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How to set milestones so even big-deal projects feel manageable

By | Published on | 7 min read
<span id="hs_cos_wrapper_name" class="hs_cos_wrapper hs_cos_wrapper_meta_field hs_cos_wrapper_type_text" style="" data-hs-cos-general-type="meta_field" data-hs-cos-type="text" >How to set milestones so even big-deal projects feel manageable</span>

Learn the right (and wrong) way to set project milestones. Hint: Don't confuse milestones with glorified tasks. 

Say you’re planning a road trip across the country—all the way from California to New York. In New York awaits the party you’ve most been looking forward to all year. You could just wing it and drive each day until you get tired. But there’s one problem with that approach: That party is your deadline. You absolutely need to be in New York by Sunday, lest you risk missing all the fun.

To ensure you get there on time (and make your journey more manageable), you decide to split up your trip using other destinations. You need to be in Arizona by Tuesday. Texas by Wednesday. Oklahoma by Thursday. You get the idea.

Whether you realize it or not, you just planned a trip using project milestones. Let’s dig into these a bit more to uncover how they work, why they matter so much, and how to make sure you set milestones you can follow to get you to your party—ahem, deadline—on time.

What are project milestones?

Project milestones are important events within a project lifecycle. They’re specific points or achievements that, when reached, confirm you’re moving in the right direction within the right timeframe (and, you know, not wandering aimlessly in Missouri). 

Basically, you can think of project milestones like mini projects or deadlines. They’re the signposts that guide the way as you make your journey from the start of your project all the way to the end. 

What’s the difference between milestones, tasks, and deliverables?

Project milestones are pretty straightforward. But they can still be easily confused with two other important parts of project management: tasks and deliverables. 

Tasks are the actual action items that need to be completed within your project. Your project milestone could be the completion of a certain task, but it’s not the task itself. Here’s an example to help you spot the difference:

  • Task example: Send final draft of ebook to client for approval. 
  • Project milestone example: Client approves the ebook draft. 

See how the task starts with an action word while the milestone indicates a specific turning point in the project?

It’s a subtle difference, but it’s an important one: it’s not just the task that’s been completed, but the impact the task has on the journey you’re highlighting with a milestone.

Now, let’s talk about deliverables. They’re the tangible outputs of your project. Again, a milestone might involve the completion of a deliverable, but the deliverable itself is something different. Sticking with our same example helps to illustrate the distinction:

  • Deliverable example: Final ebook draft.
  • Project milestone example: Client approves the ebook draft.

Why do project milestones matter?

Hashing out a project plan on its own involves a lot of work. There are so many variables to consider. Is it really worth the extra effort to identify and set milestones, too?

The short answer is yes. Think about it this way: Without milestones, you’d probably make it to New York. But the whole journey would likely feel a lot more daunting and stressful. And you might not arrive on time. 

With that in mind, here are a few reasons why project milestones are important:

  • They make projects more manageable: How do you eat an elephant? One bite at a time. Milestones break even the biggest projects into more feasible steps, which reduces feelings of overwhelm.
  • They improve planning processes: By estimating when you’ll reach each milestone, you’ll create a more accurate project timeline and be able to set more realistic deadlines.

  • They help increase motivation: Those periodic landmarks instill a sense of urgency and boost your motivation. (Think: “If we can just make it to Indiana by Friday.”) It’s all part of the progress principle, which states that of all the things that can boost your mood and perception during your workday, the most important way to boost your mood and perception during your workday is making progress in meaningful work.

  • They simplify progress monitoring: Milestones provide regular opportunities to evaluate your performance and make sure you’re sticking with your plan.

  • They provide regular chances to course-correct: Milestones also give you an opportunity to take corrective action if you realize you’ve veered off course—before you’re in way too deep. 

How to set project milestones: 3 steps to follow

Setting project milestones involves more than putting an image of your timeline on the wall and throwing a dart at it. Your milestones should be natural climaxes within your project that help you evaluate whether you’re on track.

