Season 3 Episode 34: How to Be a Better Boss
Let’s be honest: most bosses are forgettable. They’re neither terrible enough to inspire a mutiny nor brilliant enough to earn your loyalty. But the ones who do stand out? They’re either the reason you quit or the reason you stayed. This week, Jimmy and James ditch the usual rant about bad bosses (though, let’s face it, they’ve had a few) to tackle the far trickier question: What actually makes a good one?
Turns out, it’s not about charisma, a fancy title, or even a well-stocked biscuit tin. It’s about clarity—knowing where you’re going and making sure your team gives a damn about getting there. It’s about adaptability, because what works in a crisis won’t fly in a calm. And it’s about trust: not the corporate buzzword kind, but the I-won’t-throw-you-under-the-bus kind. Oh, and asking questions. Why Am I Talking? should be every boss’s mantra (thanks, James’s old boss).
But here’s the kicker: being a good boss isn’t about being liked. It’s about creating an environment where people want to do their best work—even when the system is stacked against them. So if you’re tired of pointless targets, blame games, and bosses who treat you like a spreadsheet, this is your therapy session. No fluff, no jargon, just the hard truths about leading without losing your soul (or your team’s).
Five key points:
- Trust is the glue—without it, your team’s just a bunch of people waiting for the next screw-up.
- Clarity of purpose is non-negotiable—if your team doesn’t know where they’re going, they’ll just wander into a ditch.
- Adaptability separates the memorable from the mediocre; one size does not fit all.
- Blame is the enemy of progress—good bosses fix problems, not people.
- Asking questions beats having answers; your ego is the least interesting thing in the room.
[00:03] Jimmy: Hello, I’m Jimmy. James: And I’m James. Welcome to A Job Done Well, the podcast that helps you improve your performance and enjoyment at work.
[00:15] James: Good afternoon. What are we talking about today?
[00:17] Jimmy: So today, James, we are going to talk about how to be a better boss and getting more out of our team as a result.
[00:22] James: Ah, very good.
[00:23] Jimmy: Now, we talked a few episodes ago about bad bosses, and we slaughtered loads of bad bosses that we’ve worked for—and ourselves, in fairness. But today, we’re going to focus on the positives.
[00:30] James: Right. So, of the bosses you’ve had, how many have been good bosses, and what do they have in common?
[00:37] Jimmy: We talked about this before. In percentage terms, I think a relatively small percentage were really good, a relatively small percentage are really bad, and then everyone’s just in the middle. So I think the art form here is: if you’re leading people, how do you take yourself out of the pack? Because when you’re in that pack, you might do some things right, you might do some things wrong, but you’re just in a pack of people. The memorable ones are the really good ones and the really bad ones.
[01:30] James: Yeah, go on.
[01:30] Jimmy: Hopefully, you’ve got a—
[01:31] James: I’ll have to think quick.
[01:33] Jimmy: I think it depends because it’s very individual and circumstantial. If you and I are working together in a situation where everything is ticking along really nicely, smooth and easy, you’re looking for certain things from your boss. If we’re in a different situation where the shit’s really hitting the fan, we want a different set of actions and behaviours. So I think some of it is circumstantial, and some of it’s individual. The things that you like in people might not be the things that I like, and vice versa. So I think where that draws me to is: it depends. The more helpful answer is, for me, it’s about adaptability. How do I adapt to the fact that in my team and in the circumstances I’m managing, there’s going to be a whole load of variety, and how do I deal with that authentically?
[02:30] James: Yeah. And I’m a bit more positive about it, I’ll be honest. I totally agree there are some who are standout greats, and there are some who are standout just freaking despicable. But you know who I’m talking about, don’t you?
[02:49] Jimmy: I do.
[02:49] James: But, if we were to write a list of people that we both worked with or for, and we were to rate them from who was the best boss to who was the worst, I think we’d have quite a lot of commonality. I think we would say they were over-controlling, only in it for themselves, kept changing their mind, were unhelpful, didn’t know where they were going, weak, didn’t stand up to people—those sorts of things. So if we could agree on a list of qualities for bad bosses, then I think we could probably agree on a list of good qualities for bosses.
[03:47] Jimmy: Yeah.
[03:47] James: Well, today we promised ourselves we wouldn’t dwell in the misery of bad bosses, so let’s focus on that list.
