Is your calendar keeping up with your role?

Have you ever been so certain you remembered something correctly that you didn't bother to check?

Last week, I went to the gym three times in one morning. I still didn't make it to my fitness class.

I've belonged to this gym for two years, so you'd think I'd know the schedule by now. I thought I'd signed up for the 8 am class. I'd booked the 8:50. So I went home, then came back at 9 am because, in my head, the class now started at 9. I was late. They told me the next one was at 9:40. I made my third trip at 9:50.

The same week, I missed a good friend's birthday. It was on my calendar, and I'd already bought her a present. For whatever reason, I thought it was next week.

I had all the information I needed. I just trusted what was in my head instead of checking my calendar.

It made me think about how often we operate on assumptions without stopping to question them.

I've been having a similar conversation with leaders whose responsibilities have grown, but whose way of working hasn't quite caught up.

Reevaluate what you can carry.

Ben, a sales leader I coach, recently became a player-coach. His healthy load used to be 15 to 20 deals. Now it's about six, he told me, "or other balls start to drop." When we counted, he had twelve.

He knew it was too many, but letting go of deals he'd worked on for over a year was hard. "It's a little bit harder with the sunk cost," he explained.

What got him to reconsider was recognizing what the extra deals were costing him - time with his family.

I told him that either he could make the choice intentionally or it would be made for him. By the end of our call, he'd already identified a few deals to hand off to a colleague.

Take the chips off the table (literally!)

Ben had already turned off his Slack notifications, but he still checked all day. "It feels good in the moment," he said, "because it's like you're doing busy stuff."

When I asked what had helped him break a habit before, he said, "Don't buy chips if I'm trying to stop eating them."

He realized that turning off notifications wasn't enough. So now he closes Slack entirely during focus blocks and checks it every two hours.

Research by Gloria Mark at UC Irvine explains why this matters. After an interruption, people took about 23 minutes on average to return to their original task, often doing other things along the way.

Group your meetings by the kind of thinking they need.

Dana, a senior leader I'm about to start working with, described her day as "up, down, up, down," bouncing between tactical 1:1s and strategy sessions with senior stakeholders.

"I thoroughly enjoy it, but it's very draining," she said. She's moving all her team 1:1s to Monday so she can stay on strategy the rest of the week.

Her calendar also had days with no breaks. "It's just that I let it happen," she told me. Now she's asked her admin to protect a 15-minute break every two hours.

It made me wonder how many meetings we keep accepting simply because they've always been on the calendar. If the same invite arrived today, would we still hit accept?

Move the thinking work into the workday.

Claire, another executive I coach, had pushed the industry reading and research she loves to evenings and weekends.

"This is my playtime," she said.

Just because you enjoy something doesn't mean it has to happen after hours. At her level, it's part of the job. Now she's blocking off time on Fridays for research, and she isn't letting other meetings take it.

As for me, I try to hold Thursdays for deep thinking, and I’ll admit that I don’t always hold that time “sacred.” Like Dana, I let it happen. Starting this week, I'm going to protect that time the same way I protect a client meeting.

It's easy to keep working the way you always have, especially when those habits helped make you successful. But the job changes, and sometimes the way you work needs to change with it.

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