How I Cut the Events on My Calendar by 40% and Got a Promotion

Dario De Santis
6 min readMay 25, 2022


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In 15 years of Virtual Collaboration Product Management experience, I would have never imagined to have my life completely turned upside down by being forced to work from home. However, it happened!

Those who personally met me know that I am as tall as an NBA center, a unique cumbersome characteristic that, over time, I have learned to use as a catalyst to develop professional relationships.

Therefore, my favorite professional playground has always been the office; in fact, until 2020, the days I spent working from home had been 10 or so, mostly when I was sick.

Then, the pandemic hit, and suddenly I got lost in an element so familiar and oddly unfamiliar at the same time: my home.

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Coincidentally, I had changed my role within my company and I had to re-establish a whole new set of strategic relationships with a completely new team. Quickly, my calendar got filled up by many 1:1 conversations (sounds familiar?). I thought: “it will be a temporary effect of the job change”, but it wasn’t. As the organization adapted to the new way of working, scheduled meetings replaced coffee machine talks, and popped out like mushrooms after a night of heavy rain. In Feb 2021, Microsoft estimated that meetings grew 2.5x compared to the previous year.

With more meetings filling more slots in my calendar, the time to do my work reduced dramatically, forcing me to sacrifice family time and workout to avoid falling behind with my tasks. Various recent studies estimated that overtime grew from 49 min up to 3 hours, depending on the worker’s role and industry.

It was clear to me that this way of working was not sustainable, but there wasn’t much I could do: as a Product Manager, people needed me, and, of course, I needed them.

My terrible work-life balance went on for a while, until my third daughter was born in 2021. Suddenly, my already stressful life at home became an order of magnitude more complex, and I had to find a way to eliminate overtime by keeping the same productivity levels. In other words, I had to find a solution to meeting fatigue, as soon as possible.

One of those days, during an international video call, my father saw me quite stressed and asked me why. I answered: “I am constantly in back to back meetings without being able to take a break”. He replied: “are all those meetings important? Just do less of them”.

That answer was so simple yet so powerful. Many of those meetings were indeed not important. They were scheduled in the past and now they were conflicting with other emerging priorities for the day, thus generating stress. The most frustrating aspect was that some of those meetings were completely avoidable. For example, a sales rep needed to get a hold of me to help with an ongoing negotiation, she tried to call me unsuccessfully because I was in a meeting, so she decided to schedule a 30 min 1:1 conversation, thus constraining my day and giving me one more push to work overtime.

This way of working was not sustainable, so, after a period of trial and error, I developed my own strategy to cope with it, and it turned out to be a big success!

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Today, I am able to finish all the daily tasks that matter within a 10-hour work day (down from 13 hours), and I feel much more productive!

How did I do that? I made room in my calendar to have more proactive impromptu conversations.

Step 1: Fill-in all the empty calendar slots, 2 days ahead

How do you make sure people don’t bother you with scheduled meetings? Simple: don’t let them find any availability on your calendar! Every morning, I make sure all the empty slots in my calendar for today and tomorrow are occupied by an event called “block” or “focus”. In other words, I don’t let anyone schedule any 1:1 meeting for the next 2 days. I know you are thinking: “doesn’t it also prevent other meetings from being scheduled?”. Not necessarily. Meetings with multiple parties (e.g., program reviews) appear on your calendar anyway, independently from your available slots.

Let me remind you what happens if I don’t fill my empty slots.

A sales person needs me but I don’t respond immediately because I am busy, so she schedules a meeting in the first available slot to make sure to talk to me promptly (deals are always urgent). If I refuse her invitation, I become a bad guy who is hard to work with. If I feel altruistic and I accept, I subtract 30 min of focus time from my day and increase the chances I’ll be in front of my laptop after dinner. Did this ever happen to you?

I know you’re thinking: “aren’t you also a bad guy by preventing those people from scheduling in the first place?”. Yes, unless you implement what follows.

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Step 2: Be proactive

The sales rep calls, you don’t answer, she looks at your calendar and finds out that you are completely booked. Since the matter is usually urgent, she texts you (instant message or email) to figure out when you can talk (or accommodate an earlier time than the earliest empty slot in your calendar — 3 days in the future). At that point, you surprise her: when you are free and the other person also looks free (e.g., online presence shows “available”), you proactively reach out via instant messaging, suggesting to talk right away. If she just texted you and she is likely still contemplating the message she just sent you, then call her directly.

Why this approach works

By implementing these tactics, you initially come across as busy, but you also look like a generous approachable collaborative person who cares about the business, since you proactively reach out. Usually, the other person is motivated enough to seize the moment and accept to talk to you right away.

For those who are thinking “I can’t do that, I am busy back to back all day”, let me remind you that in the previous point you have blocked your calendar and you now have plenty of time to handle impromptu conversations at your convenience.

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In the scenario I have used as an example, the combination of filling your calendar plus proactivity generated the following results:

  1. One less 1:1 meeting in your calendar, one more step towards freedom of working on what really matters.
  2. The sales rep who wanted to talk to you got an answer faster than the 1:1 scheduling scenario, at everyone’s earliest convenience.
  3. You could accomplish more in less time: the pace of your day was less dependent on the limited number of slots in your calendar. The higher resolution of your day allowed you to allocate the right amount of time to the unscheduled activities, avoiding a huge waste of time scheduling/rescheduling meetings and follow ups.
  4. You appeared as an approachable team player, which leads to better peer reviews and, in turn, higher likelihood to be promoted.

Did I tell you that I got promoted in September 2021, even though I ended up working 3 hours less per day?

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I hope you have enjoyed my true story!

For more insights, please, like Tweelin’s LinkedIn page. Very soon, we will post an invitation to an exclusive series of webinars where I will dive into more details and tactics on how to elevate your status while working less and producing more.

See you soon!

Yours sincerely,



Dario De Santis

Long-termist visionary technology Entrepreneur and Product Leader, with a strong passion for improving people's productivity through innovative solutions.