Scheduling pro-tips for calendar management

For all the ways we depend on them, and how often we interact with them, it’s kind of amazing how little attention we tend to pay to making sure our calendars are working hard for us. We’ve seen tremendous innovation in project management software, task management software, and chat apps. But when it comes to the humble calendar, most of us are calendaring much the same way as we always have. 

Maybe it’s time to upgrade our calendar management. If you’re interested in learning what calendar management is and how to improve your calendar management today for increased productivity and efficiency, read on! 

What is calendar management?

Calendar management is the process of creating and scheduling meetings, accepting meeting invites, resolving conflicts, and using your calendar to optimize time management with the ultimate goal of best utilizing our most precious resource: Time. 

Most of us practice calendar management at least daily, weekly, and monthly. 

Daily calendar management tasks include: 

• Fielding meeting requests
• Scheduling and rescheduling meetings
• Resolving conflicts
• Keeping up with OOO and holidays
• Managing time zones and working hours
• Scheduling tasks and deadlines

Weekly and monthly calendar tasks include: 

• Setting day-to-day priorities 
• Implementing time management best practices
• Strategic work

How improved calendar management can benefit you

A well-managed calendar helps ensure you’re being strategic, efficient, and effective with your time. This can benefit you in at least five ways:

1. Accomplishment

A well-managed calendar helps you achieve your key goals. Your calendar should reflect your highest priorities and ensure you have time to devote to your KPIs while also leaving time for your other responsibilities. Plus, the less time you spend scheduling and rescheduling meetings unnecessarily, the more time you have to make meaningful progress towards your bigger goals. 

2. Efficiency 

Spending time manually managing your calendar when certain tasks can be easily automated is akin to using an abacus when Excel exists. Highly effective people find efficiencies to get rid of busywork and focus on what only they can do. Automating calendar management also reduces errors and decision fatigue, which we’ll discuss in more detail later in the post. 

3. Conscientiousness 

A well-managed calendar ensures nothing falls through the cracks and no one ends up feeling slighted. Research shows that conscientious people tend to be better liked, and tend to be better employees. Improving your calendar management shows that you’re conscientious by ensuring that everyone you’re scheduling with has a pleasant experience and that you respect everyone’s time and schedule. 

4. Communication

Studies have shown that good communication can make-or-break an organization’s effectiveness. Strong relationships between colleagues is similarly important. Making time for the meetings that matter ensures you’re doing the collaborating you need to do your job well. A well-managed calendar makes time for important meetings while also leaving room for the tasks you need to complete. 

5. Record-keeping

A comprehensive, accurate calendar doubles as we record of who did what and when. This makes it way easier to look back and see what went well and what can be improved in the future. How can you know if you’re using your time wisely without good records of where your time went? A comprehensive, accurate calendar makes it much easier to track your time and improve your time management going forward. 

Tips for improving your calendar management

There are tons of ways to find efficiencies in the way you manage your calendar. Here are four tips for improving your calendar management to consider trying today. 

1. Prioritize your time slots

Your time is your most valuable resource. Does your calendar accurately reflect your top priorities? One way to evaluate whether you’re devoting the right amount of time to the right activities is to use an Action Priority Matrix. 

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Use the matrix to score tasks, appointments, meetings, and anything else you might schedule based on their potential impact and then on the effort they require. 

Make sure your calendar has lots of Quick Wins (High Impact, Low Effort), a good amount of Major Projects (High Impact, High Effort), fewer Fill Ins (Low Impact, Low Effort), and the least Thankless Tasks (Low Impact, High Effort). 

Another way to prioritize your calendar is to regularly perform a lightweight calendar audit. This can help you: 

• Understand the percentage of your time you’re spending in meetings
• Rate how essential your meetings are
• Identify opportunities to spend your time more effectively

You can perform a lightweight calendar audit in five simple steps:

1. Find a representative week on your calendar

2. Print that week or save it as a PDF you can mark up

3. Rate each recurring meeting on a scale of 1-5 in order of importance

4. Calculate how much time you’re spending in meeting types 3, 4, and 5 and delegate, be more selective, and say no more often to those types of meetings

5. Start scheduling better by only accepting type one and two meetings

For more detail on these steps, check out How and why Engineering Managers need a lightweight calendar audit.

2. Protect your Focus Time

One thing everyone needs in their calendar is time to focus on important tasks. Our research showed that Engineering Managers saw more Focus Time positively impact productivity, speed, and revenue. 

Productivity gurus like Cal Newport and Nir Eyal argue that deep, profitable work requires chunks of uninterrupted time that are at least two hours, preferably longer. Chunks shorter than two hours impose unnecessary switching costs.

Gloria Mark, a researcher at the University of California, Irvine found that most workers are able to focus on a task for about three minutes before switching to something else (usually a notification). Another recent study found that the typical worker only has 11 minutes between distractions. Other studies show that office workers are interrupted about seven times an hour, which adds up to 56 interruptions a day, 80% of which are considered trivial.

