The Most Critical Role Nobody Prepares You For
This post first appeared on my LinkedIn profile, sparked by a reflection on my own leadership journey — and what I wish I’d had back then.
I still remember the day I became a manager.
New title. New responsibilities. Same me.
No real training. No coaching. Just... figure it out.
What followed was a crash course in all the things business school doesn’t prepare you for:
- Navigating conflict you didn’t cause
- Balancing strategy and operations — simultaneously
- Shifting from managing to leading
- Supporting others while staying sane yourself
- Trying to lead even when you feel like you're guessing
Middle management is one of the hardest — and most important — roles in any organization.
When I started promoting others into their first management roles, I tried to give them what I never had: coaching, encouragement, space to grow. But I was still learning. I had other responsibilities. It was never quite enough.
Looking back, I wish I could have offered them more — something structured, consistent, and always available when they needed it most.
We talk a lot about executive leadership. But the future of high-performing teams depends on how well we support the middle.
That’s why we built Work2gether AI: to give every manager — not just the ones at the top — access to real coaching, science-backed tools, and actionable insights that help them lead better in the moments that matter.
Middle managers deserve more. Their teams do too.
Lead better. Work2gether.