Ask Christa! Am I Stuck in Middle Management Forever? (S5E51)

Introduction

Hi everyone and welcome to Ask Christa! the place where you can ask questions about how to work through business challenges and workplace issues. I'm Christa Dhimo and today’s listener question continues to address this season’s theme of Career Growth, but more from the perspective of how you manage career growth when you feel stuck, or maybe even DOOMED, in the middle.

Middle management is talked about as though it’s superfluous, “extra,” maybe even wasteful. And maybe it is if an organization grew very quickly, hired a lot, created various layers, and never tracked what was effective or efficient. Now they don’t have a middle layer anymore—they have layers and layers of middle layers, and that can choke communications, delay or paralyze decisions, and make for really slooooooow chaaaaange when it’s needed. There are indeed times when there are simply too many layers. But absent of a wasteful situation, the middle layer is a highly valuable and competitively strategic layer if you design it to be.

Listener Question

Here’s the listener question: “I’m a Director in a mid-sized global engineering company. We have about 8500 employees worldwide, with the majority of them being in the US. My role is considered middle management, where I have two levels above me to get to the CEO, and two levels below me to get to individual contributors. In my company, we have several individual contributors who are seasoned and more senior in their careers, but they do not want to manage people or they want to work in roles that offer variety and a matrixed opportunity for them to collaborate with several teams. I mention this to note that several of our individual contributors are self-directed and at my level; they just don’t have direct reports.

“My next step is a title bump to Senior Director, and I just received notice that I’ll be promoted during our current review cycle. This is exciting for me, but it also got me thinking: what do I do after that? I report to a Vice President who reports to a Senior Vice President who reports to the CEO. I haven’t wanted to talk to my manager about a career path beyond the title bump because I don’t want to appear as eager to skip levels, and honestly I’ll have a lot to learn as a Senior Director before I'm prepared for a Vice President level anyway, but there’s a part of me that’s worried I’m doomed to be stuck in middle management for several more years. What are your thoughts about middle management roles? Am I stuck in middle management forever?” 

The Curse of Middle Management (… but not really…)

I received a lot of questions from listeners feeling “stuck” in their current roles, and nearly all of them have been lingering, hovering, and in quite a few cases feeling stuck in or stalled out on positions that are in the middle layer of an organization. It’s easy to feel lost in the mix of things when you’re in that middle layer, and some might even consider this the “curse of middle management,” but I see it differently.

Career growth is about growth. It’s about learning, expanding, and experiencing new things. Stretching, elevating, and feeling more challenged with respect to the work you do. Most often, people think about career growth as promotions, and many times that’s true, but not always. Career growth is about… growth, and I encourage you to review Episode 49 where I focused on the different aspects of career growth if you’re interested in learning more.

But when it comes to middle management, most people talk about how hard it is—how thankless it can be—how challenging it feels… and that makes sense. When you’re the fulcrum of a rather large see-saw, you feel a lot of friction as the weight of one side and the other goes up and down. 

But that’s also the challenge of anyone who’s in the middle of two stakeholder groups, and the two stakeholder groups for middle managers are senior leaders steering the organization and individual contributors enabled to do the work because of how the organization is being steered... at least, in theory.

Opposing Forces Connected by The Middle Manager (a “Hub Role”)

In general, I have observed three factors that make a middle manager position more challenging that it needs to be: 

First: most people in management positions do not adequately learn how to be an effective manager. Episode 18 in Season 2 answers the question Does Management Training Matter? And.. yes… yes it does.

Middle managers are in fact managers, and if you aren’t prepared to be effective… you won’t be effective. A lot of people talk about how hard a middle manager role is, and yes. It is—largely because you’re managing other good humans, and humans are messy. We’re incredibly dynamic, we make the world go around, and we get a lot of good work done… but we also create chaos, lose our abilities to regulate our emotions from time to time, and have lives outside of work that impact… our work life. A 100% people position, like middle management, needs consistent and ongoing upskilling and cross-skilling of what it takes to manage good humans to do their best, every day, whatever that “best” looks like.

