Middle management can be a tough seat to occupy—often caught between the needs of individual contributors (ICs) and the expectations of leadership. When everything aligns, it feels effortless. But when things are misaligned, your role can become one of the hardest in the room.

In this post, I'm sharing my experience navigating one of those misaligned moments—what I learned, what I wish I'd known, and how it shaped me as a leader.

The Challenge

Our team was tasked with adding an input field for landlords to provide renter information when posting a Zillow listing. On the surface, it seemed like a simple, straightforward feature. But beneath that simplicity lay deeper issues—overlapping priorities, misaligned expectations, and a lack of clarity around the project's broader purpose.

My team viewed it as a quick, lightweight task. My manager, on the other hand, questioned its value and struggled to see how it fit into our larger strategic goals. Initially, I sided with my team—but I also recognized my manager's perspective. They were zoomed out, thinking about the bigger picture and long-term impact, while my team was zoomed in, focusing on the immediate ask.

That moment highlighted a common tension in middle management: balancing the micro with the macro, translating between strategy and execution, and helping both sides see beyond their immediate vantage point.

Navigating the discomfort

Things came to a head when my manager told me the design wasn't strong enough. At the same time, our product partners and engineers were waiting for final designs—any changes now meant delays. To make things more complicated, the feedback wasn't specific, and I struggled to translate it for the team.

I remember being visibly upset in a meeting with my PM, designer, and content designer. I couldn't articulate the reasoning clearly—because the concerns weren't mine, they were my manager's.

So I asked my manager, "How should I handle this? My team would rather hear this feedback directly from you." She replied, "You should make it your idea, not mine."

That's when it clicked: Middle management isn't about relaying messages. It's about owning decisions. You need your own vision, your own stance. That's what it means to lead from the middle.

Turning the corner

Even though everyone was frustrated, I knew I had to take action fast. I jumped into Figma and gave direct, visual feedback to clarify what wasn't working and why.

Sometimes words aren't enough. You have to show it.

The team made updates that resulted in a more scalable and streamlined experience. By recognizing how this project connected with another initiative, we also reduced development time—a win we wouldn't have seen otherwise.

Key Takeaways

• Middle management is hard. You're constantly balancing the perspectives of leadership and your team. It's your job to interpret, align, and lead through ambiguity.

• Make the feedback your own. Don't just repeat what leadership says. If you agree, own it. If you don't, push back. Your team needs to trust that you believe in what you're asking of them.

• Confidence is contagious. People can sense uncertainty. When you stand behind your decisions, it helps your team stand behind you.

• Communicate in multiple ways. Words don't always land. Show your thinking. Use visuals, examples, or storytelling to make ideas tangible.

• Create psychological safety. Your team needs to feel safe to disagree with you. That's where the best ideas—and the fastest progress—come from.

• Leadership is not a popularity contest. It's a balancing act between being liked and being effective. Choose effectiveness. Choose clarity. Choose quality.