What To Do When Your Calendar Gets in the Way of What’s Most Important

Mar 28

When you open up your work calendar or list of priorities, do you feel a sense of overwhelm, exhaustion, or even dread? Do you feel like you can’t make time for what you need to get done? This is a very common problem, especially for leaders of large teams.

Common management advice is that you can’t figure out how to use your time most effectively without first knowing where you currently spend your time. They say, only once you know where your time goes can you do something about it. This seems to make sense, until you try it. It typically results in making minimal improvements like removing a meeting here or there and maybe delegating a thing or two. It’s almost never that helpful unless it’s used after or in conjunction with what I’ll outline below.

In this article, I will describe a shift in mindset away from reactivity and towards proactivity with how you use your time. I’ll also provide some principles and tactics you can use to more fully adopt this proactive stance.

The drawbacks of analyzing how you currently spend your time

When you’re unsatisfied with where your time goes and with your ability to get the most important things done, it’s typically due to some combination of:

Actual or perceived demands on your time from other people
Activities (including meetings) that used to make sense, but no longer do
Avoidance or lack of clarity of what’s most important
Lack of delegation

People on your team, your peers, and your boss all ask for or demand your time. Questions get sent to you directly in Slack or over text messages, 1:1 requests come to your email or administrative assistant, and new meetings pop up on your calendar — constantly. You have old meetings or responsibilities that no longer make sense since your role has evolved. Your team has grown, yet you are holding onto areas that could be delegated. You put multi-hour blocks on your calendar that say “Strategy Time”, “Actual Work”, “Please Ask Before Booking”, or maybe even you’ve stepped up the assertiveness by calling the blocks “Do Not Book”, yet people (including you!) book meetings over those blocks all the time.

Unless you do something about it, your calendar is always going to be something that happens to you.

Starting with what happened to your calendar as a baseline is going to leave you feeling stuck and result in minimal improvements. Maybe you can prune off 10% of your meetings, but will that really take you from being overwhelmed to consistently getting the most important things done? When you are so deep in what happened to you, it’s hard to see where you want to go. Analyzing where your time currently goes pushes your brain deeper into what happened to you and the status quo.

So if you’re not analyzing where your time goes and pruning from there, what do you do?

Objectives should drive your calendar, not the other way around

The purpose of your time at work is not to spend X% on activity A, Y% on activity B, and so on.

The purpose of your time at work is to achieve objectives, both large and small. As a leader your objectives are often your team’s objectives, which you contribute to. An objective could be to turn a company that is bleeding cash into a profitable one, to hire a director of infrastructure engineering, to set clarity on a yearly plan for your team, to fix red-tape in the expense reporting process, to give context to someone you are delegating an area to, or to launch a new revenue generating product feature.

Objectives can be steps that lead to a larger objective. For example, creating the first draft of a yearly plan for your department, which won’t drive impact to the company top-line results right away yet is a key step to putting your team on a path to do so. These objectives don’t always have to be easily measurable, for example your objective for hosting a skip-level 1:1 may be to build trust with someone important in your organization.

Every activity you do, whether it’s one-time or ongoing, is useful only in how much it drives forward important company objectives in an effective and efficient way. Activities can be done alone (thinking while walking, drafting a quarterly plan), in small groups (codifying core values with your leadership team), or with the whole company (presenting at an all-hands meeting).

Too often, what happened to your calendar drives what objectives get done instead of having what objectives need to get done set your calendar of activities.

The key is to not start with where your time currently goes, but to flip it and start with what the most important objectives are for you and your team to achieve. This—and this alone—should be the driver of what activities are on your calendar.

I often hear the phrase “be defensive with your time”. Unless you’ve determined your most important objectives and the activities you need to do to achieve those objectives, how will you know which particular times to defend? To know what time you most need to defend, you have to start by being clear to yourself what’s most important to get done. In other words, start by being offensive with your time, before you get defensive with it.

Effective leaders are THE decision maker for their time

A great employee (managers and individual contributors alike) is one who maximizes their positive impact towards the company’s mission and goals.

The company hired you (or, if you are a founder, your investors invested in you) to take inputs and make decisions about what objectives to drive and what activities you need to do to achieve the objectives. Colleagues who are asking for your time have little context on your priorities, how much bandwidth you have, and how you can most effectively drive impact. It’s on you to make the call where you spend your time. No one else can do it. Not even your boss. No one else has the right combination of breadth and depth of knowledge for your particular role to make a better decision on your time than you can.

