Your Middle Managers Are Drowning (And You Know It)

Seventy-seven percent of CHROs lack confidence in their leadership bench strength. Meanwhile, 40% of middle managers are planning their exit.

Your leadership pipeline isn't empty because of a talent problem—it's empty because you're burning out your current leaders before they can develop.

In this episode, you'll discover:

→ Why the gig economy changed everything about middle manager retention (28% of knowledge workers are already freelancing)

→ The Five Executive Actions Framework that reduces burnout without requiring board approval

→ How to have the hard conversation with your board about "doing more with less"

→ The career-risk decision every executive faces: hit targets by destroying your team, or build something sustainable

If you're an executive watching your middle managers struggle while your board demands more with less, this is your wake-up call.

The Five Executive Actions Framework (Colby Morris)

Action 1: Audit Actual Workload Compare each middle manager's actual responsibilities—direct reports, meeting commitments, deliverables—against research-based effective spans of control (5-7 direct reports for complex work, 8-10 for straightforward work).

Action 2: Kill One Initiative Identify and eliminate one running initiative delivering minimal value, freeing capacity and demonstrating willingness to make trade-offs.

Action 3: Create a Stop-Doing List Work with middle managers to identify and actually stop producing unused reports, attending unnecessary meetings, and maintaining obsolete processes.

Action 4: Fix One Structural Problem Address the system, process, or tool creating the most friction in middle managers' daily work.

Action 5: Have the Board Conversation Directly address sustainability with board members: current middle managers are doing the work of 2-3 people, requiring either added resources or reduced expectations.

When to Apply This Guidance

Use the Five Executive Actions Framework when you observe:

• Leadership pipeline gaps with no clear successors for critical roles
• Middle manager retention issues or increased turnover at the manager level
• Consistent feedback about unsustainable workloads across your management layer
• Board pressure for results with simultaneous resource constraints
• CHROs reporting low confidence in leadership bench strength

Diagnostic Questions for Executives

• How many direct reports does each of your middle managers have, and how does that compare to research-based effective spans of control?
• Which running initiative delivers the least value relative to the capacity it consumes?
• What reports, meetings, or processes are your middle managers maintaining that no longer serve a clear purpose?
• Are you asking your middle managers to do the work of 2-3 people while simultaneously discussing talent development?

Resources Mentioned

Research Cited:

• DDI Global Leadership Forecast (2024) - Leadership stress, bench strength, and turnover data
• MBO Partners Independent Worker Research - Gig economy growth and high-earning freelancer statistics
• Upwork Freelance Forward Report - Knowledge worker freelancing trends

About The Things Leaders Do

The Things Leaders Do is a leadership podcast hosted by Colby Morris, COO at Apex Medical Management Partners and Founder of NXT Step Advisors. The show provides practical, immediately actionable leadership tools for leaders at all organizational levels, with episodes designed as 18-23 minute commute-friendly content that prioritizes concrete strategies over theoretical frameworks.

Connect with Colby Morris

LinkedIn: Colby Morr

• Colby's LinkedIn Profile
• NXTStepAdvisors.com

Transcript

The Empty Leadership Bench Problem

SPEAKER_00 0:00

People first leadership. Actionable strategies, real results. This is Things Leaders Do with Colby Morris.

