit targets because they know how their people will perform ahead of time. Empathic leaders will also rarely receive a surprise resignation. But of course, there is always a dark side. What is the dark side of managers acting like shields? Well, another term that is used to describe this type of leadership behavior that comes with a slightly more negative connotation is the umbrella manager. An umbrella manager will shield their team, but they'll shield them from all organizational noise. This means that team members are given fewer opportunities to learn how to navigate these difficult situations themselves. And if employees aren't forming these strong cross-functional relationships, they may have less organizational impact. It's a bit like helicopter parenting. Being too involved can mean that others struggle to be independent, to think for themselves, and that can ultimately reduce innovation, creativity, and problem solving. So for managers, it also poses a problem. It can build this perspective that all problems are theirs to solve, and over time, this inability to collaborate or ask for help can leave managers feeling overwhelmed and eventually create a bottleneck, slowing decisions and frustrating the team. It's a really, really tricky balance that requires high levels of self-awareness, continuous reflective practice and your own support network, whether that be your manager, your peers, or somebody outside of work, especially if you have a lot going on in your personal life. And this is why coaching and mentoring is so important, because it provides this place to reflect and learn and take action. So for any great manager, any empathetic manager listening, remember, you are the problem solver, you are not the solution.
Al ElliottSee, when an organization starts growing, it can be really exciting, but there's also a point to which it all starts to feel like it's falling apart. Lots of people talk about this, including Daniel Priestley, that the 13th hire is where things change and your organization will never be the same again. This is what Jonathan calls the Valley of Death. So let's rejoin the interview where Jonathan talks about the Valley of Death and his take on it. You wrote down there was like the potentially 3 ways things could go. Was that what you said before? Is there like a, is there, A recognized, okay, when you get to a point, there's 3 options or 3 roads you can take?
Jonathan BennettI think there's kind of 3 main points along the journey. I most often find myself helping people when they're in what's referred to as the valley of death. And certainly, I didn't coin that, but there's these sort of almost classical archetypal moments in the growth of a business that you have some choices. And I'll just speak about the first sort of 3. The first is, should you grow and/or scale past yourself? In other words, do you convert the thing that you own and that you're doing from a kind of freelancer, solopreneur experience? Do you decide to add anything, anyone that's not you to the mix? That is a really big hurdle. It's very, very personal and it's a big choice because it's suddenly you're deciding this isn't just all about me. I've got one other person. And it could be because you're winning too much work and you take on a contractor and you take on another contractor and then you think, why am I paying them at the contractor rates? I should, they should just be an employee. And so suddenly you think, okay, well, like, let's figure out how to do that. And you make them an employee and you somehow talk them into it and they sign, you know, they ramp their boat with yours. They say that they want their career to be in your hands. And then you do it once and you're like, oh, this is going good. Let's just do one more. That's the first big hurdle. The next big hurdle is usually at around 10 to 12 sort of people or so. And it varies across the industry. So I'm certainly not going to speak about, you know, the size of a company and what your turnover might be or anything like that. But just, we'll just talk about it in people terms. You get to sort of the 10 to 12 people mark and for a while, it's like all hustle. When you're at 7 people, you know everything that's going on. You know everybody personally. You hired everybody personally. You know, we're all on the same team. We communicate in a group chat. We have weekly meetings. We have monthly retreats. Whatever we're doing, it's like, you know, we're in this sort of tight circle and it's working. When you hit the sort of the 10 to 12 mark, it starts to break apart. That's when we need other layers of management to start to come in. You literally can't be in all the conversations. You can't, you can't know everything anymore. And so you have to start to professionalize your management structure through delegation, through communication channels, through workflow process design systems, that kind of thing. Most entrepreneurs hit the 10 to 12 mark and blow past it and wonder why this company's just not like it used to be anymore. We used to be like a family around here, or I loved it when it was small, right? And, um, and so the employees start to push back. Uh, we've grown too