This is a transcript of episode 161 of the Troubleshooting Agile podcast with Jeffrey Fredrick and Douglas Squirrel.

If your boss isn’t helping like you think she should, maybe she’s not from Mars, but actually trying to give you more autonomy. We reflect on this in light of real-world coaching stories.

Show links:

Listen to the episode on SoundCloud or Apple Podcasts.

Upcoming Events

Listen to this section at 00:14

Squirrel: Welcome back to Troubleshooting Agile. Hi there, Jeffrey.

Jeffrey: Hi Squirrel.

Squirrel: So we’ve got the busiest March ever. We’ve got two conferences as we’re speaking out toward the end of the month, you’ll find details of those on, on the events page. You can interact with us, ask us questions about us, disagree with us, all the fun things you can’t do here on the podcast. And then I’m doing a workshop also in that same week on Decoding Tech Talk. That’s all about how to talk to your tech team without going insane, which is always a fun topic. Details on that are on or link from the same events page and then Jeffrey, you’re doing conversational dojos like I’ve never seen before. You’re doing so many.

Jeffrey: That’s right. We’ve got three coming up in the rest of the month. So one on Thursday this week, the 11th, one next week on the 17th, which will be particularly focussed on building trust. And then we’ll have our regularly scheduled dojo on the 23rd. So that’s a Thursday, a Wednesday and a Tuesday to choose from. So hopefully there’s something in there for you to come and practise your difficult conversations at the conversational dojo.

Squirrel: No excuse for not showing up with a piece of paper and practising.

Jeffrey: That’s right. And as you said, these are linked from our events page.

Management Mishap

Listen to this section at 01:34

Squirrel: Fantastic. So we’ve got an exciting topic today. Remind me what it is.

Jeffrey: Oh, that’s right. You know, you had told me that we have to ask people who are encountering a boss that seems to be coming from another planet. So what do you do if your boss seems to be from Mars?

Squirrel: Absolutely! So, Jeffrey and I do some joint coaching and we were helping out a client and this client was describing how she had a boss who had just asked her to do stuff that didn’t make any sense. And it really felt like a completely different type of request. Suddenly, this boss was not saying, “hey, here’s the priority order for your work. I’d like you to stop doing X and start doing Y.” The boss said, “we’ve got to do this right now. It’s super important, the dominoes aren’t falling. The rest of the organisation isn’t getting going on X and so we need to get going on X!” Without commenting on all the other things that this person was doing. And she said, “what the heck am I supposed to do with that? This guy’s nuts. He doesn’t know what he’s doing.” What do you think about that reaction to new direction from somebody in your organisation?

Jeffrey: Well, what’s amusing me just by chance. After that, I was on Clubhouse and joined a room that was talking about what to do about bad bosses. What if you have a bad boss and as I listened to it one thing that occurred to me over my career as a manager is that I know I’ve been a bad manager for people in the ways they were describing at different times in my career. Not all the ways, there are some ways that are clearly pathological, but in the way that sort of not giving people what they expected, certainly that had happened. And it reminded me of this topic that the way that I would manage people now is very different than I would have when I was initially a first first line manager. And part of that is a function not just of experience and learning what it means to be a good manager, but there’s a much larger component, which is the different level that I’m working at, the different types of experience. And it’s just a very different thing being a manager with a group of people, the team that I work with all the time who are doing the job that I was just doing previously, where I am something of an expert, I know what they’re doing that can help coach them very directly. And where I am now as a managing director, where I have a very cross-functional group of people reporting to me. Who actually I’ve never necessarily done their jobs, so I have people who are, in sales, who are running support, who’s a director of product, I have staff engineers, I have quant researchers, just this very wide scope of functions reporting to me.

Squirrel: And I think you’re saying Jeffrey that you’ve never done any of those jobs. You’ve never been a quant researcher or a salesman running a financial sales organisation or anything like that. You haven’t done those things.

