How can I better manage my calendar?

Last week I made a call out to those who are on my email list (come join the fun!), asking them to submit a people or project challenge they were facing at their organizations (think “Dear Abby”). I promised to answer every single question, and to share my answer to one on Cresta Solutions blog this week. 

The Top Question

Dear Megan,

How can I get better at managing my calendar? 

-Unscheduled

My Answer

Dear Unscheduled,

I love your question because of its humility and universality. 

Plus, I could talk about calendar management all day, so thank you for asking! 🤓

Ultimately, you’re talking about making a change in your life, so let’s look at this through the lens of a change initiative. When considering change initiatives, whether on an individual or organizational scale, I like to use the ADKAR® Method. Developed by Prosci, a change management research organization, ADKAR is the acronym outlined below.

1. Awareness

Looking big picture, why is it valuable for people in general to manage their calendars well? Is it because calendars can be a valuable communication tool with colleagues, project partners, and family members? Is it because of professional expectations? Is it because you think people who manage their calendars well are more productive, less stressed, etc.?

Thinking about these questions might help you get at the idea of why you “should” manage your calendar well. This is an important starting point, and one that likely prompted your question. However, being aware of why one should do something doesn’t mean that you should do it. So let’s consider that next.

2. Desire

Looking at YOU, why do you have the personal desire to better manage your calendar? Why do you think that better calendar management is important for you on a daily tactical level? What difference would it make in your life? 

Having a well managed calendar can help reduce stress and increase productivity. It can mean that you don’t forget your colleague’s birthday for the third year in a row. It can help you feel less overwhelmed and more in control of your day. More in control of your life! 

As soon as you have awareness of why you “should” manage your calendar well and as soon as you truly desire to do so, go on to the next step!

3. Knowledge

Back to your question about how to better manage your calendar. While there are an infinite number of things to think about, here are a few high impact steps that I’d recommend:

• Keep everything in one place — If your work calendar is in Outlook, your personal calendar in Google Calendar, your family calendar on a board in the kitchen, and your bowling league’s tournaments noted in a brilliant array of sticky notes across your desk, get everything online in one calendar system. Link the pre-existing online calendars (to each other and in your smartphone) and put everything that’s written on dead trees into your online calendar. It’s absolutely fine to have reminders on the kitchen board and on your desk, but that should not be the only place where those events exist. 

• Schedule everything — Block out time for everything that you’re doing. 
  • By scheduling activities like grocery shopping and exercise, you increase the likelihood of getting them done. 
  • Also, rather than only adding a project deadline to your calendar, add project milestones and block off time to work on the various tasks. Did you hear that? Block off time to work on tasks. So no, just because you don’t have meetings tomorrow morning does not mean you’re “free” or “have nothing going on” or that you’re going to immediately respond to every arriving email. It means that you can block off time to efficiently do deep work. Your time is extremely valuable — protect it! 
  • If you’re really uncomfortable about blocking off all of your time, change the event setting from “Busy” to “Free” so that calendar systems and other viewers of your calendar can know if the time block is flexible or not.

• Thoughtfully review your calendar —
  • Review each day’s calendar that morning (or ideally the evening before) as a reminder of the coming day. Cancel what you can, reschedule what you must, and determine what you’re doing during any unaccounted for time — whether it’s project work, a quick task, or taking a break. It’s those unaccounted for half hour blocks between meetings that will eat up your day; be intentional about using them to be productive or to take a break, and then be proud of yourself for doing what you intended. If not, you’ll spend them chatting, looking through non-priority messages, or doom scrolling through social media.

• Zooming out a bit, consider reviewing your calendar for the week ahead (and even the month ahead, gasp!). Doing so helps you identify overly packed periods, stay on track with projects, and have enough time to plan for your colleague’s birthday.

4. Ability

Knowing how to manage your calendar doesn’t always mean you have the ability to do so. Here are a few tips to consider:

• Be relentless about your calendar — Every single time that a meeting, event, or appointment comes up, add it to the appropriate calendar immediately. You must be relentless about doing so. For instance, when you’re at the dentist’s office scheduling your next appointment, don’t just stick the appointment card in your pocket and leave. Right in that moment, put it into your calendar that you’ve linked in your smartphone. You can use the card to remind you to add it to the family calendar board, if you want, but in the end, your online calendar rules. 
  
  
• Build systems that create reality — If you plan to review your calendar every morning when you start work at 8am, but your supervisor keeps setting meetings with you at 8am, something’s got to give. You literally do not have the ability to manage your calendar well in this situation. You need to do the daily calendar reviews the evening before, start work earlier, or talk to your colleagues about protecting the first 15 minutes of each work day to get yourself situated. Manage your time proactively, communicate your expectations with others who have a big impact on your time, and build habits that make this change initiative a reality.

5. Reinforcement

Once you have your systems in place, make sure to periodically evaluate them. 

• How consistent are you? What’s helped you be consistent? 
• What’s detracted from your plans? 
• If external factors are impacting your ability to consistently manage your calendar, analyze them and respond accordingly. If you know you’ll be frequently interrupted, then proactively block out more time. 
• If you find yourself frequently drifting away from what you had planned to do, reflect on why and respond accordingly. Tweak your practices and systems over time to fit your preferences and rhythms, and celebrate when you have success. 

Ultimately, personal change efforts like this are about showing up for yourself. If you’re one of those people who would never want to let down a friend who was overwhelmed, show up for yourself in the same way to reduce your own overwhelm. Ironically enough, being relentlessly consistent in managing your calendar results in greater freedom. 

I hope this was helpful! 

-Megan

P.S. Interested in more tips related to time? Check out this short post "How to make time, when you 'don’t have time'"!

Megan E. Mozina
Founder & Principal
Cresta Solutions
she/her