big. So that happens usually at breakneck speed, and they— by the time they figured out that they've grown too quickly, they're actually on the other side of it. And so they don't really have much of a choice but to start to structure themselves in a way that is going to support their growth over the course of the next, you know, several years so they can get through what is now— they're into the valley of death. So, um, there's lots of different articles and people can find really cool stuff online about this, but anywhere from the sort of the 10 to 12 person mark up to Some folks say 40, some say 60, some say 100, but in my mind, it's sort of 50 to 60. That's a really hard size of a company to be. It's because you're not big enough to have achieved really deep efficiencies at scale, but you're still too big to keep things super small and agile. So you do need systems and processes. Um, most people that are founders and are growing companies like that, it's the first time they've done it. And so maybe hopefully they've come from a company that was bigger and they sort of know how it should look, uh, and that's very helpful. Sometimes I'm working with like, let's say, family-owned businesses and, you know, the kids come up through the family business and the family business has gone from 12 to 40 now. And that's like a whole DNA of an organization that's actually never worked anywhere big. So they don't even kind of know intuitively what it's even supposed to look and feel like. So that can be a hard journey for, you know, in that use case. But, you know, in general, getting through that is a hard push. It's a hard slog. They're a difficult few years and many companies frankly don't make it. It can be a really, really tough time. The ones that do tend to have really great workplace cultures. They tend to be obsessive about processes and systems, and they really are all in on it. And it's that structure that allows them to grow and grow past and get bigger. And the bigger they get, they start to get the economy of scale, and then they can invest back into their business with the sorts of things that a larger company can have that make people want to work for large companies. safety, professional development, a career path, more pay that comes in somewhat regular fashion, all those sorts of benefits of working for a bigger place.
Al ElliottYou used the term valley of death a couple of times before, and I'm just trying to make sure I understand. Is the valley of death between sort of 12 and 70, or where's the valley of death?
Jonathan BennettYeah. I mean, I think the literature is going to describe it in slightly different ways depending on what you're reading, but generally speaking, it's It's after you get past 10 or so and before you get to 60 or so. And that's just a really hard period in many companies' growth is to get through that.
Al ElliottSo, for anyone who's listening who might be in the valley of death, what sort of signs do you think that they might be seeing that will tell them they're in that valley of death?
Jonathan BennettIn their workplace, annual workplace culture surveys. Well, first of all, do you have an annual workplace culture survey? If you do, then you're starting to think about putting in the systems, the human resources systems that are going to support growth and that are going to support people feeling safe and accountable at work when you're not in the room. Because you can't be everywhere anymore as the leader I'm talking about. You've got to delegate leadership and you've got to create cascading systems. It doesn't, you know, like founders love flat systems because they're doers and they love to be everywhere in all the meetings and participate in all the decision-making. And, um, and sometimes they're, um, super transparent and it, to, to a point. And so when a company's small and they can, they're in the room and they can make lots of soothing noises Great. When the company gets bigger and they're not in the room anymore and they've delegated that meeting to another manager and the transparency flows down and that manager doesn't know how to handle it, then that can— that transparency, which should be an act of trust building, actually can be, if not handled well, the cause of a lot of concern and consternation for frontline staff who are just trying to sell the next product or deliver the service or whatever it is. So it's, it's, um, it's really, it's really difficult. Uh, I, I think if you're obsessive about growing good processes and systems and you build them with the people that are doing them, that's the key. It's not do it to them and not do it for them, but do it with them. Build systems and processes that allow the way that you want your company to run, to allow it to run when you're not in the room, when you're not in the office, when you're not a part of that decision-making process or that meeting, that's when it can be good.
Al ElliottNow, I have a question that I don't know whether you're able to answer, but because I didn't have the information on Laridae, but where did Laridae get to in terms of employees? Did you experience that valley of death? Did you make a decision before you got there?