[04:01] Jimmy: Well, today we promised ourselves we wouldn’t dwell in the misery of bad bosses, so let’s focus on that list then.
[04:09] James: Well, the first one for me—and it’s hardly surprising because we bang on about it all the time—is that a good boss is very clear on purpose. They’re absolutely sure where they want to be going. They’re very clear with you where they want to be going, and what good looks like. “We’re going in this direction.” And that’s great, but the really good ones, I would argue, do that about something that their teams can get excited about.
[04:36] Jimmy: On this one, we definitely completely overlap. But I do think it’s a nuance on what you said: it’s the what good looks like as well. So I think, yes, having a clear, bold, compelling vision that they get everyone engaged in, that’s part of it. Some of the best bosses I’ve worked for are very clear on what good looks like for me and for my team. I think that takes a lot of the ambiguity and the politics and the trying to figure out stuff—
[05:04] James: Yeah. And actually, a lot of frustrations at work are when people are clashing over what the purpose is.
[05:13] Jimmy: Just on that, James, I worked in the same organisation for a while. For the first, I think probably two years, we had a clear purpose, a burning platform, and we had to solve that, and the whole organisation was galvanised around that. Year three, we had solved the problem, and we didn’t clarify a new direction. The organisation drifted a little bit. People’s different agendas started to creep in, and their politics started to creep in, and the games playing started to creep in. Then when we restated what we were there for, again, back on track. So it was the same people, same situation. It just really depended on whether we had that clarity.
[06:00] James: Yeah. People collaborate much more if they’ve coalesced around a purpose.
Early in my career, I worked in research and development, and I worked for a boss, and he was golden so long as you were doing something that was innovative. Well, makes sense when you work in research and development, yeah? He moved on. We then got a new boss, and she was only interested in cost savings. Do what you like as long as it was saving the organisation money. What was interesting, though, was the team. You go work in R&D because you like innovative stuff. It’s not because you like cost-saving stuff. So everybody—it didn’t appeal to the team. So I think there are two things to it: clarity of purpose and it being something the team could feel they were doing good with.
[06:49] Jimmy: And, just on that second bit, James—was that where you built up your or started your allergy towards cost-saving initiatives?
[06:58] James: Futile in the extreme. Have I told you the story about Forrest Mars? I worked for Mars. I’m sure you’ve heard that bit. But I worked—
[07:05] Jimmy: You, we spent the first 12 months of working together, and everyone used to take the piss.
[07:10] James: Yeah.
[07:11] Jimmy: James—
[07:12] James: Yeah.
[07:12] Jimmy: I worked for Mars, Lawther.
[07:14] James: I have met one of the Mars Brothers, Forrest Mars. It’s a privately owned business. And these guys were billionaires, and there’s this damn fool Yank wandering around the plant in the most God-awful jumper you have ever seen in your entire life. It was a crime against style. And I said to my boss at the time, I said, “Who the hell’s the Yank in the jumper?” And he says, “Oh, that’s Forrest Mars.” Anyway, I only had one conversation with Forrest Mars, and that’s where he took me aside and he said, “James, what you don’t realise is you don’t save yourself rich.” And then he turned tail and walked off. That’s the only conversation I’ve ever had with a billionaire, American or otherwise, but that is one of the reasons why I’m a bit anti cost-saving.
[08:04] Jimmy: You worked in an environment where they wanted more innovation. People want more of this. This is changing. The world is changing. All of those things require a level of experimentation and testing. When stuff goes wrong, how do you respond to it? A good boss will respond to it positively and help the teams and the people learn from what’s gone wrong. A bad boss goes and seeks out the villains of the piece and starts casting blame, which immediately creates defensiveness and a complete unwillingness to—
[08:38] James: Totally agree, and it’s not just about innovation. Stuff goes wrong. You’ve got competitors doing things. You’ve got people in other departments doing things. You can’t control it all. You’re a fool if you think you would. You’ve got the old Mr. Six Sigma coming here, but you’ve got variation going on left, right, and centre. You cannot control it. Stuff goes wrong.
I worked for a bloke once who, anyway, when things went wrong, particularly if it got to his boss, he’d find somebody in his team to blame. Now, did that—
[09:09] Jimmy: Really?
