From Burnout to Breakthrough: Master Your Calendar

Keith Cowing: 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 burn out in the process. 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.

Keith Cowing: 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. 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, 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.

Keith Cowing: 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. In the spreadsheet, you want a column for the following things. One is meeting type — is it a one-on-one, a small group, a large group? Then attendees — is this your team, you and your boss, the board, you and direct reports? Then remote or in person, if relevant. Then the goal — what was the goal of the meeting? Then these are the key ones. One column that says energizing or draining. I want you to list for every meeting whether you left that meeting more energized or drained. And then the last one is needle mover or process. Is this something that really moved the needle? Or was it just process — 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.

Keith Cowing: Now it's time for step two, which is to analyze the results. Put together a pie chart — a now pie chart and a goal pie chart. For the now pie chart, the trick is finding what the different components are. How much time am I spending outside the building? Meeting with customers, meeting with industry partners? How much time am I spending with my team? With cross-functional teams? On vision and strategy? On operational projects? On recruiting? Where is the pie chart today? And then another pie chart of where do you want to get? What would ideal look like?

The next thing is I want you to write down two truths — just facts that you see based on the patterns. 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 six or more people drain me. That might be something you write down if it's relevant. Or maybe when you start your day with solo time, the whole day is better. Write down two truths about what gives you energy, what drains your energy, and what's driving the needle and what's not.

Once you have those two pies and those two truths, that's going to give you a compass. I hear from executives that most of the time 10 to 20 percent is how much of their time is spent on truly strategic needle-moving energizing activities. So what we look for is 10 to 20 percent of stuff that we can shift. If 90 percent of your job is staying afloat, all we need to do is shift 10 percent and we double your velocity of moving forward.

Keith Cowing: Okay, so you got your pie charts, you got your truths, now it's time to change the game. First, look for things to delete, delegate, diminish, shrink, change. I was just talking to somebody who said, what drains me is all these status meetings. Okay, great — how do we fix that? Instead of four status meetings a week, write a weekly email that does status and get those four meetings down to one. Now you can spend more time with customers. At the end of the day, we're looking for an hour a day. We change an hour a day, we change your life.

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 working on something strategic. If you had a meeting with the CEO and you were in a status meeting that was running late, you would just announce, hey, I have a meeting with the CEO next. And you would stand up and walk out. 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.

Another trick: raise your team up. Look through your calendar and say, where could I pull somebody else in to either collaborate or take it over? Something that to you feels painful and like process, to them may be strategic and needle-moving because they're learning that next thing.

And then the final one: set boundaries and change your mindset. A boundary is not the edge of your yard where somebody can walk on it if they want to. A boundary is a hard wall. Look at the highest performers, happiest people that you know. Do they show up to everything that people want them to be in? Or are they frequently the ones that aren't there? You focus on the things that are important, you set boundaries that other people can't break, and you hold firm.

Keith Cowing: So go run this playbook: audit your calendar, analyze it, come up with a couple truths, come up with a couple pie charts. And then 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.