Too often, leaders make themselves a second-class stakeholder of their time and make everyone else first-class stakeholders. This is evident when you see someone consistently book over their own weekly “Strategy Time - Do Not Book” calendar block. There is good intention behind a manager who values other people’s time above their own since unblocking your team is one of the best ways to help your team drive positive impact. Yet, this unblocking of your team can take away from what your team really needs, which is often for you to set a vision, set up a more efficient operating model, or make a key hire. All of this requires significant “thinking time” on your calendar.

Not only should you promote yourself to be a first-class stakeholder of your time, you should become THE decision maker for your time.

Think big on how to maximize your impact

Our current calendar, the routines we have, and perspectives we see our work through can place artificial constraints on how we drive impact, leaving us stuck in a local maximum. To help us think outside these artificial constraints, ask yourself these two questions:

The first is, “What are the most impactful things that can be done for the company right now?”

When asking yourself this question, don’t explicitly consider what you’re good at, your place in the org chart, or your current set of objectives since all of those constrain possibilities. Push yourself to really think at the company level or at least one or two levels broader than your current scope. At this point, don’t worry if it doesn’t seem like you can do anything to push forward the most impactful things you come up with. You’ll factor that in when you answer the second question below.

For example, if you’re an engineering manager within a much larger engineering org, push yourself to think about the most impactful things for all of engineering or what would drive the most impact at the company level.

If you’re a CEO, you don’t have a scope above you to expand your thinking into, yet you may find that you get boxed in by (explicitly or implicitly) asking yourself the question “What are CEOs of a company of my size supposed to do?” instead of “What will make my company most successful?” You are supposed to do what will make your company most successful, not do what another CEO did for their company.

Write down your answer to the first question.

Then ask yourself this second question, “How can my team and I contribute to what I identified with the first question?”

Your answer to this second question will likely have significant overlap with your current objectives/priorities. However, you may find that by thinking bigger and/or outside the scope of your role results in some new ways you and your team can drive even more impact for the company.

I encouraged a VP of Engineering I was coaching to use this approach and it caused them to uncover a way their engineering team could help another department drive forward a top company goal that they originally thought engineering had no influence over.

Take the time to set your objectives

To figure out what the most important objectives are for you to get done and how to get them done, you need to be conscious about setting time aside to think this through.

It’s useful to have two timescales for which you determine your objectives, for example: weekly and quarterly. This timeframe differs by company, role, and other factors, so pick ones that seem best for you and you can modify later as you iterate on your process.

Every week at the start or end of the week, create a personal planning calendar event where you determine the most important things for you to do in the week. This is your most important event of the week. Nothing can get in the way of this. If an urgent issue or an immovable event with external stakeholders comes up, move your personal planning event, but do not cancel it.

For the longer timescale, let’s say quarterly, you can set a monthly personal planning event where you think of what the most important objectives are for you to do in the quarter.

Then you can rank or prioritize these objectives. From there, you can determine which activities are necessary to drive the most important objectives. For example, a 30 minute meeting with the Chief Product Officer to pitch a new direction on a proposed product launch, a meeting with your leadership team to get input on how to improve the performance management process, or 30 minutes alone to rehearse your part in a company all-hands meeting. These activities then take priority over every other activity.

“If I did this and nothing else…”

One powerful technique to keep you focused on how you can drive the most impact is to take the most important objective on your list and say “If I completed only my most important objective, and nothing else this week, would that be better than completing everything else but not my most important objective?” If your answer is “no”, then ask the same question for your top two objectives compared to everything else. You may be surprised to find how often it’s more important for you to get just one or two things done instead of doing dozens of other things. With the knowledge that comes from asking yourself this, think how much easier it will be to get the most important things done!

Find a way to remind yourself to focus on completing your most important objectives over everything else. A simple, effective way is to create a post-it note and stick it on your monitor. Put whatever resonates with you to remind yourself of this, for example a post-it note that changes week-to-week like “The most important thing is to hire a VP of Product”. You can also use a post-it note that stays constant reminding you to always focus on your highest priority objective. Some real examples from people I’ve coached are: “the highest leverage thing”, “the one thing”, or “be offensive with my time”.

If your most important objective for the week is to create a quarterly plan for your team, you might set a two hour block on Monday morning to create a draft plan to show to your leadership team on Tuesday. If your kid gets sick on Monday morning and you need to take them to a doctor’s appointment, the automatic (reactive) tendency is to skip your two hour block so you can make all your other Monday meetings (because those meetings have more attendees than just you). However, to maximize the positive impact you have on the company, it’s very likely that you should take a proactive stance by moving, canceling, or not attending some other Monday meetings so you can move your two hour block to later in the day to make sure you can complete the draft of your quarterly plan.

