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Why Your Team Misses Their Deadlines
missed deadlines and how to avoid them

Why Your Team Misses Their Deadlines

By Alex Dingley

About missed deadlines, English author, Douglas Adams once said, “I love deadlines. I love the whooshing noise they make as they go by.”

Unfortunately, too many of us can relate to the feeling of watching deadlines whoosh past without deliveries or milestones being met. According to PMI’s 2018 Pulse of the Profession report, roughly 48% of projects don’t finish within their initially scheduled times.  

When nearly half of all projects result in missed deadlines, you know this is an issue that cannot be overlooked. Late projects can result in increased costs and unhappy customers, which harms both your reputation and your business.  

Here are three reasons your team has missed deadlines and what you can do to eliminate these problems going forward.

1. Optimistic Planning Creates Unachievable Timelines

Did you know that it’s human nature to be overly optimistic about how long it will take you to complete a task? Even when it’s a task you’ve done before?

This unfortunate tendency is called “planning fallacy.” While it was first coined back in 1977 by psychologists Daniel Kahneman and Amos Tversky, it still holds true today.

People generally underestimate how long it takes to do something, regardless of whether it’s a simple task like preparing supper or something more complex such as building a house.

For instance, imagine your last software development project took 16 months to complete. It’s natural to assume that this time around you can do it in 14 months because now you have more knowledge and experience. But that optimism can quickly lead to missed deadlines.

Other causes of overly optimistic timelines include:

  • The assumption that the project will go as planned, with no issues.
  • Failure to assess how long it’s taken to complete similar tasks or projects.
  • Failure to factor in resource and other constraints (such as holiday shutdowns or long material lead times.)
  • The assumption that this project will be simpler than the previous ones.

How to Create Realistic Timelines

The key to a more realistic schedule is to rely on analysis and data. If you’re using project management software, and you’ve completed similar projects in the past, you can easily use these as the basis for realistic estimates. The more data you have, the more confident you can be in your estimates.

If you don’t have enough past project data to guide you, then you can use the following methods to ensure your numbers aren’t overly optimistic.

Method 1: Use a multi-point estimation technique

There are many different methods for creating more realistic estimates, including:

All of these methods take multiple estimates and combine them to arrive at a more realistic timeline. For example, a 3-point estimation requires that you estimate three different timelines:

  1. The most optimistic or shortest amount of time you think it will take.
  2. The most pessimistic or longest amount of time you think it will take.
  3. The amount of time you believe it’s most likely to take.

Method 2: Have your team create bottom-up estimates

A bottom-up approach to estimating requires that you build your timeline by estimating each individual task and then combining them to arrive at an overall project estimate.

Due to the level of detail involved, this takes more work than a top-down approach, where you simply estimate a project as a whole. However, the level of detail required is also what enables this to result in a more realistic estimate.

Bottom-up estimates ensure no tasks are missed in the creation of the timeline. Plus, by having your team contribute to the task estimates, you can increase employee buy-in and feel more confident in the schedule.

Method 3: Add reserves

By building reserves into your schedule, you can help account for known and unknown risks, which will result in a more achievable timeline. There are two types of reserves:

  1. A contingency reserve is money and/or time built into your schedule in case known risks occur.

    Let’s say you’re painting a house and you know that bad weather could delay painting for one week. Since bad weather is a known risk, you may choose to add one week to your painting schedule to mitigate it.
  2. A management reserve is for unknown or unexpected risks. It’s typically a flat 5–10% of the project cost and/or timeline added to the schedule baseline in case something unforeseen occurs.

    Imagine one day, one of your delivery drivers backs right into the house, collapsing the front porch. This event was so unlikely, it was never recorded as a risk and had no contingency. Therefore a management reserve is needed to offset it’s impact.
team meeting to fix missed deadlines

2. Unclear Expectations Result in Missed Deadlines

If your team is unclear on when a deadline is, how will they ever meet it?

The problem is that communication problems can lead to you thinking your team understood their deadline when they didn’t.

Imagine the following conversation:

You: “Can you get this back to me by Thursday, at the latest?

Team member: “Well, I don’t know. It depends on if Jan finds any defects or not. If I have to do error resolution, then I doubt I’ll be able to complete this before Monday.

You: “Look, unless they’re critical, just leave the bugs and focus on this. I really need it no later than Friday.

Team member: “Alright, I’ll try my best.

Based on this conversation, what do you think the agreed-upon deadline is?

As the boss, you may be under the impression that your team member is expected to get it done by Thursday unless there are critical defects, in which case you will accept it on Friday.

However, your team member may have interpreted it that you need it by Friday, but if there are critical bugs, those come first, so his initial estimate of Monday is still the drop-dead deadline.

How to Communicate Expectations Clearly

The deadline for a task or project may be perfectly clear in your mind, but that doesn’t mean that everyone on your team is on the same page.

Here are three ways you can ensure your team understands their deadlines.

Method 1: Use your project management software

If you assign work informally or inconsistently, it can be easily misunderstood, forgotten, or considered unimportant.

