How to take control of your calendar with a simple time management system

Face it. Your calendar is a mess. 

Let me guess. You’re struggling with a cluttered calendar and a frantic work-life balance. And you know it. You're not alone. Been there. Done that. 

In today’s issue, I'll explore some warning signs of an out-of-control calendar and I’m going to share my simple 3-D time management system that helped me regain control and find harmony in my work and personal life.

Recognizing the Chaos: Signs of a Disordered Calendar

Is this you?

• Chronic lateness: Consistently arriving late for meetings due to an overcrowded schedule, often unprepared and unclear about the agenda.
• Inability to focus: Struggling to concentrate on tasks and constantly procrastinating or seeking distractions.
• Odd hours: Regularly missing deadlines and scheduling meetings outside normal working hours, leading to an ever-expanding workweek.
• Constant rush and stress: Feeling perpetually hurried and overwhelmed by your workload.
• Neglected work-life balance: Allowing personal life and relationships to suffer due to nonstop work commitments.

If any of these signs resonate with you, it's time for an intervention and to reevaluate your schedule.

Understanding the Problem: Demands on Manager Time

 As a leader, you face various demands on your time:

• Planning
• Budgeting
• Cross-functional collaboration
• External engagements
• Crisis management
• Mentorship and team development
• Stakeholder management
• Personal development
• Administrative tasks

These demands lead to an array of meetings, ranging from one-on-one sessions to group meetings and ad-hoc discussions, that just keep on piling up.

I will argue that the larger the team, the less meetings you should have.

A simple litmus test: scroll your calendar 3 months from today. Sum the hours of meetings excluding personal time in that week. If more than 12, you are already overbooked. I just checked my calendar: I only have 6 hours pre-booked. 6.

My 3-D Time Management System

I analyzed a year of meetings. I found 3 core activities that I have to perform and built my system around them.

1. Deep work

This is the “big rocks in a jar first” concept to solve problems that matter most. Schedule "deep work" time for focused, uninterrupted work on complex tasks and critical thinking alone. Set up a few slots in your calendar per week, ideally 60-90 minutes long, at about the same time every day to build up the mental habit. Late morning is my most productive time. I block every day from 11 am to 12 pm.

During these sessions, turn off all distractions (slack, IM, emails, etc). 

2. Dive-in

Identify the 3-5 important initiatives you want to see succeed. This might be your top-level OKRs, priority projects from using the Eisenhower Matrix or any method to distinguish between urgent and important tasks.

Schedule a 90-minute block for diving into the work. This is not about getting a status update from the team but engaging with them. On agenda can be reviewing KPIs, assumptions, models, demos, impediments, customer feedback, and anything else driving decisions.

3. Dependency squash

As a leader, your output is the sum of the output of your teams. When they are stuck, you are stuck. Being available to make a quick decision or solve a problem you cannot delegate but blocks someone in your team is crucial. Block whole sections of your calendar as “office hours”. Invite people to connect with you for a quick chat (slack, call). A 5-minute conversation can cut hours of waiting.

When demand is low, use the free time to engage in a "gemba walk" to observe and understand your team's work firsthand. Ask if someone has a few minutes for a sync, or join meetings unannounced. Listen. Ask what pain points exist and what you can do to help.

Implementation and evolution

Aim to have a system to manage your time. You don’t have to copy mine. Keep it simple. Share it with others. Encourage others to do the same. This cultural norm will change you and your organization.

Block your calendar for designated hours, including lunch, end-of-day cutoff, deep solo work, collaborative work, and open hours. Stick to it.

Evaluate your setup on a regular basis. Adjust the framework before changing your calendar. 

Pro-tip: delete all meetings once a year. And rebuild from scratch.

Workspace setup

I work mostly from home. I’m set up with 3 computer screens to match my time management.

Central screen (laptop): One app open for single-tasking. For deep work, this is usually a browser for research and writing thoughts down (Google Doc / Sheet).

Left screen: asynchronous apps (calendar, email, task manager). I check them on a regular basis, but not so often.

Right screen: Synchronous apps (slack, IM, zoom). Open mostly during office hours.  

Takeaway

By recognizing the signs of a chaotic calendar, understanding the demands on your time, and implementing a strict time management system, you will regain control of your schedule, enhance productivity for both you and your team, and improve your work-life balance.