Remembering Middle Manager Reality

Why Managers Leave Faster Now

The Real Cost Of More With Less

Executive Burnout And Value Erosion

Five Actions To Fix The System

Choosing Targets Or Sustainable Work

How To Support And Stay Connected

SPEAKER_01 0:11

That's the percentage of CHROs who lack confidence in their leadership bench strength for critical roles. According to DDI's Global Leadership Forecast, more than three out of four chief HR officers look at their leadership pipeline and see nothing. No one ready to step up. No one developed, no succession plan that actually works. And if you're an executive, you probably already know why. Your middle managers aren't sticking around long enough to develop into anything. 40% of them are actively planning their exit while you're in board meetings talking about talent development. You want to know why you don't have bench strength? Because you're burning out your current leaders before they can become your future leaders. These people running your operations, the people managing your teams, the people who are supposed to be your leadership pipeline, they're all planning their escape routes while trying to look engaged in your all-hands meeting. 71% of leaders report increased stress. And those stressed, burned out middle managers, they're not developing. They're surviving. And look, I I know you know this. You used to be a middleman. You remember what it felt like. That squeeze from both sides, the impossible workload, the expectation that you just figure it out and make it work. You swore that when you became an executive, that you'd do things differently, that you'd protect your people, that you wouldn't let them go through what you went through, but here you are. Making the same decisions, creating the same pressures, watching your middle manager slowly burn out while you tell yourself there's nothing you can do about it. Except there is. You're just not doing it. Today I'm talking directly to executives about the middle manager crisis you're creating. Why your leadership pipeline is empty, what the real cost of doing more with less actually is, and what you can actually do about it before you lose every good manager you have. Because the truth is this you have more power to fix this than anyone else in the organization. You're just choosing not to use it. So let's talk about it. Hey leaders, this is Colby Morris, and you're listening to the Things Leaders Do podcast. Again, I have 20 to 30 minutes of, you know, specifically for executives this time, leadership advice for people who are watching their middle manager struggle and wondering what to do about it. Okay, and there are no corporate platitudes in here. Okay, no nonsense. Just real talk about the decisions you need to make. All right. Let me take you back. You remember being a middle manager? You remember the meetings that consumed your entire day, right? Back to back from nine to five, sometimes eight to six. Once you had a meeting to prep for another meeting about whether you needed a third meeting, you remember the impossible workload, the boss who kept adding more to your plate while your team kept needing more support. You get that message at 4 47 p.m. on Friday, hey, got a minute? Just thought of something we should add to the roadmap. And you remember working nights and weekends, answering those emails at 10 p.m., skipping lunch because there was always that one more thing. Your family probably stopped asking if you'd be home for dinner because the answer was always probably not. You remember feeling stuck. Like you were responsible for everything, but in control of nothing. Like you were just trying to survive until Friday, but then starting the whole cycle over again. And you remember the executives above you. The ones who seem completely disconnected from what was actually happening. The ones who would announce new initiatives without adding resources. We're launching a customer service experience transformation. Also, we're not backfilling Sarah's role when she leaves, but we're confident you'll make it work. Yeah. The ones who would talk about doing more with less, like it was some kind of inspirational challenge, instead of an omission that they, you know, just weren't willing to invest in their people. Like you were supposed to get pumped up about working twice as hard for the same money. You remember thinking, when I'm in that role, I'll do it differently. I'll remember what this feels like. I won't put my people through this. And then you became an executive. And at first, you did try to do it differently, didn't you? You protected your team. You fought for resources. You you pushed back when the board wanted to cut headcount. You advocated for realistic workloads and sustainable expectations. But then something happened. The board kept pushing. The shareholders wanted better margins. Your peers at other companies were somehow doing it with fewer people, or at least that's what they were claiming in their earnings calls. Spoiler alert, they were lying. Or about to have a mass exodus, or probably both. You started getting pressure to optimize and streamline and all those other euphemisms for, you know, make people do more work for the same money. And slowly, so slowly you barely noticed, you became the executive you swore you'd never be. You started saying those things like, well, maybe we do need to do more with FLAS. You started approving org chart changes that eliminated layers without redistributing work. You started expecting your middle managers to just figure it out. Just like your executives expected you to figure it out when you were in their shoes. And now your middle managers are drowning. And you know it. Because you've been there. You know exactly what they're going through. But here's where you're getting stuck. You pushed through, right? You survived it, you persevered, and eventually you made it to where you are now. So why can't they? Why does this generation seem to struggle with what you just handled? Why are they talking about burnout and work-life balance and boundaries when you just had to put your head down and did the work? Well, let me tell you why. Because it's a different world now. When you finally decided you'd had enough, when you hit your breaking point as a middle manager, what did you do? You started looking. Right? You update your resume, you reach out to your network, you apply to jobs, you go on interviews, you wait for callbacks, you negotiate offers. And it took forever, didn't it? Months, probably, maybe six months, maybe a year. The whole time, you were stuck in that miserable job, grinding it out because you had no other options. You had a mortgage, you had bills, you had responsibilities. You can't just quit without something else lined up. So you stayed. You persevered. Not because you were tougher or more committed, but because you didn't have a choice. But today, Gore Middle Managers have options you didn't have. The gig economy has exploded since COVID. Full-time independent workers at more than doubled from 13.6 million in 2020 to 27.7 million in 2024. Over 70 million Americans, 36% of the total US workforce now participate in freelance work in some capacity. And this isn't just delivery drivers and rideshare workers. 