Second? The number of stakeholders. You can’t keep everyone happy, and it’s not your job to even try, but some might thing it is. Your job is to manage all around you, 360 degrees: up, over, down, and around, and that’s because most middle managers are the hub to a lot of workstreams. As part of that, and by definition, each of those workstreams has different owners and different stakeholders with different views on what success looks like. If you’re the hub of THAT? It can be rough.

Third… politics. Season 4’s Episode 43 answers a plea for help because the listener hated politics, and I get it. COMPLETELY. In that episode, I talked about thinking of of politics as influence. Not all politics are bad or toxic, and if you’re the hub to that many spokes—that many stakeholders—that many needs… it means you’re the hub to a lot of influence needs. You also have a team you are managing to enable their success as much as possible AND you’re balancing that out with the success of many around you—including your own success in partnership with your own manager, depending on the kind of manager you have.

Of course, culture and commitment about “hub roles,” as middle management tends to be, matters. If you’re in an organization that doesn’t support a Hub Role, then expect things to be tough, but if you understand the value of a “hub role,” then you have the foundational perspective to be successful in that role.

To recap: What makes a middle manager role more challenging is: Lack of preparation, either because there is no or very little training or sponsorship or mentorship or ALL OF THE ABOVE; the sheer number of stakeholders and needs or expectations you have to manage up, over, down, and around; and the politics and level of influence needed to keep those expectations where they should be while making space for new expectations or effectively pushing back on unrealistic expectations. You are, after all, focused on the success of your team just as much as you’re focused on the success of your leaders, your peers, and of course, yourself.

The Middle Manager Role Isn’t Going Away: the Task Manager Role Is

Now, there have been several news releases in the last many years that talk about companies doing away with the middle management role, but I don’t see that happening. What I see happening is a lot of companies are doing away with the Task Manager role: roles that organizationally fit in the middle of the organization, but really focus on getting the work done as a matter of tasks versus getting the work done as a matter of organizational performance, and overall? Here is where I see the biggest blind spot and knowledge gap when it comes to organizations appropriate preparing their middle managers, then actually LEVERAGING that layer as a strategic strength.

Think about the best sports teams as an example. If the owners and team administrators are the senior level leaders, and the specialty coaches and athletic trainers are the front-line leaders interfacing the most with everyone on the team, you could argue that the Coach is the middle manager.

Some may push back on me and argue that the Coach is a senior leader—but that’s only because of perceived decision-making capabilities and their authority as a prized and revered leader to the team.

And that’s my point.

Organizationally, the coach is in the middle layer. They are the ones that bridge between the top leaders making large strategic decisions and managing the team. Sure, they have a lot of say in how certain strategies go, but that’s because of their knowledge and experience in how the game is played and how well they can play certain plays based on the talent mix of the team. It’s also based on how good their front-line leaders and supervisors are as it relates to developing the talent of the team while keeping them healthy enough to play the plays.

If more organizations embraced the middle management layer as a strategic fulcrum—the part of the organization designed to take the most friction, the most weight of the organization and balance the needs of senior leadership with those closest to the customers, they’d receive the strategic value—AND competitive advantage—of excellence at that middle layer.

But instead, what a lot of organizations do is put their middle management layer into Task Manager roles. Unfortunately, this not only dilutes the strength of that middle layer, but also creates a middle layer that supervises the work instead of strategically managing the talent to run the best plays for the organization each day while satisfying senior leader expectations and offering the best work experience for the team.

Middle management is a necessary layer in an organization-- some companies have to "right size" or think about whether that middle layer is so big that it hinders progress or prohibits front-line employees from feeling empowered enough to make decisions in the moment. But if that middle layer is expendable in your organization, it’s because you either don’t know how to make the layer a competitive advantage, run a more transactional business so you don’t NEED that layer as a competitive advantage-- at least not a big layer of it-- or you have a highly matrixed organization where the hierarchy associated with a middle layer doesn’t fit the needs of your business. It just... slows you down. And yes, that happens.