Spotting those turning points involves some strategy. Here are a few simple steps on how to do it, along with some project milestone examples to provide even more clarity. 

1. Create your project plan

Identifying your milestones is not your first step when planning a project. In fact, you want to have most of your project plan worked out before zooming in on milestones. 

Think back on our road trip example. Before you picked your pit stops, you already knew your starting point, your destination, your deadline, and who was coming along for the ride. The same applies to any other project. As you pull together your plan, make sure you can answer questions like:

  • What’s the project goal?
  • What is/are the deliverable(s)?
  • What’s the timeline?
  • Which team members and stakeholders are involved?
  • Which tasks need to be accomplished?

Let’s say that you want to create a customer-facing knowledge base. Here are the nuts and bolts of the project you’ve worked out: 

  • Goal: Create a knowledge base to empower customers by providing them with easy-to-access information.
  • Deliverable: Public knowledge base on our website.
  • Timeline: Knowledge base will be live by October 1, 2022.
  • Teams: Sales team, customer support team, and marketing team.
  • Tasks: Generate a list of FAQs, draft supporting documents, design knowledge base, etc.

2. Look for the highlights

Milestones should feel somewhat natural—they’re those big moments that indicate you’ve reached a major achievement in your project. 

As you look at your overarching plan, some project milestones might jump out at you right away. But, if you’re struggling to parse out some of those turning points, here are a few key points that can help you determine your project milestones:

  • The project moves into a new phase
    • Project milestone example: Your knowledge base moves from the drafting stage to the design stage.

  • The project is handed off to another team
    • Project milestone example: The development team takes over from the design team.

  • A project deliverable is completed
    • Project milestone example: The first drafts of all the support articles are finished.

  • The project reaches an important event
    • Project milestone example: The drafted knowledge base articles receive leadership approval. 

3. Space out your milestones

You’ve pulled out all of the big moments within your project. Now, should they all be milestones? How many should you have?

This can be tricky. Too many milestones will kill momentum and slow down your progress. But too few will leave everybody feeling confused about where the team stands. 

There isn’t one right answer for how many milestones your project needs—a lot of that depends on the complexity and duration of your project. A major project that lasts a year might have a milestone every quarter. Or maybe every month. But a smaller project that lasts for one month might have a milestone every week. 

As you evaluate whether something should be set as an official project milestone, ask yourself this: Why does it matter that we’ve reached this point in the project?

For example, getting leadership approval on the drafts matters because you need that thumbs-up before moving forward with anything else. But having the development team take over might not be as big of deal, especially since the design team will continue to be involved.

If you don’t have a solid answer to the “why does this matter?” question, you’re probably not looking at a suitable milestone—even if it is a bigger moment within your project. 

With all of that in mind, you could end up with the following project milestone examples for our knowledge base project:

  • Milestone #1: Knowledge base categories, topics, and questions are identified.
  • Milestone #2: Knowledge base support articles are drafted.
  • Milestone #3: Knowledge base support articles receive leadership approval.
  • Milestone #4: Knowledge base site is designed.
  • Milestone #5: Knowledge base site is launched.

Setting project milestones in Trello

If you’re using Trello to track your project, both the timeline view and the calendar view of your board will make for a handy visual reference—like a map on a road trip—to help you keep track of your project milestones.

Insert project milestones into the timeline view to have a clear visual layout of upcoming due dates. This video clip from Atlassian University demonstrates how to map your project milestones in a Timeline view in Trello:


HubSpot Video


Or, try the Calendar view to help you see cards in a monthly, weekly, or daily format. Like this:


HubSpot Video



Note: We’ve recently upgraded the Board view experience! As a result, some of the screens in the videos above may look different. With the new update, you will be able to toggle between board views from buttons along your top menu bar. Read more about it here. 

Screenshot showing toggle view

To learn more about improving your team’s projects, workflows, and tasks, take the Atlassian University course that includes the videos above and much more . (P.S. Not sure you’re a Trello admin? If you manage a board, you’re an admin!)

See all Atlassian University courses now


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