28% of U.S. knowledge workers, the professionals, consultants, managers, they now operate as freelancers or independent professionals. And over a third of full-time workers are actively considering making this jump. This isn't just side hustles anymore, y'all. High-earning freelancers, meaning they make you know$100,000 or more, surged from$3 million in 2020 to$5.6 million in 2025. And by 2027, get this. Freelancers are projected to make up over 50% of the U.S. workforce. Read that again. I guess I should listen to that again. Over half the workforce. If one of your middle managers hits their breaking point today and they don't have to spend six months and interview hell while staying in a job that's destroying them, yeah, they can put in their two weeks, sign up for DoorDash or Uber or Instacart, and they can make enough to cover their bills while they figure out their next move. They can freelance, they can consult, they can take contract work, they can patch together income from you know multiple sources until they just find something better. Is it ideal? No. Is it stable? Well, not really. But is it better than staying in a job that's burning them out to them? Absolutely. And here's the kicker they're not afraid to do it. Your generation stayed because leaving felt risky. Their generation leaves because staying feels unbearable. They've watched people get laid off after, you know, decades of loyalty. They've seen companies eliminate positions without warning. They've learned that corporate loyalty is a one-way street. So when they hit their limit, they just they just leave. They don't wait for it to get better. They don't give you more than six months to fix it. Okay, they don't tough it out until they have another job lined up. They're gone. And they're driving for DoorDash or walking dogs or doing freelance work while they figure out what comes next. If they don't want to be there, they don't have to be. And that should scare the daylights out of you and your organization. Because if your organization treats people this way, if you keep squeezing your middle managers until they break, you're going to wake up one day and realize you don't have a middle management layer anymore at all. They're all gone. They're all out there delivering groceries or consulting or working for your competitors. And as the executive, you need to speak up. You need to stand up for your people. You need to go to your board, your CEO, your fellow executives, and warn them if something doesn't change, we're going to lose everyone. And not eventually, but soon. This isn't a generational weakness. It's a generational option. They can leave easier than you could, and they will. But the question is, what are you going to do about it? Let's let's be real about something because I'm not here to just beat you up for 20, 30 minutes. You're under pressure too. I get that. The board wants growth without investment. Shareholders want you know better margins. Your peers at other companies are somehow doing it with fewer people, or at least that's what they're claiming. You're in meetings where someone shows a chart with a line going up and another line going down and says, we need to close this gap. Closing the gap usually means cutting costs, which means cutting people, or at least not hiring the people you desperately need. You make the case for hiring, right? You explain that your middle managers are at capacity. You show the data on workload and span of control. You cite the research on effective team sizes. You've got slides, you've got metrics, you've got everything except the word yes. And they say, everyone's doing more with less now. We need to stay competitive. Or they say, well, let's wait until next quarter and see how the numbers look. Next quarter has been just around the corner for three years now. It's like, you know, waiting for Godot, except Godot is head accounted. Or, and this is my favorite, they say, can we just you use AI for some of this? As if AI is going to magically solve the problem of humans managing humans. As if Chat GPT is going to, you know, give performance feedback or mediate team conflicts or have difficult conversations about career development. Hey, AI, can you tell Marcus his attitude is affecting the team? I'm sorry, I can't do that, Dave. So you go back to your team and you eliminate a layer. You ask your middle managers to take on more direct reports. You launch another initiative without adding headcount. You approve a new system implementation that's supposed to create efficiencies, but really just creates more work. And another training they had to complete, and another dashboard they have to update. And you tell yourself it's temporary, just until next quarter, just until we get through this rough patch, just until the market improves. Except it's never temporary. Okay, there's always another quarter. Another rough patch, another reason to delay. Next quarter is the executive version of the check is in the mail. And meanwhile, your middle managers are working themselves to death, trying to deliver on expectations that were impossible from the start. And I get it. You're stuck between the board's demands and your team's capacity. You're trying to keep the company viable while also keeping your people from quitting. It's an impossible balancing act. You're juggling chainsaws while someone keeps throwing more chainsaws at you and yelling, you know, just be more agile. Here's what you need to hear. The cost of doing more with less isn't just showing up in engagement surveys. It's showing up in your leadership pipeline, in your retention numbers, and the quality of work being produced and the health of your organizational culture. You're winning