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Working Conversations Episode 271:
Middle Manager Caught in the Middle on AI? Here Are Your Three Moves

Working Conversations Episode 271: Middle Manager Caught in the Middle on AI? Here Are Your Three Moves

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If you are searching for middle manager AI adoption strategies, you are probably living the reality this episode is built around: pressure coming from above to get your team on board with AI, and resistance coming from below that tells you something more complicated is going on. You are caught in the middle, and the usual advice does not quite fit your situation.

Here is what most organizations are getting wrong. They are treating AI adoption as a technology deployment problem, the same way they would handle rolling out a new version of software. But this is not that. Asking your team to enthusiastically embrace AI tools when they have spent two years hearing that AI is coming for their jobs is not a tech rollout issue. It is a change management problem, and it requires an entirely different set of solutions.

In this episode, I walk you through three specific moves for the middle manager who is stuck in this moment. The first is about managing up: how to reframe the conversation with senior leaders so you are positioned as a strategist surfacing organizational intelligence, not a squeaky wheel delivering bad news. The second move is about managing down: how to close the perception gap with your team by having the real conversation about what AI actually means for their roles. The third move is about shrinking the ask, making it specific, completable, and safe to report back on.

I also dig into the research from Harvard Business Review and Columbia Business School that reveals a striking gap between what executives think is happening with AI adoption and what frontline employees are actually experiencing. That data alone may change how you talk about this upward in your organization.

If you are an individual contributor trying to navigate this too, there is something in here for you as well. And if you are a senior leader wondering why adoption is stalling, this episode will reframe the problem in a way that points toward real solutions.

Listen and catch the full episode here or wherever you listen to podcasts. You can also watch it and replay it on my YouTube channel, JanelAndersonPhD.

EPISODE TRANSCRIPT

My company's just invested in AI tools, and leadership keeps pushing for adoption, but my team just won't get on board. What am I missing? Well, if that sounds like you, just know that this pressure to adopt AI is landing squarely on the shoulders of middle managers. They are getting pressure from above, and you, if you are a middle manager, are getting pressure from above and resistance from below, and that's putting you in a catch 22 That is putting you in a really, really difficult position. And you might be wondering, well, Whose problem is it to solve, is it my senior leaders, or is it the people who report to me, or is it my problem to resolve?

And I'm going to say it's kind of everybody's problem, but you, middle manager, if you are a middle manager, are really stuck in the middle right now. So I'm going to give some strategies in this episode that are going to help you, as the middle manager, if you are an individual contributor reporting to one of those managers or supervisors who's feeling a little stuck in the middle, you may want to go back and listen to last week's episode, but I'm going to give you some good strategies for you in this episode as well, and if you're one of those senior leaders who is wishing that people will get on board faster than they are, I've got some ideas for you as well, so you might also be feeling like, well, our company rolled out AI last year and told we told everyone to start using it, and some people are, but most people aren't. And how do I fix this?

Or again, you might be feeling caught between executives pushing for AI adoption, and then your team who's resisting, and how do you handle both sides of it? So again, we're going to get into it from all the different angles, but the real problem here is not the technology, and it is not that your team is being difficult. Here's what's actually happening: your frontline employees have been, have heard for the last two years that AI is coming for their jobs. I mean, we've seen it in the headlines, it's been all over the news that you know entry-level positions will be entirely obliterated and eliminated because of AI, and in the same breath, leadership is handing them an AI tool and asking them to adopt it enthusiastically.

So think about what that's actually asking people, it's not just learn a new tool, it's really to not only be complicit in the, you know, potential demise of their own role, but to actively participate in the demise of their own role, so that just makes no sense, and you can see why an individual contributor could be particularly resistant to adopting new AI tools. Now, that might not be the even an underlying concern. It might just be like it's one more thing, or it might be that you've got folks on your team who are resistant to technology, and or have other reasons to be pushing back against AI technology, but it would be a completely rational response for somebody to not want to not only complicitly but actively participate in something that could be their own demise, so that really I think does help go a long way towards understanding the numbers, so I'm going to get into a little bit of research here.

So just a few months back, Harvard Business Review published an article that was based on a Columbia Business School survey of 1400 US employees and in leaders, and in that study they found that 76% of executives believe that their employees are enthusiastically embracing AI now. When they asked the employees the same question, only 31% of employees were actively, positively excited about AI and using it. And then the middle managers were really right there in between 51% of middle managers thought that the frontline staff were actively embracing AI, so we see this huge disparity where you've got the senior leaders thinking everybody, not everybody, but senior leaders thinking 76% are on board of the actual people who we're talking about, only 31% of them are on board, and then the middle managers in between think maybe like half half the folks are on board.