[09:09] James: God’s sake. So how did that go? A, you wouldn’t tell him when things had gone wrong, and B, everybody thought he was a fool. And there is that thing about when—fortuneately, I’ve never done it, but in the First World War, when they were fighting in the trenches, how many people are you gonna send over the top of the trench for? And yeah, this guy wasn’t one. So there you go. Don’t blame people. Stop looking for villains.
[09:31] Jimmy: Just on that, that last point. I think that willingness to unlock the discretionary effort for a boss, I think that’s always a good measure of a good boss. If you find yourself running through walls for someone—
[09:46] James: Yeah. No, I think that is a very good test.
[09:49] Jimmy: Yeah.
[09:49] James: Well, I think a good boss isn’t just focused on their bit of the organisation. They stand back and they look at the whole picture, and they’re in a better position to do that than you are because they are the boss. But on a link to what we’ve just said, you know, all the activities that happen in an organisation, they’re all linked. They don’t happen in isolation. And so if you want things to run smoothly, having a boss who can stand back and look and understand the bits upstream and downstream is really all-important.
So I’ll give you an example. It’s a very obvious example. One organisation I worked for, I was in charge of complaints, would you believe? So I’ve got a team handling complaints. They had a target—oh, I don’t know, some ridiculous target, 80% of complaints had to be handled in 14 days or something ridiculous. We never got anywhere near it. And that’d be very easy to jump up and down on people’s heads and say, “Well, why didn’t you get the complaints? What’s stopping you?” The reality is, they were handled by a call centre somewhere else, where they’d incidentally put in some cost-saving initiatives, and then they just dribbled through as and when they could get by to us. But once you stand back and you look and you understand the system and understand what’s going on, then you can start to act and smooth things out, which the people who are working for you don’t have the opportunity to do. So I think that’s the thing I’d say: pay attention to what’s going on and look at the wider picture.
[11:12] Jimmy: Another angle to being a good boss is you start off your career, invariably, you have a deep level of expertise in quite a narrow field.
[11:23] James: Yeah.
[11:24] Jimmy: What happens to us, and then you build your reputation. When I worked for a betting company initially, I knew everything about the customers and the events and the stuff that we’re doing. So I was successful because I had deep expertise in that. And then all of a sudden, you get promoted to a level where the breadth of what you’re looking after, you can’t have that same deep expertise that you once made your name on. The change for me with somebody who’s a good boss is: are they able to do that pivot where you’re going deep on something, and all of a sudden you’ve gotta go really shallow on lots of things? Now, the implication of that is you’re not gonna know everything, so it can be a little bit uncomfortable when you’re used to being a deep expert. And secondly, you have to build up levels of trust and ability to ask the right questions of the people who are the deep experts. Otherwise, you add no value. You just get in their way.
[12:31] James: Well, yeah, and so I think that links really nicely to my next point, which is a really good boss asks questions and doesn’t think he’s got all the answers. It’s not about his or her ego. They realise that they don’t know anything, and they spend their time asking questions and finding out what’s going on.
[12:49] Jimmy: We should also plug the episode we did with Reinberg last year on the power of questions. It’s worth having a look at that, ‘cause that is a really underused skill.
[12:52] James: That’s great.
[12:52] Jimmy: Reinberg last year on the power of questions.
[12:59] James: One of my bosses, he had this lovely acronym. He said, “James, you’ve gotta remember the acronym WAIT.” W-A-I-T: Why Am I Talking?
[13:10] Jimmy: Oh, I like it.
[13:12] James: Very similar to what my wife says to me, which is, “Why are you talking?” Anyway, but it’s really powerful, because a really good boss knows what they know. They should be far more interested in what you know, because that’s how they will learn something. So some really simple questions a good boss will ask are things like, “What would make it easier?” or “What’s getting in the way?” as opposed to, “Why aren’t you doing that?” And it links a wee bit to that point about blame, but just that whole thing about understanding. A really powerful question I used to use was, “How can I help?” or “What would you like me to do?” And most bosses don’t say that because they’re scared that they’ll get lumbered with a whole load of extra work. But the reality is people like to be self-determining. They want to take control of their own destiny. So actually, the act of saying, “How can I help?” They invariably say, “Well, it’s all right. I think we’ve got it covered. We don’t need your help, thank you very much.”
