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Project Portfolio Management

Six Common Project Management Milestone Mistakes – and How to Avoid Them

Published By Team AdaptiveWork

Milestones have been a basic staple on the project management landscape for, well, forever.

Indeed, just as you can spot economists at a party because they’re the ones saying “all else being equal,” and you can identify the IT specialists because they’re passionately talking about “cloud migration,” you can point out the project managers because they’re chatting about milestones.

However, sometimes this chatting is more of a confession, because virtually every project manager has, at one time or another, made one, some, or likely all of the following milestone mistakes:

  • Not Creating Enough Milestones

It’s important to be selective and take a “less is more” approach when creating milestones, since they’re only supposed to mark important and noteworthy events in a project task (or a group of tasks). However, this minimalism can sometimes lead to a scarcity of necessary milestones, which means that projects can veer off track and stakeholders can underestimate or overestimate where they’ve been, where they are, and where they’re heading next.

  • Creating Too Many Milestones

On the other end of the spectrum, creating too many milestones adds needless schedule complexity, as stakeholders struggle to focus on those that matter, and filter out those that don’t. In addition to being a logistical headache, this error often makes smaller projects — or phases within projects — seem larger than they truly are, which triggers procrastination (i.e. people think they have more time then they actually do) and fatigue (i.e. people think there’s much more work than there actually is).

  • Not Proving Enough Information

Milestones on the side of the road provide very basic information, like the name of a city or the distance to a landmark. But milestones in a project often need to be associated with supplemental or background data, such as contracts, meeting minutes, reports, and so on. Avoiding this error is essentially impossible for project managers who are saddled with tools like spreadsheets, or who obligated to use conventional (read: prehistoric) project management software that was not designed to capture the reality that milestones are signs, not stories.   

  • Not Communicating Milestone Information

Once milestones are defined, they need to be shared with appropriate internal and external stakeholders. This is a tedious, time consuming, and often error-prone task for project managers that cannot easily connect and collaborate with colleagues, customers, vendors, service providers, and so on.

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    • Not Using Milestones as Motivational Tools


    Project managers should — but often don’t — use milestones to celebrate wins and motivate team members. Even a quick mention at a daily stand up or a weekly status meeting can boost engagement and unity.

    • Not Monitoring and Optimizing Milestones


    Milestones aren’t set-it-and-forget it project elements. Project managers need to regularly monitor milestones and, like gardeners, prune those that are no longer valid, cultivate those that are flourishing, and plant those that need to be part of the landscape.  

    The Solution

    The key to avoiding all of these errors — and turning milestones from a liability into an asset — is using a cloud-based project management solution like Planview AdaptiveWork that empowers project managers to:

    • Accelerate and simplify the milestone planning process by accessing full visibility into task progress and other factors that affect milestone identification and completion.
    • Add and edit milestones that team members and authorized external stakeholders can view in real-time.
    • Add documents and meeting notes to milestones to provide background/supplemental information.
    • Create a single, easy-to-manage source for up-to-date milestone information.
    • Convert existing project tasks into new milestones, which is especially helpful when managing several sub-projects within a larger project.


    Learn more by scheduling your live guided demo, or launch your free 30-day fully-fledged trial of Planview AdaptiveWork today.

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Written by Team AdaptiveWork