Avoiding “Death by Calendar” as an Engineering Manager

It’s Monday and you’re opening your calendar with dread. Whilst pouring a cup of coffee you prepare yourself for the work ahead of you. Or nay — it’s not work anymore. It’s a goddamn RACE from 9 am until the day is over. Tuesday doesn’t look much better. You sigh and realize you won’t make it to the gym today either. Now you’re at the point where you’re wondering when you’ll even have time to go to the bathroom?

Sounds familiar? I’ve been that manager. I’ve been the manager to that manager. How do you break the cycle? Here’s a few learnings from the trenches.

First, a bit of tough love and words on Why to build up strength, when it feels overbearing to break the vicious cycle.

As a leader you are a role-model

You likely go to work every day and tell your engineers to say no, to prioritize, to avoid context switching, to focus. Consider how your actions matches your words.

You’re not that important, and everything is not equally important

The world does not rest on your shoulders. Most teams will be fine without you, short term. If what you’re doing is roaming around from meeting to meeting, you’re probably too stressed to provide any real true value anyway.

Your job is to ignite change

How much of a change maker are you able to be if what you’re mostly doing is scattered work, running around to catch up on context? And frankly, as a manager you’re measured on how much change you’ve been able to accomplish (I hope!) — not how busy you’ve been.

You are not shackled to your calendar

The calendar is a tool to help you plan your time. Not to have your time planned for you. So cancel. You’re a grown-up. There’s a button for it. Use it.

So how do I do it practically? Here’s how I’ve approached it.

Save first, then spend

It’s easy to think you’ll do deep work “when time permits”. How often do you end up with a free 4 hour slot? Didn’t think so. Treat your time the same way you treat your salary. Save first. Book recurring slots in your calendar for yourself. Consider what time of day, to ensure that your brain is in the best state to accomplish something. For example, Monday morning is better suited for me than Friday afternoon.

Earmark time and NAME it to make it clear what you’re compromising if cancelling

Protect your time

I name the slot with what I will focus on. It’s a way for me to protect that slot from myself and others compromising with that time. When I had a generic “Focus time” block in my calendar I would often get asked if people could schedule something over it. And I would always say yes. It doesn’t happen as frequently when I name the event “Strategy presentation” or “Recruitment pipeline work”. It makes it clear to me what I will be sacrificing when asked to use that time for other things.

Establish your baseline

I try not to muck around too much with my 1:1s. Keeping that schedule is a foundation of trust with the people that you manage. That said, not all people need to have equal priority in your work life. Some of my directs I need 1 hour weekly with, because they or their team are going through change. Others might only need 30 minutes every third week with you.

Set your goals

Compare your goals to your calendar. Where does change need to happen? If the most important thing you can do this quarter is to turn around a dysfunctional team, your calendar should reflect that. If those two are not aligned, you have some adjusting to do.

De-frag and Communicate

Remember the first paragraph about being a role-model? A couple of phrases to practice:

“Hey team, I really want to focus on getting X done this week. Therefore, I will down-prioritize Y and Z and won’t be in those meetings. Let me know if you need me”.

“Hi, I got this meeting invite. How urgent is it? Can we solve (part of) it async and I’ll respond later?

“Hi, I got this invite. Am I needed in that meeting? Can I provide my input to you and skip?

This is you actively role-modeling prioritization in action. When your focus time is on — mute your notifications, and don’t check emails.

Remember

You might not save this week. But start protecting slots three weeks from now.

Maybe you roll your eyes at this point, thinking “well, this is not possible in my situation”. Yep. Sometimes it’s just calendar management. But you’re right, it might also be that your calendar dread is a symptom of something else, where defragging won’t work. More to come on that in another post.