Today’s blog post is about—you guessed it—more calendaring and scheduling stuff. This time I want to focus on one of the most unbelievably wasteful uses of time: time spent scheduling meetings. It’s a necessary evil, but can we at least optimize it, and get the lesser of the evils?
Here’s the short version: I suggest we can avoid a ton of wasted time by preferring (in order) to keep calendars open, share your calendar’s free/busy, use meeting slot tools, or as a last resort have an assistant do your scheduling.
With that in mind, the following are my suggestions for how to Do Better, because we can’t do worse.
Scheduling: The Most Ironic Waste of Time
The inspiration for this post is the many times I’ve interacted with profligate scheduling ceremonies. Whenever I have to engage with someone’s executive assistant it astonishes me what an antediluvian process this is. “Alice is available today at 3pm, tomorrow at 11:30am or 1:30pm.” “I’m not available then, but…” It’s incredible how wasteful it is to engage in this activity. It can easily take 30-45 minutes of calls and emails to schedule a 30-minute call. And that’s with just two people; it’s much worse with three or more. Have we benefited nothing from advances in technology? Is this really the best we can do? It blows my mind.
The default scheduling algorithm between two humans seems to be a random activity mostly caused by inability or unwillingness to actually share information.
Blindly scheduling meetings because you don’t have access to calendars is like playing Battleship:
P: “Sent an invite for next Tues. Does that work?”
Me: “Hit and sink! You took out a 1:1 w/ my direct report.”
Another comparison I’ve seen is to the game of Tetris.
Calendar Tetris is my least favorite kind of Tetris
Default To Openness
The first problem in scheduling is trying to find matching slots in calendars about which you have no information. Thus, a first optimization is to make your calendars as open as possible. For most people, in most organizations, a fully open calendar is the best default setting. Just let everyone see everything! There’s no reason not to!
Aaron P Blohowiak
Open calendars increase information exchange velocity, accelerating progress.
With open calendars, anyone can use their “find a time” feature in pretty much any calendaring app and… find a time. It’s almost like magic, except it’s not magic, it’s just basic information-sharing.
But, in a lot of organizations, transparency and openness aren’t the default. And yeah, I get it, some people like CEOs can’t just share their calendars. People would freak out if they took a peek and saw how a CEO spends their time. So, some of us have to limit access to our calendars, for legitimate reasons or otherwise.
Next Best Thing: Share Free/Busy
The fallback compromise for most people who can’t just make their calendars public is to make their free/busy public. This can be really easy to do. With Google Calendar, for example, you can share free/busy publicly, then get a shareable URL. First, open the calendar’s sharing settings:
Then make free/busy available publicly. You’ll see that, regrettably, I’ve had to make my calendar non-open within my domain. If you don’t see this checkbox or it’s grayed out, it’s probably disabled in your Google Apps domain or organization.
Finally, copy the share URL and save it:
Now you can share this URL with the person you’re scheduling with. Instead of listing times you’re available, just send them the URL and let them see what works for them. They’ll be able to see your free/busy in their timezone and avoid asking you when you’re free. In my experience, this does two things:
- Reduces a huge amount of slow back-and-forth.
- Reduces a lot of mistakes caused by timezone miscommunications.
To make this even easier, you can make the URL easier to share. Create a shortcut in your keyboard settings, which expands into the share URL. Or, go to TinyURL and create a short URL, but give it a memorable name that you can easily type without looking up.
Too Much Openness Is Dangerous
But as I mentioned above, too much transparency can be dangerous in some cases. At the same time, some things you think are open might not be, or vice versa, which can cause its own problems. Here are cases in which I’ve seen calendars behave unexpectedly:
- Invisible automatic events. Events such as airline flights, auto-added by GMail from flight confirmation receipts, are visible to you but invisible to others. Get ready to be booked for meetings while in-flight. My solution to this is to access the event’s context menu and use “copy to calendar,” then save a copy of the event on my calendar. I delete the original.
- Public events are public. Watch out for events that someone’s explicitly set to public. I’ve had someone invite me to an event that they made completely public—such as the company’s all-hands call—and it showed up with full detail in the shared calendar link I sent to people. Whoops. Not a huge problem, though; a bit surprising but no harm was done. A small risk to take in return for saving tons of time scheduling stuff.
Use Calendar Slot Tools
If sharing a free/busy schedule doesn’t work for you, the next step is to use a calendaring tool that lets people choose from among time slots that are available. There are a lot of these available, many of them designed for salespeople. Those are useful for most people who are doing sales-like activities too, such as setting up investor calls.
Here’s a small list of such tools:
- Google Calendar appointment slots.
- X.AI—an automated AI “personal assistant.” I haven’t used this one myself.
- Mixmax—a GMail extension that inserts free slots into the email.
- Calendly—schedule meetings without back-and-forth.
- Assistant.to—similar to Calendly.
- You Can Book Me—ditto.
- Cirrus Insight—ditto, very salesperson-focused.
- Doodle Polls—set up a poll that everyone fills in to say what times work for them.
There are more; some have come and gone, such as Tungle. This category of apps and plugins will never die. It’s too useful (and yet too hard to turn into a real business).
There is bound to be one that works for you. If you’re scheduling a lot of calls and you’re doing it manually, you’re doing it wrong.
Use an Executive Assistant
As a last resort, use an executive assistant. Why do I say a last resort? I don’t have an executive assistant, but I have used one in the past. And no offense to all the great EA’s everywhere—and there are many—but adding yet another person into the mix doesn’t really reduce the net sum of time spent by all people involved. It just offloads one, or perhaps two, of the people involved. It shifts the time burden from someone whose time is extremely expensive, to someone who’s paid a lot less.
So, if your time is worth thousands of dollars an hour and you schedule a lot of meetings, sure. Use an executive assistant. But in my personal experience, adding an executive assistant may shield you from some of the work of scheduling, but you trade it for a different time expenditure: interacting with your EA. So although you may benefit from an EA, it won’t be entirely free. The EA adds some time burden themselves.
In conclusion, try to do as little of the above stuff as you can get away with. Ideally, share enough information that people can schedule things with you in a functional way. If that doesn’t work, use the most convenient and feasible alternative that does work. Apps like Calendly and similar are huge productivity boosters. Good luck scheduling, and let me know your favorite tips not listed here!
Update: important tip shared with me on Twitter.
Gwen (Chen) Shapira
@xaprb wrote tips for optimizing the time spent scheduling, But he missed the best tip: Have fewer meetings.