Why Middle Management Feels Hard (No, It’s Not Just You!)

From the brain of Jocelin. 

I still remember the drive.

I was on my way to lay someone off and it was a week before Christmas. The decision had been made in a boardroom I wasn't in, by people I wasn't with, about a person I knew and had hired. A member of a team I managed. 

When I told her, she was angry, and sad. The anger came straight at me (of course, I was the messenger). It didn’t get aimed at the people who made the call or at the budget pressures or the board or whatever had been decided upstairs. It was aimed at me, the manager. 

She wasn't angry at me personally. She was angry at the situation. But I was the only one there to receive it. And that’s the middle. You deliver what you didn't decide. You absorb what you didn't create, and somehow you're supposed to keep everyone's trust while you do it.

No one tells you that part when you take the role and step into management. 

If you manage people while are also being managed, you know this feeling. The direction comes down from above and it's your job to make it real for your team. The frustration comes up from below and it's your job to carry it upward. Somewhere in the middle of all of that, you're trying to figure out what's actually yours to deal with and how you do it with integrity.

Most people step into middle leadership because they were good at the work. Not because anyone sat them down and said, “Here is what it actually feels like to lead from inside a system pulling in three directions at once. Here is how to know what is yours and what isn't. Here is how to stay standing when the anger lands on you.”

We just figure it out as we go, and some days that works and some days we drive home and feel really alone. 

What you're experiencing isn't random and it isn't a reflection of how capable you are. Barry Oshry studied organizational systems for decades and found that the same patterns show up everywhere. Hospitals, universities, corporations, nonprofits. Different organizations, same experience. People at the top hold information close and feel the weight of everything. People at the front line feel unheard. The people in the middle carry the gap between those two realities every single day.

It's structural, but it feels personal.

When you can see the system clearly and create an appropriate emotional distance from what the system creates, you get to make different choices. You get to decide what is yours to carry and what you need to put down. You get to lead with intention instead of just reacting to whatever lands on you that day.

The role doesn't get easier exactly. But it does feel lighter.

I'd love to hear from you,  what's the hardest part of leading from the middle right now? Drop it in the comments or send me a note at jocelin@reimaginework.ca.

On October 6, 2026, we’re hosting our “Leading from the Messy Middle” workshop at KWENCH. Are you a middle manager trying to figure things out? Then this workshop is for you. I hope to see you there.