Show me your calendar!

It’s Friday afternoon, and Jakub is at home preparing his third cup of coffee. He runs on caffeine because either the kids, or Pager-Duty, keep him up at night. He sprays the coffee beans with water since he saw it in a YouTube video, but he can’t tell the difference. “Moisture,” he thinks, “such a friendly word.”

He checks the kitchen clock and realizes he is 1 minute late for his one-on-one meeting with Mike “The Fly”.

Jakub is the director of Infrastructure at a large tech company in Illinois. Mike reports to him, and also happens to be a friend of his. “It’s not nepotism,” he always justifies. “Mike is solid, and he was the best candidate for that position.”

They always start the one on one with some small talk. “How was your weekend?”, “And the kids?”, “Nice, send my regards to Angela.”. All very cordial, like when they were in college. But past the pleasantries, they both adopt their roles extremely seriously, like that Stanford prison experiment. And this week, Jakub has something important to discuss with Mike. Costs keep racking up, and Mike is not doing anything about it.

“Look Mike, I know you are trying, and you are a good guy. Yeah, great guy. Very solid. But if you don’t put your shit together, I will have to let you go. And trust me, this is the last thing I want to do.” Jakub is originally from Poland and learned English by watching American TV. His way of speaking is very cinematic. He squints his eyes and talks with that whispery voice that no one uses in real life. “The costs keep being higher than expected, and management is not happy. My ass is on the line here.”

Mike is not sure what to say. He rubs his hands nervously, and then he covers his face with them. The Fly. This is how he got the nickname, but no one ever told him, so he keeps doing it.

“I am trying my best, Jakub. Really. I’m just swamped with meetings, you know? Keeping The Lights On and all that.”

Jakub sighs. He will have to pull a Coaching Move on him. He hates doing this, but desperate times call for desperate measures.

“It’s all-right Mike, I’m here to help. Just... Show me your calendar.”

The air in the room is heavy. Mike is clearly tense and uncomfortable and hesitates for a moment before clicking the share screen button.

“Can you see my screen?”.

“Yes, I can. We always can. Why do we always ask?”

A horrendous calendar shows on the screen. It’s a mess. Like an enraged Mondrian.

“Jesus Maria!” Jakub yowls. That’s a common Polish way to express dismay, but they pronounce it like “MA-ree-ah”, not Maria.

“This is a problem, Mike. This is a big problem. But we are going to fix it. We are going to fix it together.”

Mike nods. He is ashamed.

“I’m going to categorize all those meetings and see what we can do about it.” Jakub opens Google Sheets and starts typing stuff. “Can you see the problem?”

“I can’t see anything, actually.” Mike interrupts him.

“Oops, sorry. I’m sharing the wrong screen. Now… So, you know that your number one priority is to fix the costs. We agreed on this one month ago. And yet, you only have 13 hours a week for it. And most of it is divided into blocks of 30 minutes scattered here and there. You are not in control. The calendar is.”

Mike looks down.

“From next week onwards, you are going to block 5 hours every day, from 9am to 2pm. And you will tell everybody that you are not available during that time. Screw them. It’s your calendar, and if your calendar does not reflect your priorities, then they are not your priorities. Time is the most precious resource we have.”

“Got it, Jakub. I will try. It makes a lot of sense when you put it this way… Now, just be honest with me. Is this some sort of Coaching Move?”

“Sorry Mike, I have to leave you. I have to pick up the kids and I’m late already.”

Fall came in, and the leaves turned yellow, orange, and brown. Mike The Fly successfully cut down the costs, and Jakub kept his job, but not for long, since Google poached him with a better offer. “That’s a hell of a logo. It will look good on my resume,” he thought. “And their offices are nice, too.”

He brought in Mike and cashed $10.000 from a referral bonus. “He is solid,” he told the recruiters. “I’ve known him since college.” This time around, though, he would not report to him, which is better, since their friendship has weakened over the last year.

Jakub started to drink more and more coffee, but he is not moisturizing the beans anymore: time is too precious. The job is more intense than ever, and his third kid is on the way. He is always stressed. Running late, running crazy.

One day, they both met by the water cooler, “where serendipity happens,” as management would say. They started to do some small talk. All very cordial, like when they were in college.

“How’s it going, Jakub?”

“Pretty good, Mike,” he lies. “How about you?”

“Much better, Jakub. Things are going great here at Google. Thanks for the referral, mate.”

“You’re welcome, Mike. The bonus helped, but you know, I would do it anyway.”

“I know... I know. Are you sure you are ok? You look tired.”

“Yeah... you know, the kids.”

“What about them?”

“They are great. I love them above all else. But work is work, you know? I don’t find the way to balance it. I am trying to be a wonderful dad, but every day something else comes up. A conference, a meeting, a call.” He is mumbling, like he is trying to convince himself.

Mike has never seen him like this. He starts rubbing his hands again, but this time he doesn’t cover his face. The Fly is gone; he is just The Mantis now.

“This reminds me of something I read once,” Mike says. “The correct way to fill up a jar is to start with the rocks, then the pebbles, and you finish with the sand. If you do it the other way around, the rocks won’t fit. It looks like you know what’s important to you, but you are leaving it for the last.”

Mike is not rubbing his hands anymore. He is smiling. They both know what comes next.

“Jakub, why don’t you... Show Me Your Calendar?”

The room goes dark and a lightning strikes across the room. A droplet falls from the water cooler, somewhere a bird takes off and flies away, and a leave falls from a tree.

Jakub has been Counter Coached.

Show me your calendar was one of the most interesting prompts I’ve been using as a CTO. Time management is one of the harder skills for managers to master and one of the most important ones. You can raise money, you can save it, you can invest it, and make it grow. But you can’t do any of that with time. Time just goes away, like water in a river. You either use it wisely, or waste it.

In your one on ones, ask what the priorities were for the upcoming month. That already triggers the most interesting conversations. Top-down priorities are not always the same as bottom-up ones, and the truth often lies somewhere in the messy middle.

Once you agree on the priorities, you can ask to see their calendar for the upcoming month. Things will get ugly: Business As Usual eats time like a black hole. People set up recurring meetings with good intentions, but when you let other people set your schedule, it’s not your schedule anymore.

Ironically, at a personal level, I was failing at time management myself. It’s easier to solve someone else’s problems than your own, I guess. In my case, work was creeping up and taking over my calendar, despite telling myself that it was not my number one priority. This lead to neglecting health, friendships and hobbies, so I applied what I preached and contrasted my priorities with my calendar. I’m still trying to figure things out, but that’s for another story.