Your Calendar is a Cage and it’s a Systems Problem
If your calendar is full from 9 to 5 but your team still feels behind, the problem isn’t your time management. The problem is that meetings have become your company’s only way of doing work.
In this environment, nothing moves unless people are talking to each other in real-time. Decisions only happen on calls. Information only gets shared on calls. People only feel "accountable" when they are staring at their boss on a screen.
This is a fragile way to run a business. It makes everyone feel exhausted and "busy," but actual progress stays stuck.
Yesterday, I wrote about how to rebuild a team’s operating system from scratch. In that post, I broke down how to clarify who makes decisions and how to hand off work without it falling through the cracks. If you want the step-by-step "how-to" guide, start there.
Today, I want to talk about the "why." Why does meeting overload happen in the first place, and what is it telling you about the cracks in your business?
The Executive Who "Became the System"
When I was an Executive Assistant, I supported a high-stakes team. In my first week, I saw the chaos immediately. Meetings were happening with just vibes, no agendas, and people hopping on and off haphazardly. Calendars were double-booked. My executive felt he had to be in every single meeting just to make sure things were moving. He didn't trust the system to work without him, so he became the system. He was the human glue holding everything together.
I didn't "clean up" his calendar by deleting invites. I rebuilt the way the entire team worked. I created a standard way for people to share updates in writing and built a simple process for following up on tasks.
The goal wasn't just to have fewer meetings. The goal was to have a team that could run without needing to talk about every single detail live.
The Data Shows We Are Guessing
Recent data shows that work is becoming more reactive:
Microsoft found that 57% of meetings are now "on the fly" calls without an invite, and 1 in 10 are booked at the last minute.
Atlassian reported that in teams with poor meeting cultures, people spend 50% more time in unnecessary meetings than on their actual high-priority work.
Decisions take forever, and your best people end up working late at night just to do the "real work" that meetings interrupted during the day.
Why Meetings Become the "Default"
Meeting overload happens when your company is missing the basic tools it needs to function. We use meetings to fill four specific gaps:
Confusion over who decides: If nobody knows who has the final "yes," we call a meeting so everyone can weigh in and share the blame if things go wrong.
No way to see progress: If there isn't a central place to see the status of a project, we call a meeting just to ask, "Where are we on this?"
Information is scattered: If notes and context live in people’s heads or private DMs, we call a meeting to get everyone on the same page.
No follow-through: If we don't trust that people will finish their tasks, we call a meeting to create a "forced" sense of urgency.
Meetings are the glue holding these gaps together. This is why simply telling people to "have fewer meetings" never works. You're removing the glue without fixing the holes.
Three Types of Meeting Waste
You don’t need a consultant to tell you which meetings are bad. You just need to recognize these three patterns:
The "Update" Meeting: This is just people reading reports to each other. If it could have been an email or a written post, it’s a waste of time.
The "Waiting" Meeting: This happens when work stops until the next scheduled check-in. If a decision has to wait five days for a "sync," your momentum is dying on the calendar.
The "Just in Case" Meeting: These are meetings with 15 people where only 3 actually talk. People are invited so they don't feel left out or to "keep them in the loop."
One Question to Fix Your Calendar
Before you send a calendar invite, ask yourself this:
"Can we achieve this goal in writing within 24 hours?"
If the answer is yes, do it in writing. Use a shared doc or a project tool. If the answer is no (because the topic is too emotional, complex, or requires a hard debate), then schedule a small, focused meeting and make a decision.
A Quick Self-Check for Founders
If you feel like a prisoner to your calendar, one of these is likely true:
You haven't told people exactly what they are allowed to decide on their own.
You can't "see" the work, so you have to "hear" about it in a meeting.
Your team doesn't have a standard way to send written updates.
This is the diagnosis. The cure is building a system that makes progress visible and decisions fast—without forcing everyone onto a call.
In Part 2, I’ll share the playbook: which meetings are actually worth keeping, how to end every call with real follow-through, and the "two-week reset" to get you out of calendar jail.