How to Schedule a Perfect Meeting

Matt Hubert / strategy / October 19th 2015

Almost everyone has meetings, sometimes despite their wishes. The lucky few only have an occasional call or in-person, but the rest of us often spend all day on the phone with customers. If you're like me and run a back-to-back schedule, you want to minimize your meeting snafus and focus on having as many productive conversations as possible.

Every no-show, reschedule, delay, bad call connection, or other meeting hiccup can create anything from a minor annoyance to a scheduling disaster, throwing off the rest of your day. It drives me crazy when I spend fifteen minutes of a half hour call just trying to get a screenshare working, not to mention the potential lost revenue from a cancel or no-show.

I've spent years developing a process that helps my calendar run like clockwork. It's saved me countless hours, and I'd love for you to give it a try and see what you think.

1. Propose a Time

All right, let's do this. It's time to schedule a meeting, so first thing's first, we need to pick a time. This is the hardest part, so I've broken it down into subsections with an example.

Rule #1: Usually the first person who offers times gets the better schedule, so be proactive and offer some timeslots. Don't wait! Your first email should include specific time slot offers, instead of unhelpful invitations such as "my whole Tuesday is open".

Rule #2: Offer half hour blocks. All meetings should default to 30 minutes unless you know for certain they will be longer (like an onboarding call). In that case, offer hour blocks, and be explicit that this meeting will take an hour.

Rule #3: Propose two slots per attendee. If you're meeting with one person, offer two times. If you're meeting with two people, offer four. Every attendee increases the complexity of scheduling, so save yourself an email thread from hell by offering lots of time.

Rule #4: Add a timezone! The world is big, and even if you're certain your contact's office is in San Francisco, that doesn't mean they aren't travelling in Taipei right now. If you're certain where your contact lives, propose the time in their timezone so they don't have to convert. If you have no idea, using yours is fine. Just don't forget one. If you're really generous you can even add both: "How is 12PM PT / 3PM ET"?

Pedantic Personal Request: Unless it's actually relevant, there is no reason to use Daylight Saving modifiers in your timezone. Pacific Time should be abbreviated "PT", Eastern Time "ET". If you get in the habit of writing "PDT" or "EST" and don't have the Daylight Saving dates tattooed in your brain (which you shouldn't, because they change every decade anyway), you'll technically be an hour off for half the year. Just leave it off and let your calendar do the hard work.

Rule #5: This also goes both ways: When somebody proposes a time with a timezone, pay attention. I've had meetings get rescheduled because somebody claims they thought the time was in Eastern instead of Pacific, even though I specified the timezone clearly in the email and invite. Always be aware of the proposed timezone, and if they don't propose a timezone and you're not 110% certain of their location, ask before accepting.

Rule #6: At the end of your time proposal, specify explicitly that "I will send an invite". Invites are they key to meeting success, and this clears up an entire round trip regarding how you will actually contact each other.

Here's an example, putting this all in action:   

Third party: "Matt, I'd like to introduce you to Sally, our head of product. She's interested in what you're working on and would like to learn more."

Matt: "Sally, pleasure virtually meeting you. (Moving to BCC)* I'd love to find a time to chat. How is 9 or 9:30AM PT on Tuesday the 22nd? Let me know and I'll send an invite."

Sally: "9AM on the 22nd works great. Looking forward to chatting more."

* In addition to proposing a time, move all non-scheduling-dependent parties to BCC. They'll thank you later.

Sweet, we've proposed a time. Let's get the details locked down.

2. Block Off Time Proposals in Your Calendar

In my example above, I got lucky and Sally responded accepting my proposal immediately. This basically never happens, so to avoid double booking, put two calendar events in your calendar called "TBD Sally" for 9AM and 9:30AM. That way you know you have an outstanding proposal, and don't accidentally offer it to somebody else.

3. Always Be Inviting

Calendar invites are the crux of business communication. The only invention greater than invites is the telephone itself. To remember when to use them, check out this helpful guide.

