How to use timeboxing to tame your calendar

If you’ve been on the receiving end of Nat’s obnoxious travel updates (☀️🍍🏖️) and Kristen’s view into the Canadian wilderness, you’ll have noticed that we’re currently in two very different parts of the world.

This geographical switch-up doesn’t just impact the quality of our Zoom backgrounds (why don’t hotels have better lighting?), it also means operating in different time zones. A sudden shift in working arrangements is usually enough to induce perimenopause-level migraines, but we’ve adapted almost seamlessly. After swapping phone calls with voice notes, and home offices with cocktails in fruit caravans and Airbnbs, it’s basically business as usual. 

It’s your calendar, stupid

On a call last week, a Powrsuiter claimed she’d never be able to travel and work like us – too little structure, too much upheaval. That got us thinking, why do we find it relatively easy? The answer lies in our calendars.

In the past, we’ve shared simple calendar hacks to live by. One of those hacks, timeboxing, has enabled us to work largely asynchronously. We treat our calendars as open to-do lists, scheduling our work and keeping each other across everything on our individual plates. Like most planning, it creates a time dividend – a little bit of time invested upfront saves a lot of calendar mashing, rushed deadlines and ball-dropping later. 

It takes the mental load out of managing your to-do list and creates the structure that we need to move out of the busyness trap and into effective mode. And it’s a simple process. We run it almost without thinking now, every time be commit to a new piece of work or one-off training session, and at the start of each week: 

1. Work back from the delivery date

If you’re a Powrsuit member, you probably define your work using the labels rocks, pebbles and sand. And you’ll know that all your big tasks should be broken down into smaller pieces that you can complete in one calendar block. 

Now all you need to do is work back from the delivery date and schedule time in your calendar for each piece of work. For example, for this newsletter, we plot three blocks leading up to the send date:

1. First draft (Friday – 1 hour): Jot down the key points and form the article structure – without formatting or punctuation. Why Friday? So our subconscious continues working over the weekend.
2. Second draft (Monday – 2 hours): Turn the notes into a first complete draft.
3. Final edits (Tuesday – 1 hour): A final edit with fresh eyes to spot all the times we use ‘career’ three times in a sentence. 

Those three calendar blocks are locked in every fortnight, so all we need to do is check our calendar to know when it’s time to get cracking. 

2. Budget a realistic amount of time for each task

Review each time block and ensure you’ve estimated how long each one realistically needs to be. 

One of the benefits of timeboxing is that you build your work-sizing muscle. Because you’re tracking how long things actually take, you get better at estimating. This helps you manage your own workload, while also building decision-making skills – sizing work is an important component of cost/benefit analysis.

Padding is a good thing – it’s always better to finish earlier than wind up running out of time. But expect to get it wrong a lot, too. We underestimate our timeboxes all the time. Case in point: After twenty four meetings and events in Singapore, Nat scheduled a measly 1.5 hours to send thank yous and follow-ups. A day and a half in, her calendar was chaos.

That’s ok – next time, budget more time.

3. Invite others early

You know how you just blocked out time in your calendar for each task? That also allows you to give other people plenty of notice when you need time in theirs. 

You know you’ll need a review of your first draft in 4 weeks’ time, and be in a position to give a status update two weeks later, so schedule those meetings now. You’ll minimise last-minute calendar wrangling while staying true to our (very effective) stakeholder management philosophy: No surprises.

4. Add in other stuff

Sadly, real life is never as tidy as a framework would have you believe. Call these extra bits ‘sand’, life or BAU, but there’ll always be other ‘stuff’ that needs to get done. Think LinkedIn scrolling, checking email, exercise, kids’ sports days, travel between meetings, last-minute requests, dinner with friends.

A lot of these things are predictable, so in the calendar they go. 

Bonus points if you’re in a formal leadership position and role model the juggle. Don’t hide school pick-ups, haircuts, or a late start after a 10pm work call. Normalise results, not time spent at your desk.

5. Use descriptive titles and agendas

This one’s simple: Make sure every calendar block title accurately describes the task you’re doing.

During a recent mini-masterclass on running one-on-ones, one of the top questions was “how do you fit work in progress updates into crowded schedules?” Well, your calendar should be shouldering some of the burden. By using detailed calendar titles, you create a living status update, which saves meetings for collaboration. 

And speaking of meetings – ensure the timeboxed calendar invites you send to others are specific, too. Even if you have recurring meetings set up, ensure agendas and calendar titles reflect the updates, decisions and questions you need to cover (don’t forget to include documents, links etc). Detail helps busy people prepare and stops your slot from being booked over by perceived ‘higher priorities’.

Let your calendar take on the mental load

Last week, we covered work on your plate vs the mental load. Most of us have far too much of the latter, so let your calendar take some of it off you. Timeboxing means that whatever comes up and wherever you are in the world, you still know exactly what you need to get done.