From Burnout to Breakthrough: Master Your Calendar

Feeling like your calendar is running your life? In this episode of Executives Unplugged, executive coach Keith Cowing shares a battle-tested playbook to flip the script. Learn how to audit your schedule, spot energy-drainers, and make small but powerful changes that double your strategic time without burning out.

You’ll discover:

How to run a calendar audit step by step

The “two truths and two pies” exercise

Simple psychological tricks to protect your focus

Why just a 10% shift can double your momentum

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Chapters:

(00:00) Intro — Is your calendar running your life?

(00:51) The Tetris analogy: when meetings feel like blocks falling

(02:20) Step 1 — Calendar audit explained

(04:06) Step 2 — Analyzing results: the two pies and two truths

(07:53) Step 3 — Making changes and mindset shifts

(09:04) Protecting your focus like it’s a meeting with the CEO

(11:11) Setting boundaries and saying no with confidence

(12:48) Closing thoughts — audit, analyze, shift

Full Transcript

Keith Cowing (00:00)

Do you feel like your calendar manages you instead of the other way around? No breathing room, no opportunity to work on that big strategic project so you can really move the needle and achieve those goals that you have for the quarter. I see this all the time and if you don't fix it, the costs are huge. You either end up missing out on huge achievements that you could have accomplished or you

yourself in the process and you end up burning out.

and we don't want either of those two to happen. So today, I'm running through a playbook that I run frequently with CEOs and CPOs and CTOs, and it completely changes how you think about your relationship with your time and your calendar, so that suddenly you can have the freedom to get those things done that you need to get done and stay sane at the same time.

Keith Cowing (00:51)

This is Executives Unplugged. I'm Keith Cowing, your host and executive coach, and today we're talking about managing your calendar and how you can flip the script to take more control back than you realize you can. I got a text the other day from a client while I was at the gym and had my AirPods in, and she's an executive at a private equity-backed company, reports to the CEO. She has a very busy schedule, and she took a screenshot of her calendar and sent it to me.

and said, is this what everybody's dealing with? When am I supposed to get my work done? Siri read the message to me and said, your client sent you a long message and an attachment of a screenshot of a video game And this was a pretty good analogy at the end of the day. Now, Siri is not the most intelligent AI and joking on that aside,

The analogy of a video game to your calendar is actually an apt one. That's what it feels like to many of us. It's this game of Tetris. These blocks are falling from the sky that we don't control. We're scrambling to try to fit them in, to try to catch up, and if we don't, the screen fills and it's game over. So how do we change that? I'm gonna walk you through something in 10 minutes and it will help you completely change how you think about this, and at the end, I've got some psychological tricks to be able to change your relationship with your calendar.

And I've seen this drive huge results with only small adjustments in your schedule and in your work. So let's jump in.

Step one, very simple, do a calendar audit. Go through the past two weeks of your calendar and identify every single meeting and then open a spreadsheet. I do it in Google Sheets, but you can use whatever you'd like. And in the spreadsheet, you want a column for the following things. One is meeting type. Is it a one-on-one? Is it a small group? Is it a large group?

Then attendees, just list generally. Is this your team, you and your boss, the board, you and direct reports, et cetera. Then remote or in person, if it's relevant, if all of your meetings are remote or all are in person, this isn't relevant. Otherwise, mark that. Then the goal, what was the goal of the meeting? Then these are the key ones. One column that says energizing or draining.

And I want you to list for every meeting whether you left that meeting more energized and you had more energy or drained and you had less energy. And then the last one is needle mover or process. Is this something that really moved the needle and changed your strategic goals and outcomes? You achieved something and closed the deal with a customer. You got a new hire on board that's going to change your life. You got a new product out the door. What was that? Or...

Was it just process? It's something you feel compelled to do, that you have to attend because it's part of your job. But when you look at your goals for the quarter, none of them moved as a result of this meeting. And that's all you need for step one. Go through the last two weeks. If it's an anomaly because you're at a conference and it was only one week a year that you're at a conference, then pick a different week. And if you have to, can just use one. I find that using two weeks gives you a pretty good pattern. But one is actually typically enough. So go through your calendar.