Jonathan BennettYeah, we slammed right up against it. So we hit 13, literally we hit 13 employees and And it started to fall apart at the seams. I was no longer able to be everywhere any longer. There were a few external factors and we went through a rough patch and it was really tough. So we actually shrunk and it was what we needed to do at the time. I would say the quality of the work was starting to suffer. Hopefully, the clients didn't notice that, but I felt as the owner that it was. And so we restructured and we took a beat and, um, refocused and kind of got back down to around 8. And that was what— where we needed to be. We had lots of subcontractors and other people delivering things for us, but like as a kind of core team, uh, that was where we needed to be. And, um, we purposefully stuck there for the next few years. And, uh, and some of that was through the pandemic. And so, uh, that was also— there was that layer of complexity on the business at the time. But yeah, we really hit it. And I think that I did not know— theoretically, I knew this because I've been talking about this for a long time and I've seen it in my consulting work. But when it happens to you, you think you're special and you're different and that somehow it's not going to apply. It completely applied. And I immediately had not, you know, I knew like we just had not built out, especially for us, it was the sales and marketing systems to support our growth. Everything had been inbound organic based on the quality of work relationships, like classic service-based business. And it was doing awesome work, still is by the way. It's a fantastic company and it's still doing amazing things. So yeah, I'm talking about it kind of historically now. This is sort of going back maybe more than 5 years. Um, and you know, when we hit that point, it was because we were just flat out, we had too much work. And then suddenly we didn't have too much work and we had too many staff, and we just had not built sales processes. We were just in response mode, like rookie mistake, and yet happens so frequently. There are some wonderful examples of companies and company cultures that have been designed in ways, uh, that, that are not all about how big they are or about, um, yeah. And, and, and, and a lot of private company, uh, success is hidden from us. You know, we don't really know what's, what's going on. And so, you know, we don't really know what's going on. Uh, they might be doing amazing things and grinding their people into the ground, and it's a horrible place to work. Or, uh, you know, they might not be that profitable, or they might be wonderfully profitable and a wonderfully mature, grown-up, sensitive, psychologically safe workplace. These are hard things to know, and it would be wonderful if some of these narratives weren't quite so dude bro culture stuff. Like, I just, I don't have any time for any of that. Like, I would much rather see us brag about the kinds of places that our workplaces are. and the kind of people that we attract to work with us. And I think increasingly, that's what employees are looking for. They're looking for a values alignment. They want to see the company that they work for and the work they do be an extension of their own identity and their self-expression.
Al ElliottSo, Leigh, let's just talk about this for a second. Why is it that teams change? The original people Start to feel a little bit like everything's going wrong. What is the actual psychology behind this?
Leanne ElliottWe are asked about this quite a lot, aren't we? And I think a useful starting point is the psychology of groups. So, if we start right at the beginning, evolution. Forming groups simply allowed humans to deal more effectively with our enemies, with predators. It increased our chance of survival living in these, in these groups. And over time, that's turned into just an innate human drive, need to form strong and positive relationships with others, or a term that's used more in organizational psychology, to belong. Groups also help us to understand the world around us, to interpret the behaviors of others, and to reduce ambiguity. So put really simply, groups make us feel safe. And then we have the complexity that as the size of the group increases, there's a need for organizations to have more leadership in place or middle management in place. There's a German sociologist called George Simmel, and he argued that as a group becomes greater in terms of number, those individual benefits that we saw reduce. The individual becomes separated from the group. It grows more alone, more isolated and segmented. So all those benefits that we mentioned in terms of group membership, in terms of safety, in terms of a lack of ambiguity, they start to diminish. So, our drive is to replace this, to regain this out of instinct, and we do that by splitting into subgroups, or in organisational terms, teams. So, teams are a good thing. They keep organisations agile, they enable fast decision-making, and then create environments where these strong bonds can continue to exist between colleagues, with managers, and that is really critical for performance and engagement and wellbeing. And it's also why great managers are so important, because the research shows us time and time again that performance soars when teams in a larger organization are united in a shared vision and have clarity over their role and know how their role contributes to mission delivery. The issue is not large groups splitting into smaller groups. It's— the challenge is maintaining that collective vision and making sure that all the teams, all individuals understand their role in delivering it. And the key to that, the way to solve that, is to make sure that this vision is refreshed and how it's delivered is refreshed as your organisation grows. And importantly, that is articulated with your team. If that's done right, that when— then even when splits happen in the organisation, everyone's still on the same page. And it's worth business owners, entrepreneurs remembering this when they start to feel like they're losing the original culture. And we've had many questions along this line, as both through our consultancy and on the weekly Workplace Surgery. You are losing the culture you originally built because it's evolving, and it needs to. Like everything, we all need to evolve to survive.
Al ElliottSo, we've talked about the lone leader, we've talked about the valley of death. After the break, we're going to talk about the third characteristic, which is the selfless Did you know that the UK's number one management podcast—
Leanne Elliottthat's us, by the way— and the UK's number one marketing podcast are both on the same podcast network?
