Beating the “Messy Middle”: How to Break Any Project Down into (Actionable) Tasks

Originally published by Jory MacKay on July 10th 2018 2,266 reads

This guide runs you through everything you need to know about task management, from what it is, to the methodologies best suited to your team, what tools you’ll need, and how to organize, prioritize, delegate, and track tasks. Tasks by their very definition are tiny. But the return they bring you and your team are massive. Instead of huge, vague, and unclear project goals, tasks are clear, descriptive, step-by-step instructions. By breaking down every part of your project into a detailed task, you get a better picture of how you're bringing it to life.

@JoryMacKay
Jory MacKay

Copywriter, growth editor, and content strategist

Tasks by their very definition are tiny. But the return they bring you and your team are massive.

One of the hardest things about running any project is dealing with the messy middle. You might have a vision of what things should look like when you’re done, and a good idea of where you are now. But getting there? It’s safe to say even the best teams can get lost along the way.

Luckily, there’s an easy tool that can guide your team through the messy middle: Task management.

Instead of huge, vague, and unclear project goals, tasks are clear, descriptive, step-by-step instructions. By breaking down every part of your project into a detailed task, you get a better picture of how you’re going to bring it to life. Otherwise, it’s like trying to do a puzzle without any idea of what it looks like.

In this post, we’ll run you through everything you need to know about task management, from exactly what it is, to the methodologies best suited to your team, what tools you’ll need, and how to organize, prioritize, delegate, and track tasks.

First off, what is task management?

Task management is a pretty simple idea. But simple doesn’t always mean easy.

In its most basic form, task management is the process of managing a task through its life cycle — from planning, testing, tracking, to reporting on the outcome.

Task Management involves managing all aspects of a task, from its status and priority, to the time, human, and financial resources it needs.

When you’re working with a team, proper task management is the foundation for productive days. Task management tools and techniques give you a detailed and up-to-date view of all the moving parts of a project. It helps everyone on your team stay in-sync, productive, and on schedule.

And as an added bonus, breaking projects and milestones down into specific tasks can be a huge motivator.

When researchers Teresa Amabile and Steven J. Kramer looked at all the things that make great teams succeed, they found that

“Of all the things that can boost emotions, motivation, and perceptions during a workday, the single most important is making progress in meaningful work.”

Task management lets you and your team see that progress. And like Newton’s first law of motion tells us, once your team is moving, it’s easier to keep them going.

What task management software should you use?

A powerful task management tool or software is your best friend when it comes to organizing, assigning, tracking, and reporting on tasks.

Not only will it keep all your info in one place that’s visible to the entire team, but it also lets you see your task and project progress and where you might be overcommitting resources.

There are lots of options out there for you to pick from, but we built Planio specifically to be a flexible, customizable, and simple to use task management tool (built in to a broader project management tool).

Planio lets you follow project and task management best practices. So while we’re going to use it as an example throughout this guide, the methodologies behind what we’re saying can be applied to whatever system and tool works for you.

» If you’d like to try Planio out for your team, you can sign up for a free 14-day trial here.

Task Management Best Practices

So, now that we understand why task management is so important to running projects, what’s the best way to go about actually doing it?

The basics of task management are to capture, organize, and assign everything that needs to get done to complete your project. The more detail you can get upfront, the more people will know what needs to be done.

As with everything when it comes to project management, the only method that matters is the one that works for your team. So while this guide will give you everything you need to know to start properly managing tasks, make sure to experiment and see what your team likes or doesn’t.

Organizing tasks: How to break bigger projects down into prioritized tasks

Any project, no matter the size, is just a series of small steps.

And the first thing you need to do in task management is gather all of those steps together. Don’t worry about organizing them into any sort of order at this point (we’ll get to that next). Right now, all we’re concerned with is getting everything out there.

And we mean everything.

The key to successful task management is having every step clearly laid out. Otherwise you might miss a step and end up down the wrong path. Even better, by keeping all your tasks in a centralized location (like your project management software), you greatly reduce the cognitive load on your brain and are able to focus more on what needs to be done now.

