The Management Squeeze: Why Capable Managers Struggle, and What Actually Helps
About the Author
Ashley Fina is the Co-CEO of Oxygen and former CEO of Michael C. Fina Recognition. She helps founders, executives, and high-growth companies build stronger teams through practical, people-first management training. Ashley has coached and advised more than 35 companies across industries and serves on multiple boards focused on business leadership and human capital development. Follow her on LinkedIn @AshleyFina.
Key Takeaways
Most managers don’t struggle because they lack effort or talent; they struggle because they’re stuck in the middle.
The “management squeeze” happens when managers are pulled between team needs, executive expectations, and company priorities.
Moving from individual contributor to manager is a career change, not a simple promotion.
The most effective way to unlock manager performance is through clarity, shared language, and practical management skills (not more pressure).
The Management Squeeze
As CEOs and senior leaders, we often look to our managers as the backbone of the organization. They’re the ones translating strategy into action, supporting teams through change, and keeping the day-to-day running.
So when managers start escalating everything, avoiding hard conversations, or defaulting to doing the work themselves, it’s natural to wonder what’s actually going wrong.
In my experience, most managers aren’t failing. They’re just stuck.
Specifically, they’re stuck in what I call the management squeeze: caught between their team’s needs, leadership expectations, and the realities of running the business. And most were never given the tools, language, or support to navigate that tension well.
I recently shared this short video about why managers get stuck. It struck a nerve, because it names something a lot of leaders feel but don’t always have language for.
▶ Watch the 60-second video here:
In this post, I want to explore this more deeply: what’s really happening beneath the surface, and why this problem shows up so consistently in growing organizations.
The Real Problem: Managers Are Trapped in the Middle
When someone steps into management, the role itself is often undefined.
Overnight, they’re expected to:
Support their team emotionally and professionally
Deliver results on tight timelines
Translate strategy into clear execution
Push back on unrealistic expectations — without creating friction
Make decisions that used to be made for them
This is the essence of the management squeeze. Managers sit at the intersection of team needs, executive demands, and company priorities. Unlike senior leaders, they often lack:
The authority to change the rules
The full context behind decisions
The language to push back or realign expectations productively
Left unaddressed, that tension doesn’t disappear. It accumulates, and eventually shows up as overwhelm, hesitation, or disengagement.
Why High Performers Feel the Squeeze Most
Ironically, the managers who struggle the most are often the ones promoted for all the right reasons.
They were strong individual contributors. They took ownership. They moved quickly. They delivered results.
So when the role changes, they lean on what’s familiar:
Doing instead of delegating
Fixing instead of coaching
Saying yes instead of prioritizing
Under the management squeeze, this behavior can look like commitment. Over time, it leads to exhaustion, unclear accountability, and teams that rely too heavily on the manager instead of growing.
From the outside, it may look like a performance issue.
From the inside, it feels like carrying too much with too little guidance.
The Costly Myth: “They’ll Figure It Out”
Most organizations promote managers and then move on.
There’s an unspoken belief that if someone was good at their job, they’ll naturally figure out how to manage others.
But management isn’t an extension of individual contribution. It’s a career change.
We don’t expect a great engineer to instantly become a great product leader. Or a top salesperson to intuitively know how to coach a team.
Yet we routinely expect new managers to:
Give effective feedback
Navigate conflict
Set clear expectations
Manage up
Prioritize competing demands
Trying to do this while operating inside the management squeeze, often without training or peer support, is rarely about capability. It’s about lack of preparation and structure.
What the Management Squeeze Looks Like in Practice
Managers rarely say, “I don’t know how to do this.”
What they say instead sounds like:
“I’m constantly putting out fires.”
“I don’t have time to actually manage.”
“My team needs more from me, but leadership wants faster results.”
“I’m not sure what I’m allowed to say no to.”
“Everything feels urgent.”
These are not individual failings. They are predictable symptoms of the management squeeze — a system where expectations are high, but clarity and support are low.
Why More Oversight Makes Things Worse
When managers struggle, the instinct from senior leadership is often to step in more closely.
More check-ins. More escalation. More control.
But pressure without clarity doesn’t build capable managers. It creates dependency.
Over time, managers stop making decisions. They wait for direction. They manage defensively instead of confidently.
The result is slower execution — not because people aren’t working hard, but because decision-making becomes bottlenecked.
What Actually Helps Managers Break Free
The answer isn’t motivation.
It’s not more content.
And it’s not telling managers to “be more confident.”
What helps managers move out of the management squeeze is shared language and practical structure.
Managers need support in areas like:
Managing up without sounding defensive
Saying no while staying aligned
Prioritizing when everything feels important
Giving feedback that actually lands
Coaching instead of correcting
These aren’t soft skills. They are core operating skills.
When managers share common frameworks and language, something shifts:
Decisions get faster
Conversations get clearer
Confidence replaces anxiety
Not because the work gets easier, but because managers know how to navigate it.
The Organization’s Role: Build Capability, Not Control
Companies don’t resolve the management squeeze by hovering. They resolve it by investing in the environment managers operate in.
That means:
Acknowledging that management is hard
Treating manager development as foundational infrastructure
Creating space for managers to learn alongside peers, not in isolation
When managers feel supported instead of scrutinized, they lead differently. And when managers lead differently, teams perform differently.
The Power of Management Training
If your managers feel overwhelmed, reactive, or hesitant, it’s not a character flaw.
It’s a signal.
A signal that they’re carrying responsibilities they were never trained to hold alone.
The fastest way to improve performance isn’t replacing managers.It’s equipping them.
Because when managers move out of the management squeeze, the entire organization moves forward.