• Stef the PM
  • Posts
  • What My Week Actually Looked Like (And The System That Keeps Me Sane)

What My Week Actually Looked Like (And The System That Keeps Me Sane)

How I manage 10 engineers and 3 roadmaps without losing my mind

Author

Stefanie Brown
September 26, 2025

👋 Hey friends,

Someone asked me this week what a PM actually does all day. People think we just write features and tell engineers what to build.

Here’s what my Tuesday actually looked like:

9 AM: Customer call where they kept saying our new dashboard is “confusing” but couldn’t explain why. Spent 20 minutes asking different versions of “what specifically feels off?” before we got to the real issue.

10:30 AM: Forty-five minutes translating “the button should be more intuitive” into something our designer could actually work with. Turns out “intuitive” meant “like the old version but better.”

12 PM: Dug through usage data trying to figure out why a feature that killed it in beta is getting ignored in production. Still don’t have a clear answer.

2 PM: Had the same alignment conversation with three different stakeholders because everyone heard something different in Monday’s meeting.

Most of PM work isn’t writing specs. It’s detective work and connecting dots between conversations that happened in different rooms with different people.

The Problem: Everything Feels Scattered

A year ago, this scattered approach worked fine. I had 3 engineers and 1 designer. I could keep track of everything in my head and have quick conversations whenever something came up.

Then I picked up an extra team. Three engineers became six, then recently a whole new team joined. Now I’m working with 10 engineers and still that same 1 designer.

The casual “hey, quick question” conversations were constant. By Friday, I’d realize I had no idea what half the team was actually working on.

My Solution: Meeting Marathon Mondays

Every other Monday, my calendar is straight meetings from 10:30 to 3:30. 1:1s with each engineer, project check-ins, alignment conversations. It sounds terrible, but it’s become my favorite system.

Monday = Download everything from the team The Monday 1:1s are mostly casual updates and project “whats.” What are you working on? What’s blocked? Where are you in the timeline?

But also the practical stuff: Who’s taking time off next week? Are we waiting on that other team for the API specs? Do we have capacity for the urgent request from sales?

Tuesday-Thursday = Clean focus time This is where the scattered conversations from my Tuesday example happen. Customer research calls, writing specs, digging into data, having those alignment conversations. The actual thinking work that requires focus.

Friday = Upload everything to my manager It’s a typical 1:1: this week, last week, priorities. But the best ones are when we dive into a specific problem or idea for broader strategic thinking.

I come prepared with actual context instead of just reacting to whatever fire felt biggest that week.

The conversations still happen anyway. The system just makes them way more productive.

💡 Quick tip: The key is separating information gathering (Mondays) from problem-solving (the rest of the week). When everything’s mixed together, you’re always context-switching.

Here’s what changed for me: that random Tuesday afternoon technical question now happens when I already know everyone’s workload from Monday. Instead of spending 30 minutes getting context, I can immediately help prioritize and loop in the right people.

💡 Quick tip: One silly thing that’s been a game-changer: I ask my team to use a siren emoji 🚨 for truly urgent “quick questions” and a different emoji (something silly like 🦄) if it can wait until later. Sounds dumb, but it works.

Why This Actually Works

Better problem-spotting: When you talk to everyone regularly, you catch patterns. Three people mention the same API issue? That’s not a coincidence.

Less reactive firefighting: Problems surface in planned conversations instead of crisis Slack messages.

The magic isn’t the specific schedule. It’s creating predictable information flow so you’re not always playing catch-up.

The Reality Check

Does this solve everything? Absolutely not. I still have days like that Tuesday example where everything feels chaotic.

But I’m no longer managing 10 people’s work through random conversations and hoping I didn’t miss something important.

The hardest part about scaling as a PM isn’t learning new frameworks. It’s building systems that help you stay connected to the actual work without drowning in it.

Quick Reads for PMs Managing Bigger Teams

This Week’s Challenge

If you’re feeling scattered or reactive in your current role, try this experiment for one week:

Pick one type of conversation (status updates, customer feedback, design reviews) and batch it into dedicated time instead of letting it happen randomly.

Track the difference: How much thinking time did you create? What problems did you catch earlier?

Even if you’re not managing a team yet, this skill of creating information systems will serve you in any role where you’re coordinating between different people or projects.

The goal isn’t to eliminate scattered conversations. It’s to make sure they’re happening in addition to planned ones, not instead of them.

Managing multiple projects or stakeholders in your current role? I’d love to hear what systems are working (or not working) for you. Hit reply and share your approach.

See you next Friday,

– Stef

📬 Know someone juggling multiple teams or projects? Forward this newsletter to them. Organization systems are always better when shared.

💬 What’s your biggest challenge with staying organized? Reply and tell me. Your struggle might become next week’s newsletter.

📬 Other Newsletters You Might Like

If you like Stef the PM, here are a few other reads worth checking out:

The free newsletter making HR less lonely

The best HR advice comes from those in the trenches. That’s what this is: real-world HR insights delivered in a newsletter from Hebba Youssef, a Chief People Officer who’s been there. Practical, real strategies with a dash of humor. Because HR shouldn’t be thankless—and you shouldn’t be alone in it.

Register for Pioneer: A summit for AI customer service leaders

Join the brightest, most innovative voices in customer service at Pioneer, a summit for exploring the latest opportunities and challenges transforming service with AI Agents.

Hear from leaders at companies like Anthropic, Boston Consulting Group, and more on how they’re building smarter support systems and why customer service will never be the same.