Leadership
Your Calendar Is Lying to You
Jun 22, 2025
(And What It Says About Your Culture Might Surprise You)
A while back, I canceled a recurring Thursday sync no one liked, no one needed, and no one had the nerve to kill.
Nothing broke.
One of my engineers messaged:
“Thanks for the air.”
That single line told me more about our team’s culture than any values deck ever could.
Your culture isn’t what you say. It’s what you schedule.
What Your Calendar Reveals
We all say we value trust, autonomy, and deep work. But our calendars often tell a different story:
Back-to-back meetings
Bloated standups
Skipped 1:1s
Focus time that’s fractured into 30-minute scraps
These aren’t just annoyances. They’re signals.
Skipped 1:1s? Growth is optional.
Over-invites? Presence matters more than impact.
No strategy time? Urgency wins over direction.
Your team watches what you do—not what you say.
When I Got It Wrong
In my first year managing a distributed team, I overbooked myself into oblivion. Like many new managers in enterprise tech, I thought presence was leadership—until my schedule started breaking the team.
Daily syncs, project reviews, open DMs—I thought availability was the job.
The result?
No strategic margin
A disempowered team
Slower execution
Canceling one sync didn’t fix everything. But it gave us room to reset. I reclaimed six hours a week. No one noticed. Everyone felt the difference.
Why This Still Matters in 2025
Despite years of remote and hybrid work, the problem hasn’t improved. If anything, it’s worse:
Meeting load is up 13.5% since 2020
Knowledge workers now spend nearly two-thirds of their time in meetings or messaging
Just two meeting-free days a week increased productivity by 71% and engagement by 55% (MIT Sloan)
And for distributed teams, it’s even harder. Sync time shrinks. Async noise grows. Calendars stay bloated either way.
Our tools have evolved. Our habits haven’t. Calendars have calcified—and they’re quietly draining performance.
Culture Drift Is Calendar Debt
Culture doesn’t collapse. It drifts.
Not through crisis—but one calendar invite at a time:
“Let’s keep it just in case.”
“We’ll reschedule the 1:1.”
“Let’s sync on this instead of writing it up.”
This is calendar debt. Like tech debt, it compounds silently until teams feel overwhelmed, unproductive, or disconnected.
Eventually, the structure meant to support good work becomes the thing preventing it.
The Real Problem Isn’t Time. It’s Insecurity.
We blame the meetings.
But often, it’s fear underneath:
Fear of being out of the loop
Fear of missing a signal
Fear of being misunderstood
So we schedule. We sync. We protect our inboxes instead of our impact.
Organizational psychologist Adam Grant said it well:
“If you want people to think for themselves, you have to free up their time to do it.”
Treat Your Calendar Like a Product
Your calendar is a daily-use interface—for your leadership, your values, and your team’s autonomy.
Is it intuitive? Is it intentional? Does it reinforce the culture you say you want?
If not, iterate.
A Five-Step Calendar Reset
Audit Intentionally. Kill dead meetings. Shrink bloated ones. Rotate or combine what’s left.
Color-Code by Intent. Use labels such as Strategy, Execution, Coaching, Admin, and Async Prep to reveal imbalances at a glance.
Block and Defend Focus Time. Start small—two hours, twice a week. Guard it visibly. Model it for others.
Communicate the Why. Let your team in: “I’m canceling this sync to create space for deep work. Let’s try async updates.”
Run a Calendar Retro Quarterly. What’s working? What’s noise? What’s no longer necessary?
Quick Calendar Audit: 3 Questions
Use this before accepting your next invite—or in your next retro.
What decision or outcome requires this meeting?
Who would notice if we canceled it for a month?
What would happen if we made this async?
Small questions. Big clarity.
The One-Meeting Challenge
Want a quick win?
Cancel one recurring meeting
Use that hour for strategy, coaching, or deep execution
Ask your team what changed after one sprint
Small move. Big signal.
Final Thought
If your calendar looks like chaos, your culture probably feels like exhaustion. If your values say “trust,” but your schedule screams “control,” your team will believe the schedule.
Don’t start with a new mission statement. Start by canceling one meeting.
Then use that hour to build something better.