Al ElliottWe actually have a lot in common. We both use behavioural science to help people do better at work.
Leanne ElliottAnd we both had to wrangle Rory Sutherland on an episode.
Al ElliottAnd 2 out of 3 of us are devilishly good looking. And you're not gonna say which. Phil, host of Nudge, UK's number one marketing podcast. It's brought to you— we need to do this in threes—
Leanne Elliottthe HubSpot Podcast Network, the audio destination for business professionals.
Al ElliottSeamless, seamless. Tell us about your latest episode, Phil.
Jonathan BennettUh, we've just done an episode on fake fandom and how New York indie bands are paying agencies to create fake TikTok videos about how much they like their work. And we talk about the behavioral science behind fandom and how that encourages people to enjoy the music and all of that good stuff, and do some big things about how this affects the world of politics, business, and brands as well.
Leanne ElliottIt is, it's such, it's such a good show. Of course, you'll hear all the stuff you want to hear about how to grow your business by using behavioural science in your marketing. But there's also just some really interesting episodes that will be right up your street. Personally, I enjoyed Can Balsamic Vinegar Make Beer Taste Better?
Jonathan BennettIt can.
Leanne ElliottAnd Are We All Just Status-Seeking Monkeys?
Jonathan BennettI am.
Al ElliottGo and listen to Nudge wherever you get your podcasts.
Leanne ElliottBut come back.
Al ElliottYeah, come back.
Jonathan BennettDefinitely come back because Nudge isn't as good as this. So come back.
Al ElliottI'll cut that out. Keep that in. Welcome back. The 3rd characteristic of a great leader in a growing organization is the obsession with putting the team first, this selfless path. While psychological safety is one of the secrets, Jonathan has more advice for you. So let's get back to the interview and hear what Jonathan's got to say. You used a phrase there, psychological safety, which I'm not a psychologist. My wife and co-host is. She's amazing. And she would kick my ass if I said to you, that sounds like a bullshit buzzword. So tell me why that's not a bullshit buzzword, psychological safety.
Jonathan BennettYeah, it's not. There's some decent and emerging literature in it. I think, and just encourage everybody to read Amy Edmondson's book called Psychological Safety. It's a really solid read that I think sort of unpacks and founds this sort of concept. I think if you can show up to work and feel safe enough to describe the things that are happening to you in a way that is not going to cause your self-harm, or you won't be shamed, or you won't have suffered negative consequences, um, and you're doing it because it's in the best interest of yourself, your team, and the company, then you're in a psychologically safe place. Uh, too often we go into work, it's competitive environment, there's zero-sum games happening, everybody's out for themselves, and/or the manager is fighting for their life and they just push that down. These are unsafe environments and they are sadly all too common. And I think that what Amy has given us as just sort of like people out here doing this kind of work is a framework and a set of tools to think about how to describe both what we think can look good and also what happens out there when it's not well. I'm going to tell you a story. A while ago, I'm going to say maybe 5 years ago, I was at a business meeting in Ottawa. And this is a personal story. It was about the company that I was running at the time. I was at a business meeting in Ottawa and I'm waiting for the person that I was meeting to come for lunch. And I was checking my phone and there was a text. And it was just a bit ambiguous from one of the folks that worked at, you know, one of my colleagues. And I thought nothing of it. And I just said, sounds good, or something. And then I couldn't let it go. And so, During the meal, I'm like, I checked my phone. I think I asked even. Let's hope I asked. And I checked my phone and I'm like, what was that? And they said, oh, so-and-so, you know, happened— something happened with their kid. And so they couldn't travel up to the other place. So, so-and-so subbed off and we made this switch. And then this person is now doing that. Don't worry. They're getting briefed on the way and everything's good. So, I described this to the person I was having lunch with. I was saying— and so I just sort of said, oh, turns out it was nothing. They just had to make a big switch out on the team and the person, like, hadn't done this before, but they got briefed. And this person looked at me astounded and they said, do you realize that you have a self-organizing, self-healing team? That is at the pinnacle of what you can achieve. So he said, you should remember this moment because it may pass and your next iteration of the team may not be this good. And I have always thought about that because I don't think I really realized until that moment what we built, what the culture was, that everybody cared about everybody else enough that they made decisions that were in the best interests of themselves, their team, and the company overall. And that was a collective cultural response in all situations. And so that's, I think, what we look for when we're looking for psychologically safe environments. You want teams where people can express themselves in a professional way, in a professional context. You want there to be no harmful repercussions to somebody putting up their hand and say, you know, I'm not sure we're doing our best work here, or could we take another look at this system that doesn't seem to be working well, or I've got this client feedback. And not feel like they're going to get growled at by their team members, or there's going to be eye rolls, or there's going to be, you know, some kind of pushback. And if you can create an environment where those things are going on, then the outcomes and outputs and results go up. And the things that you're trying to avoid, like turnover and all kinds of other negative human resources consequences to not having good workplaces All of that goes down.
