Scheduling Savvy

time to schedule concept clock

Lesson two: Scheduling!

Back to the nuts-and-bolts, folks! In the spotlight today: scheduling.

This is the cornerstone of executive assistance: effectively managing your boss’s time.

How many of you thought, when I said, “scheduling,” that this would be a blog post about how to set appointments? Well, we will indeed go over best practices for that most basic and necessary of EA tasks, but the meat of this post is about how to own your executive’s schedule.

Step One: Prioritize 

Make a list of all the things your exec spends time, or should be spending time, doing.

Sit down with your exec on a regular basis and have her/him put that list in order from most to least urgent.

Step Two: Create and keep an accurate calendar / agenda 

Block out chunks of time for your exec to focus on those things, in your new prioritized order. The deep work, i.e. the most thought-intensive tasks, should come first. As the day wears on you can work in other necessary tasks that cannot be delegated.

Remember to schedule in things like lunch, travel time to/from offsite meetings, and to leave breathing room for your exec to brainstorm, write up notes after important meetings, etc.

It’s a good idea to make a list of all repeated meetings such as one-on-ones and staff meetings, and their default timing, with the understanding that they often need to shift to accommodate more urgent activities. I like to keep a default weekly calendar so I can see what it “should” look like before it gets changed to accommodate shifting priorities.

Things will of course come up, and the schedule will necessarily shift to accommodate important meetings, etc. But armed with your list of priorities, you will know better than to bump a high pri task for a lower pri meeting, etc. And so long as you stay on top of changing the calendar to reflect what actually occurred, you will have an accurate record from which to…

Step Three: Draw up a monthly “time spent” chart

This chart is your measurement for how closely you and your executive are sticking to that list of priorities from step one. And that is your measuring stick for effective time management, which is arguably the most important part of your job.

This is especially important in a start-up, where there are never-ending distractions and rat-holes for your exec to fall into. Because there are so many things that could be getting done, it is imperative that you keep the boss focused on what needs to get done, and what can be done only by her/him.

Unfortunately, there is no app (yet–attention entrepreneurs!) that will seamlessly tally up time spent in predetermined categories. So here’s the system I’ve worked up:

At the end of each month, I go through and code each calendar event by number, for example 1 = HR, 2 = Sales, etc. [Note: I don’t do this as I go because it would be confusing for outside guests.] Then I use GCal2Excel to create a spreadsheet and sort by number. Finally I make a pie chart of time spent by category and compare that to the ideal time spent chart I keep by my desk.

Now I have a visual aid to bring into my next 1:1 to show Bossman how closely (or not) he is keeping to his stated priorities, and we can troubleshoot as needed.

Once you’re doing all that, you’re ready to start scheduling some meetings.

Scheduling 101

Meeting requests can come from many directions (sometimes simultaneously). Your exec may ask you directly to set up a meeting, someone else may make a request to meet with your exec, or you may simply discover an email thread in which a meeting is mentioned. In any of the above cases, the next steps are the same.

You will need to identify:

  1. The purpose of the meeting, its urgency and importance

  2. How much time is needed

  3. Who is to be involved and what time zone they’re in

  4. What kind of meeting it is: In-person? Phone call? Video conference?

  5. Any special considerations

Once you’ve established all that, you can start looking at your exec’s calendar to find some good time slots. Keep in mind:

  1. If anyone on the call is in a different time zone, you’ll need to find something that makes sense for everyone, even if that means asking your exec if they’re willing to do an early morning or late evening call.

  2. If it’s an off-site meeting, plan for travel time to and from.

Aggregate a list of possible dates and times, and email it to all those who need to be involved. Other information you will want to ascertain at this stage:

  1. If it’s a phone call, who’s calling whom?

  2. If it’s a video conference, do you have the ID’s of everyone involved?

  3. Also, it’s a good idea to get a mobile phone number in case of technical difficulties.

  4. If it’s an in-person meeting, will food be involved? Do you know the dietary restrictions/preferences of those involved?

This is where Boomerang comes in handy. I click the box that says “boomerang in [2 days] if no reply” before sending. That way if I don’t get a response right away, the thread will come back to the top of my inbox so I can follow up with a revised set of options.

Once you have agreement on a day and time, I recommend sending a confirmation email before you create a calendar invite. For example:

CONFIRMED: 2/22 at 10:00am PST, Google Hangout Invite to follow

This gives your invitees an opportunity to correct any misunderstandings or typos before you create the calendar event.

If it’s an in-person meeting you will also need to include the address, along with tips on finding the place, where to park, and how much parking will cost attendees.

When you do make the meeting invitation, copy/paste the entire thread into the “details” section. Invite everyone involved, and consider whether or not you will need to reserve a room for this meeting.

Finally, you will need to follow up with external invitees the day before the meeting in question. Easiest way to do that is simply to do a search for the thread in your email and reply all with a quick message such as: “Just a note to reconfirm your meeting tomorrow at 10 am. Elizabeth looks forward to speaking with you then.”

The purpose of this is 3-fold.

  1. It brings the email thread to the top of their inbox, reminding them of the meeting and making it far less likely that they will simply space it.

  2. It refreshes their memory as to the purpose of the meeting, increasing the likelihood of preparedness.

  3. It gives them an opportunity to reschedule if that time is no longer convenient, saving everyone time and frustration.

If this is an important meeting, it’s a good idea to follow up with a thank you note, and to schedule in time for your exec to write up some notes and send any follow-up materials afterward.

These are my recommended best practices. Would love to hear yours!

Live bravely, work deliberately, and eat good chocolate.


#calendaring #Organization #scheduling

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