[14:06] Jimmy: Yeah. I’d argue that with that slightly, James. I don’t think it’s they’re motivated by not wanting extra work. I think they’re motivated by the fact that a lot of people think they know the answer. The reason they don’t ask questions is because they’re too busy telling people what they should be doing and how they should be doing it. That ego of whether it’s born out of arrogance or insecurity—“I’m the boss, I should know the answer, shouldn’t I?”—it still comes from the same place.
[14:35] James: Yeah, but a little humility is a fabulous thing. And there’s this quote, isn’t it? If you’re a good boss, your job is to make the room smarter, not to be the smartest person in the room. So yeah, how do you get all that information out? It’s about asking questions and burying your ego. So I think that makes a good boss.
[14:54] Jimmy: And one that we almost certainly will disagree with each other on: I think you’ve got to build and maintain relationships with your team.
[15:04] James: Ah, you’re wrong, mate. They’re just a bunch of spreadsheets. You need to treat your team like spreadsheets, and you’ll be okay.
[15:09] Jimmy: But in all seriousness, I think people want to have individual relationships, and their boss is a really important relationship. So ask yourself stuff about your team members’ kids, their partners, their pets, what they get up to outside of work. It means a lot when you say to somebody, “How’s your dog?” You know, “I know your dog’s been ill. How’s Bear doing?” It means a lot to somebody. Whether you care deeply about the future of their dog, whether you’ve ever met their dog, it’s almost irrelevant. It’s just being interested in them as a person, because A, that will matter to them, and B, it creates an environment where they feel like they’re—
[15:55] James: Yeah. Well, people want to matter. They need to be relevant. So yeah, I would say to me, this is important. You’re absolutely right. It’s very important because people need to matter. And there’s another bit to this as well, which is a little bit more transactional, but it’s very easy to think you understand what your team’s motivations are and what their desires are, and who will want this project and who wants to do that. You don’t know. If somebody’s having a divorce, that’s very different to somebody having a poorly child. Their motivations and their actions will be totally different. So understanding your team is all-important.
[16:30] Jimmy: And equally, you need to let them understand you. We tend to try and be this absolutely perfect—nothing ever goes wrong for me, I can handle everything, show no vulnerability—whereas actually, you’ve got to let them see that you’re human.
[16:46] James: Yeah, no, totally agree. A lot of management is about measures, and actually, the way you as a boss use measures is all-important. So if you use them carefully, I think that can put you in a really strong position. And it’s your point about understanding. Using measures to understand what’s going on and help test things and try things is absolutely important.
[17:13] Jimmy: What?
[17:13] James: Now—
[17:14] Jimmy: Setting—
[17:14] James: Using targets—no, no. Dig away. Dig away.
[17:19] Jimmy: Using targets—
[17:20] James: No, no. Dig away. But yeah, targets just bugger things up. The number of times I’ve had a boss give me a target, and it’s been an objective or something like that, and it’s some mundane thing, but because it’s been written in PowerPoint, we’ve got to hit this flipping number, and just that complete lack of understanding of what’s going on and just the obsession with hitting the target, because hitting the target makes you look good. So using measures is all-important, but just getting obsessed about targets is a bit pointless.
[17:52] Jimmy: We did an episode early on about gets done, so it’s worth checking that out.
[17:54] James: Yeah.
[17:54] Jimmy: But would it help your therapy if we did—
[17:59] James: Yeah, we can do—
[18:01] Jimmy: Just allowed you to—
[18:03] James: Yeah, pointless targets. Pointless targets. But I think the thing here is teamwork is more important than targets. So you’re setting people individual targets and individual measures. But that’s not what being a boss is about. The point about being a boss is to coordinate and get teamwork. So I think, yeah, understanding metrics and using them to understand where things are going badly and what we need to do differently is all-important. But if you care more about the metric than the behaviour, then I think you’ve got a bit of a problem.
[18:33] Jimmy: Next one is back to that environment you create around your team. In today’s world, if you’re gonna be successful, you’ve got to be improving. You can’t stand still. There’s always a relentless need for better performance or new innovation or stuff that’s happening in the market. It’s never-ending. And the only way you can really tackle that successfully is to create an environment where people can learn. So that’s about being open, observing, listening to people, looking up, looking out, looking around, and learning, and encouraging your—
[18:57] James: Yeah.
