Sarah was your third hire. Brilliant developer, solved problems nobody else could touch, the kind of person who made everyone around her better just by being there.
Two years later, she’s managing a team of eight engineers. She’s miserable. Her team is frustrated. And you’re wondering what went wrong with someone who used to be unstoppable.
Welcome to the middle management squeeze… the inevitable growing pain that catches every scaling company off guard.
The Promotion Trap
Here’s how it happens: your best individual contributors become your first managers. Makes perfect sense, right? They know the work, they understand the company, they’ve earned the opportunity.
Except being great at doing the work and being great at leading people who do the work are completely different skill sets. It’s like promoting your best chef to restaurant manager and expecting them to automatically know how to handle suppliers, staff schedules, and customer complaints.
Your star performers suddenly find themselves spending their days in meetings they don’t understand, having conversations they’re not trained for, making decisions about people instead of products.
And the worst part? Nobody prepared them for this transition. Not you, not them, not the company.
When Your Best Becomes Your Bottleneck
Sarah used to ship features. Now she’s trying to figure out why Tom isn’t meeting deadlines, how to motivate Lisa who seems disengaged, and whether she should approve Jake’s request to work remotely three days a week.
She’s drowning in one-on-ones, performance reviews, and team dynamics. Meanwhile, the technical work she loves and excels at gets pushed to evenings and weekends, because “manager stuff” fills her days.
The person who used to accelerate your company’s progress has accidentally become a constraint on it. Through no fault of her own.
The Ripple Effect
It’s not just Sarah who’s suffering. Her team feels it too.
They’re getting less technical guidance from someone they respected as a peer. They’re watching their former colleague struggle with management tasks while the work they need direction on piles up. The clear communication and quick decisions they used to get are replaced by hesitation and overthinking.
What used to be your highest-performing team is now your most frustrated one.
And you’re stuck in the middle, watching great people become miserable in roles they never asked for but felt obligated to accept.
The Multiplication Crisis
As you grow from 50 to 150 to 250 people, this pattern repeats across every department. Your best salesperson becomes a sales manager. Your top marketer leads the marketing team. Your most reliable operations person suddenly oversees operations.
Each promotion creates the same challenge: exceptional individual contributors trying to figure out leadership on the fly, while the company desperately needs both their expertise and their management skills.
You end up with a layer of reluctant managers who are overwhelmed by people’s responsibilities and disconnected from the work they’re passionate about.
The Skillset Switchover
The cruel irony is that everything that made Sarah great as an individual contributor works against her as a manager. Her perfectionism becomes micromanagement. Her deep technical knowledge makes it hard to delegate. Her focus on getting things done clashes with the messy, slow work of developing people.
Nobody taught her that management is a completely different discipline. That leading people requires different tools than solving technical problems. That her job is no longer to be the smartest person in the room, but to make everyone else smarter.
What Actually Works
The companies that navigate this successfully do three things differently.
First, they separate the management track from the technical excellence track. You can be senior, respected, and well-compensated without managing people. Not everyone who’s great at their job needs to become someone else’s boss.
Second, when they do promote people into management, they treat it like learning a new profession, not a natural evolution of their existing role. Management training, mentoring, and gradual responsibility increases. The whole works.
Third, they get honest about what they’re asking people to give up. Sarah isn’t just taking on new responsibilities, she’s stepping away from the work that energized her. That’s a real loss that needs to be acknowledged and addressed.
The Growing Company’s Choice
Every growing company faces this moment: your best people need to become leaders, but leadership will fundamentally change who they are at work.
You can stumble through it, promoting people and hoping they figure it out. Watch them struggle, their teams suffer, and your growth slow down as your rising stars burn out in roles they weren’t prepared for.
Or you can be intentional about it. Build development systems that prepare people for leadership transitions. Create paths for expertise that don’t require managing others. Support your new managers through the hardest professional transition they’ll ever make.
The middle management squeeze is inevitable. But the casualties don’t have to be.