Get this in and then we're ready for step two.

Keith Cowing (04:09)

Now it's time for step two, which is to analyze the results. And there's two things that I want you to do. So as you read through this and you start to notice what the patterns are, I want you to look for two different things. And the first one is put together a pie chart and you're going to have a now pie chart and then a goal pie chart. And for the now pie chart, the trick is finding what the different components are. You'll use your best judgment to put in how you're spending your time.

And this isn't about getting exact. So don't worry about if it's 10 % or if it's 15%, just estimate, but create a pie chart and you can either just do it by hand or roughly, or do it right in the spreadsheet that you're in. And when I was a head of product, for example, I would put in this pie chart, how much time am I spending outside the building? Meeting with customers, meeting with industry partners, et cetera, to really understand what's going on. How much time am I spending with my team? How much time am I spending with cross-functional teams or with the executive team?

How much time am I spending on vision and strategy and storytelling? How much time am I spending on operational projects? How much time am I spending on recruiting and bringing on new team members? And those things will change. Sometimes you go through flows of trying to find the roadmap and really going out there and being strategic and understanding what's going on and doing customer discovery. And then sometimes you know exactly what you need to do and you really double down on execution. You're going to go through waves. So it'll never be the same, but it's important to know the facts.

Where is the pie chart today? And then another pie chart of where do you want to get? What would ideal look like to you? The next thing is I want you to look at your calendar and I want you to write down two truths, just facts that you see based on the patterns of what you did, who was in the room, what the goals were and how you felt about it. So I'll give you an example. At the beginning of the year, I went through this and I wrote down that large zooms

where I'm with a whole bunch of people call it six or more, drain me. And I really don't like those. That might be something that you write down if it's relevant. We're just starting with facts. It's not about whether or not we can change it yet. You might write down, hey, when I start my day with solo time, I was just talking to somebody who starts his day with meditation. And he now has noticed that when he starts his day with meditation, the whole day is better. Or maybe it's kicking off with a big group, if that's where you get your energy from.

So things like the beginning of the day, the end of the day, how does that change? How you feel throughout the sequencing of the activities? Who's in the room? Write down two truths about what gives you energy, what drains your energy, and what's driving the needle and what's not. Because you can learn a lot by just looking at your calendar and processing it. Once you have those two pies and those two truths, that's going to give you a compass because you will, after that, know what you need to subtract.

what you need to protect and what you need to add to your calendar to not be an infinite shift. We're not talking about flipping it on its head. I hear from executives that most of the time 10 to 20 % and it tends to err on 10 % is how much of their time is spent on truly strategic needle moving energizing activities. And so what we look for is 10 to 20 % of stuff that we can get rid of, change or shift and change into needle moving.

energizing activities because if 80 to 90 percent of your job is just staying afloat, just staying with your head above water, and 10 percent is moving forward, then all we need to do is shift 10 percent and we double your velocity of moving. Think about it that way. We're looking for that 10 percent gain. So do the analysis, come up with the truths, then we're moving to step three where we're really going to make the psychological shift that's going to help us get there.

Keith Cowing (07:56)

Okay, so you got your pie charts, you got your truths, you got your analysis, now it's time to change the game. First of all, let's look for things to delete, delegate, diminish, shrink, change. I was just talking to somebody, they looked and they said, hey, what drains me is all these status meetings. Okay, great, how do we fix that? How do we help everybody be up to date on status so you can spend your time making decisions talking to customer shipping product? They also noticed that...

Talking to customers was right now what was giving them energy and what was moving the needle. And so instead of four status meetings a week across different things, which sometimes you honestly don't realize, until you take a step back, take a breath, and just look at the calendar, and then you notice these patterns and all of a sudden it's super easy. you know what? I need to write a weekly email that does status and I can get those four meetings down to one. Now I can spend more time with customers. Instant change. And at the end of the day, we're looking for an hour a day.