[18:57] Jimmy: Team to do the same.
[19:10] James: Yeah, and I don’t think—well, I think so few managers realise that their staff want to improve their lot. They want to get better, and the only way you can do that is by learning. I totally agree. The alternative, of course, is just to sit on your hands and not do anything, but your staff won’t like that. So it is about moving forward in the direction you’ve talked about and learning, improving stuff, seeing what works and seeing what doesn’t. Which then, of course, leads us back to that whole point about observing and going and looking. So I think that’s all-important.
[19:42] Jimmy: Yeah. And I think one of the good challenges if you’re running a team of people: ask yourself how much time you’ve spent this week sitting next to somebody while they do their work. You know what I mean? Just observing what they’re doing, chatting to them about what they’re doing. And not just your direct reports, but right at the people on the frontline serving your customers or executing your process, whatever it is that you’re doing. Have you observed them doing their work this week? Because that’s where you learn, ultimately.
[20:15] James: Yeah, which kind of—there’s a management guy, and he said the three things a good manager does is: purpose, which we talked about, or direction, space, and resources. How do you know you’re getting people the right resources if you don’t know what they’re doing? Being close enough to understand it without telling people what to do is absolutely all-important, which kind of brings us back to the whole point about learning. But you don’t get the learning, of course, if you haven’t got an environment in which people trust you.
[20:45] Jimmy: And equally, you’ve got to trust people that A, they can get on and do their job, trust their capability. They’ve got to trust you on how you’re going to things.
[20:54] James: Yeah.
[20:55] Jimmy: So back to your point about the boss who always threw somebody under the bus. Well, he had zero trust with his team. They didn’t trust him to not throw them under the bus. So, funny enough, they’d never—
[21:08] James: Yeah, and you know, you then get—we’re getting to the other thing, my other trigger word here, which is performance management. But if you can’t trust your staff, if they are useless, get rid of them. Don’t hang back, just get shot of them. But you need to be in a position where for your team, you’ve got people you can trust and you can let them get on with it, because you haven’t got time to be doing everything else.
[21:29] Jimmy: Yeah, and just one small point, James. We’ve done two episodes on performance management, and it’s still—it’s deeply triggered. So I don’t think the—
[21:38] James: Well—
[21:38] Jimmy: Joy—
[21:39] James: We could do a targets and performance management double header.
[21:42] Jimmy: Moving on.
[21:43] James: It’s this thing about treating people fairly and just respectfully. Oh, here’s a story for you. We had one organisation I worked for, they had a stupid rule. There were lots of people travelling everywhere, and the trains get delayed, and there was the whole delay repay thing. You can claim money back on the train. So HR put out a rule, which was that if you were delayed on a company-paid-for train, you had to make the reclaim, and then you had to use that reclaim for company business.
[22:13] Jimmy: No.
[22:14] James: No, I’m not. So I kid you not, this is what they—
[22:19] Jimmy: No.
[22:20] James: That was the expenses rule. And I had a guy come talk to me, and he said, “I don’t travel as much as you do, James, but I’ve got £200 worth of vouchers because I keep getting stuck in Manchester at 11 o’clock at night when I’m trying to get home.” And I just looked at him. I said, “Well, go and spend the money. Take your wife somewhere. You have that money.” Because it’s absolutely out of order for the company to think it’s okay that if you’re sitting there at 11 o’clock at night on some bloody train that’s not moving, and you’re going through all of the pain, the company’s got the rights to have that money? That very act of treating people fairly does a huge lot for what the teams think of you.
[22:58] Jimmy: Yeah.
[22:58] James: The company’s got the—
[23:06] Jimmy: You can get your money back for your ticket. Does that suddenly make your company more successful and more profitable? Because I guarantee you, the £200 that you got back from his vouchers versus how pissed off—
[23:17] James: Oh.
[23:18] Jimmy: He was—
[23:19] James: Yeah, absolutely.
[23:20] Jimmy: £200.
[23:20] James: It’s very easy. That whole point about trust is very easy to dissolve some trust by pissing people off. Which leads us quite nicely onto, I think, my next one, which I’ve talked about in the past, which is the whole management umbrella. A good boss, I think, stops people from getting wet, but they should know it’s raining. So it’s just that whole balance of shielding off the corporate excess and shielding off the organisational barons who are jumping up and down, whilst at the same time getting people to realise it’s a bit painful. So I think that’s quite an important role of a good boss.
