TL;DR: Why Scheduling Is Killing Your Momentum
If your team’s losing speed waiting for meetings, here’s the fix:
- Default to now. If both people are free, talk immediately instead of scheduling later.
- Protect deep work. But don’t let “focus time” become an excuse for delay.
- Short beats scheduled. A 12-minute chat today beats a 30-minute meeting next week.
- Momentum matters. Don’t let energy die waiting for a calendar slot.
- Culture counts. Make it normal to say both “let’s talk now” and “not right now.”
How many times a week do you find yourself saying, “When works for you?”
Ever had an idea, felt the spark, and then watched it die waiting for a calendar slot?
UGH.
I recently read Jason Fried's post about ditching the calendar dance and just calling people when you need to talk. His take:
"Don't schedule, don't send me a link to pick a time, just pick up the phone and call."
It got me thinking about how much time we waste on calendar bureaucracy, especially with our own teams.
The Everyday Example
Here’s a conversation that happens at least three times a week:
Team member: “Hey, when are you free? I'll book some time in your calendar to discuss the new feature.”
Me: “We're both free right now. Let's just huddle.”
And BOOM — 12 minutes later the decision’s made, instead of waiting three days for a formal meeting that would have been dragged out to fill the full 30-minute slot.
The Scheduling Tax We Don’t Talk About
Every time someone says “Let me send you a calendar invite,” here’s what’s really happening:
- Momentum killer: The urgency dies.
- Time inflation: A 10-minute discussion becomes a 30-minute meeting.
- Decision delay: What could be solved now sits in limbo for days.
- Context switching: You’re thinking about it now, but by Thursday you’ll have to reload everything.
Think about it—when was the last time a scheduled 30-minute internal meeting actually needed 30 minutes?
The Magic of Right Now
There's something powerful about catching someone when they're already in the right headspace.
When someone says “I need to talk through this pricing change,” they're already loaded with context. Their brain is fired up about the problem.
Schedule it for Thursday at 2 PM? Now they have to:
- Remember the context
- Reload all the details
- Get back into problem-solving mode
- Fill whatever time was blocked
But grab them now? The conversation is focused, urgent, and efficient.
You get clarity in 10 minutes instead of dragging through 30 just because the calendar says you should.
The “Just Call” Rules I've Adopted
Here’s what’s working for me and my team:
- When something comes up, and both people are available, default to a quick huddle.
- No invites, no links — just a quick “Quick call?” in Slack.
- If it takes longer to schedule the chat than to have it, just have it now.
- And if someone brings up a problem, that’s your signal: their energy and context are peaking right now. Don’t lose that momentum or opportunity.
Of course, not every moment’s the right one. If someone’s deep in focus, respect that boundary.
But most of the time, the fastest way to move forward is simply to start talking.
When This Doesn't Work
Let's be realistic — this approach isn't universally applicable:
- External meetings: Clients and prospects need structure and respect for their time.
- Large group discussions: You can't just “huddle” 8 people without warning.
- Complex topics: Some conversations need preparation and dedicated focus time.
- Different time zones: Obviously harder to “just call” when half your team is asleep.
- Deep work protection: You don’t want to interrupt someone mid-flow just because you’re ready to talk.
The point isn’t to abandon structure. It’s to stop defaulting to it.
We’ve confused being busy with being productive, and our calendars are the proof.
The best work doesn’t happen when the clock says it should — it happens when the energy’s there.
The key is making it culturally acceptable to say both “let’s talk now” and “can’t talk now.”
That’s when communication becomes real collaboration.
The Results
Since ditching the calendar shuffle, our team moves faster, and it shows.
- Decisions happen faster
- Conversations are more focused
- Team momentum stays higher
- Calendar stays cleaner for actual deep work
Sure, sometimes you can't reach someone immediately. But Jason's right — it usually works out. And when it does, you get the best version of the conversation.