Jeffrey: I’ve done some of them, but many of them I haven’t. So I’m running a product organisation that I’m familiar with. I’ve been an engineer, though, never a staff engineer so some at least commonality there. But these other ones are very different from my experience. The kind of relationship I have to their decisions, the relationship I have to the work that they’re doing and I think most relevant here, the kind of trade offs that they need to be making, I just can’t provide the same kind of input and insight. And so I don’t try to I behave differently and I don’t try to make decisions on their behalf. And I think that’s part of being a good manager in this case, where I’m providing them information rather than trying to do the role for them. But that might be a bit of a shock, I think, for people who are not used to managers who aren’t overseeing their work directly.

Squirrel: It certainly was a shock to the person we were talking to. It really sounded like she was suddenly hearing this message from this other planet. I have an interesting experience that from my very first management role that I always use as the reference for the case where you’re kind of that, you called it a “player coach” Jeffrey, where you’re kind of knowledgeable about all the work of the people underneath you. When I was very first managing, I’d just taken on a totally new type of role. I was organising a team to get a task done by a certain time, and I’d never done that before. And the person who was managing me said, well, Squirrel, what you should do is just take this group of very junior folks who know just a little bit less than you start at one end of the row, they were sat in a row on the on the desk and there were four of them in a row, and start with number one, ask her where she’s stuck, get her unstuck and get her working, and then go to number two and get him unstuck, figure out what he’s doing, make sure he’s on track. And by the time you get to number four, it’ll be time to go back to number one. So just keep going along the row, helping each of them and, take a break for lunch. But otherwise, that’s what you do all day. And that was a very good model for that type of leadership and the that type of management. And I think that’s what our kind of less junior version of this was, what our coachee was expecting. She was expecting someone to come along. It was when it was her turn on the row, the manager would give her some direction, would say “do this one and not that. And you’re doing this correctly, good for you, and change this one.” And that wasn’t what he was doing. And it’s that shift that I often see as a shock to people in that situation. And suddenly they’re functioning very, very differently.

Making the Shift

Listen to this section at 07:35

Jeffrey: And one of the things that happens that makes this change is that it comes with becoming more senior. It comes often with, maybe it’s not a promotion, but being given more responsibility. And that’s where you would expect that now you’re going to have more things delegated to you. And this is growth, this is what growth looks like. But it can be uncomfortable because it means now taking responsibility for decisions that normally or previously you wouldn’t have had to make on your own. I’m thinking of the situational leadership model, which I’ve been talking to some people about recently. And the idea of situational leadership is that as a manager, you interact with the person based on their readiness level. And so there’s a time in the relationship where you’re just telling the person what to do. If they have no idea if there’s things that are holding them back, you might just be very directive. Then you move into a position of selling them where you’re sort of teaching them what to do and selling them the benefits of a particular approach. Then you have a supporting phase where you are helping them think it through but basically the decisions are really coming from them and you’re just facilitating and then finally reached this level of delegating where it’s like, “OK, look, you can handle this” and the trade-offs involved and more of it now goes to the person to run independently. And that last one is the real big shift because you no longer have the sort of psychological safety net you had before of the manager being a partner in the decisions. And I think that can be a bit disorienting. How does that match your experience from coaching?

Squirrel: Oh, absolutely. That’s often exactly what I’m helping people through and helping them at both ends of it. So I have people who are moving along that situational leadership path, we’ll put a link in the show notes, of course. But there’s a famous picture that kind of looks like a winding path and there are people who are moving along that themselves. So I’m telling them to do things, one of my favourite things to do is tell people to go on a listening tour. So I say your job is now not what it used to be. It used to be that kind of going along the line, telling the next person in order what to do. Now, your job is much more about alignment. So go and listen to this group of people that you’ve never talked to before who are not in your organisation and understand what they need. I’m going to have somebody I’m going to be talking to later this morning who’s in the middle of that and finding it really enlightening. So that’s one of the parts that I’m helping people on, is helping to become that leader who is functioning in the new situation and performing more alignment tasks and giving less immediate direction and may not know how many of those folks do their jobs. And the other thing is being, as you’re doing, that you’re also adjusting to new levels of leadership and new types of leadership from those above you in the organisation. So I’m often helping people on both sides of it.