How to capture all your tasks in one place

It’s time we addressed the elephant in the room. The reason the messy middle is so difficult in projects is because most of the time you don’t actually know what all the tasks that need to be done are!

But that’s ok. There are a few techniques you can use to help tease out all of the many tasks that make up your project:

Start at the end and do a brain dump: Sometimes it’s easier to start at the end rather than the beginning. Imagine your finished project. Now what steps needed to happen to get there? Start high-level and work your way backwards. It might also be easier to visualize your tasks at this point on a mind map. This is where you write down each step on a piece of paper or whiteboard and then break them down into the smaller steps required to get there.
Engage your team to see what you’ve missed: Don’t try to come up with all your tasks in a vacuum. Your team are the ones who will be working through these tasks and so they’ll probably have a pretty good idea if you’re missing anything. Once you have the high-level approach done, bring them in to help fill in the holes and ask questions.
Break multi-step tasks down into single-step ones: At this point, you’ll also want to make sure you don’t have too many big tasks (or “mini-projects”). The goal here is to create tasks that are actionable. If a task feels too big, break it down. What are all the components of it? Each one should be its own task.
Group tasks into milestones: Some of your tasks make sense to be grouped together. And creating a milestone is a great way to get more detail into each step and measure your progress along the way. We’ll cover how exactly to create milestones later on, but it’s a good idea to start grouping tasks into categories that make sense early on. In Planio, you can assign tasks to specific milestones via Settings → Milestones. This way you can quickly view your progress in the Roadmap tab.
Ask an expert: If you’re taking on a brand new project, you and your team might naturally miss some key things that have to happen. If you can, bring in an expert who has gone through the process before to let you know if your list of tasks look good — or at the very least, discuss together at your next team meeting and reach group consensus on the best possible breakdown.

What information should each task include?

Each individual task should go into enough detail that anyone looking at them knows what needs to be done, how important it is, when it’s due, and who’s working on it. Your task management software should give you all of these options (and more).

In Planio, you can create a new task simply by pressing the + button in the top left-hand corner. When filling out your task, start with the basic information like the task subject and a detailed description:

Next, go into detail about task status, priority, assignee (aka, who’s responsible), category, milestone, start and finish dates, estimated time, and progress:

Finally, you should attach any supporting documents and files, as well as select other teammates who should be updated on changes or progress made on the task:

Don’t worry if you can’t do all of this right away. But the goal is to make every task ultra-clear about what’s being done, who’s doing it, and when it’s done so your entire team has visibility into the project’s needs.

How to properly prioritize tasks

You can’t just look at your giant list and assume you’ll know what to do next. Instead, every task needs to be properly prioritized to know what needs to happen to keep the project running smoothing. But this isn’t always easy.

Some tasks will naturally be higher priority than others. But there will also be some nebulous ones that you’ll be stumped by. You’ll want to start by defining the scale you’re going to prioritize on. Something like:

Finish Projects on Time and Budget. With Planio.

Alternatively, you might choose a numbered system (if you have more layers of priorities). That could be:

P1
P2
P3
P4
And so on… (with P1 being the highest priority)

When it comes to actually assigning priorities to tasks, one of the best ways is to use a system like the Eisenhower Box, which classifies task priority by importance and urgency.

In this scenario, you would give your highest priority rating to tasks in the Urgent and Important box. Your second highest rating to Important, but not Urgent. Third highest to Urgent, but not Important. And lowest priority to Neither Urgent Not Important.

If it still feels like your tasks aren’t fully prioritized, or you have too many Urgent and Important tasks, you can break them down a step further.

One way is to prioritize within each category. So, let’s say you assign a letter to each category with A being highest priority and D being lowest. Within each letter category, you can then assign a numbered priority. So A1 would be your most prioritized task, while A24 is still a higher priority than B1.

This might sound a bit complicated, but the goal you want to set here, is to make your tasks (and your priorities) super clear, so that everyone knows what should be worked on first.