These brief attention shifts can cost as much as 40% of your productive time. “Attention residue” is what researchers call what happens to your productivity when you switch tasks. It takes a long time (around 20 minutes) to get back to your previous level of efficiency before the interruption. ​​

Make sure your calendar isn’t too packed with meetings to focus. Many companies, including Clockwise, use a No Meeting Day to help protect focus time.

When Newport looked at 25 profiles of famously prolific, creative people he found they spent an average of 5.25 hours per day in deep work. Most of us, Newport argues in Deep Work, have about four hours of deep work in us per day. Newport himself works in two 2-3 hour chunks per day.

Here are three tips for getting more focus time in your day:

1. Swerve

Learn how to ignore people

Delaying your responses to incoming messages not only creates better responses, but more thought-out, thorough responses can also reduce the total number of messages required to get a point across. Ideally, you can spend less time on messaging total while still communicating as much as you need to. 

Instead of switching tasks to respond to messages immediately as they come in, try setting aside some time once or twice per day to respond to all incoming messages. This helps you stay in the loop while preserving your focus. You can also try scheduling multi-stakeholder, complex planning and strategy discussions rather than responding to messages as they pop up. It might be even faster to replace constant Slack chatter with Scrum standups. Lastly, try setting professor-style office hours for synchronous chats.

(Read more: Yes, I am ignoring you. Here’s why.)

2. Stack

Schedule your meetings back-to-back in your calendar

Every week, make a habit of taking a few minutes to look at your calendar and re-arrange events to maximize your (and your team’s) productivity.

For example, scheduling your meetings back-to-back can open up longer blocks of Focus Time. Wouldn’t you rather have one two-hour chunk of focus time than four 30-minute blocks between meetings when all you have time for are low-level tasks like email and Slack?

(Read more: Why focused work time is so important)

3. Schedule

Block off Focus Time on your calendar

Once you’ve created more focus time by setting up office hours and stacking your meetings, now it’s time to protect your focus time. Blocking out time in your calendar for focus helps signal to yourself and to others that this time is valuable. To maximize focus, make it clear that you’re not available to meet or be interrupted during your Focus Time. To take it a step further, put your phone on Do Not Disturb and sign out of your social media accounts during this time.

3. Automate calendar management

There was a time when nobody thought of an abacus as particularly manual. It was far more automatic than doing calculations without it. But then along came the calculator.

Today’s default calendar apps are a little like abacuses. They’re far less manual than paper calendars. But there are new calendar apps and extensions that can automate some of the manual work of calendaring. And just like automating data entry reduces errors, automating your calendaring can actually help you create a more optimized calendar than you could create on your own.

One way to start automating your calendaring tasks is to use a time orchestration platform slash scheduling assistant like Clockwise. When you want to schedule a meeting with one of your team members, the scheduler surfaces the best times for everyone based on everyone’s working hours, meeting hours, time zones, focus time, and more. For scheduling with people outside your organization, avoid the back-and-forth with Clockwise Links, a Calendly alternative, which uses AI and your preferences to show when the best time to meet is, not just the next time you’re free. When you let Clockwise help you find the best times to meet you reduce decision fatigue so you can use your brainpower where it’s needed instead of on menial tasks like scheduling. One more tip: Save more time on back-and-forth by allowing other users to modify your events. This one click has saved Nathan Feger, Director of Engineering at Schoology, a lot of time and hassle.

Clockwise also allows you to make your internal meetings flexible. It will automatically move your flexible meetings to the best time for you and your colleagues, no manual effort required. 

Clockwise also:

• Syncs your work and personal calendars
• Creates a shared team calendar with everyone’s holidays, OOO, and No Meeting Days
• Color codes your calendar
• Schedules travel time
• Integrates your calendar with Zoom and Slack for even more automated workflows

4. Use your calendar for task management

One way to make sure you have time for all your tasks is to schedule them on your calendar like any other appointment. Time blocking your calendar can help you stop neglecting your highest priority tasks, spending too much time on less-important tasks, and wondering what to work on next. Just ask ‍Elon Musk, Bill Gates, and Cal Newport, all of whom time block their calendars. To help you get started, check out these time blocking apps which can help automate the process for you. 

While you’re time blocking your calendar, you’re also timeboxing your calendar. When you schedule a task, you’re also deciding in advance how long you want to work on that task, which helps ensure you avoid Parkinson’s law. 

You can also supercharge your time blocking and timeboxing with time batching. This is when you group like tasks together on your calendar to reduce the amount of context switching you have to do in a day. So if you have a group of tasks that all have to do with accounting and another group of tasks that all require writing, schedule the similar tasks right after the other. 

If you’re an Asana devotee, Clockwise’s Asana integration is the easiest way to schedule tasks on your calendar.