The Engineers Guide to Calendaring For Productivity

10 calendaring techniques you can apply today to maximize your impact

Hey Y'all, excited to share all of my calendaring best practices. Many of these are trivial to implement and will yield immediate value in how you optimize your time. Let me know in the comments what other techniques you are using!

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Calendar management is a skill just like writing or coding that if mastered, will enable you to stay more productive.

These are techniques that I use for calendar management. For each technique I’ll provide what it is, motivation/example, and where possible/needed screenshots and examples.

Disclosures: I have Executive Assistance support. I still leverage these tips and so does my EA and they will be beneficial for all technical staff. However, having EA support makes cross-functional management and proactive scheduling conflict resolution significantly streamlined.

Reference Calendar

We will start with a week view, that we will reference several times through this post. I will post each day vertically so it’s clear to read.

Monday

Tuesday

Wednesday

Thursday

Friday

Top 10

1. Almost nothing should be open - Make it clear to your stakeholders when you are available, by booking every minute you work. You are the most important person, so book the most time with yourself. In the example above, we’re aggressive but for you, you may want to make available time each day. I would suggest optimizing for making yourself available when you are less productive (allowing you to focus productivity on creative/technical tasks). Book your personal time, activities, travel/commute. Because you are mostly unavailable, people will book over focus blocks but will most likely reach out first, allowing you to consider alternative times more akin to your working model.

   1. I use subject line tags like like “Not Available” (inflexible except in emergency’s or VP+), Focus Time (“talk to me first”), or Work Block. Ideally when

2. Make your Calendar Visible Internally - Yes, I know there are privacy concerns. But having your calendar visit will result in less people overbooking your most important time. When you say not available, it’s a stronger signal then a calendar that just shows the word private. Private calendars prevent schedulers from optimizing focus time.

3. Propose A New Time That Optimizes for Both - If sometime sets up a meeting that doesn’t work, propose a new time (built into Google calendar). One thing I do (esp for 1:1s), is optimize for “back to back” meetings. If someone books over a focus block, ill look for when they are in a block of 1:1s and suggest a time before/after it. Then ill message on slack mentioning how i found a time that may be less interrupt. Don’t underestimate the power of the Slack follow up.

4. Meeting Batching - One of my favorite techniques is batching like meetings. I try to stack like meetings (e.g., have all 1:1s back to back same day or program meetings). This helps reduce context switching. If my primary program is DDoS, then let’s have all meetings on the same day, ideally consecutively.

   1. For program meetings you don’t own, ask the organizer to stack them with other program meetings (e.g. if im on a program with 3 track syncs, and a leads meeting, ill ask to batch them during the same work block).

5. Meeting Colors - This is an easy one, but helpful. I color my meetings based on 1:1s, focus, program meetings, Business reviews, etc. A rainbow colored day tells me I’ll be probably fragmented and heavy cognitive load. Single colors or long streaks of the same colors, good sign of low cognitive load and context switching.

   1. Example Colors

      

6. 5 Minutes After - Google has this feature called “speedy meetings” when meetings end 5 mins early. No one follows it, meetings run up to the hour. But if you start your minutes 5 mins after, almost no one will be late and you’ll get a chance for a stretch and a bio break if you are in back to back meetings.

7. Super Batching - This is a new experiment I’ve been running with EXCELLENT RESULTS. I call it super batching. 1:1s, program meetings, and other meetings I have any scheduling power over, I batch Tuesdays/Thursdays every other week. This means 2 weeks a month I know I’m going to have a pretty heavy meeting day Tue/Thur. But the other weeks, I’m in very little meetings. As a result I have a fair bit of focus times every other week to really hone in on deep work.

   1. Another three dimensional chess move - Make Monthly’s, Bi-Mont’s, Quarterlies, all fall on the same Thursday. That way they don’t scatter your low meeting weeks.

8. 1:1 Super Tips - For any 1:1, ask if you can share ownership so that you have some flexibility in scheduling. Wherever possible ask yourself, could I meet with this person less (either frequency or length of meetings). Ask your 1:1s to make sure to try to get agenda topics a day before you meet, that way if there is nothing to cover, you can cancel. If my 1:1s have empty agenda and I don’t have topics, I suggest a slack ping and a cancel.

9. Be Flexible For Where It Matters - None of these rules should be applied without context. When you are meeting with a c suite executive, an expensive cross-functional meeting with lots of stakeholders, and 1:1s with senior leaders, optimize for their schedules. An executive’s calendar is built out very far in advance, and rescheduling meetings with a lot of attendees can disadvantage folks who may have conflicts or have to adjust other meetings to accommodate you.

10. Book Full Days or Weeks - I do a lot of swarms and hack-a-thon style work blocks. I find for me, having a full day or two of no meetings or interrupts allows me to get a lot more work done, especially if it’s technical/complex work or requires a lot of creative thinking. I usually do this weeks out (i’ll try to carve a full day or two, marking myself as not available, and treating it as a P0 priority to deeply focus on a problem set).

11. Bonus Experiment - Almost No Reoccurring 1:1s - I tried this in Q2, it went pretty well (considering it again). Cancel most reoccurring 1:1s (sans essential) and ask to move to ad hocs. This is a bit of a forcing function for folks to really prepare a worthwhile agenda. Its also a chance to practice async communication and “just hop on a for a quick sync” style collaborations, which more mimic how it used to be when we were in office and could pop by a co-workers desk for a ~5 mins syncup.

Band Practice - Apply 3 Hacks

This week, I want you to implement the following techniques:

1. Fully book your calendar, so that each hour has something scheduled. If you need to have flexibility, you can mark 1 hour to 90 mins per day for “open for meetings”.

2. Adjust any meetings you own to start 5 minutes after and end ‘on the hour’.

3. Determine your “meeting categories” and color code your meetings. Are you seeing a lot of rainbow days, try to adjust things so that your colors are in larger blocks or more single color days.

Band practice is more fun with friends, so ask a colleague to also try some calendar hacks Let me know in a few weeks if this was helpful in creating more focus time.

S.B.