[23:57] Jimmy: Yeah. So where does that lead?
[23:58] James: Well, I don’t know. I suppose you’ve got to pick your favourite things. What would your summary be?
[24:03] Jimmy: Well, the interesting thing going through this episode is there’s loads of stuff out there about good bosses and bad bosses and all this sort of stuff. So we’re just giving today our take on what we think makes a good boss.
[24:16] James: On, just before we go, let’s not decry it. Between us, we’ve had the thick end of 70 years’ worth of working for people. So, you know.
[24:22] Jimmy: We know our stuff, but we have definitely had some horrors, and we’ve had some very good bosses. So, you know, if anyone wants to explore it more, they’re knock yourselves out. So go on, James, what were your top takeaways from today?
[24:37] James: I think the one that’s really important for me is a bit biblical, but treat people the way you’d like to be treated yourself. Nothing very clever about it, but I think that is a really important thing. The second thing I think is just ask, don’t tell. Because you know what you know, but if you ask people, you’d be amazed what you can learn. Get people the things they need to do their job. I mean, a lot of being a good boss is just about getting people the resources they need, and also just the ability to stand back and look at the big picture and help people negotiate their way through the organisation. So those would be my four things.
[25:14] Jimmy: I think they’re good things. I would have—
[25:15] James: No, there’s a go. You’re gonna disagree with me, are you? Go on.
[25:18] Jimmy: Yeah? Well, no, not actually disagree, but I think you should treat people as they want to be treated. Because if you take you and me, we’re completely different, right? And we’d like certain things. If you always treated people as if they were James Lawther, Jesus Christ, that would—
[25:34] James: Yeah, right.
[25:35] Jimmy: Last a little while. You know what I mean? So it’s back to my point about understanding people as individuals. I think the second thing for me is I’d agree. I think creating that real sense of direction, getting people bought into that sense of direction, I think is massively important. One area—this is a passion of yours—which is just understand how the environment impacts the people that are working for you. Because I think we overestimate, or certainly I’ve been guilty of overestimating, the importance that people have—the system around them, and the system around them can boost them up or stop them dead. But unless you are conscious about that, you can get people as geed up and ready and capable and fired up as you want. If the system completely takes them off their knees, they’re not gonna get very far. So I think understanding that environment, and the fourth one for me was really: listen more, tell less.
[26:32] James: So final thoughts. I think really, and I would say this, right? But it’s all about the system. So I just think as a boss, your job is to create an environment where people can do their best work. I’ve said it before, I’ll say it again, but that’s the job. It’s not to tell people what to do. It’s about creating that environment.
[26:49] Jimmy: Yeah, and like I said, Jones, that was one of the points I brought out. I guess I have a bit more of a view that it’s a balance between getting people fired up and capable and the system itself. And if you can do both of those, you’ll be golden.
[27:03] James: Super. So we don’t need any feedback on how good we were as bosses. Thank you very much. If you’ve got those sorts of comments, you can keep them to yourself.
[27:10] Jimmy: Which part of the good bosses was that? Is that open?
[27:13] James: I was learning.
[27:14] Jimmy: That was—
[27:14] James: I’m too old to be learning now. Yeah.
[27:17] Jimmy: Well, it’s all—
[27:17] James: So all right, yeah, there’s no—
[27:20] Jimmy: You’re all—
[27:20] James: Cool.
[27:21] Jimmy: All right.
[27:22] James: Speak to—
[27:22] Jimmy: Thanks, everyone.
[27:23] Speaker 3: We cover a whole host of topics on this podcast,
[27:26] Speaker 2: from purpose to corporate jargon,
[27:28] Speaker 3: but always focused on one thing: getting the job done well.
[27:32] Speaker 2: Easier said than done. So if you’ve got unhappy customers or employees, bosses or regulators breathing down your neck,
[27:41] Speaker 3: if your backlogs are out of control and your costs are spiralling, and that big IT transformation project that you’ve been promised just keeps failing to deliver,
[27:50] Speaker 2: we can help. If you need to improve your performance, your team’s performance, or your organisation’s, get in touch at jimmy@ajobdonewell.com or james@ajobdonewell.com.
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