So and if you are the middle manager, you know the pain of living in that gap every single day, because you know your senior leaders are investing all of this money and talking about the great change that AI is going to bring to your organization, and then you see your staff really reluctant to get on board, and then also, when you think about what you're tasked with as a middle manager, it's not just like use AI, it's drive AI integration into the products and services that we put out into the marketplace, and so it's not even just for your own personal use, a lot of you are tasked with really revolutionizing the products and services that your organizations develop and sell, and by incorporating AI into that, so that's a lot to take on.

So the question underneath the question here is not really, how do I get my team to use AI? The real question is, do you understand why they're not using AI, and what might you do to actually help alleviate their concerns, or get at what the root cause is for why they're not using AI, and then help them along the way, now again, we're going to talk about this from a couple of different angles. If you are that individual contributor, what can you do to get on board? And again, I want to also point you to episode 270 that came out just one week ago, that gives you four places to just, you know, four tactics, four things that you can try to step into a little more AI use, or if you haven't used it at all, to just get started.

So, we'll link that one up in the show notes. This is episode 271 so that is Janel Anderson forward slash Janel anderson.com forward slash 271 for episode 271 and 270 would be the URL for the show notes for the previous podcast, and and if you prefer to watch, we also have this on YouTube, so you can find my YouTube channel and look it up there again. We'll link that up in the show notes as well. Okay, so a organizations are treating AI adoption as like technology deployment. When I think it's not just so simple as like here's this new tech tool, like we've upgraded to the latest version of Microsoft 365 it's not that at all.

This is very, very different. A tech tool or using a new piece of software, it has completely different problems associated with it than implementing AI across your organization. When we think about this, and like, I've been thinking about this a lot, because I was at a conference, I don't know, like two months ago, a big tech conference, and as one of the sessions was a panel discussion of chief technology officers of a bunch of very large corporations, and they were talking about this very challenge about how much they're investing in AI, and how frustrated they are that frontline employees, individual contributors, are not using AI, and they're just seeing it as like one more thing, and then those AI tools are essentially collecting dust, and so they're like, how do we, how do we fix this, how do we remedy this?

So, again, I saw it firsthand, and I hear it firsthand from from the folks that I talk to when I'm out speaking and training, and so forth. We've got these really enthusiastic senior leaders who are putting a lot of money behind it and really hoping it will revolutionize their business and that they'll see great return on investment. And then again, we've got the frontline staff who are highly resistant to using it, so again, we can't just think about this as a tech tool that's being rolled out. I want you to be thinking about this more macro. This is really a change management problem, because we're not just asking people to use a new tool, we're asking them if they really do embrace using that new tool, which is generative AI.

We're asking them to rethink their job, and again, if you've heard some of my earlier episodes on AI, I'm completely of the persuasion that AI is not going to take your job unless you are refusing to learn AI, in which case you're going to lose your job for a variety of reasons, not that AI is necessarily going to take it over, but somebody who knows how to use AI will be a much better candidate for your position than somebody who is completely resistant to using AI at all. So, that's that's my stand on it, and that stand doesn't, doesn't change. But did you hear what was in that? That what I'm, what I'm proposing is that again? AI is not going to take your job, but it's going to, if you really embrace it, is going to fundamentally change your job.

And a lot of that might come down to you figuring out which pieces of your own job could be automated with AI. And then, once you implement those things, if extra time shows up on your calendar, what are you going to be adding to, and you know, how can you continue to add value and bring value to your organization in your role by doing some other things, and so again, this is a fundamental change in how we work, not just rolling out a tool, and I think this is the where middle managers are getting caught in the midst of it, because I think you probably sense this, even if you hadn't put the exact language that I just put to your problem. I think you've, you probably went like, oh, exactly, she just nailed it, that's exactly what I'm experiencing.

So I want us to be thinking about this holistically again, from the individual contributor role, the job is going to be redesigned as a result of using AI, and it might be that individual contributor who is in charge of doing that redesign, because the middle manager can't be redesigning everybody's role as well as their own and pushing AI into the products and services that your company produces. Okay, that is just too much for the middle manager, so if you are that individual contributor, what I want you to do is really take charge of adding AI into your role and thinking about how you can redesign your role, which pieces of what you do can AI safely and responsibly either replicate what you're doing, be your thinking partner in what you're doing, so it speeds things along, or perhaps automate some pieces of what you're doing altogether.