short-term margin improvements at the cost of long-term organizational capability. You're optimizing for this quarter while destroying your ability to compete three years from now. And at some point, some point, you're going to have to decide, are you going to keep playing this game? Are you going to do something different? Let's talk about something nobody really wants to admit. You're burned out too. Not in the same way your middle managers are burned out. You're not drowning in operational work. You're not managing 15, 20 direct reports, you're not in meetings from 8 a.m. to 6 p.m. with no time to think. But you're carrying a different weight. The weight of making decisions that affect hundreds of people's lives. The weight of knowing that every choice you make, every headcount freeze, every restructure, every optimization, that has real consequences for real people. And hey, you're you're a people first leader. You actually care about your team. You don't see them as resources or FTEs or line items on the budget. You see them as humans, okay, with families and mortgages and dreams, which is exactly what makes us job so exhausting. Makes this so much harder. Because you sit in board meetings listening to conversations about margin improvement and cost reduction. And all you can think about is Jessica in operations, who's managing 12 people, when she should probably, you know, maybe only have six. Or Marcus in sales, who's been working 60-hour weeks for eight months straight. Or Priya in product who had to cancel her vacation because you didn't or couldn't backfill that role in someone. You're nodding along to the CFO's presentation about efficiency gains while mentally calculating how many more people are going to quit when this one gets announced. You know what you're asking of your people is unreasonable. You know the pressure is unsustainable. You know you're losing good people because they can't keep doing this. And you feel terrible about it. You lay awake at night thinking about it. You wonder if there was a different decision you could have made. Your question whether you, you know, you should have pushed back harder in that board meeting. You replay conversations in your head at 2 a.m. like they were, you know, bad movie sequels nobody asked for. But then morning comes. And you go back into the office and you make the same impossible asks because you don't see another option. And that's its own kind of burnout. The slow erosion of the leader you wanted to be. The gradual acceptance of things that you swore you'd never accept. The compromise of values in service of survival. You wanted to build a people-first culture. You wanted to be the executive who did things differently. You wanted to prove you could deliver results without destroying your team. But the system doesn't really allow for that, does it? Or at least that's you know what you tell yourself. At least that's what helps keep you sane. And the worst part? Your middle managers don't see your struggle. Okay, they just see the decisions. They they see the headcount freeze, they see the restructure, they they see the new initiative with no additional support. They don't see you fighting in board meetings. They don't see you pushing back, they don't see the proposals you submitted that got rejected. They don't see you losing sleep over this. They don't see the email you drafted at midnight advocating for them that you never sent because you knew it just wouldn't they just see the results. And from their perspective, you're part of the problem. And maybe you are. But maybe you don't have to be. All right. So what can you actually do? What changes can you make that will help your middle managers survive? Let me give you five specific actions, not theory, not consider doing this someday. Things you can do this month. First, audit your middle manager's actual workload. Not their job description, but their actual workload. How many direct reports does each middle manager have? What meetings are they in? What are they actually responsible for? Then compare that to research on effective span of control. The research says five to seven direct reports for complex work. Maybe eight to ten if the work is straightforward and people are experienced. If you've got a you know middle managers with 12, 15, 18, 20 direct reports, you don't have a performance problem. You have a structural problem. No amount of coaching or development is really going to fix that. You can't coach someone into having more hours in the day. You can't develop someone into being three people. You need to either reduce their span of control or accept that the work isn't getting done. Those are your options. Pick one. Second, kill one initiative. Right now, today, pick one initiative that's running and kill it. I know you can't kill all of them, okay? I know they all seem important, but your middle managers are drowning in competing priorities, and every initiative you launch is one more thing they have to deliver with the same resources. So pick one. The one that's delivering the least value, the one that's, you know, with someone's pet project, but isn't actually moving the business forward. The one that made sense six months ago, but just doesn't anymore. One that's been launching next quarter for like two years, kill it. Free up capacity. Show your middle managers that you're willing to make you know those trade-offs instead of just adding one more to their plate. And yes, someone will be upset about it. Someone will say, but we already invested so much. Too bad. Sunk cost fallacy isn't a strategy. Third, create a stop doing list. You're really good at creating start doing lists. Okay, new initiatives, new priorities, new ways of working, but you never create a stop doing list. So all the old work stays. While the new work gets added, it's like hoarding except with tasks and instead of new pay newspapers from 1987. So sit down with your middle managers and ask, what are we doing that we could stop doing? What reports don't actually get used? What meetings could be eliminated? What processes could be simplified? I guarantee you someone is still producing a weekly report that literally no one reads. Someone is attending a meeting that should have been an email. Someone is updating a dashboard that was built three years ago for a project that doesn't exist anymore. Then actually stop doing those things. Don't just talk about it. Actually stop. Delete the recurring meeting invite. Turn off the