Collaborating: Assigning tasks, estimating time, and scheduling your project

With your huge list of prioritized tasks ready to go, it’s time to start assigning them and seeing if you have the resources to get the project over the finish line in time.

At this step, you’ll start to get a better idea of how all your tasks fit together and where you might be overcommitting either time or resources.

How to estimate the time each task will take

We’ve already done the hard work of deciding what needs to get done and breaking each task down into its smallest part. So we should be able to accurately estimate how long each of those parts will take.

However, if you’re working on tasks that are completely new or unfamiliar, there are a few techniques you can use:

Estimate time and use timeboxing: Some tasks — especially creatives ones like writing, designing, and coding — will take as long as you give them (psychologists call this Parkinson’s Law). In these scenarios it’s important to give limitations to the time for the task. In Planio you can include an “estimated time” for each task and then compare that to how long it actually took. You might be off, but you’ll get a better understanding of how long certain types of tasks take.
Build in buffers for unfamiliar tasks: If you’re working on a task for the first time, you need to start with a guess of how long it will take. However, underestimating time too much can bring added stress to the entire project. That’s why it’s important to build in time buffers to your task management. Typically, you’ll want to add x1.5 the estimated time for tasks you haven’t done before but have a good idea how they can be done. And x2 the estimated time for tasks that seem doable but need research on how to actually complete them.
Ask an expert: Just like you can bring in experts to help you with task creation, they’re also a great source to help with time estimation. Ask people who have done similar work how long it took them. Each team is different and you have to take your individual team mates and skill levels into account. But this should give you a good starting place for estimating task time.

Use your time estimates to prepare your schedule and allocate resources

It’s important to remember that time estimations are just guesses.

You’ll probably hit a few roadblocks along the way and your estimations might get completely out of whack. But the goal of estimating task time isn’t just to show your boss how long a project will take. It’s also to see how much you’re committing individual team members to.

Once you’ve taken a first pass, look at the tasks you’ve assigned to someone and the time estimation. (You can filter tasks by assignee in Planio!)

Is that reasonable?

Do you have places where you need to move or reallocate resources to help them out?

Task management isn’t just about having a giant list of tasks to do, but spreading them out evenly and in the way that makes the most sense and ensures the project can actually get completed.

Tracking: Grouping tasks into milestones and managing task status from start to finish

Once you’re actually working on your project, task management becomes even more important.

You need to be able to know what team members should be working on, the status of every task, and what’s coming up in the future and will need your attention. This means grouping tasks together to see the milestones of your project and then using a task management methodology to track your progress.

How to break tasks down into milestones

Milestones are simply a collection of tasks that represent some piece of your project puzzle being completed. It could be finishing coding a feature or redesigning a landing page — anything that marks an achievement or end of a chunk of work.

Milestones are important because they let you zoom out from task-level view and see the real progress you’re making. If tasks are the smallest possible steps that need to get done, Milestones are like the giant leaps.

To create a new Milestone in Planio simply go to Settings → Milestones. Each Milestone should have a name, short description, and be made public if you want everyone to be able to see it. You can then assign specific tasks, feature requests, and even bugs to that Milestone.

So, let’s say our Milestone is to release a mobile app. In the example below, we’ve created our Milestone and we can see that there were 14 issues and tasks assigned to it. And that they’ve all been completed!

Milestones are a great tool for tracking task status. But they’re also fantastic for maintaining focus and boosting motivation. To get the most out of your Milestones, you should make sure they’re:

Specific: Every Milestone should be properly scoped out and descriptive.
Attainable and timely: There should be a start and end date that you think you can reach.
Progressive: Milestones should build on each other. Once one is finished, it should be 100% done and the next one should be 100% doable.
Significant: Don’t make Milestones too small or your project will look bigger than it actually is. Make sure that the end of each Milestone feels like you’re completed a respectable portion of the project.

Choose a method for tracking your milestones, task progress, and task status

There are tons of ways to manage your tasks and milestones so that you can unlock more time to pursue other meaningful company objectives like establishing partnerships or generating more leads for your business. And at the end of the day, what works best for you, will come down to the size of your team, the complexity of your project, and how you work best.

