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

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 .

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:

  1. 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.
  2. 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.
  3. 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 SettingsMilestones. 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:

  1. Specific: Every Milestone should be properly scoped out and descriptive.
  2. Attainable and timely: There should be a start and end date that you think you can reach.
  3. Progressive: Milestones should build on each other. Once one is finished, it should be 100% done and the next one should be 100% doable.
  4. 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 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.

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