Al ElliottWhat's the best way to incorporate new employees into this? If we— I feel that if you bring even just one wrong person into a 20-person organization, you could seriously fuck things up.
Jonathan BennettYeah, I'm a bit obsessed with onboarding. I think that we think about onboarding all wrong. Mostly, our onboarding strategy is, here's the binder. Here's the passwords to your computer and the tech. Watch these 6 videos. Go through these 3 checklists. And then good luck. We'll just drop you in the deep end and see if you survive. That's most people's experience of being onboarded. I like to think about onboarding the same as, like, Pediatricians talk about attachment theory with infants. So I think that it takes about a year for an employee to fully attach to a workplace and a team. I think the first 3 months, a whole bunch of things are happening in their mind. They're wondering whether or not they've made the right decision. They're trying to figure out What are the rules around here, the unwritten rules around here that happen? Am I safe? What happens if I screw up? Will they figure out that I don't really know what I'm doing? Will they support me to learn that I'm, you know, doing something or a bunch of things for the first time, or I'm doing them in a completely new context? And so I have to learn new ways of doing old things. They're in a kind of fight-or-flight response for the first 3 months. Listen really carefully for when people's language shifts from you to we. That's the triggering moment that you know that they're attaching. Because every new employees, their small talk, they're telling you the story of who they used to be. They're telling you about the last place they used to work. They're doing compare and contrasting things, like when you're on a vacation and you spend the entire time thinking about the difference in prices at this location to where you live at home. That's what they're doing. Eventually, they stop that. Eventually, they start to relax. Eventually, they start to think, you know what? I have made a good decision. My career is relatively safe. My manager is mostly pretty good. I pretty much like most of my teammates. I think I can grow. And they start to like actually relax into the job. That's when they can start thinking. That's when they can start actually contributing properly. So you're at somewhere like the 6-month mark. And not until mostly you've been through an entire year's worth of cycle, whether it's a business cycle, whether it's, you know, you've got some seasonality in your business, that they've actually kind of gone once around the mulberry bush and they've actually figured out, okay, I think I kind of got it now. I can actually make improvements incrementally, you know, support my team in new and different ways. It's not 2 weeks. I think that that is a huge disservice that we do to people, and we should be thinking about how do we support people on a year-long journey. It doesn't mean that they need to be coddled or wrapped in bubble wrap or anything, but it does mean that there should be more frequent check-ins, that they should have somebody on the team that's a designated, like, partner to them. So they, you know, so I can ask the stupid question, not out loud but quietly after the meeting's over. Somebody that can just check in and see how they're doing and, you know, where are they struggling. Mostly we don't do these things in companies, but companies that do that really well, companies that take a very slow burn approach to allowing new employees on to, you know, to onboard deeply and properly, they stay. They stay, they stay, they stay. And I'll tell you another story. If you've ever been to a retirement party, It doesn't happen much anymore, but people used to work somewhere for 40 years. And those employees that have been there for 40 years, they stand up in the lunchroom and they tell one story inevitably, how they got hired. 40 years later, they will tell you who hired them, who was there for them in the first year. And then they'll skip forward 10 years and they'll tell another anecdote, and then they'll skip forward to who's in the room right now. Everybody's origin story is essential, and yet somehow we leave the origin story and the onboarding to chance. I think that's wrong. I think we should be thinking about it like an infant attaching, and they need all the care and support and love that we can give them. And so when the 1-year mark happens, they're thinking, great, I'm safe here, I'm going to stay. And then all that investment, we know how expensive it is to replace an employee and to find a new one, will actually pay off and you'll be able to get the dividends on that employee.