Jeffrey: The thing that occurs to me is as we talk about this is how frequently the people I’m working with who are experienced in this haven’t really been trained in being a manager. And the people managing them, haven’t been trained in being a manager. So one of things that we do and we go and talk to them is we bring in all these frameworks as well as experience and say here’s how you can make sense of what’s happening. By the way here’s the transition you’re going through or if you’re helping someone else through the transition, here’s how you can help them through it. But it’s often the case then the people are going through this transition from someone who’s leading them through it, actually, who’s not leading them through who who is who is going through their own transformation, their own transition, and isn’t as consciously thinking about what the person who’s new to the role is going through. So this makes sense that we’re describing this in terms of ‘yes there’s this management theory to explain what to do and we might help guide people through it’. But it’s often the case, and this goes back to the idea of the conversation about bad managers I was listening to last night is the people listening had high expectations of what their managers already knew. But my own experience is that it’s very rare for organisations these days to invest a lot in actual formal training of managers. And that leads to people behaving bad in all kinds of ways because there’s a lot of things you need you to be a good manager and you miss any one of them and you can be a bad manager in some way. And so there’s that element. One of things that occurred to me as I was listening to it is it’s actually very useful for people, even if they’re not managers, to learn some management theory, to help understand what is actually happening to them, what they’re going through.

Squirrel: Excellent. Well, you can certainly follow the links in the show notes to learn more about situational leadership. You can ask us for more information. And there’s certainly lots of podcasts we’ve done on leadership. So go back to some of the episodes that we’ve done in that in that area or pick your favourite book on this topic. There’s so many there’s absolutely no shortage. So if you’re an individual contributor, one of the things you might do, whether or not you ever intend to be a manager, is to pick up some of the theory. And for me, I don’t know if you agree, Jeffrey, It almost doesn’t matter which one you pick up because they’re all going to give similar sorts of messages. And if you have any framework for what’s happening, if you have any context to put that message from Mars into, then it will feel less like it’s from Mars and you’ll be able to function better with it. What do you think?

Jeffrey: Exactly right. And you begin to develop one of the things we talk about a lot on the show is empathy. You’ll be able to develop some understanding of what your manager, what your boss is going through. And that’s going to be very helpful for interpreting what you’re hearing. So it’s like you’re learning a bit of Martian, which can can really be helpful.

Squirrel: Exactly. And the last thing I would note here is that we picked this up as we were coaching our friend last night. One of the things that can happen is that the messages you’re getting from Mars will sound like a bad boss. It’ll sound like the wrong thing because it would have been the wrong thing in the previous context. So this boss sounded like he was doing a bad job, not giving this person priority direction, not helping with understanding of the of the work that she was doing. But in fact, at this new level of this boss was functioning exactly as he should and in fact, doing a very good job of alignment and giving direction about which tasks were most important at that time and how the context was changing. So if your boss sounds bad, if your boss sounds like he or she is from Mars, get some theory. It may actually actually be able to translate the Martian and understand that. But what you’re hearing is actually very valuable.

Squirrel: All right, well, thanks, Jeffrey! If listeners want to disagree with any of that, want to argue with us, tell us that they are boss actually is bad, we would sure like to hear about that. You can find us, as we are noting at the top at, there’s a list of events there, including the dojos and the workshop and the two conferences and whatever else we think up by the time this goes live. So we’d love to hear from you there and you’ll find our Twitter and email and carrier pigeon and whatever else strikes your fancy there to hear from us. And we’ll see you again next Wednesday.

Squirrel: Thanks, Jeffrey.

Jeffrey: Thanks, Squirrel.