Defrag Your Calendar

Jason Craft
6 min readFeb 24, 2019

Managing your calendar is an important part of every tech manager’s role. It’s all too easy to allow meetings to pile up until you’re stuck working between them and not really accomplishing anything due to the constant distractions flooding your office. That’s when you know it’s time to take a step back and defrag your calendar.

It will be a difficult task, but it’s worth it in the end. You’ll be able to focus and enter a deep-work state of mind more often, enabling you to be much more productive. You’ll also find that most of the meetings that you’ve pushed around or canceled weren’t producing anything of value to you anyway.

If your calendar looks like this, you have a problem.

Your Calendar

I realized one day that, after running through my upcoming week’s calendar, my schedule was a daily barrage of interruptions that left me without any significant chunk of time to accomplish my goals for the week. I laughed about how much my calendar acted like an old platter hard drive after severals months of use. Bits of data were strewn here and there and slowed everything down. It was time to defrag.

Just like hard drive defragging, my goal was to group all my meetings together and leave myself at least half the day to focus on my important work. It was tough, I contacted dozens of people to coordinate and move meetings around, but at the end of it, I had solid chunks of time that enabled me to get my own work done. I was able to keep most of my meetings, and had enough time to get into the zone.

Tech management, much like software engineering, is an art form and requires space for creativity. Trying to focus with a fragmented calendar will make you feel like your head is constantly under water and you’re gasping for air. Your calendar must include time for entering a deep-focus state.

Think about how much time you need to really focus on getting a task done and don’t allow meetings to cut into that threshold. For me, I need at least an hour for a simple task and half a day for more complex tasks. If I’m thinking about new service architecture or how to refactor some existing pain points of the system, that’s when I need at least a half of a day to dive in and think through everything uninterrupted. That’s also what I consider to be highly valuable work and I don’t allow any meetings to disrupt that.

I also enjoy putting as many meetings on Mondays as I possibly can. That way, every week, I’m prepared for Mega Meeting Monday, and don’t plan for much highly valuable work to get done. Now, Monday isn’t long enough to house all of my meetings, but I was able to get the majority moved, which freed up the rest of my week to be placed into nice, half day chunks. Now I have the right amount of time for executing on my team’s goals and for coordinating the flow of information for the meetings that remain on my calendar.

I encourage you to go through the same though process and reflect on how the time during your week is spent. Are you letting too many people pull you in too many directions? Are interruptions taking over your professional space, leaving you without any recourse for stemming the tide? Are you attending meetings that should really be emails? Answer all of these questions and determine what really important enough to make it onto your calendar.

Everyone has 24 hours in a day, and you need to maximize that time. Don’t be afraid to refuse meetings. Not every meeting is worthwhile. In the corporate world, entirely too many meetings become soapboxes that people exchange places on to see who can bore the room the most. In the tech world, information is king and meetings that produce valuable outcomes by the exchange of information should be prioritized over meetings that produce nothing.

It’s also worth noting that you shouldn’t feel the need to know absolutely everything that goes on throughout the company. You are tasked with managing a small part of the grand corporate vision and you don’t control much outside of that. Too much knowledge will ultimately lead to seeing frustrating situations that you know you could resolve, but have absolutely no power to. You should refuse any meeting where you have little to no decision making power, because they often lead to these situations. Just because some other part of the company may be dysfunctional, doesn’t mean you should attend meetings that only serve to frustrate you over it.

When it’s time to start grouping your regular meetings, don’t forget about the mental setup and teardown time that accompanies them. Take into account a 5–10 minute window before and after all meetings on your calendar. If you have an hour’s worth of work time sandwiched between two meetings, you’re losing at least 10 minutes of that due to the office walking and context switching. You need at least a 1.5 scheduled hours of work time between meetings to guarantee yourself 1 hour’s worth of work time.

Once you’ve optimized the work time on your calendar into sizable chunks, don’t allow anyone to cut into that time. Your work will suffer if you do, because you’ll either work inefficiently during the day, or put in extra hours at night. You’ll be surprised how much better you are when focused on your tasks and not just waiting on your next meeting.

Your Team’s Calendar

Not only are you the boss of your team, but you are the boss of their calendars as well. You should regularly check in on your team’s calendars to ensure they have a productive calendar, just like yours. Ultimately, you answer for your team’s performance and if their calendars aren’t faring better than yours, then the team’s performance is hurting.

Most tech managers understand that software engineers need plenty of uninterrupted time to get in the zone and enter the deep work state that powers their best insights. Programming is a creative art and creativity simply cannot thrive while surrounded by distractions. The easiest way to note distractions your team is facing is to review their calendars and them defragged.

The vast majority of your team’s time should be dedicated to programming. If they are being pulled into every little tech committee and info gathering meeting, then you can be sure that their best work is being subverted, even if it may be by good intentions. It’s your job to reclaim that sacred time territory and give it back to the team. You don’t necessarily need to step in and be the bad guy for them, if that’s not how you operate. However, you at least need to set expectations for what their calendars should look like and help them achieve the optimal schedule.

I’ve explained my defragging system to the engineers on my teams and it worked well. Just telling them to not worry about attending every single meeting invite gave them the power over their own workday and boosted their productivity. You would be surprised how much better engineers work when they are in charge of their schedule. They take ownership and make the most of their days.

Another tip I’ve learned is to not allow unfettered access to your team members. If someone wants to schedule a meeting with an engineer, they need to justify the time they will be taking from the team’s productivity. Just because someone in marketing has a great idea for a new product, doesn’t mean they should be allowed to disrupt your team’s work. If you notice others in your company abusing your team’s calendar, then step up and kindly ask if they can stop setting meetings without your approval. That will add a layer of both visibility and vetting before the meeting gets set.

Work to make sure you manage you and your team’s time well. Build in time for deep focus and the results will speak for themselves.

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Jason Craft

Software Engineer at Realself with a penchant for writing about the process.