Take control of your calendar

Tame meeting chaos and live with more sanity

Oct 05, 2020

“If there’s a common denominator in happiness, it’s that people want to control their lives.” -Morgan Housel

The tyranny of modern work is that we are tethered to our relentless calendars. We conflate busyness with productivity and importance, when it actually means you have less time to think. Less time to think means decision quality goes down.

To do our best work, we have to take back control of our calendar. Different types of work require different types of calendars. Do you do individual work, or do you work through others? In the words of PG, are you a maker or a manager?

As a PM, I am both. I need focus time to figure out what to build and when. I also need to work with others to validate the what, when, and how. For the latter, meetings are a medium for work (but certainly not the only one)!

Left on its own, calendars evolve from the open pastures of the maker to the caged world of the manager. As you become known, there will be more calendar demands, even if you’re not a manager. This is especially tough for makers like engineers and designers who need generous stretches of time to make meaningful progress.

Here’s a guide on how you can tame the chaotic beast that ravages your day. As an introverted PM, this has been key to my survival.

Identify what is critical

Audit your calendar and identify the job of each meeting. A meeting is critical if it serves a necessary job in improving outcomes. I have seven(!) types:

Planning (to set vision, milestones, and roadmap to reach them)
Standups (to get updates on weekly sprint)
Working session (to edit scoping and designs)
Features (customer interviews, kickoffs, handoffs, launch demos to ship quality things)
Leadership readout (to provide updates on milestones)
1:1s (to build trust, discuss personal and professional goals)
Interviews (to build a world-class team)

There are three things you can do with a meeting:

Cancel it
Improve quality
Edit frequency/duration

I find the first one most satisfying, but unless your calendar is littered with aimless meetings, the other two paths will be more commonly used.

Improve quality

Every meeting (unless social hour) should have an agenda. The purpose of an agenda is to clarify the end goal, the options that can be taken, and the roles of each attendee. Here’s an example:

Sometimes asking for an agenda shows the meeting isn’t needed. Here’s an example:

You: Thanks for setting up time, can you share an agenda so I come prepared?
Meeting owner: Oh, no need to prep, just wanted to pick your brain.
You: Ah ok, why don’t you ping me your questions when you’re ready? Happy to chat live if I can clarify.
Meeting owner: Ya I’ll think about it...
<meeting is cancelled>

Nothing wrong with bouncing off ideas, but if you’re going to spend 30 minutes together, you can spend 3 minutes preparing an agenda. Maybe the person just wants to hang out with you. That’s cool too. Call it a catch-up and you can go in with the right mental space.

Synchronous time is expensive, especially if you have many attendees scattered across time zones. The best use of synchronous time is to discuss important topics, make decisions, and build trust. They all benefit from focusing on what’s relevant and actionable using an agenda. Even better, send a pre-read (Loom, Figma, document) along with the agenda, and ask attendees to review before discussing. This allows you to dive right in, and reduces the likelihood of random tangents.

We are in Peak Collaboration. There are so many ways to work with others, let’s save meetings for when tools fall short.

Edit frequency / duration

An agenda will also help determine how long a meeting needs to be, and whether it needs to recur.

Ever notice the default Google Calendar invite is set for 1 hour? What would happen if the default started at 15 minutes? Or if it showed you the estimated cost of a meeting based on duration and # attendees? Meetings are gifted at filling the time and invite list they are given, so it’s important to be thoughtful, especially if it’s recurring.

A recurring meeting for which the only job is to update others assumes that people can’t be trusted to work autonomously. As the meeting owner, reflect on what you are most concerned about. Design your agenda to focus on these areas. As your confidence rises, consider lowering the frequency. As the meeting attendee, focus your updates on what the owner is concerned about. You will alleviate concerns by being consistent; if you don’t, then the meeting shall persist :)

As an example, we reduced our daily stand-ups to twice a week. People were thrilled, and productivity was, thankfully, not sacrificed.

Recurring meetings are useful when you’re on a tight timeline, and need to stay close to the progress of the work. They can quickly expose blockers or dependencies that save time for everyone. They’re not all bad, they’re just overdone.

Cancel with grace

It’s hard saying no. Unfortunately, when you don’t say no, you dilute your impact across all your commitments. People tend to be forgiving when you frame it that way.

Here are some graceful examples of saying no, and one CEO’s library of let-downs.

Turning people down is not the best way to start something new, but will be necessary as you progress in your tenure. If you’re worried about ruffling feathers, get your manager’s advice, and observe the culture around you.

Eliminate last-minute distractions

For a while, I found myself at the mercy of random invites (usually with no agendas) that were booked same-day. First, I tried putting DNS (do not schedule) blocks for thinking time. Before long, people started apologetically booking over it.

Then I developed my master stroke: a day or two before, I plan how to spend my time and create meetings with myself named after the task. The day of, my calendar is entirely booked. No room for last minute distractions. I don’t follow the bookings entirely, but they give me the air cover to pursue the most important things. I also end up with a reliable time log.

Here’s a snapshot of my (scary) calendar. Can you tell which are self-meetings?

If you find yourself answering the same question, write a document and share that instead. If you find yourself answering different questions in the same vein, set up office hours people can attend. Create ways to scale yourself.

Your calendar is yours to shape

My hack is a poor man’s version of the true ideal: shaping your calendar into the maker and manager blocks you need to do your best work. When I have <30 minutes between meetings, I end up walking to the fridge. When I have a few hours open, I’m more likely to work on something ambitious and impactful.

How long does it take you to shake your distractions and get into flow? Based on that, try to consolidate meetings and thinking time into uninterrupted blocks. Move things around to fill dead time. It’s not always possible, but it shows how you prefer to structure your time, and others will be more likely to work with it going forward.

Focus is in short supply. Lowering the friction to doing meaningful work should be more widely adopted. An uncluttered calendar does for you what an injury-free season does for athletes. Let’s stop getting in each other’s way.

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