How to Do Timeboxing Right / by David Sherwin

Timeboxing

Timeboxing is the use of short, structured sprints to achieve stated goals. Here’s how to get the most out of this technique in your daily work.

Time. When pursuing our personal and professional goals, it’s the most precious commodity we have. We obsess about how to make the most of it, treat it like it’s a tangible resource we can invest. We don’t want to fritter our time away in life, but treating our time too tangibly puts us in a double-bind situation. If we want a creative idea or team project to yield a meaningful result, we need enough time to take risks and explore new pathways. Yet if we give ourselves too much time for undirected exploration, we can end up having little to no time to create a product we can stand behind. We feel this tension in every project that we take on, and it’s a primary contributor to our anxieties in work and life.

In 2008, overwhelmed by the stress of a fast-paced job in a design studio, I decided to do something about it. After a few months of research into time management techniques, I wasn’t much better off than when I started. If you've used strategies like the ones provided in David Allen's book Getting Things Done, then you've spent time focused on how to process and organize the things you need to get done. While such systems are good at helping you prioritize what needs to be done, such systems have little to no advice about how to complete a creative task individually or as a team.

At the time, I was working on multiple software development projects with contrasting methodologies: waterfall and agile. I wondered what would happen if I took the concept of timeboxing from agile—the use of one to two-week sprints to scope and deliver units of work as a team—and scaled it down for use in ten-minute increments? Over two years, I experimented with using this technique for creative problem solving in individual, team, and classroom settings. When I saw consistent results, I shared it in my book Creative Workshop, talks, free publications, and training workshops.

Fast-forward to 2019. Timeboxing is now part of the public lexicon, from its use in Design Sprints to Harvard Business Review articles, from Medium posts expanding on the technique to apps that visualize your timeboxed productivity. I continue to see organizations and teams advocate the use of timeboxing as beneficial, and it’s being applied to a wide range of activities beyond design.

However, almost everything I’ve seen about timeboxing in the past decade is missing something critical: Timeboxing isn’t just task chunking. (Sorry, Elon Musk.) People may think timeboxing is about checking tasks off the to-do list, or chopping their days into 5-minute increments. Yes, it’s easy to tick the box on short, clearly described tasks. However, it’s hard to make sure we’re completing relevant tasks in pursuit of the right goals.

In what follows, I’m going to update what I’d originally written about timeboxing in 2009, taking into account what I’ve learned in the past 10 years teaching the technique with my partner Mary Sherwin. It’s my hope that this will help you put timeboxing into practice more effectively, no matter whether you’re individually tackling problems or seeking to improve how you work with your team.

Timeboxing: Short, Structured Sprints to Reach Stated Goals

My definition of timeboxing is this: Timeboxing is the use of short, structured sprints to reach stated goals. Let’s look at a few of these words more closely.

By short, I mean that each task you’re completing is ideally no longer than 10 minutes. The more time you give yourself in a time box, the less likely you’ll be able to focus on finishing the task.

By structured, I mean that there’s a range of actions in a sprint that’ll help you accomplish your goal. These actions include setting goals, completing tasks in pursuit of that goal, taking breaks, and so forth.

By stated goals, I mean that you and your team should know exactly what you’re trying to create in each sprint at the desired fidelity. At the end of the time box, you should be able to say with certainty whether you accomplished what you’d intended or not, and why. Only start a sprint if you know exactly what you’re trying to achieve in that time period, and that everyone participating has agreed to give it a try.

There are three benefits of using timeboxing: Time constraints create extreme focus when you’re trying to accomplish tasks. You’re forced to regularly re-evaluate if you’re heading in the right direction. And it’s easy to course correct.

Timeboxing is best applied in the following situations:

It's hard to focus on getting things done. Timeboxing can help you start creating something right away on a project, so you won’t fall prey to the “uh-oh effect”.

A deadline is rapidly approaching. Timeboxing is a way to design your own deadlines, so you aren’t procrastinating until you need to deliver something to others.

You need to align and motivate a group. If you’re in a workshop or meeting, timeboxing can keep everyone focused on what needs to be accomplished (in bite-sized increments).

The topic or problem seems too big to tackle. Timeboxing is a great way to put structure around a problem and take your first steps towards solving it.

Timeboxing doesn’t work in all circumstances, as there are many activities that require sustained attention to achieve results. For example, timeboxing doesn’t work well when you’re in the throes of executing detailed production work. So don’t oversell its benefits.

The Process of Timeboxing: Plan, Act, Evaluate

To explain the process of timeboxing, let’s see how a single timebox can be used to align and motivate a group.

When timeboxing, be specific about the required output and fidelity of what you’re creating. Over time, this will help you estimate how much you can accomplish when you take on certain tasks. It will also create shared accountability when timeboxing as a team.

When timeboxing, be specific about the required output and fidelity of what you’re creating. Over time, this will help you estimate how much you can accomplish when you take on certain tasks. It will also create shared accountability when timeboxing as a team.

Planning the Timebox

Imagine you’re working as a designer on a product team. In a meeting, you’ve shared three design ideas with your team leads, which somehow turned into a long debate about which idea would be best to implement. You’ve only got 15 minutes left in the meeting. You can use timeboxing to work your way towards a resolution:

“Let’s timebox this. For the next eight minutes, we’ll individually write on sticky notes three pros and three cons for each design option. When we’re done, we’ll read what everyone wrote and make a decision on what to implement. Want to try it?”