automated report. Archive the SharePoint site that nobody has accessed since 2022. Because every hour you free up is an hour your middle manager can spend on work that actually matters. Or sleep or their families. Or literally anything other than producing reports nobody reads for meetings nobody wanted to attend. And then fourth, fix one structural problem. You know what they are. The systems that don't work, the processes that create unnecessary work, the approval chains that require 17 signatures for a$200 expense, the tools that make everything harder instead of easier. Pick one. The one that's creating the most friction, the one that makes your middle managers want to throw their laptops out the window. Maybe it's the expense system that requires manager approval, then director approval, then VP approval, and then finance approval, and then accounting approval, then a blood sacrifice and a permission slip from your third grade teacher. Maybe it's the project management tool that's so complicated it requires a training course just to create a task. And then, of course, another training course to figure out why the task disappeared. Maybe it's the annual review process that takes 40 hours to complete and produces insights like continue developing leadership skills. Okay. Fix it. Allocate the resources. Make it a priority. Show your team that you're willing to invest in making their jobs easier, not just in making them more productive. And then fifth, have the hard conversation with the board. Yeah, this is one you don't want to do, is it? But it's the most important. You need to go to your board and say, we're asking our middle managers to do the work of two or three people. They're burning out. We're losing really good people. Our leadership pipeline is empty. Okay, this isn't sustainable. We need to either add resources or reduce expectations. We can't keep doing both. And yeah, they might say no. They might tell you to make it work. They might point to other companies that are doing it with fewer people. But at least you'll have said it. At least you'll have tried, and maybe, just maybe, they'll listen. Because the alternative is watching your entire middle management layer quit over the next two years. And then what's your board going to say when you don't have anyone left to run their organization? Well, at least our margins look good for those six quarters before the company collapsed. All right. So, real talk. Sometimes the answer isn't do more with what you have. Sometimes the answer is we can't do all of this. And that's a hard thing to say, especially when you're in a growth mode, especially when competitors are moving fast or when the board has expectations. But you have to make a choice. You can't have aggressive growth targets and sustainable workloads. You can't launch five major initiatives and expect your middle managers to deliver all of them well. You can't eliminate layers of management and expect the same output. Something has to give. The law of physics still apply, even in corporate America. And the question is, what are you willing to give? Are you willing to tell the board that you're going to hit 80% of the target instead of 100% because you need to protect your people? Are you willing to delay a product launch because you don't have the capacity to do it right? Are you willing to say no to a new opportunity because your team is already maxed out? Those are the hard decisions. Career risk decisions. The kind of decisions that might get you fired. But you know what else might get you fired? Losing your entire middle management layer? Having no one capable of running the business, watching your organizational capability crumble because you optimize for short-term results. Or missing every target for the next three years because everyone quit. And honestly, even if those decisions don't get you fired, they might make you quit. Because at some point, you have to decide what kind of leader do you actually want to be? Do you want to be the leader who delivered the numbers by destroying their team? The one people talk about in hushed tones at industry conferences. Yeah, they hit their numbers, but at what cost? Or the leader who built something sustainable, even if it meant missing a quarterly target. The one people want to work for, the one who actually lives the people first values instead of just putting them on the wall in the lobby. Look, I'm not saying this is easy. I'm not saying the choice is obvious. I'm saying you have to make a choice. Because right now, you're trying to have it both ways. You're trying to hit the targets while also being people first, and it's not working. Your middle managers are leaving, your culture is suffering, and your leadership pipeline is non-existent. It is empty. And something has to change. And you're the only one with the power to change it. Before we wrap up, I want to remind you that I'm working on creating a second episode that will launch every week, one where I interview leaders and try to find the best tools and leadership tactics from them and be able to start sharing that with you. Again, as I said last week, it's proven to be a little tougher than what I said to organize given my schedule, but I am working on it and I want to bring that to you. Now, if your organization is struggling with middle manager burnout or leadership pipeline development or even building sustainable leadership practices at skill, I would love to help. That's what I do, whether it's coaching, speaking, training, whatever, I would love to help you out. Connect with me on LinkedIn or you can visit my website. Both those links are in the show notes. And if this episode challenged you, would you do me a favor? Would you mind subscribing to the show wherever it is that you're listening to this? And please, please leave a review. This is what helps me get the show out there, find out more about who you are, and helps more leaders become better leaders faster. And share it with another executive who needs to hear this. Please keep protecting your people. Keep making the hard calls and keep being the leader you needed when you were coming up. And you know why? Because those are the things that leaders do.

SPEAKER_00 29:41

Thank you for listening to Things Leaders Do. If you're looking for more tips on how to be a better leader, be sure to subscribe to the podcast and listen to next week's episode. Until next time, keep working on being a better leader by doing the things that leaders do.