We change an hour a day, we change your life. That can be two 30 minute meetings, one 60 minute meeting, so we're hunting. First off, delete, delegate, diminish, automate, what can we get rid of or shrink? The next one is how do we protect your focus?

my challenge to you is a simple mental trick. Treat your most important time blocks as if they're a meeting with the CEO.

or the board.

It doesn't matter if it's a personal thing like going to the gym or having dinner with your family or working on something strategic that is gonna drive your goals and your outcomes. Because if you had a meeting with a CEO and you were in a status meeting and it was about to run late, you wouldn't sit there and squirm and.

kind of wonder if it was gonna run over and say, I think I'm wasting my time. You would just announce in the middle of the meeting, hey, by the way, I have a meeting with the CEO next. It's really important. If you are the CEO, you can consider it your board. And in the middle, you'd say, hey, I have this important thing after. Let's make sure we wrap this early. And it might even motivate everybody to wrap it a few minutes early. And whether or not it's done, you would stand up with your chest up and you would just walk out the door and you would go to that meeting with the CEO or the board, whatever it is that's truly critical.

But we don't treat our critical time blocks as if they're critical. We just let them get run over. And it's not because people run them over. It's because we let them get run over. And so this is where we protect your time. Treat those blocks as if they are meetings with the CEO or the board. And another trick here is to raise your team up. So look through your calendar and say, hey, where could I pull somebody else in to either be able to collaborate on this or just literally take it over?

because very frequently, if you have a team reporting to you, they're looking for more things and you're trying to stop from drowning. And so something that to you may feel really painful and like process, to them may be strategic and needle moving because they're learning that next thing. Look for those. And then the final one here is set boundaries and change your mindset. So setting boundaries does not mean that you're asking other people to respect boundaries. A boundary is not the edge of your yard.

where somebody can walk on it if they want to, you're just asking them not to. A boundary is a hard wall where they literally can't get through it. And so you have to set these boundaries, you have to protect your time. And the mindset, look at the highest performers, happiest people that you know. They're both happy and high performing. They do not show up to all of the things that you want them to come to if they don't wanna be there and they don't think it's important. Observe it, just pay attention for a week.

the happiest, highest performers? Do they show up to everything that people want them to be in, or are they frequently the ones that aren't there? So now, it's your turn to be that person. You're in a job that's unfair, so you have to play unfairly, which means that you focus on the things that are important, and I don't mean be selfish. I mean drive your goals and empower and lead your team by setting boundaries that other people can't break.

prioritizing this stuff as if it's a meeting with the CEO or the board and just holding firm to it. And you just have to get really good at drawing those boundaries and saying no to things by saying yes to the most strategic stuff that you need to stick in your calendar. And you don't have to do this for everything because it's impossible to change all of your calendar. There is a little bit of Tetris going on, but we're gonna avoid

everything being Tetris because most of us think of the world as outside in and it's happening to us. And the second we decide, no, it's my calendar. I own it. You can make that shift and you can make that shift today, which will help you be more decisive, help you get your work done, eliminate zombie meetings and have an energizing day that moves a needle and keeps your energy up past dinner and into the evening. So you just feel like a totally new person.

Keith Cowing (12:48)

So go run this playbook, audit your calendar, analyze it, come up with a couple truths, come up with a couple pie charts, what it looks like today, what you'd like it to look like. And then third one is make changes and change your mindset. Don't let your calendar manage you. Don't let other people set your priorities. Set boundaries, decide your own priorities, and go out there and make these shifts that will totally change your goals, your sanity, and your happiness in life. And by the way, let me know how it goes. I would love to hear...

what you find that works, what you find that doesn't work. And if you have specific questions that are relevant to your calendar, your environment, feel free to reach out and subscribe. I will be sharing these playbooks and conversations with top executives every week.