When should I send a calendar invite?
A) Always
B) Every Time
C) Upon Scheduling Each Meeting
D) All of the Above

It is crucial that you send an invite to every attendee of the meeting. This automatically blocks off the time in their calendar so they don't forget, as well as provides all requisite information on how to actually have the meeting. For more information about what actually goes in this invite, read on. 

4. Invite Details are King

The details you provide in the calendar invite are the ultimate source of truth regarding where, when, and how to meet. It is important that you fill them out accurately.

#1 Subject: This is ironically one of the less important pieces in the invite. A subject covering the basics is sufficient: "Bitmatica / Intro Call" is fine, just remember to include both parties' names in the subject. If everybody sent me an invite called "Bitmatica Intro Call", I'd have five hours of Bitmatica intro calls.

#2 Time: Pretty straightforward, just remember to add accurate start and end times in the invite, including the correct timezone. Their calendar will automatically translate your local times into their local times. Always make sure the length is correct: 30 minute meetings should be scheduled for 30 minutes, not the often default time of an hour. Nice feature: Most calendaring software lets you set your default meeting length to 30 minutes.

#3 LocationThis is the most important field in the invitation! This is the part where you specify how you'll actually meet. Provide a dial-in with a phone number and access code, or a link to GoToMeeting, or a physical address with floor number. Whatever it is, just make sure it's clear and complete. 

Good locations:

Conference Bridge: (415) 555-5555, Access Code: 12345
535 Mission St, 17th Floor, San Francisco Link:
Matt to Call Sally: (212) 555-5555

Bad locations:

Conference Line (what is it?)
Coffee (where?)
(415) 555-5555 (who is supposed to call this number? both of us? one of us?)
Our Office (where is your office?)
Empty (please don't leave this field empty!)

Pro Tip: After years and years of failed meetings, I have a mountain of anecdotal evidence that telephone is far and away the best communication mechanism. Many people request to meet over Google Hangouts, Skype, and other pure-VoIP solutions. I cannot count the number of times I've had to install plugins, failed to hear people over bad Internet connections, had their computer crash, or endured countless other glitches.

Telephone is still hands down the most reliable communication channel, so always offer a POTS-based dial-in first and foremost. If you plan on screensharing, it's often better to offer a screenshare link after everybody has joined the telephone line, that way you can troubleshoot in real time when inevitably somebody's computer can't see your screen. I often just read a link over the phone -- it works nearly 100% of the time.

#4 Description: This is where any details go, such as the agenda. It's very helpful to provide an agenda if you can, and for larger meetings with >4 attendees, I'd almost require it just to be respectful of everybody's time. You can also add semi-important details such as "Check in at reception on the 14th floor when you get here". Anything that can't be figured out three minutes before the meeting, however, should be part of the Location Field (such as "access code 12345"). Some peoples' calendars don't show Description as prominent as they should.

#5 Attendees: And of course, remember to actually add everybody to the meeting. Mark their participation as optional if they aren't required to be there. Nice feature: If you use Google Calendar and want to invite a Google Group to an invite, you can just add that group name, and all email addresses will populate automatically. 

5. Accept the Invite

When you receive an invite from somebody, make sure to click "Yes". That way the organizer knows you received the invite, confirmed the time, and are actually coming.

If your attendee doesn't accept the meeting and subsequently doesn't show up, half of the time they'll probably claim they never received an invite. Nine out of ten times that's probably not true and they just forgot, but if they accept the invite, at least you know they got it. And if they don't accept the invite...

6. Send a Reminder

This one is challenging for people with busy schedules. It's hard enough to actually attend all of your meetings, let alone remind everybody to show up. If you have an executive assistant, have them send out a reminder a day before confirming everybody's attendance. If you don't, try to go through your meetings a day before and find ones with unconfirmed attendance to send reminders to; it's possible your invites actually went to spam.

Interesting Anecdote: I've noticed a small trend where sometimes reminder emails actually cause more no-shows than normal. My theory goes that if you give somebody the opportunity to cancel the meeting, those previously on the fence will actually take this chance to cancel / reschedule because you're providing a convenient opportunity. Whereas if you say nothing, those on the fence will sometimes attend anyway instead of going through the effort to reach out and cancel. Take that for what it's worth.

