Conquering Your Calendar

While I intensely dislike the slogan “Work smarter, not harder,” the phrase resonates with me when it comes to managing your calendar.

If you have ever felt like your calendar leads you around like a dog on a leash, or you’ve felt a rush of dopamine because you figured out how to squeeze another meeting into an overloaded schedule, today’s post is for you.

Your Ideal Calendar

If your calendar is overflowing with meetings and you have no “productive” or “think” time, it’s time to remodel. I choose that term deliberately. This is not canceling a meeting here or there. This is tearing it down and rebuilding it as you want it to be.

To do this, forget everything about your existing calendar structure. Forget the constraints you know (or believe) are non-negotiable. If you had the power to rebuild your calendar from the ground up however you wanted, how would you design it? Consider the following:

  • How many blocks of uninterrupted “focus time” do you need in your week?
  • What do you want your “working hours” to be? What’s the earliest meeting you’d like to have? What’s the latest time of the day you’d have an appointment?
  • How many breaks do you need in a day? Where would you slot them? Do you have a dedicated break for lunch?
  • At what time of day is your energy level highest? How would you arrange your schedule to take advantage of this?
  • Do you want to batch 1:1 meetings together on a single day or spread them throughout the week?

In particular, ensure you have two or three dedicated “focus time” blocks on your calendar. It will never happen if you don’t proactively block this time and treat it as sacred. A word of caution on this. If you are in 6-8 hours of meetings per day right now, you will have difficulty permitting yourself to block out as much focus time as you need to succeed. If you struggle with this, find a coach or an accountability partner to challenge your thinking. 

My ideal calendar as a Product Management executive
My ideal calendar as a Product Management executive

Assess Your Current Calendar

Chances are, your ideal calendar looks radically different than your current one. It may feel like a bridge too far. Before you remodel, do some detective work on your existing calendar to identify opportunities for change.

Put each meeting under a microscope. Ask yourself the following questions:

  • Is this meeting a valuable use of time? Rate the value of each meeting on a scale of 1-5.
  • If you scored the meeting low, how can you change it?
  • Should you be attending this meeting?
  • If not, why are you attending?
  • Do you need to delegate attendance to someone else?
  • Do you need to ensure the meeting owner publishes outcomes to people who need to be informed?
  • Is this meeting the right length of time? Can it be shortened? Can it happen less frequently?
  • Could this meeting be replaced with another mode of communication (Slack, Email, Video Message)?

If you are ruthless in your evaluation, you will find many opportunities for remodeling.

This is an excellent opportunity to re-evaluate your 1:1 meetings with your direct reports. See my 1:1 101 post for tips on how to make this time more effective. I shifted that time to mentoring and coaching and reduced the frequency from weekly to fortnightly.

Many meetings have too many participants. This can indicate a FOMO (Fear of Missing Out) culture – people fear they won’t know what decisions were made unless they attend the meeting. Whenever I see this, I ask the leader to reboot the meeting, limiting it to the required participants. I ask them to commit to publishing decisions and action items from the meeting to everyone who wants to be informed. I ask them not to accept additional participants who don’t need to be there but want to “listen in.” (Pro tip – Outlook and Gmail both have settings where you can prevent participants from forwarding your invite to someone else).


With your ideal calendar and your existing analysis completed, the next step is negotiating your current calendar with the desired state. In their book Make Time: How to Focus on What Matters Every Day, Jake Knapp and John Zeratsky have a tactic they call “Bulldoze Your Calendar” (this is tactic 10 of 87). Imagine a mini bulldozer driving around your calendar, freeing up the space you need.

  • Move meetings over to other slots.
  • Eliminate meetings you don’t need to attend.
  • Shorten meetings or move to a less frequent cadence.

Have courage. You’ll be surprised how many people will shorten a meeting or shift to accommodate your schedule if you take the time to ask and explain your desire to be a more effective leader.

If you can’t make this happen in the coming weeks, I invite you to jump ahead four weeks. While the near-term may be booked solid, you probably have more flexibility when you start looking out four weeks or more. Draw a line in the sand and remodel your calendar beginning at that point forward. You’ll be there before you know it.

If you haven’t already done so, I also recommend you enable short meetings, giving yourself and your colleagues 5-10 minutes between meetings, so you have a few minutes to collect yourself. 

Putting It Into Practice

Here’s a quick list to put these techniques into practice:

  • Build your optimal calendar from the ground up, including dedicated blocks of focus time.
  • Assess the value of your existing meetings.
  • Look for opportunities to eliminate meetings, reduce the number of participants, or reduce the frequency.
  • Remodel your calendar to align with your optimal calendar.
  • Enable short meetings.
  • If your next few weeks are set in stone, put this in place beginning four weeks from now.

You have much more control over your calendar than you think, but it requires courage, a willingness to say no, and a touch of ruthlessness when you see poor meeting behaviors. The impact on your productivity and your sanity will be well worth it.

Schedule time with Josh.

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