And then in the gap of time that is then created the positive, that positive gap where you now have more discretionary time. What can you do to add greater value in your role? So again, this is you redesigning your role, and a lot of times it's not even going to be like, and then here I rewrote my job, my position description, probably not. I mean, eventually that those pieces will catch up, but for now I want you, individual contributor, to just be finding ways to use AI to automate things, to accelerate things, and so on, and then in the additional time that you have, and again, it's going to be a little bit of a lift at first, and you won't have that additional time, but once you get some things in play, then you will have discretionary time, and then you can think about how you can add more value to the to the role that you're already playing.

Okay, so that is your task. Now, middle managers, you've got a little bit of a different task here. You need to first of all understand some of the underlying concerns of why your staff is resistant to adopting AI, and then you, in that middle management position, you are totally in the messy middle. You absolutely are in the messy middle of this, and I want to give you some strategies on how to handle that messy middle, okay. So, here we go. Let's get into the, let's get into the very specific things that you can do. So, if you are that middle manager, I want you to think about being the translator, not the messenger, as you think about sending messages upward in the organization.

So, this is all about managing up now. The fear that most middle managers have around AI is this: if I tell my executive team that my team isn't enthusiastic about AI, that my team isn't embracing AI, then I become the problem. It seems like I'm not doing my job, and so a lot of middle managers will stay quiet, they will absorb the pressure, they will just stay in that messy middle space, and they won't, you know, they'll keep promising upwards, like, oh yeah, we're doing better, we're doing better, I'm getting people on board, while they know that they are absolutely not doing that all. So, what your role is, middle manager, is to reframe this entirely from an AI adoption and, like, a tech rollout, a tech tool rollout.

Your job is again not to be the messenger that says, "My team isn't embracing this, but your job is to be the translator. Your job is to explain to senior leaders that this isn't just a new tech tool, that this needs to be governed by change management. This needs to be thought of more as like a communication and an innovation issue, not rolling out a new tool, because you know, as I just described it, fundamentally changing people's positions is that that's not something to be taken lightly, that is not something that's just like a new tech tool. Okay, so the most important translation that you can make is this one, like, let your senior leaders know we're treating this as a technology deployment problem when it's actually a change management problem.

And they need very different solutions, because a deployment problem gets solved with, like, mandates and you know access to things, but change management problems get solved with communication, with explaining the context, with sometimes training and with an appropriate expectation of how long something is going to take, so this framing in and of itself is going to change the conversation from why isn't this working to what kind of a problem are we actually trying to solve here, so when you bring that kind of a diagnosis upward, paired with any specific signals or recommendations on training, or whatever you might have to accompany that, you're shifting the conversation from delivering bad news upwards to being, you know, to offering strategic intelligence and alliance with your senior leaders.

If you can come to them with the problem. I mean, they know that individual contributors are not embracing AI in the way that they had hoped, in the way that they had thought. I mean, if they're reading any of the research studies, and, like I said, when I sat in on this panel discussion of chief technology officers, you could, I mean, their frustration with the lack of adoption was palpable, so they're feeling it. If you can show up as the bridge between, hey, I know what's going on over here, and we need to treat this problem differently than we have been, and we need to resource it differently, and we need to come at it with different types of solutions. Now you are definitely putting yourself in the seat of the person who is, and again, this is classic managing one on one, managing up one on one is to say here's the problem.

And in fact, in this case, you're not even saying here's a problem, you're saying we've been treating the wrong problem, this is a tech deployment problem, this is a change management problem, and I have some ideas on how we can address it, and then again, you move from being like the squeaky wheel to being the person who has a strategic solution for a problem that's literally been keeping them up at night, okay. So you're going to start off with something like this. Hey, what I'm seeing is, and then you'll explain what the, you know, what your staff is or isn't doing in terms of adoption, and then, and then you want to shift to, well, and the reason I think this is happening. So, you're going to start with what you're seeing, then you're going to go with why you think this is happening.

And here is where you're not being, you're not defending them, but you're making a diagnosis. You're saying, you know, they don't have a use case tied to their actual work, and some of them are scared about what this means for their role, and you're explaining the why for the reasons why they're not adopting AI at, you know, the pace that senior leaders would expect, and then you're going to now offer solutions. So, what I need is, and don't make it vague, be very specific. What I need is someone to come in and do some very specific platform-based training on this, or what I need is extra time to roll this out, or what I need is maybe you have some staff who are really tied to that position description. What I need is to partner with Human Resources to help do some redesign.

