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Well, hello. Welcome to another edition of Pivotal Conversations.

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I've recorded several of these today, so I have nothing zany to say.

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What do we got going for us, Richard?

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Yeah, so this time we have a few different guests with us that we can quick introduce,

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talking a little bit about frozen middles and not necessarily in Popsicle format.

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So we have Dormaine here.

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Hello.

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What do you do here?

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I do product marketing.

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At Pivotal.

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They just throw any product at me and I'll market it.

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That's it. She markets it like crazy.

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We have Rachel.

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Hi, I'm Rachel Stevens with RedMonk.

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And we have Steven.

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I'm Steve O'Ready, also with RedMonk.

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All right.

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So I thought we'd have a little bit of a chat for a few minutes about this idea of the frozen middle.

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We heard it at SpringOne last year when the city executive type, Brad, I don't remember what his title was,

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talked about some of their transformation, some of that challenge.

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And frozen middle, I guess, is a term from the 80s that automaker examples were.

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And the idea is that the frozen middle is those middle managers that kind of push back and create some of this organizational inertia.

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And all that change that you want to enable at the top kind of gets stuck there.

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And then when the grassroots stuff happens, it kind of gets blunted before it actually makes it to the top.

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So if you don't change the frozen middle, I think the hypothesis is then your change kind of dies on the vine.

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So can we just have an empathy moment for those middle managers?

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Because I think like it's, you know, we're putting a lot of focus there.

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And it's sort of there's a tendency to to make that sort of maybe maybe blame even, if you will.

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But like the middle management life is tough, right?

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Like you're why?

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Well, it's like you're still you're still kind of like playing, right?

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You're still you're still getting stuff done.

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But you're also you're managing.

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You're not getting to like make the big decisions.

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You're you're trying to execute it, but you can't necessarily do it all yourself.

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So you've got to make sure that all these people below you are executing it.

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I just I just wanted to like start with an empathy moment for, you know, the reality of that's hard for any business person.

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If you've grown up in a particular environment, you're used to a particular environment, you're dropped into all of a sudden a completely new environment.

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It's hard.

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Change is hard.

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Doesn't matter who you are.

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I mean, you and I talked a little bit about, I think, incentives as well as what sometimes causes things to die there.

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Or is it, you know, are middle managers incented the right way to, you know, take some of this change from their developers and their ops staff?

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Or is it more about just kind of keeping things status quo?

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And they're also trying to absorb these maybe lofty objectives from a manager and executive.

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I mean, do you think there's an incentives challenge there that makes it where things get stuck?

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In theory, I think that a middle manager is the person who's supposed to be able to help you go over your entire organization and have some kind of strategic view.

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So your top is the people who have this strategic vision.

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The people at the bottom are the people who do the work.

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And the people in kind of that middle layer are supposed to be the ones who help translate like that.

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And so, like, the people at the bottom maybe don't necessarily understand the implications or the wider implications of what they're doing.

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And the people at the top don't really understand what the specifics of what they're asking.

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And so the middle managers are really there to help translate between the groups.

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And I think that that's a really challenging role.

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And it's particularly challenging to incentivize that.

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That's pretty fair.

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How do you – I mean, so in IT teams, you know, I think you all see how either both web companies as well as enterprises who want to be web companies kind of start to do this change.

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So, you know, how does that start to thaw, I guess, is the idea in the tech – you know, in a technology world where you have tech middle managers who, again, you have, you know, potentially a manager of ops who is paid on stability.

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And, therefore, they do not want to introduce change.

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And I have a dev manager who's incented to ship software.

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And so that's their incentive.

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And so you have this kind of clash over and over again.

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How do you see companies start to bust that?

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Well, I mean, do you want the positive answer or the negative answer?

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I want both.

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The positive answer is that in some cases, you know, you do have organizations, consultants, you know, sort of outside resources, you know, sort of in some cases that's technology, in other cases that's services or people and so on, you know, whose job is essentially to assist with the transformational process, right?

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To go in and basically say, look, we're not just going to, for example, come in and, you know, drop in, you know, some new platform or some new piece of technology.

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We're going to, you know, work with you to retrain, essentially, the organization around sort of this change, right?

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That's the positive spin.

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The negative spin is, is that there's a great Max Planck, a famous scientist quote, that the opponents of new scientific theories are never sort of correct themselves.

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They just eventually die off.

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And, you know, within, you know, some organizations, certainly what you end up seeing is, is that, you know, with a sort of quote unquote frozen middle, they just get routed around.

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And eventually they become obsolete.

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And that's typically not good for your long term employment.

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Yeah, I just finished a good book, The Art of Action, which looked at the Prussian army in like the 1800s and how that translates to business today, which is, again, thrilling read and fun at parties.

