The Big Squeeze – Managers in the Middle
Middle managers live in the tension between the demands from above and the needs of the team below.
They’re expected to translate strategy into action while supporting individuals, resolving conflict, hitting performance targets, and maintaining morale.
It’s a lot.
Often, these managers are promoted from within. They know the work, they’ve earned trust, and they’re seen as dependable. But that very familiarity can complicate their transition into leadership. One day, they’re shoulder to shoulder with their peers. The next, they’re expected to lead those same colleagues - sometimes without clear guidance, authority, or the confidence that they’re “doing it right.”
The shift from being part of the team to leading it can be disorienting. The social contracts they built others as “one of the gang” can feel like something they need to protect. This can lead to hesitation around holding boundaries, having hard conversations, or asserting authority. Add to that the pressure from senior leaders to deliver results, and it’s no wonder middle managers often feel squeezed from both sides.
What makes the difference?
Not a one-day course. Not a checklist. Not crash course training.
Real leadership development takes time.
It requires space to reflect on personal patterns - how one reacts under stress, how decisions are made, and how communication shifts in different environments. It involves seeing where trust breaks down on a team and understanding what drives - OR - derails collaboration.
It takes courage to look in the mirror and ask:
Where am I getting in my own way?
How do I lead people who are different from me?
What kind of leader do I actually want to be?
The best learning opportunities don’t flood people with content - don’t even get me started on content! As a society we are overrun with hacks and how to’s, digital boards and save lists that are overflowing but not being utilized.
The best learning opportunities - create stretch moments.
They invite challenge, yes, but also provide space to practice, to misstep, and to try again.
They build awareness around different workstyles and motivators, help identify emotional triggers and strengths, and deepen insight into how trust is built (and broken) in teams.
This kind of paced learning helps a manager move from managing the work to leading the people.
If we want our middle managers to grow into senior leaders and not just survive the squeeze, we need to invest in learning that’s intentional, paced, and rooted in real-world application.
Their development isn’t a checkbox. It’s a commitment.