Or maybe you're bringing in an outside consultant, or whatever, because I mean HR is tapped to the max too, so we don't necessarily need to put one more thing on their plate, so maybe you're bringing in an outside consultant to rewrite job descriptions, to reconfigure work, to reimagine what some roles would look like, and then recast them in different language, and again, so what you're doing is you're reframing the problem upward, and then explaining exactly what you need from senior leaders, and I think if you're explaining it that way, they're going to be much more likely to be on board now. If you happen to be a senior leader and you're listening to this episode, I want you yourself to start rethinking about this tech adoption from lower levels in your organization, not as a tech deployment, but as a situation of change management.

And when you're rolling out massive change across your organization, you don't just expect everybody to get on board right away, or if you do, I would say you're totally mistaken, but for the middle manager, this kind of structure, where you're managing up and explaining what's underneath the issue, is really protecting you politically, because now you don't sound like the squeaky wheel, you are a strategist, you are surfacing organizational intelligence, you are not an obstacle to AI adoption, in fact just the opposite, you are there to help get AI adoption moving in the organization, and this is going to give your executives something to act on, instead of just more evidence that adoption is lagging, and if they really want to see that ROI on their investment into, in AI, in generative AI, they need to make sure that it is deeply integrated into the organization, because that's where they're going to see scale and efficiency, and all the things that AI can actually do for us.

Okay, now if you are that middle manager, your work is not done just by managing up, you need to also do a couple of things to manage down. So, I want to give you two more things you can do. So, the first one is managing up, as we just talked about, reframing from a tech tools conversation to a change management conversation. So, the second thing you need to do is to close the perception gap with your staff, so you can't close a gap that you haven't measured. So, most managers, when they find out that their team is struggling with AI adoption, respond by sending more information, more tools, more links, more tutorials, more encouragement, getting trying to get people to just simply try it, but that doesn't work, because information isn't the problem.

The move here is to have an actual conversation and surface people's fears, concerns, and anxiety. So, if they have heard for the last two and a half years that AI is going to take their job, and then they're being told to use AI, well, again, we don't need to be a genius to put that together, and know that, like, that is going to be the cause of some trepidation. Now, the headlines are starting to shift around this, and I don't know if you've heard this, but just within the last couple of weeks, Sam Altman, who's the CEO of Open AI, that is the folks who bring us Chat GPT, has changed his tune, and he's now saying, I mean, he was saying for the last couple years that AI was going to eliminate entry-level jobs, and now he's reversed course on that.

He doesn't think that's going to be the case anymore. So, make sure that your staff are hearing that research and hearing those, well, that's not necessarily research per se, but it's based in his experience, but that they're hearing those headlines and saying, like, hey, if you heard that AI was going to take your job, well, that attitude is not as prevalent anymore, and what's what's going to happen is your job is going to fundamentally change, and so let's find out what concerns you have, what parts of your job do you think could be automated, and let's, let's like have some dialog around it, but you want to really surface their concerns first, because you can't address a concern that you're not aware of.

So you might be thinking their issue is one thing and it's totally different, so you really do need to surface their concerns first by having an actual conversation, and you know, what have you tried, what's getting in the way, what does it feel like from where you sit to start using some of these AI tools, or why haven't you used them, what you know, what are your concerns, so resurfacing that is something that so many managers are skipping these days, because the answer is quite likely going to be some version of I'm really worried about my job, and that AI is going to replace me, and that's an uncomfortable conversation to have, but again, if you are the manager, I want you to start redefining that conversation and saying, like, no, AI is not going to take your job, but somebody who can learn AI will take your job if you don't get on board.

And you know, and again, don't say it in a threatening way by any means. We don't want this to be coercive unless it absolutely has to be, but we want to be supportive of somebody and say, like, you know, AI in and of itself cannot do all of your job, but let's find the ways that we can streamline your job. Let's find the tasks that AI can do or help you with to make you more efficient, because then that will open up more and different types of work that you can be doing to again add more value. So, when you acknowledge the fear directly, like, hey, I know there's a lot of noise about AI taking over people's jobs. I want to talk to you, what that means for us specifically in your job, specifically.

Now you're changing the context here, so to one of potential fear, this unknown fear that maybe hasn't even been specifically voiced in your organization, to a conversation that is much more wrapped in psychological safety, because it is all about, like, I want you to ask me the dumb questions, I want you to ask me the things that you're concerned about, so that we can talk about them together. And there is no, you know, fear of retribution here. We're not going to, you're not going to get fired for asking a dumb question about AI. You want to treat your staff as adults who are allowed to have a complicated reaction to a complicated piece of technology that's what is going to earn you the trust that you actually need to move adoption forward in your organization.

