Confessions of a Middle Manager: Secrets, Regrets and Guilty Pleasures

The unspoken truths of middle management

Feb 20, 2025

Middle management is a world of contradictions: Rewarding yet exhausting. Empowering yet disheartening. Strategic yet reactive.

For more than two decades, I’ve navigated the trenches of the corporate workplace—sometimes as a front-line manager, other times as the leader of large, matrixed teams spread across geographies. I’ve reported to over 15 different managers, often juggling multiple reporting lines at once. I’ve been at the center of strategy discussions while also managing the day-to-day chaos of execution.

And through it all, I’ve come to realize something that rarely gets discussed: middle management is one of the most misunderstood, undervalued, and paradoxical roles in an organization.

Who is a Middle Manager?

When people hear the term middle manager, they often picture someone with a title like Manager or Senior Manager. But in reality, middle management could span a wide range of titles and levels—from frontline supervisors to directors and VPs—and varies widely depending on the size of the company (with more layers of middle management in larger companies.)

A middle manager is the bridge between strategy and execution, sitting between executive leadership and frontline employees.

Being a middle manager means existing in two worlds at once.

As a middle manager, you’re expected to turn high-level strategy into actionable steps for your team while shielding them from the unpredictable demands of senior leadership.

You’re expected to deliver bad news, enforce policies you didn’t create, and fight battles your team will never know about—all while trying to maintain some semblance of motivation and direction.

Yet, despite its importance, middle management is often dismissed as bureaucratic red tape, a “layer of fat” that companies experiment with removing.

If you’re with me so far, stay tuned as I pull back the curtain on some of the unspoken truths of middle management.

These are the confessions—the secrets, regrets, and guilty pleasures—of a middle manager.

Confession #1: Balancing Act - The Tightrope Walk Between Leadership and Team Needs

I remember a time when my manager assigned me to a project with an aggressive project deadline, one that I knew was unrealistic given our current workload. At the same time, my team was already stretched thin, with some members on the verge of burnout.

I found myself in the impossible position of needing to deliver results while also protecting my team from being overworked.

So, as any sane manager would, I tried to negotiate with my manager for more resources. Unsurprisingly, the response I got was: “Just make it happen.”

This is the balancing act of middle management—being the bridge between leadership’s vision and the team’s reality.

It’s a tightrope walk, one where you constantly have to translate strategy into execution while keeping your team motivated. When you’re squeezed from both sides, it’s easy to feel like you’re failing someone, no matter what you do.

My Takeaways:

Be honest with your team about the challenges while maintaining a solutions-oriented mindset. Don’t glorify the vision: your team is not stupid, and they know when you’re not being genuine.
Never commit to a project without first discussing it with your team. Your team should understand the vision, the “Why”, and feel included in the planning process. Once they are aligned with the goals, they will work hard to meet the timelines.
When caught between conflicting demands, seek clarity from your manager. That’s their job, after all.

Confession #2: Empty Rhetoric - When You Don’t Fully Believe What You’re Saying

I’ll never forget the all-hands meeting where I stood in front of my team, sharing some “exciting updates” about the company’s future—talking about growth, opportunities, and upcoming projects.

But behind closed doors, I already knew that a major restructuring was on the horizon, one that could potentially impact some of the very people I was speaking to.

As I spoke about future plans with a confident smile, I felt like I was betraying their trust. These were people I worked with every day—people who counted on me for honesty. Yet, there I was, delivering a carefully crafted message, knowing full well that change was coming. I wasn’t technically lying, but I wasn’t being fully transparent either.

And that’s what made it so uncomfortable.

Every middle manager has faced this dilemma—having to sell an idea they don’t fully believe in. The challenge is walking the fine line between loyalty to leadership and maintaining trust with your team. While I try to be as authentic as possible, there are times when I’ve had to play the role of the enthusiastic messenger, even when my gut said otherwise.

My takeaways:

If you don’t believe in an initiative, ask leadership for deeper insight before passing it down. You deserve to know the background (and your leadership owes it to you.)
Frame messages in a way that aligns with your team’s interests and motivations.
Be genuine—if something doesn’t resonate with you, be pragmatic rather than overly enthusiastic. As I mentioned earlier, your team is smarter than you think, and you can’t bluff your way out of this.

Confession #3: The Illusion of Control - When You Feel Powerless

There was a period when my team was affected by a major restructuring, yet I had little say in the decisions. I attended meetings where executives discussed organizational changes like they were moving chess pieces, while I sat there knowing the real impact on the ground but with little say in the decision itself.

My team looked to me for answers, but I had none.

Have you faced this situation before? I have, several times over.

Middle managers are expected to lead, but in reality, we often have limited control over major decisions. We are held accountable for results, yet have little authority over the big levers that shape our work. It’s one of the most frustrating parts of the job—feeling like a decision-maker while realizing you’re mostly an executor.

