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Deadline Management Dilemmas? Tame Your Task List: 101

Deadline dilemmas stressing you out? Manage your team's deadlines without the headaches with this 10-minute guide to better deadline management.

Haylee Read
Writer at Motion
Mar 27, 2024
Table of contents

There’s nothing like the dread you feel the night before that deadline you just know your team will miss. Not to mention the chain reaction it’ll cause if you miss the deadline entirely.

Maybe you did everything possible to meet it, but it wasn't possible.

Or maybe they weren't as focused as they could have been because life just got in the way.

If you find yourself wrestling with the complexities of deadline management, this 10-minute read will equip you with the essential strategies for navigating, setting, managing, and easily meeting tight deadlines.

Whether you're a seasoned project manager or a budding entrepreneur, mastering deadline management is essential for building trust with clients relying on you to deliver what you promise.

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7 underlying issues that could be causing widespread missed deadlines

If your team continually misses deadlines, it could be down to poor time management, or there could be something else going on behind the scenes, like:

1. The planning fallacy muddying reality

The planning fallacy says we greatly overestimate our ability to get things done within a timeframe.

Sometimes, it pays to be a pessimist. At least, that’s what the Harvard Business Review says when planning for better deadlines. Assume the worst and add buffer time just in case, like when you add extra time to drive somewhere, knowing traffic could be bad.

But don’t go overboard. We all know the longer we have to complete a task, the more we procrastinate. If you have 14 days to do a task, you know you’ll take the whole 14 days, even if you could have achieved the same result in 2.

In addition to being overly optimistic about how long a task might take, there are quite a few reasons we miss deadlines. Here are just a few of the underlying issues that could be leading to widespread deadline issues in your team:

2. Scope creep (adding invisible load)

Things can get out of hand when a complex project grows out of control without us realizing it. If you keep adding more tasks or more powerful features as you go, it can kill your timeline (big time). Especially if they conflict with dependent tasks.

We get how easily it can happen. For example, you’re in a client meeting about a website, and your client asks if they can change one small part of an existing page (since you’re already there doing other work). You’re eager to please because it’s a new client, so you agree to do it just this once. Suddenly, at every meeting, there is one small addition, and before you know it, you and your team are doing unpaid work on features you didn’t build in the first place.

Not only are you adding work, you’re detracting from the true project.

Scope creep isn’t just a drain on your resources. It also removes opportunities to cross-sell and up-sell additional work that you could tackle much better when you have the time to do it right.

3. Communication breakdowns throughout project execution

Things can easily go off track if you’re not keeping everyone in the loop. You need clear channels for effective communication to make sure everyone knows what's going on.

In your business, this might mean using a communication tool like Slack, with separate channels for each development team, creative team, and management team.

Behind the scenes, it could mean time tracking tools to get oversight into where time is going.

It could also mean weekly client progress reports updating on the status of critical tasks and explaining if there have been any changes to the planned dates. Keeping clients in the loop reduces the back-and-forth and maintains trust, even if you miss a deadline.

But it also goes both ways. If your clients aren't providing what they agreed to by their deadlines, you're wasting valuable time chasing them up.

All parties (or stakeholders) must meet deadlines, including your clients.

4. Resource constraints

Resource allocation (or costs) is a key piece of the project management iron triangle, which boils down to three key things:

  • What needs to be done (scope)
  • When it needs to be done (time)
  • How much it's going to cost (cost)

A triangle with a header at each point.

‎When altered, each of these key constraints will affect the quality of the work you’re doing.

Continuing with our website example, adding extra work would increase the scope, affect the project timeline, and increase the cost.

Continuing with our website example, adding extra work would increase the scope, affect the project timeline, and increase the cost. This, in turn, would affect the balance of the iron triangle and the quality of your output.

Now you're not only delivering late, but you're delivering lower quality and losing money. Not great, right?

5. Dreaming too big

Sometimes, we set deadlines that are just way too ambitious because we want to go the extra mile for our clients. But you must be realistic about what you can achieve at any time.

When setting deadlines, keep the planning fallacy in mind, review past projects to see how long things took, and learn from past mistakes.

If you’re unsure how to measure how long your future projects should take correctly, try the Critical Path Method and plot all your crucial tasks and task dependencies on a PERT chart.

‎While you might be shocked to see how long something takes, undercutting that to impress a client will only cost you in the long run. In project management, going the extra mile means being able to say no when it’s necessary.

6. Risks becoming issues

Sometimes, things just go wrong and are out of your control. Risk management planning helps you account for things that could happen throughout your project with pre-planned contingencies that you can enact should the worst happen.

An iceberg above and below water with words around it

‎For example, few saw the pandemic coming. Now that we've experienced one, you know that should it happen again, there are ways of working to keep work moving at the same pace.

You should have the same level of risk planning for any potential project risks you’ve identified.

7. Prioritizing speed over quality

Sometimes, we rush to get things done and sacrifice quality, but that tends to bite us in the long run (and burn more time).

To tackle this, you need to face this head-on. That means better planning, communicating more, setting realistic project goals, ensuring we have what we need, and being ready for curveballs.

Deadline management is as much a company culture thing as time and project management, so have an open conversation with your development team, find the underlying issues, and solve them together.

5 steps to setting better deadlines — without the headaches

Setting effective deadlines for your creative team is crucial for creating a culture of productivity and completing projects successfully. Here are some tips to help you set better deadlines:

1. Understand the project you’re scheduling

Before setting a deadline, ensure you fully understand the task or project. This includes knowing the scope, requirements, and any potential challenges that may arise (risk planning).