Al ElliottI want to know, what else do we need to know about onboarding that you've not just said?
Jonathan BennettIt starts before the job ad gets posted and before you know any of the candidates. It shouldn't start with, oh no, Mary in accounting's leaving. We need to fill Mary's job. It shouldn't start with, uh, we're bursting at the seams here, let's add a person to the sales team or to the marketing team or to the product development or whatever. It's about a wholesale integration of a new human into a culture, and every touchpoint along the way is a judgment point of that new employee Picking up information as they go through the process. How's the website look like? What was the job description like? What was the job ad like? What was the first reach out from the company like? Had they, you know, like, did I feel seen? Did I feel taken care of? Did I feel like I, like there was a healthy process here? That it was, that the process was going to be fair. All of these steps along like what are kind of normal HR sort of, you know, like perfunctory steps. I think if, if you put a sales lens on that, you're thinking about a customer journey. Like, think about what it's like to go into a Costco anywhere in North America and probably all around the world. They have thought of every single last step and thing that you're going to see and look at, and they incredibly precisely place things in the most annoying ways that you have to travel the entire distance of this warehouse just to get milk. Well, why don't we come— why don't we think about hiring in the same way? Like, we want to win through this. We want to get a great person who really wants to come and stay with us a long time. We know their origin story is important. We should be thinking about what their experience is at every step of the way. What those reach out, what the touchpoint, what the reference check is like, what the first interview is going to be like, what the follow-up after the first interview is going to be like, what the second interview is going to be like, who's going to be there. Not ad hoc, not could you do this, the thing. Do you have any questions? Oh my God, we didn't write any questions. Let's get these questions with for the last job and the wrong job, like make it up. Candidates sense all that stuff, and even if they end up getting hired, in the back of their mind they're like, this place is, you know, not perfect, it's a bit broken, the things. I just think that there's just so much more rigor that we could be doing, and the benefits and the knock-on effect is huge to attaching, to building a culture that people think that they can be really proud of. And it starts way earlier than I think most people think about.
Al ElliottThere you have it. If you have— I'm laughing because Leanne always takes the mickey out of me saying, there you have it. But there you definitely do have it. If you have thoughts or want to know a bit more about anything we've talked about in this episode, then head over to LinkedIn and join the conversation. Just search for Truth, Lies, and Work. Next week, we have another great guest who's doing something bit different. Jeff Roberts is the co-owner of Outsetter, where everyone earns $210,000 a year and can work wherever they want and as many days as they want. Yeah, it sounded a little bit ridiculous, so I had to get an interview with him. So subscribe to the podcast and ensure you won't miss our interview next Thursday with Jeff Roberts.
Leanne ElliottBefore we go, here is a final word from Jonathan explaining how you can find out a bit more about him The most common place people reach out to connect is on LinkedIn.
Jonathan BennettAnd I am a real human, I return DMs. And the first thing I normally do when I'm going to work with a new founder or CEO is hang out for an hour and, and just allow them to experience me doing my work. And there's never any cost to that. So if that sounds like something you're interested in, reach out.
Al ElliottSo thank you for listening. Thank you for subscribing. I hope If you have already. If you haven't, you know what to do. We will see you on Tuesday for our normal Tuesday episode, and then we'll see you next Thursday with the amazing Geoff. Anything to add before we say goodbye, Leanne?
Leanne ElliottNo.
Al ElliottGood. Bye then.
Leanne ElliottBye.
Al ElliottBye-bye. Uh, we have the, uh, the world-famous Workly Weekly Workly Play.
Leanne ElliottThat's gonna— I've lost my place. Sorry, I just fucking went off on one then, didn't I?
Al ElliottWelcome back. The 3rd characteristic of a great leader of a growing organisation is don't know.
Leanne ElliottAn umbrella manager will shield their team, but they'll shield them from— shield, she'd—
Jonathan BennettSheedle.
Leanne ElliottSheedle.
Al ElliottA few weeks ago, and we're going to join the interview now as we're going to meet— I'm not looking at the camera.
Leanne ElliottThere you have it. Of course you do. There you have it. So.