The Middle Manager Dilemma
- Samantha Riel
- Jul 15
- 3 min read
Updated: Jul 30
Middle managers don’t get enough airtime.
They’re the ones sitting between strategy and execution. The ones translating big goals into daily actions. The ones holding it together when things start to stretch.
And yet, they’re often the most overlooked and under-supported layer in a growing company.
This topic has been on my mind for a while. So I took a beat to dig into it on the podcast. No guests. Just me, reflecting on what I’ve seen—and what we so often miss when it comes to the people in the middle.
Here’s what came up.
Middle Managers Are Often Set Up to Struggle
Many middle managers are promoted because they’re great individual contributors. But once they’re in the role, the job changes. Now they’re navigating personalities, giving feedback, managing up, and helping others grow. It’s a completely different skill set.
And too often, they get no real training or coaching.
They’re expected to juggle priorities, keep the team moving, and absorb pressure from both sides. That pressure builds. It leads to confusion, burnout, and turnover.
It’s not about blaming founders or execs. It’s about recognizing that this layer is critical, and it needs support just like any other part of the business.
People Don’t Leave Companies. They Leave Chaos.
We’ve all heard the saying, but here’s the nuance. People leave when they don’t feel supported. It's death by 1000 papercuts, and often, that lack of support comes from a manager who’s struggling quietly.
Managers are trying to shield their teams from everything swirling around them while still delivering on goals they had no part in setting. They’re caught in the middle, and if no one is checking in on how they’re doing, things start to unravel.
Retention issues. Slow execution. Low morale. These don’t always come from the top. They often start in the middle.
Culture Isn’t Defined by Executives. It’s Lived by Managers.
Founders set the tone. Leadership teams outline the values. But the actual experience of your company lives in how managers lead their teams: how they run meetings, how they give feedback, and how they make space for growth, conflict, and clarity.
If you want to know what your culture really feels like, ask someone who reports to a middle manager. Or better yet, ask the manager how supported they feel. When managers feel empowered and confident, that shows up across the team. When they’re confused or overwhelmed, that does too.
The Emotional Load Is Real
One thing that stood out in this episode is how little we talk about the emotional weight middle managers carry.
They’re often the buffer. The ones trying to protect the team from instability while still meeting leadership’s expectations. That creates a lot of tension.
Sometimes, it can be hard for this groups to to raise concerns without feeling like they're being difficult. It’s hard to admit they're struggling when the assumption is that they're the ones who are the frontline leader.
If we want more resilient teams, we have to start by creating space for our managers to be human, to say what’s working and what’s not. To have permission to lead, not just manage.
How to Provide Real Support
Middle managers don’t need grand gestures. They need consistent, practical support that helps them succeed.
A few examples:
A clear role description that outlines what they’re accountable for and where they have authority
Manager-specific training focused on real-life situations, not just leadership theory
Offsites to think strategically, not just tactically
A community of peers and mentors to talk through challenges, without judgment
A chance to contribute to strategy, not just receive marching orders
Encouragement to lead in their own voice, not just copy what they’ve seen modeled
These changes may feel small, but they compound and can completely shift how a manager shows up for their team.
If Something Feels Off, Start in the Middle
When a business starts to feel disjointed, when communication breaks down, or when execution slows, it’s easy to look at the top or the frontlines.
But often, the answer is in the middle. Are your managers clear on what’s expected? Do they have the resources to lead well?
Because the truth is, you don’t scale a company by pushing harder. You scale by supporting the people who carry the weight every day.Middle managers are often the glue that keeps things moving. Let’s make sure they’re not the ones holding everything together without a net.
Listen to Episode 5: The Middle Manager Dilemma
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