Managing your calendar in the age of constant busyness

Do you ever find yourself at the end of a work day after having 7 Zoom calls, totally exhausted, and not sure where all the time was spent on? It's a feeling that a lot of managers and startup founders are familiar with.

I am a complete nerd when it comes to managing my emails (Link to the article), so it might not come as a surprise that I'm hyper vigilant about my calendar as well. For me it comes down to making sure that:

1. I spend my time on right things and use my time in the most effective way
2. I allocate enough time to rewind and take care of myself and don't overwork
3. I free up headspace – instead of remembering what I need to do and when, I do the planning in advance and keep every appointment in the calendar

Here are some principles and tips that help me manage my calendar and don't feel overwhelmed.

#1. Email slots

I wrote about it in my previous article about managing emails. As a part of my job, I get 60-80 new emails every day and this can take up a lot of time. To avoid any distractions during the day, I turn off all email notifications and check my inbox only during dedicated time slots:

1. 1-hour kick-off session in the morning – I usually start my day at 8.30-9am and try to avoid any calls before 10am. That gives me around an hour to plan my day and sort through emails.
2. 30-minute slots after lunch and after 5pm – I use this time to focus on a couple of emails that require a long or a well-prepared reply.
3. If necessary, a 15-minute email break – depending on my workload I might add an additional email break, limiting it to 15 minutes max and only doing a very simple "delete - forward - reply later" scan through my emails. Typically it happens when the company is going through busy times, like hiring or PR / marketing campaigns.

I block slots in my calendar to keep myself in check and simplify the routine.  

#2. Deep work slots

Similarly to email slots, I make sure to have 2-3 slots (3 hours/each) during a week that are dedicated to deep work. This could be working on a new sales strategy, preparing fundraising materials, or doing a market research – anything that requires no interruptions and a couple of hours of focused work.

Personally, I typically schedule these deep dive slots in the early afternoons – that's when I'm most creative and productive.

The trick is to have these slots blocked out in your calendar as a recurring event (ideally ending on 31 Dec) to avoid skipping it or double-booking.

#3. Calendar review & Friday planning

One important ritual that I adopted recently is a calendar review. I do it twice a week and the goal is to make sure that my calendar still reflects the key goals for a given week.

It all starts on Friday afternoon (a 30 mins blocked slot), when I reflect on a previous week and plan the upcoming week. I simply write down the top-3 worries and the top-3 priorities – usually, they are fully or somewhat aligned. Based on these priorities, I review the calendar and check every booked slot – Does it reflect my priorities? Should it still be kept in the calendar?

For example, if my key priority is hiring a new Head of Sales, I cannot justify spending 40% of my time on investor calls. Think of it as "Marie Kondo-ish" approach to time spent: "does it bring value?"

In the past, I often find myself struggling with keeping up with this approach throughout a week and by Thursday my calendar will be out of control. So I've added a shorter 10 mins. check-in meeting on Wednesday morning to make sure that nothing managed to sneak into my calendar.

#4. Calendly

Calendly and other scheduling solutions became somewhat controversial in the past couple of years. Some like them, others feel insulted and refuse to use them.

Personally, I see a lot of value in such tools. Not only do they simplify the scheduling process, but most importantly they allow one to have more control.

Currently I have several Calendly links for different purposes, shared with different people and using different settings.

• Regular 1-on-1 meetings with the team – two time blocks per week to account for different time zones of my remote team. The link is shared with the team, so everyone can book time with me. I pair it up with a Slack bot that reminds a team member (every 5 weeks) to book a call.
• External meetings – two separate Calendly links for sales / partnership meetings and for any other meetings. Different available slots in the calendar and meetings no longer than 25 or 30 mins.
• Community or "Pay back" meetings – I keep 2 hours every week available for early stage founders or others in the community building something exciting and reaching out to me for help or advice.

The key is to set up available time slots wisely and avoid having too many available slots.

#5. Self-care and thinking time

Over the last year – with the pandemic, lockdowns and working from home – I found it especially hard to not overwork. Nowadays, I block out the early morning (6-8.30am) and lunch to make sure that I have time to take care of myself. No meetings can be scheduled during these blocks and it allows me to fully focus on a morning jog, meditation, or lunch without worrying about the next meeting.

Similarly, I schedule free time during the day to go for a quick walk or just think and reflect on the company's progress.

One might say, that it's overkill and over-optimisation to have these in a calendar. Perhaps. But I find comfort in structure and it's easier to block it in the calendar and let my Calendly do the job.

I gained a lot of valuable insights and adopted some of the routines, described by Mathilde Collin, the co-founder and CEO of Front, in an article titled "The Founder’s Guide to Discipline".  I love the overall "discipline over passion" approach and can highly recommend tips on how she manages her calendar.