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But what it was often about was how do you translate down and how do you actually arrange for agility and empower people in that middle layer so they don't feel like they're beholden to these instructions they can't achieve from the top.

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And yet they're also kind of crippled from the bottom.

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Have you seen Dormain, you know, pillow runs with a lot of individual cells and teams?

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So there's not that, I don't think, traditional middle management layer here because sometimes the teams are self-sustaining and they've got their own little unit inside.

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I mean, do you think there's a, I guess, DevOps sort of way that you start to break that down because you don't just have this layer of middle management?

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Or is it just moved to a different place?

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Does DevOps fix the frozen middle?

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I don't know.

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No.

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I would argue no.

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No.

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I don't think there's anything necessarily that fixes the frozen middle simply because the frozen middle is the product of, you know, really that sort of, as we said, you know, it's a sort of very human emotion, like a fear of change.

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Right.

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And can, you know, I think the other related question is, can DevOps help?

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And I think certainly in certain cases, sure.

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Right.

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Because, you know, in other words, if you can get to the point where, let's say you've been tasked with modernizing your software organization.

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Right.

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And you're part of the sort of frozen middle.

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You have no idea what's going on.

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You're used to doing things a certain way.

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If DevOps or the process of going down that path can begin to show some immediate results and you can begin to see this change, maybe then you buy into it.

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Maybe it's less scary.

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Right.

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Because it's not just this weird new thing.

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And, you know, frankly, many of the sort of people who are scared of this have heard claims like this for literally decades.

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Every year somebody has some brand new technology or product or methodology or process or whatever it is, it's going to fix everything and so on.

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So maybe, you know, certainly as you see DevOps implemented and rolled out, you begin to see some of these results and you buy in.

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But I don't think there's any sort of, I don't think there's a cure, you know, so to speak.

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What about like actually what we were just talking about downstairs in terms of sort of rotations within an organization and how when you start to rotate people around and thinking about that at that middle management kind of layer, that all those rotations kind of, it's basically forcing change.

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Because every time you make a rotation, you're like, I'm getting handed a brand new pile of problems I got to go solve.

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Brand new pile of problems, brand new environment.

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Yeah.

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So I can sort of think about what I did over here, but I'm going to have to adapt on some level.

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And if you do that enough times and that kind of becomes the culture, then each one of those is like, okay, we're just going to get used to change.

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And at each point you have to, you have to look at what's, what's actually happening in the here and now.

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Yep.

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Because you're, you're coming into it with a fresh pair of eyes.

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Yeah.

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So I don't know, just like a hypothesis about, you know, rotations and it, and it also kind of breaks some of those silos.

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Cause I think one of the reasons why they're, that doesn't happen is because people sort of have this notion of expertise, right?

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Like a friend of mine is a, he's, he's a data scientist.

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And then, um, now he manages a team and he's got like 20 something people below him and he's, he's essentially kind of in one of the, now in some kind of middle management layer, he's constantly trying to stay on top of his, you know, data science chops, right?

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Like it's a highly technical field, but he's also got to like play the politics and figure out all these other things going on.

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And then, you know, it's tricky because you take someone who's got literally decades of training in that like field, like data science and like where are you going to rotate them around into?

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Like the guy has, you know, written like how many papers on this topic?

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I mean, maybe that doesn't apply to all corners of, you know, IT and development.

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That's kind of an extreme corner case, but you know, in other places, yeah, it's like someone who's, well, I understand this application or like this.

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I work with this line of business and I really understand their needs.

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Like maybe that's part of the problem is like, you're not looking at it with a fresh pair of eyes, but there's this perceived notion of expertise that you don't want to let go of.

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Yep.

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That's, that's pretty fair.

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Um, certainly cultivates versatility, you know, if nothing else, right.

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In terms of being sort of rotated around, you can't become too comfortable, you know, certainly where you are and, you know, Hey, you know, we've always done things in this, you know, particular department or BU, wherever it is.

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Um, because you know, Hey, I've been here for a year and I was somewhere else a year before that and somewhere else a year before that.

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Um, so yeah, I can certainly see that as a working hypothesis.

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And I've definitely seen just in my own experience, the hoarding of organizational knowledge as a source of job security.

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And so the rotation thing can definitely help with that.

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Doesn't a lot of this come down to though, it's got to be safe to fail to some extent.

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You would think that middle managers often get so atrophied or so terrified because, you know, they, they worry that they didn't translate the top level objectives, right.

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So they're just going to try to play it safe and they don't want to get it wrong.

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And so, I mean, there's a lot of this have to be that it's okay to make a mistake so that you, again, you do allow people under you to be a little more risky or ambitious versus stunting any sort of innovation they're trying to do.