If you agree to a complex project without completing the required risk planning and timeline calculations (PERT, CPM), you’re setting yourself up to fail.

You need to ensure that your deadlines are Specific, Measurable, Achievable, Relevant, and Time-bound (SMART). This helps clarify expectations and keeps everyone accountable.

‎If your client is too busy to allow you to complete these vital tasks, educate them on the value of planning and discovery (include some real examples of what could happen).

If they want to rush, it might be ‌time to consider moving on to clients who value your process, which is there to serve them better (not a waste of time).

2. Break down the task and make room for opportunity:

Look at your project like a chain reaction of task dependencies. What happens if one task is late?

Break larger, more challenging tasks into smaller, manageable chunks. This makes it easier to set realistic deadlines and track progress. Then track these dependent tasks individually rather than tracking against larger milestones (which have too many moving parts).

Task tracking is the key to project success. After all, these tasks are the links in the chain that pull your project across the finish line. If one link breaks, the project breaks.

Instead of manual tracking, use a task manager to understand better how long things take. Then add buffer time in the future.

3. Consider individual workloads:

Consider each team member's workload before setting deadlines. Everyone has different responsibilities and commitments. Make sure the deadlines you assign are fair and doable based on what else they have going on.

By using a task tracking tool (vs. manual tracking), you can get real-time reporting on each team member’s schedule.

Then you can distribute even the most difficult tasks effectively so deadlines are met without causing too much stress or sacrificing quality (remember the Iron Triangle). It's all about finding that balance for a productive team AND a happy customer.

4. Communicate clearly

Communicate deadline expectations to your team and your clients. You can do this with progress reports or weekly status meetings.

Every stakeholder needs to be held to the same standard. Your client expects you to deliver what you promise on time, and vice versa.

Communicate these standards early (and often) so there is no tension when you have to remind a client that any delay in them providing the information you need (like logins, access to tools, documents, etc.) will also affect your timelines.

‎It’s not your job to absorb time lost by stakeholders. It’s your job to ensure it doesn’t happen in the first place.

5. Be realistic — don’t overpromise

When setting deadlines, be realistic and avoid overpromising. Don't set overly ambitious deadlines that are impossible to meet. Consider factors like complexity, available resources, and potential obstacles.

Rushing through urgent tasks due to unrealistic deadlines can lead to mistakes or delivering tasks late — which is ultimately a waste of time. Setting achievable deadlines gives you and your team a better chance to deliver quality work without unnecessary stress or disappointment.

It's all about finding the right balance between ambition and feasibility.

3 pro tips to make deadline management a breeze

We’ve given you plenty to think about already, but just to put the cherry on top, here are three pro tips you can use right now to make your project deadline management even easier:

1. Get your stakeholders on board

  • We can’t stress this enough. If you agree to unrealistic deadlines to try to win business, you’ll, you’ll not only lose clients when you can’t deliver what you promised but also the staff that are being burned out.
  • Be realistic when setting deadlines so your clients will learn to trust your word and your team can provide the highest quality work the first time — without rounds and rounds of revisions because they felt forced to rush.
  • The little pushback you dread when telling clients it'll take longer than they would like is nothing compared to the pain of pushing deadlines once you start work.

2. Create a culture of productivity — not hustle

  • There's a big difference between creating a high-performing team that loves what they do and producing a task factory that pumps out work under the risk of punishment.
  • Focus on creating an environment of open communication where deadlines can be discussed freely and moved when there are real issues.
  • When there are genuine concerns about multiple people missing deadlines (especially top performers), it’s time to take a good look at your planned versus actual progress over time to determine if the problem is your team's time management or unrealistic expectations.

3. Let task-management tools act as a second brain for complex tasks

  • Gone are the days of paper to-do lists, manual task managers, or just working at the whims of your inbox.
  • You need smart task management tools with powerful features to set the optimal schedule for you and your entire team in real time, so all you have to do is log in and get to work.

  • ‎Focus on project management software that allows your project team time to focus on deep work and productivity rather than just being busy — there's a big difference.

Don’t let tight deadlines get the best of you and your team. Delegate deadline management to an AI-driven assistant instead.

Meet Motion: Your project deadline management assistant

No more struggling with impossible deadlines and trying to keep everyone on track! Meet Motion, your project assistant dedicated solely to managing deadlines and schedules without all the stress.

This isn’t your typical project management tool. Imagine this: no more last-minute rushes or missed deadlines. With Motion, you can manage your entire team's schedules seamlessly.

Once you've set your task deadlines, Motion gets to work. It's like having an expert scheduler on hand, making realistic daily plans that meet your project timelines and balance their day for better focus.

And the best part? If things change unexpectedly, Motion is there to help. Its advanced task-tracking capabilities are great at adjusting task deadlines. Keep your project teams moving forward while Motion auto-adjusts their schedules for better focus.

Consider how much better it'll feel knowing you're working towards achievable project goals. With Motion, you can say goodbye to chaos and hello to getting things done.

Ready to take control of your deadlines? Try Motion FREE today!

Haylee Read
Haylee is a versatile writer with ten years of experience. With a background in marketing and writing for large SaaS companies, Haylee brings her passion for the written word to diverse projects ranging from blog posts and ebooks to direct marketing campaigns.
Written by Haylee Read