And when what you learn in these conversations is also going to give you exactly what you need to use in advocating upward in the organization, because maybe it's training, maybe it's time, maybe it's whatever it is you're going to find out by having those frank conversations with your staff. Okay, and then a third thing that you can do as a manager to get that AI adoption rolling a little bit more, and this is very similar to something I talked about in episode 270 is to, you know, shrink the ask. Don't ask somebody something like, you know, use more AI or use the AI tools that you have, instead. Again, that's going to land as amorphous, ambiguous, and just one more thing. And it's not necessarily very actionable, so maybe you're, you know, as you shrink the ask, you're asking them to use AI in one specific capacity of their job.

And so instead of saying something like, I want everybody using AI by Q, I mean that's completely meaningless, that's compliance theater at its best. Instead, I want you to come up with a specific thing that they could use AI for. I want each of you to find one recurring task that moves, that takes 30 minutes off of your plate each week, and try it this week with AI. Now, they might not necessarily know that somebody's going to take 30 minutes off of their plate, or it might actually take them two hours to figure it out, such that next week it takes 30 minutes off of their plate. So, maybe it is using AI to streamline status reports, or maybe it is using AI to summarize to review meetings that they weren't able to attend, or whatever it is, but pick a specific workflow and make the ask very compatible with a workflow.

Give it a deadline and make it explicitly safe to come back and say, I tried it and I got stuck, or I tried it and didn't really seem to work, or it took me three hours to set up, and I don't know if I'm going to get the payoff from using it every week, that's information, and that information is what you need, not only to help your team, but also again to continue to do that translation upwards. So, shrinking the ask also gives you something very concrete that you can report up the chain, so you can let your, your senior leaders know, hey, we're working, not just something broad, like we're working on AI adoption or deployment, but hey, three people used it in their status reports. They spent, you know, a disproportionate amount of time upfront to get that set up, and now that they've used it for two weeks, we're starting to see the payoff.

Okay, so again, let get some data, and then you can have it be a data-driven decision as you're talking upward in the organization. All right, so now as we wrap this episode, we are going to figure out here on the Working Conversations Podcast how to put it to work. Put it to work. So we're going to take the tips and strategies we've been talking about, and put it to work, and I want to give a quick shout out to my audio engineer, Ken. He started, he sent me this message the other day about how I always like to end the episodes with a call to action, and he's like, that call to action needs a name. So, Ken, this one's for you. We're gonna, from now on, we're gonna be calling it Put It to Work.

Okay, so this is where you are going to put to work the ideas and actions that we've been talking about, or the ideas into actions as we wrap the episode. Okay, so this week I want you to have one conversation with somebody on your team, not about AI tools, but about how AI feels to them from exactly where they sit. What are they worried about, what have they tried, what would help. And then take what you learn into a conversation with your manager. Again, it's not going to be a complaint or a problem, it's going to be a translation. So, I want you to do, if you're that middle manager, I want you to be working both sides of the equation. Here, you're going to be having a conversation down with one of your direct reports, or multiple of your direct reports, an honest conversation where you're finding out what's underneath their concern.

And then you're going to have the conversation up, you're going to put it to work and have the conversation up to let your senior leaders know what's going on that is getting in the way of AI adoption, and again, I want you to be that translator, I want you to be talking about how this isn't just tech deployment, this absolutely is a change management issue, and we need to treat it as such. All right, and if you are an individual contributor listening to this, your action is to send this episode to your immediate supervisor, so they can listen to it, because I guarantee they are going to understand the dynamics of the situation that they're stuck in right now very, very differently after they've listened to this, and I think they can be a much better support to you personally if they understand that they are absolutely in that messy middle.

And if you are a senior leader, your job is to reconfigure this whole thing as from tech deployment to change management and start moving things in in the direction of a change management problem and the solutions to a change management problem. So again, if you are in that messy middle, you are not stuck between your executives and your direct reports. You are the connection. So there's not a problem here. You are the solution. You maybe didn't know it yet, but being that connective tissue between senior leaders and the individual contributors who are getting the work done, that's your job. That is middle management at its best. So, that is your job. So, again, put it to work, my friends. Go out there, take some action on this episode, and I love to hear your successes or your failures. If something's not working, shoot me a message, so you can find all my contact information over on the show notes page or on my website, so Janel anderson.com forward slash 271 for the show notes for this particular episode. And if you're listening on YouTube, you can send me messages directly through YouTube as well, so multiple ways to get a hold of me, but I want to know how it's working for you. Okay, my friends, be well, and we'll catch you next week.

 


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