Getting input from up, down, and across your organization

When you become the decision maker for your time, it’s still important for you to get input and information from elsewhere in the organization (and even outside the organization from advisors, customers, etc.).

The big shift here is: instead of having people give input directly into what objectives you take on or to what activities you do, you treat their input as information that you can use to determine which objectives you and your team can take on to drive the most positive impact for the company.

If you have a manager, it’s important to align your objectives and their priorities with your manager, especially if your objectives end up being different from what they proposed. Good managers will typically be happy if you come up with something you or your team can do that’s even more impactful than an original priority.

You may wonder, “If I’m the decision maker for my time, how does that relate to my manager’s staff meetings which I have to attend?” Your contribution to your manager’s staff meetings is typically an important activity to drive impact at the company. If you find that staff meetings don’t seem to be very valuable, you could be missing a perspective that your manager has on how the staff meetings are valuable and/or your manager may be missing your perspective on how the staff meetings could be more valuable (in which case you can share your perspective with them on how to improve the meetings).

Delegating your objectives

Once you’ve determined the most important objectives for you to achieve, you can go through the exercise of figuring out which objectives or which parts of those objectives can be delegated to members of your team. I recommend reading this article on the 3 Delegation Traps to help you identify additional things to delegate.

Other tactics to help get the most important things done

Here are a few additional tactics you may find helpful:

In most cases, a manager needs to think very differently from an individual contributor, but you can learn something from your time as an individual contributor. If you were a software engineer, your most important output was the code you wrote. What would your manager say if you wrote no code for the week because you were doing other things instead? If you were a customer support specialist, what if you answered no customer tickets for the week? Your manager would probably tell you to stop doing all the other stuff and do the most important part of your job. Remembering this analogy can be helpful as you’re figuring out what your calendar should look like.

I’ve found it helpful for myself to create a task list that is roughly ranked in order of priority. Then I add another section for things that I consciously decide not to do this week (often they are important, non-urgent tasks). Then whenever I feel the urge to do something that I consciously decided not to do, I re-read my task list and remind myself “yes, I made the conscious decision not to do this task this week”. This relieves stress by helping keep this important, non-urgent task off my mind for the week.

At times, I’ve shared the above list with peers and my manager for feedback. I’ve also used a peer in a different department as an accountability buddy.

Set calendar events for specific objectives, not just a blanket “Strategy Time”. This makes it less likely for you and others to book over it.

Google Calendar has an auto-reject setting for invitations. Block time on your calendar for your most important objectives with auto-reject on. I’ve found that this prevents people from trying to book over my events. I’ll admit it can also be oddly satisfying to see someone try to book over an important event on your calendar and see Google send an instant rejection.

Batch checking email into just a few time periods per day. Turn off all email notifications on your phone and laptop.

When you are working on something, turn off Slack and close out of email. This seems almost too obvious to write, but I see this come up often with leaders when I begin coaching them. Your team can go two hours without you. And if they can’t, then your most important objective might be to make it so they can. You can also have a different way for team members to contact you in an emergency, for example by calling or texting you instead of direct messaging you on Slack.

Put your phone in another room. Take Slack and email off your phone completely. Turn your phone display to grayscale to make it less alluring. I’ve done all of these when appropriate. Do whatever makes sense for you. One CTO I coached would lock their phone in a specially designed box that would only open after a certain period of time. It can be easy to fall into the trap of “I should be able to have email on my phone and not check it constantly”. Don’t feel bad about not being able to stop checking your phone. It doesn’t matter how you stay focused, as long as you stay focused.

Summary

Instead of starting by analyzing where your time goes, figure out what is most important for you or your team to do to make the company successful and use that to determine your activities. Have your objectives drive your calendar and not the other way around.

Stop being a second-class stakeholder of your time and promote yourself to become THE decision maker for your time. No one else can decide where your time should go more effectively than you can.

Create personal planning events where you plan out your objectives and do not cancel these events. Think big when determining what objectives you can take on to make your company as successful as possible. Do whatever you need to in order to minimize the distractions that keep you from driving your most important objectives.

All of this will help you move from being reactive about your time to proactively maximizing your positive impact to your company and its mission.

Insight and Action

Answering these questions will help you generate insights and actions that are specific to you, which will help you get more of the most important things done.

What are the 1 or 2 biggest insights you got from this article?
What actions(s) will you take based on these insights and by when will you do them?
What “quick win” tactic can you implement right now to help you make consistent progress each week on your most important objectives?
Which timescale(s) will you use for your personal planning events? (weekly, bi-weekly, monthly, quarterly, etc.)
How will you remind yourself to stay focused on your most important objectives/priorities?

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Kevin Rice