The above statement contains your plan for the timebox and has all the essential ingredients you need to get moving: what to do, how long you’ll do it, and the desired output.

Acting on the Plan

Say that your team agrees to this plan. Now you act on it, carrying out the task you’d agreed upon. Set the timer for eight minutes and go!

Evaluating What’s Been Done

Six minutes have elapsed so far. If you’re leading the timeboxing activity for the team, you would evaluate the team’s progress towards the output. Is everyone on their way to completing the task? If not, why? Do they need more time to complete it? Or was there something that you’d missed that needs to be addressed?

This is the most critical step of the timeboxing process: Using what you’re learning from completing the task to adjust what you’ll do in the next timebox. In some cases, what you learn in the activity can cause your team to entirely re-evaluate what you’re trying to accomplish.

This is where timeboxing moves beyond mere task chunking and becomes a powerful learning tool. You’re not timeboxing unless it includes planning, action, and evaluation.

Timeboxing isn’t about just checking things off a to-do list. Always include time for planning, action, and evaluation after each task. That said, it’s rare that a team can timebox for more than an hour without a break. Use your breaks to refuel, recharge, and reflect on what’s working and what you might do next.

Timeboxing isn’t about just checking things off a to-do list. Always include time for planning, action, and evaluation after each task. That said, it’s rare that a team can timebox for more than an hour without a break. Use your breaks to refuel, recharge, and reflect on what’s working and what you might do next.

Constructing Timeboxes that Lead to Great Results

Now that you understand the process of timeboxing, let’s look more closely at how to construct individual timeboxes. Including the following ingredients will help you consistently create great results.

What to Do: The Task That Needs to Happen

For each timebox, describe the exact task that needs to happen. The range of tasks you can take on is only limited by your imagination: generating questions, identifying audiences, brainstorming of ideas, giving and receiving feedback, sharing your work, and so forth. No matter what task you choose, it should always be clear how each it contributes to the success of your project. (Pro tip: Sharing and discussing work out loud always takes longer than you plan, and can bias your decision-making based on who’s the most verbally proficient on your team.)

Duration: How Long We’ll Do the Task

Try to keep yourself at 10 minutes or less, and be clear about what tasks aren’t included. Make sure there’s just enough time before the task to agree to your plan, and after the task to evaluate what happened.

Required Output: How Much You’ll Create at the Desired Fidelity

No matter what the task is, it should always have a tangible output. Be specific about the output, and how much of it you plan to create. You should be able to definitely say that you did it: In eight minutes, write eight ideas on individual sticky notes as words and sketches. Yes, we did that.

By requiring specific output, people are forced to be concise and consistent. A good rule of thumb is this: The lower the fidelity of what you’re creating in a timebox, the more of it you’ll be able to create. When you increase the fidelity, you increase the challenge. This is part of the reason why timeboxing doesn’t work well for more production-oriented tasks—it just takes longer than ten minutes to do certain tasks, like editing a piece of writing, creating detailed designs, or producing audio or video.

Don’t treat timeboxing as a rote recipe for task completion. You want to treat it flexibly, like you’re cooking a meal based on the ingredients at hand. Over time, timeboxing can become a mindset for how you respond to everyday challenges:

“I don’t have enough ideas yet for this project. I’m going to timebox myself to come up with 10 additional ideas in 10 minutes, one per page in my notebook…”

“We need more ‘How Might We?’ questions before we can start brainstorming. Let’s each generate five questions in the next five minutes, one question per sticky note…”

“Let’s timebox this debate to ten minutes. Each person will get 2 minutes to share their point of view, and I’ll write your key points on the whiteboard…”

Timeboxing Can Help Break Down Ambiguous Goals

Now that you’ve seen how to construct individual timeboxes, let’s briefly look at how to use them to break down and work towards fuzzy, ambiguous goals.

Imagine you’re working at a food delivery startup that’s struggling to reach its quarterly targets. Your CEO swings by your desk and says you’ll be taking on a crash project to develop three new revenue-generating opportunities that customers will love… oh, and you’ve got till the end of the week.

The ask isn’t totally clear, and if you pulled together a team to tackle this they would have a ton of questions. Just a few timeboxes could help you and your team break down this challenge by:

Asking questions to better understand the problem. You could write a list of questions that, if answered, would help everyone decide what problems you’re trying to solve.

Defining what the end deliverable should include. You could list what elements these revenue-generating opportunities will need to include when you present them.

Listing criteria that you’ll use to evaluate your ideas. You could determine what makes for a good (or not so good) idea, before everyone starts generating them.

Creating a draft plan for the week. You could list what needs to be accomplished in order to deliver on the ask, then prioritize which of those actions to take on first.

On every project that you work on, your approach is going to look a little different—and that’s okay. You’ll discover the best path to your goal as you go, and have the flexibility to adjust based on what you discover along the way. Due to this, timeboxing is different from certain trendy time management techniques that encourage you to schedule 25- to 30-minute time blocks for completing groups of tasks. Timeboxing helps you break down those big blocks and make the best use of the time inside them.

Got 10 Minutes? Give Timeboxing a Try

During the past decade, timeboxing has helped countless people be more productive in their professional and personal lives. If you haven’t used timeboxing before, take a few minutes today to try it out.

If you’d like activities to practice timeboxing on your own or with teams, check out Turning People into Teams and Creative Workshop. And if you’d like to train your team in using timeboxing, contact me at questions (at) askthesherwins (daht) com.