Some task management systems are more flexible and visual (like Kanban), while others are simpler (like your basic to-do list).

We’re going to assume that you’re working with a team of people on a project that needs more visibility than a simple to-do list can provide. Which means there are a few task management methods you should consider:

Kanban

Kanban is a visual task management method where tasks are defined on “Cards” and then moved left to right on a board through each stage. This could be as simple as “To do”, “Doing”, “Done” or broken down into whatever stages you need.

Here’s what a Kanban board in Planio looks like:

The great part about Kanban is that it gives you a quick big-picture overview of all the tasks you need to complete and what their status is. You’ll have all your tasks, due dates, progress, and task status in front of you. The only downside is that because task details are contained within a card the details can sometimes get lost.

Gantt Charts

Big projects often lend themselves to stages or milestones, where some tasks need to be done before others. In this case, using a Gantt chart is a great way to organize your tasks.

Gantt charts have been around for over 100 years and are a great way to visualize all your tasks, when they’re due, and who’s working on them to see how many resources you’ll need and monitor progress.

Again, Planio lets you quickly create Gantt charts for your tasks that look like this:

Gantt charts are great as they let you quickly visualize the Milestones and related tasks to see how progress is being made and who has too much on their plate. They’re also a powerful way to see dependencies on projects (i.e. “I can’t do X until Jon does Y”).

However, if you have a very complex project with tons of tasks, they can get a bit messy and hard to comprehend.

Adjusting: How to adjust tasks (when your situation changes)

No project ever goes exactly as planned. But that’s what makes task management so fantastic.

When you have a deep understanding of all the things that need to get done to hit 100% and can visualize them all in one central place, you have a better chance of seeing when problems might arise and adjust accordingly.

Situations change. A team mate might quit or need to take time off. Or some new user research might come in that changes the scope of your project. Heck, your company might even pivot! In all of these cases, you can use your task management system to take stock of the situation, adjust, and get back on track.

Here’s a few final tips for making the most out of your task management when things change:

Always have a full view of the project: Whether this is through a Kanban board, Gantt chart, or some other method, it pays to always be able to zoom out and get a full view of the project. Task view is great when you’re in the thick of a project. But too much time spent on the small details (especially as a project manager) can make you miss the forest for the trees. Periodically step back and reassess your task priorities, milestones, and the overall flow of your project and assess how upcoming changes might affect it.
Be proactive about seeing and adjusting to shifting priorities: The importance of task priority can’t be overstated. When you say something is critical or A1 or whatever task priority system you’re using, you’re setting the path for your team. But that doesn’t always mean that path is the right one. Be proactive about looking for potential priority shifts. Talk to other managers or team leads. Planio also lets you filter tasks by priority and any other criteria. The better you can prioritize, the more productive your team will be.
Always be able to connect tasks to project and company goals: Just like the last point, connecting your tasks to project and company goals is a compass check to make sure you’re still going the right way. We’ve written about the power of OKRs in the past and this is no different. Make sure tasks align with company goals as much as possible.
Remove tasks that aren’t being actively worked on from immediate attention: Task management is as much about what’s not there as what is. If a task is no longer relevant due to a change in priority, get rid of it. Too many tasks on a board (or chart) add an unnecessary cognitive load to your team. You want them to see progress and feel motivated. Not bogged down by endless tasks.

Tasks by their very definition are tiny. But the return they bring you and your team are massive.

Take the time to break down tasks into their smallest pieces, prioritize them ruthlessly, and find a task management software that gives you visibility, flexibility, and awareness (like Planio) and you’ll be on your way to turning that big, scary, audacious project into an actionable, step-by-step plan.

Hey, I’m Jory!

I help companies and interesting people tell their stories through smart and focused writing. Want to work together? Email me at [email protected]

A version of this post was originally published on the Planio blog. Check it out for more essays and actionable tips on project management, building a remote team, and thriving as a startup.

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