My takeaways:

Focus on what you can control—team morale, communication, and execution.
Never pretend that “everything is in control.” Acknowledge uncertainty, and prepare your team to handle situations that you can anticipate.
Increase your influence over time by learning to navigate power dynamics. This will help you regain some of the lost control. Check out 6 Simple Strategies to Navigate Office Politics Like a Pro for some inspiration.

Confession #4: Tough Love - Giving Feedback That Hurts

I remember many years ago, I had a ‘genius’ engineer on my team. He was technically brilliant: he could solve complex technical problems in minutes and write code like he was an AI bot (which didn’t exist at the time, btw!) Many even called him the “god of software development.”

Except, there was a slight problem.

His communication was rough and unprofessional, and he appeared to be too full of himself whenever he opened his mouth. While working with others, he often ended up saying something that was rash or disrespectful, which led to a spiral of escalations.

Don’t get me wrong: I loved him, and didn’t want to lose him, but as his direct manager I had to have a conversation with him to make sure he knew the ‘other side’. That conversation was one of the hardest I’ve had because I knew it would sting.

And it did.

Giving tough feedback is an inevitable part of management, something middle managers need to embrace as a regular part of their job. It’s never easy, especially when you know it could hurt someone’s confidence. But leadership isn’t about being liked—it’s about being fair, direct, and invested in people’s growth.

It’s about doing what’s right.

My takeaways:

Approach feedback with empathy but clarity—don’t sugarcoat, but don’t demoralize.
Focus on behaviors, not personality, and offer actionable ways to improve.
Check out How to Deliver Tough Feedback in as Little as 5 Minutes - Even If You Dread Confrontation for some inspiration.

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Confession #5: Imposter Syndrome - The Fear of Not Belonging

Even after years in management, there are moments when I wonder, Do I really deserve this role? I look around at other leaders and sometimes feel like they have it all figured out, while I’m just figuring things out as I go.

Imposter syndrome is real, and it doesn’t go away with experience. The higher you climb, the more you realize how much you don’t know.

But the truth is, most leaders feel this way at some point.

Middle managers sit in a uniquely challenging position. Unlike individual contributors, our work isn’t always directly visible—our success is measured by our team’s output rather than our own. This can create a sense of detachment from achievements, making it harder to internalize success.

Additionally, middle managers operate in ambiguity, and navigate the messy, uncertain space in between executives and the teams. This uncertainty can make us feel like we don’t have control or that we’re just “winging it.” And when you constantly feel like you’re figuring things out on the fly, it’s easy to assume that everyone else knows what they’re doing—except you.

My takeaways:

Remind yourself that you earned your position through experience and skills. Promotions don’t happen by accident. You are where you are because someone saw potential in you. Trust that.
Seek mentorship and peer support—most leaders have experienced imposter syndrome at some point. Talking to them can help normalize your feelings and offer valuable perspective.
Accept that you don’t need to have all the answers, just the ability to find them. That’s your fundamental job as a manager.

Confession #6: Office Politics - Getting Caught in the Middle

I once mediated a conflict between two senior leaders whose disagreements trickled down to my team. At the time I was reporting to both of them simultaneously (in a matrixed organization.)

One believed in full transparency—sharing as much information as possible with employees to build trust. The other believed in selective information sharing, worried that too much transparency could lead to confusion or unnecessary concern. Both had valid perspectives, but their ongoing battle left my team in limbo.

I found myself caught in between, trying to balance the competing expectations of these senior leaders, each of whom expected me to ‘take their side.’

This is the reality of office politics for middle managers. Unlike senior executives, we don’t set the strategic direction, but we are expected to uphold and implement decisions. Unlike individual contributors, we can’t just focus on our work and avoid the politics—we are directly affected by leadership decisions and the power dynamics that shape them.

Middle managers are often the middlemen in power struggles—they are often the diplomats, the negotiators, and the peacekeepers. It’s exhausting but necessary to keep things moving forward.

My takeaways:

Don’t take sides—focus on solutions, not personal battles. When senior leaders are at odds, avoid getting emotionally invested in their conflicts. Your job is to keep your team productive, not to act as a referee in leadership disputes.
Build alliances but be neutral where possible. Networking is crucial. Strong relationships with different stakeholders can help you navigate office politics more effectively.
Pick your battles wisely. Not every political game is worth playing. Check out 6 Simple Strategies to Navigate Office Politics Like a Pro for some inspiration.

Confession #7: Bending the Rules - When Doing the Right Thing Isn’t ‘Right’

Early in my career, one of my star performers needed a few extra days of leave for a personal emergency.

The company’s leave policy was rigid, with no room for exceptions, and I knew HR would reject the request outright. But this employee had always gone above and beyond for the team, often working late and covering for others when needed.

I knew in my gut that turning down his leave request would be unfair, and just wrong. So, I found a workaround—shifting responsibilities, adjusting schedules, and reclassifying part of the leave under another category.

Technically, I wasn’t breaking any rules, but I wasn’t exactly following them either.

Did I follow company policy to the letter? No. Did I do the right thing for my employee and the team? Absolutely. And I’d do it again.

Sometimes, being a good manager means bending rules that don’t make sense. It’s a fine line between discretion and bending rules, but at the end of the day, leadership is about people, not policies.