For everyone, however, it's useful to set a reminder in your calendaring software between 3-10 minutes beforehand. That way you never forget.

7. T-Minus 5 Minutes Until Meeting Time. Man Your Email!

Here's one that drives me crazy. You're three minutes into a half-hour meeting and can't connect to the provided conference line. You email the attendees asking for or providing an alternate. Three more minutes go by. Silence.

When you're about to hop on the phone with somebody, watch your email like a hawk. Inevitably somebody will be running late, or their phone will die, or your WebEx link will break. When this happens, it's critical that you get the details squared away over email as if you were on instant message. Every minute you wait for somebody to respond is cutting into a thirty minute block that took you four months to schedule.

8. Meeting Time! Dial Whatever is in the Location Field of the Invite.

As I said before, calendar invites are king. The Location Field should specify exactly what you need to do or where you need to go to close this deal. Don't call their signature, don't call their cell, don't email them with your Skype handle, don't send them a request for a Google Hangout. Click the link or dial the phone number in the Location. If it's not there, somebody didn't follow Step 3.

In the (unfortunately common) case where the Location is empty or wrong, email them asking for their preferred dial-in information.

In the (still unfortunately common) case where they didn't follow Step 7 and don't respond to your email, do then try to call a number in their signature or whatever contact information you can find. A late meeting is better than no meeting.

In the (even still unfortunately common) case where they don't pick up, leave a voicemail for posterity, and forward them this blog post

9. Please be on Time.

Early is on time, and on time is late. So be early. If you're meeting in person, at least ten minutes early. I promise you'll first get lost and then end up in the longest security queue the lobby has ever seen, so be early.

Pro tip: When you're scheduling an in-person meeting, make sure to plan travel time to and from the location. Don't book two back-to-back in-person meetings at offices across the city. You'll never be on time.

10. Please End on Time.

The length of the invite in your calendar is the length that the meeting should run. Meetings run over all the time, but only go over time if both parties agree. Otherwise, offer to schedule a follow up -- and take the last three minutes of the meeting to schedule it in real time over the phone! That way you hang up with another invite on the calendar ready to go.

Also, if you accept an invite for 2-3PM, it's rude to say you have a hard stop at 2:30. If somebody proposes to meet for an hour and you can't or don't want to, ask to reschedule ahead of time. Otherwise they may waste their time preparing an hour of content for no reason.

Bonus #11: I'm Running Late and Need to Reschedule.

That's cool, it happens. Just email the organizer / attendees as soon as possible letting them know, and propose an alternate time to meet. If you're running late, email the attendees saying so, and let them know when to expect you. If you think you might miss more than 15% of the meeting, propose a time to reschedule instead.

If you can't make a meeting, please don't just decline the invite and say nothing. It's far more important to propose a new time than to just decline the invite. In fact, I rarely decline invites unless I said ahead a time that I will not be joining. Instead, if a time doesn't work for me or I need to reschedule, I simply don't accept until we've arrived at a time that works.

Note for Outlook users: Outlook supports a wonderful "Propose Alternate Time" or "Counter Proposal" feature, which is a great way to propose a time that works, except for one small problem: Google Calendar users can't actually see the new time that you propose! They just receive a blank email. So unless you have an attendance of 100% Outlook users, you'll have to stick scheduling over plain old email.

If you are the organizer, please do not cancel the meeting if you cannot attend. It automatically removes it from everyone's calendars without record, and now I can't easily reference the information to reschedule. Instead, propose an alternate time and reschedule the same calendar event. Avoid making new ones if possible because it's preferable to have a record of the same invite being changed.

Meetings sure are a lot more complicated than they seem! It may be a lot to remember, but if you stay vigilant and try following this process as closely as possible, you should end up with a far more productive calendar in short order.

As you can tell, I spend way too much time thinking about the optimal way to schedule a meeting. If you have any more tips on how to optimize meetings, we'd love to hear them!


Matt Hubert
Co-founder of Bitmatica. Super powers include catching falling objects and occasionally having perfect pitch.