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I mean, do you see that?

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I think around here, when you were talking, all of a sudden I hit this realization.

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I think I'm middle management now, which really just freaked the hell out of me.

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But part of that was, I mean, I think pivotal makes it a pretty safe place to fail.

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And I don't think you can fail repeatedly doing the same thing, but that gives you a certain freedom.

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I think that's the definition of insanity.

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Yeah, that's true.

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Yeah.

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But, but do you see that?

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I mean, does that have to be rotations?

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Great.

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I think all empathy is great.

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You understand all the different roles, but does some of this have to come down that you feel like it is safe to be curious?

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I think certainly the larger the margin for error that any individual employee has, the more open I think they'll be to change.

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And the reverse is true, right?

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So in other words, basically you have no margin for error if the first thing that goes wrong, you're out.

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Well, you know, guess what?

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You're going to be pretty resistant to any change whatsoever, you know?

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So, yeah, I think it's, it's, you know, absolutely there's a correlation there in terms of, you know, having a tolerance for maybe not everything going perfectly correctly.

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And, you know, hey, we're going to try this.

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If it works, great.

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If it doesn't, then that's okay, too.

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Yeah, I can definitely see that.

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You know, you know, I don't remember the only encounter I've had with Prussian military theory, which was really bizarre, was in that Lean Enterprise book.

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And I remember coming across and being like, wow, this is an odd thing to come across.

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But it does seem like, you know, when I talk with people who are frozen, and all of y'all have hit on this stuff a lot, it seems like, to some extent, at least in not even a stereotypical way, but the way we think about middle management is, to the point of the frozen metaphor, we're setting into stone a process.

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And middle management is in charge of making sure that process is followed and executed.

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And it seems like, you know, that's sort of nice, and more of what we want to shoot for is at least, like, a slushy middle management, where, like, their job is more to sort of, like, to use another metaphor, you know, smell the cheese often and see if it's gone bad.

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Like, they need to be more of a monitor of, like, are we meeting the ends that we want, which is the point of not being able to fail constantly.

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And then also, like, how do I manage the change to the new way of doing stuff?

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And I don't know if middle managers typically think of themselves that way, like, they almost expect, and you still need this, they need the higher level managers to pass down the, you know, time to change or whatever.

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And so maybe that's, like, I think, especially in the tech industry, the frustration we have with a lot of middle management people is they don't change on their own.

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And I think part of it is, like, that's not their job description.

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I mean, and as an example of that, like, I think to turn a sarcastic joke into a positive, right, like, after, like, three or four years of Spotify culture presentations, you realize that, like, having no culture is their culture, right?

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Like, they just change it and adapt it around as needed on an annual cycle, and obviously I'm overstating it.

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But it's sort of like, it seems like what we would want middle management to get more comfortable with is, like, yeah, we should change things around all the time to meet whatever goals we want.

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Not gratuitously, but if we need to change things around, we should monitor for that.

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And if things are going poorly, we need to change how things operate.

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Yeah, that seems fair.

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Yeah, I mean, I don't know if you've ever read, I haven't finished the book, Holacracy, you know, these ideas of having truly almost self-organizing stuff where there is no management and teams figure out what they do, and it's extremely fluid.

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There's some success, and it sounds like some terrible failures with that.

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But, you know, do we think that in tech, that role of middle management doesn't have to be a complete slog, that there can be something where you actually might aspire to doing that and not fear that you've just, you know, completely torpedoed your career?

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I think so much of it honestly depends on the organization, right?

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It depends on sort of the wider culture of the organization, you know, because, look, middle management, you know, on some level, you know, per Rachel's description, I think, which is very apt, which is, look, you know, it's not that different from, for example, in the military, you have officers, right?

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You know, sort of, you know, according to, you know, a lot of definitions of officers, officers are there to essentially hand down orders.

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They go down to the non-commissioned officers, the sergeants, and they're the ones who figure out how everything actually gets done.

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And part of, you know, the officer's job is effectively to run interference, right, so that, you know, you can actually get done what you're supposed to get done.

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That's, you know, not dissimilar from what you see within, I think, a lot of organizations, right, which is, okay, I'm going to actually take care of politics so you guys can, you know, sort of be effective, right?

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So what is that, that depends on having a culture where you buy in and where you want to take care of, where you care about the job, you care about the people and everything else, you know, versus organizations where you don't care about the job, you don't care about the people.

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Well, you know, basically you're just there, you know, pushing, you know, pushing things around your desk and, yeah, I don't, I don't, so, yeah, I think the answer to me is that it really depends on the culture of the place.

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Yeah, collecting TPS reports.