When you hand out assignments verbally, people can easily forget about what was discussed or misconstrue your words. For instance, if you say, “I’d like to see this by the end of the week,” a team member may see that as a request and not a hard deadline.

However, when their name is assigned to a task in project management software, the end date in the system allows for no question as to when their deadline is. Plus, you can use system features such as notifications to ensure team members don’t forget what they’ve been assigned and what due dates are approaching.

Method 2: Implement a closed feedback loop

A feedback loop, or communication loop, is a simple process for ensuring what you’ve communicated has been heard and understood.

To ensure your employees share the same understanding, you can ask them to repeat back to you what their deadlines are. In the hypothetical conversation above, imagine if the team member was asked what the agreed-upon deadline was and replied: “Friday, unless there are critical defects, then Monday.”

You would know before he ever left the room that your understanding was not shared, and you would have the opportunity to clarify expectations before missed deadlines.

Method 3: Incorporate periodic check-ins

The last thing you want is to discover after the deadline was missed that there was a misunderstanding as to when it was.

By incorporating periodic check-ins into your schedule, you’re achieving three things:

  1. Creating additional opportunities to remind employees of a deadline.
  2. Re-communicating the importance of that deadline.
  3. Creating opportunities for additional feedback to ensure they understand the deadline.

Check-ins can also help you identify potential problems and warning signs before it’s too late, without having to micromanage your team.

3. Poor Time Management

If you asked your team members how many hours a day they spend doing productive, project-related work, what answer would they give?

Assuming an 8-hour workday, they may guess 7–8 hours. But, research shows that this is a drastic overestimate.

In fact, during an average 8-hour workday, most people only accomplish 5 hours of productive work. To make matters even worse, those 5-hours include multi-tasking and constant interruptions from email and instant messaging apps. This means in reality, your team is achieving only about 12.5 hours of uninterrupted productive work each week.

When you’re assuming a 35–40-hour workweek and only achieving 12.5–25 hours of work, it’s no wonder there are missed deadlines are missed!

How to Improve Employee Time Management

Here are three ways you can help your team better manage their time and become more productive:

Method 1: Reduce time wasters

Toggl is a free time tracking tool that your employees can use to record what they spent their time doing.

By tracking their own time for a few days, your team can discover time-wasters such as spending too much time on social media or surfing the web. They may also discover bottlenecks in the process, such as the time they’re forced to sit idle while waiting for reviews or approvals. Another potential time-waster is time spent in unproductive or unnecessary meetings.

Once these time wasters are identified, you and your team can work together to resolve the issues and improve their efficiency. For instance, StayFocusd is a Chrome browser extension that you and your team can use to block out time-wasting websites during the workday.

Plus, you can ensure that employees are only invited to meetings they are directly impacted by and that any unnecessary ones are canceled.  

Method 2: Eliminate distractions and interruptions

How much of the day do your team members spend with their email and instant messenger app open on their desktop or mobile? And how quickly do they respond to messages and requests when they come in?

It can seem natural to be so connected and accessible in this day-and-age. And while this can boost collaboration and communication among the team, it can also detract from productivity.

Every time we’re interrupted, it destroys our focus. Even if it’s just a simple glance at your inbox, it can pull you out of “the zone,” drastically reducing your productivity. Considering that US employees check their email roughly every 15 minutes, you can imagine how much time is lost. Time that could otherwise be used to meet project deadlines.   

Here are three ways you can help your team eliminate distractions and interruptions:

  1. Encourage time blocking.
  2. Recommend employees only check email and IMs at designated times.
  3. Provide a quiet, isolated space such as an empty office for employees working on anything complex or high-priority.  

Method 3: Avoid overloading your team

Even when time wasters are removed, and distractions are eliminated, you may find that your team is still over-allocated. After all, you can’t completely remove emails, meetings, and other interruptions.

So, even if you can help your employees achieve 30 hours of productive work a week, you’re still overloading them by assuming a 35-40-hour work week in your schedule.

When team members are overallocated, they cannot get everything done in the time allotted to them. This creates competing priorities. This means that either your team will be forced to work overtime or deadlines will slip.

If your team members have too much on their plates, you will need to either increase the size of the team or push out the timelines. If some of their workload is for another project or manager, ensure everyone is aligned on what is prioritized, and work together to agree to an attainable schedule.


Missed deadlines are all too common across all industries and businesses. If your team is one of the nearly half of project teams with missed deadlines, it’s due to one of three problems: overly optimistic estimates, unclear deadline expectations, or poor time management.

Fortunately, all three of these are avoidable. By following the advice provided above, you can ensure that your team doesn’t miss another deadline from here on out.


Alex is the Director of Customer Success at Workzone. He oversees the training and implementation of Workzone’s project management software for new customers. Prior to Workzone, he spent 7 years with Apple, Inc. as a trainer in the retail stores and at their corporate headquarters. He’s also a recording & broadcast engineer, musician, and volunteer with the Big Brothers, Big Sisters.