My takeaways:

Understand company policies deeply—many allow for discretionary decisions. Before bending a rule, check if there’s built-in flexibility.
Weigh risks before bending rules, and be prepared to justify your actions. I like to document my reasoning in case I need to explain my decision later.
When possible, push for policy changes rather than working around them. This is especially true if you’re having to make the same exception over and over again (and there’s a high likelihood that other managers are doing the same.)

Confession #8: Playing Bad Cop - Enforcing Unpopular Policies

Nothing makes you more unpopular than delivering bad news—budget cuts, hiring freezes, reorgs, policy changes, and the list goes on.

I’ve had to sit in meetings where employees looked at me with frustration, as if I was the one making these decisions. I’ve had to announce layoffs, justify why raises weren’t happening, and explain why new company-wide initiatives (that didn’t make sense to my team) still needed to be implemented.

Each time, I could feel the silent judgment of my team that perhaps I wasn’t fighting hard enough for them.

Being a middle manager means owning decisions you don’t always agree with. It’s an uncomfortable position—we act as the face of decisions made at a higher level, even when we have little or no say in them. Employees expect us to advocate for them, yet leadership expects us to execute. This is where many middle managers struggle: How do you maintain credibility with your team while enforcing policies that frustrate them?

My takeaways:

Acknowledge frustrations, but don’t pass the buck. It’s tempting to say, “I don’t agree with this either,” but that does more damage to your own integrity than it helps with trust. Instead, acknowledge their feelings: “I understand that this is frustrating, and I hear your concerns.”
Provide context—people accept change better when they understand the why. Remember the unpopular decisions that just “slide in” without any explanation? If your leadership doesn’t provide enough context, ask for it, and then have the courage to stand in front of your team and provide them the context. Trust me, they’ll understand.
Don’t just enforce changes, offer support to help your team navigate through them. For example, if you’re rolling out a hiring freeze, help your team find ways to redistribute their workload.

Confession #9: Guilty Pleasures - The Little Wins We Don’t Talk About

Let’s be honest—middle management is tough. You’re juggling competing priorities, managing expectations from all sides, and often working longer hours than you’d like.

So, it’s no surprise that middle managers, like everyone else, have their guilty pleasures—the small, unspoken indulgences that make the job just a little more bearable.

I’ll admit it: there are moments I secretly enjoy, even if I wouldn’t broadcast them in a meeting or to peers.

Like the quiet relief when a long, back-to-back meeting block suddenly gets canceled. Or the satisfaction of marking an “urgent” email as Unread, pretending I haven’t seen it yet because I just need a breather. (Did I just catch you secretly smile on that one?)

Sometimes, it’s the joy of skipping a non-critical Zoom call while catching up on actual work—or, let’s be honest, just sipping coffee in peace.

There’s also the pleasure of delaying bad news by a day because I know it’ll ruin someone’s weekend, or leaving my status as “In a Meeting” when I’m really just catching my breath.

And who hasn’t skimmed a 50-slide deck five minutes before presenting it, hoping for the best? I certainly have.

My takeaways:

Don’t beat yourself up. Everyone needs small escapes to stay effective. As long as they don’t compromise your work or your team’s trust, they’re harmless.
There’s a difference between self-care and neglecting responsibilities. If your guilty pleasures are becoming daily habits that hurt productivity, it’s time to reassess.
If you’re constantly seeking shortcuts, it might be a sign of burnout. Instead of dodging work, find sustainable ways to manage stress—whether it’s taking a real lunch break, blocking focus time, or simply logging off on time.

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Summary: Confessions of a Middle Manager

Middle management is a role defined by contradictions—leading without full authority, advocating for your team while aligning with leadership, and juggling expectations from all sides.

Confessions of a Middle Manager: Secrets, Regrets and Guilty Pleasures

In this article, we discussed confessions—secrets, regrets and guilty pleasures—of a middle manager. These are the untold truths that every middle manager faces:

Balancing Act: Constantly juggling leadership demands and team needs, often feeling stretched thin and unable to fully satisfy either side.
Empty Rhetoric: Sometimes delivering messages you don’t fully believe in, caught between leadership loyalty and team trust.
The Illusion of Control: Being held accountable for outcomes while having little say in major decisions, leading to a frustrating sense of powerlessness.
Tough Love: Giving difficult feedback that stings, but is necessary for team growth and maintaining a healthy work environment.
Imposter Syndrome: Feeling like you don’t deserve your role, fueled by the ambiguity and lack of visible success middle managers often face.
Office Politics: Navigating power struggles between leaders while staying neutral, often acting as the peacekeeper in workplace conflicts.
Bending the Rules: Occasionally bending rigid policies to do what’s right for your team, balancing discretion with accountability.
Playing Bad Cop: Enforcing unpopular policies you don’t agree with, while trying to maintain credibility with your team.
Guilty Pleasures: Finding comfort in small indulgences—like skipping meetings or delaying emails—to cope with the daily stress of middle management.