Several organizations may go through a “delayering” because they grew fast or their strategy has shifted and they have duplicative tasks (or work) taking place in different…places. The question becomes: do all these layers help or hinder performance? But in my estimation, there’s just as many instances where the organization doesn’t know how to make the layer a competitive advantage. Maybe you don’t need as many layers, OR maybe you can expand the scope of what you do and offer by making that layer a more strategic and value-add within your organization.  But… I’m a transformation professional, so I fully admit that I tend to start with how to expand organizational performance and potential using what you already have…

Growing Toward the Next Level Isn’t Always a Management Path

Now, having said all of that, I recommend to our listener that you first consider your value and the competitive edge that middle management can and may already bring to your organization. Adjust and adapt your thinking away from what you may read about and listen to with respect to middle managers, and form your OWN position on what that role is capable of for the greater good and higher value of an organization. 

Next is this: as our listener mentioned in their question, their organization includes individual contributors, and while they may be closer to the work and to the customer, they are regarded as senior and understood as experienced. Not all next-level career growth is about becoming a manager, and while this concept is only about 20 or 25 years old—if that—it’s an important one to embrace. I think part of why people feel stuck or stalled out in middle management positions is because they aren’t ready for the next step into an executive role, or frankly, that’s not where they want to be. So take a step back. What can you do with the impressive experience you have? Perhaps switch into consulting within your industry, or consider a specialized role within your organization as a subject matter expert, or consider whether a smaller organization is a better move for you—where you might manage people, but contribute your expertise in a different way.

Last: shift your mindset and resist the urge to go along with what everyone else says about middle management. We all know which organizations have little regard for a middle layer; avoid those companies. Take your newfound position on the middle management layer, create a manifesto about how YOU view the role of middle management, and plot your next step, either with or without the support of your manager. As we’ve talked a lot about, it’s always nice to have the support and knowledge and sponsorship and expertise of your manager when it comes to your career development, but it’s not necessary. Go to a mentor, take advantage of the many online platforms available, join a networking group, or tap on someone you used to work with. Remember: career growth is growth, so again, resist the urge to accept what you hear about middle management and make your own way. Sure, maybe you spend a certain amount of time in a middle management position, but the moment you feel “stuck,” or become afraid of becoming stuck in middle management, my guess is that’s more about career growth overall in your organization than the actual layer you’re in. 

Additional Resources

For your resources, located in the show notes, I included an article from the Academy to Innovate HR from November 2024 called, “What is delayering? Definition & Examples,” and I included it because it is a super-efficient read, with a section that provide a quick overview of what delayering is, which is essentially flattening out the hierarchy we see in a lot of businesses, often because of fast growth or breadth of scale across a large number of products. They review the difference between delayering and downsizing, which is an important distinction, then they talk about the advantages and disadvantages of delayering, which is an important perspective to learn, especially if you’re in that middle management layer and continue to hear about lay-offs. Having a level of knowledge and perspective always helps in determining various aspects of your career development.

Next up, and in line with having perspective: an insightful article from Harvard Business Review called, “Middle Managers feel the least psychological safety at work.” It’s from this month, October 2025, and it reviews how the risk profile or feelings about risk changes once someone is promoted into a position where you have having multiple stakeholders all around with different needs and expectations. It’s particularly prominent when someone in the middle has been newly promoted. The article quickly reviews the various factors of what’s behind psychological safety, such as fear of making mistakes, and structural isolation where there are so many stakeholders it’s hard to build camaraderie among peers.

The last article is from the Indeed Editorial Team, with an article also from this month, October 2025. The article is called, “A guide to the role of middle management (with job titles).” It reviews the important functions of a middle layer in an organization, reviews various skills required, and yes—also includes some job titles. Some of them might surprise you, like being the Head of a Division.

Wrap Up & Submitting Your Questions

And that’s a wrap for episode 51 in Season FIVE, focused on Career Growth! 

You can submit YOUR question on my show’s site, AskChrista.com, that’s Christa with a C-H, where you will see all my episodes listed based on category and season. While your there—sign up for my More Answers… newsletter, where you will receive additional content on Sunday nights to set you up for the work week.

As always—thank you for your support. And remember, if you have a business challenge or a workplace issue—Ask Christa!