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Exactly.

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Yeah, in other words, that's the, that's the canonical example.

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Do you think domain middle management doesn't have to suck?

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No, it doesn't have to suck.

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You know, I think a lot more people need to aspire to it because there's going to be a lot more people in it.

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Yeah.

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Like, there's just no way around it, so we have to make it not suck.

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I'm saying that as like a, more of like a mission statement than like an actual truth.

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But, you know, if we think about it, like, we do have to fix that, right?

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So that it's like the only people who end up in middle management are either like pushing things around their desk or they're just trying to figure out how they can climb higher up the ladder and like step on whoever they need to to get there.

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Like, if we just, you know, keep going down that route, like, this is never going to get better.

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Yeah, and I know even the book on the Prussian military, which again, I'll refer to again, clearly a great read, Art of Action.

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But it made the point that sometimes it's easy to say like, hey, you know, we don't want managers, we want leaders.

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And that can be super cliche, but you actually need managers.

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Like, you need people who know how to help people execute on a particular path and get things out of their way.

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And it's not just about ambitious, motivational statements and attaboys and let's go.

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It's actually about people who know how to execute.

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So I know it's easy to be kind of, I don't know, talk down about management, but it's super important.

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It's just maybe not as sexy as somebody who can go up there and deliver a fiery speech that gets everyone out.

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I was going to say, I think a lot of the organizations, not all of them, of course, but a lot of the organizations that decided that they didn't, you know, sort of at the outset that they didn't need managers, turns out they needed managers.

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Right.

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And, you know, those transitions in many cases have been painful.

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And, you know, like I said, it's not that there can't be exceptions, you know, that are able to function without it.

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But, you know, at a certain level, you have to be able to process, get things done.

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And they're just like in any group of people, there's going to be politics and, you know, sort of differing agendas and so on.

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And how does that get juggled?

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Well, you know, if you're a developer, you really don't want to deal with that.

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Yeah.

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So it'd be really cool if there was somebody whose job it was to deal with that for you so that you could actually get your shit done.

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Well, I feel like this has probably been very helpful for Richard, who seems to have recently had this dark epiphany that he is middle management.

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So I think along with his fascinating bedtime reading, it sounds like, his Prussian whatnot, like I think he's got some good stuff to chew on here.

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So why don't each of you tell us, like, if people want to, like, find you more on the Internet or whatever, where they can go to look for you.

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We'll start with Rachel.

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Rachel, you can find me over at Redmonk or on Twitter at rstevensme.

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Dormain.

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Oh, yeah.

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So if you just look for my name, which is D-O-R-M-A-I-N, but if you Google that, you just get a lot of people who mistyped domain.

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Did you mean on your own name?

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You do.

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I do.

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And only if it's just my first name.

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And then, so that, I'm just going to tell you right now, is not how to find me, because you'll just get a lot of people with fat fingers.

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And it's kind of, it's actually like a big word for the Internet.

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Like, apparently there's some relationship between the two.

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So, nonetheless, that happens.

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So you've got to go with the whole Dormain Dreywitz.

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I know it's a lot to remember, but, you know, Twitter, at Dormain Dreywitz.

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Some robot got at Dormain, probably thinking, like, gosh, this is really close to this other word that seems really popular.

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So I, unfortunately, didn't get that one.

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Nice.

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Yourself, Steven?

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I'm at redbuck.com, and I'm on Twitter at S-O-Grady, S-O-G-R-A-D-Y.

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Well, good.

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Well, hopefully we've, you know, I don't know if, dear listener, if you're a part of the world, you have something called a Sonic.

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But, like, at a Sonic, they have something called a slushy, which is a divine drink.

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Hopefully we figured out how to freeze middle management, at least into that.

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If you get the lime one, they put, like, a half lime at the bottom.

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It's a fun exercise to see if you can, like, suck out the lime without destroying your teeth with all the ice in it.

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You do that when it's really hot.

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But, as always, this has been Pivotal Conversations.

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You can find all the latest episodes that we have at SoundCloud.com slash Pivotal Conversations.

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If you subscribe to the feed that's there, you don't have to worry about anything.

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It'll just be downloaded automatically, and you listen at your leisure.

252
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It'd be delightful.

253
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Also, if you haven't gone into iTunes and left a reviewer rating or gone into Overcast and clicked the little recommend thing, that would be great to do.

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Or it's also nice just to tell us you listen and recommend it to your friends and help us promote it.

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It's promoted everywhere, because we really are just doing this, you know, to know that people are listening to it.

256
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Otherwise, I could sit here and talk into an empty coffee cup.

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It'd be kind of the equivalent.

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But with that, we'll see everyone next time.

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Bye-bye.