Optimize your workflow with these 9 deadline management tips

Do you manage a team that has deadlines? Are you someone who has to complete business tasks on a schedule?

If you answered “yes” to either, you likely already know the pain of meeting deadlines.

Somehow it hardly seems to matter how much time a task or project is given. As any deadline nears, we humans seem extremely adept at missing them or at least coming close to doing so.

If you’re looking for help setting or meeting deadlines or improving your deadline management skills as you juggle projects with competing priorities, this article is for you.

Ready to take back your workflows and lessen that end-of-project stress?

Let’s jump in!

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Why we all struggle to set realistic deadlines

We all — every last one of us — struggle to set realistic deadlines (says the author with only hours to go before this very article is due).

Why?

Well, because we’re human.

There are all sorts of reasons we struggle with this. In business contexts, these are some of the most common:

• Inexperienced with a type of project: Sometimes we fail to set and manage deadlines because we don’t fully understand the effort and time required to complete tasks we’ve never attempted before.

• Failing to set deadlines in the first place: “It’ll get done when it gets done” may make your creatives happy, but it doesn’t lead to reliable or timely results.

• General disorganization: Sometimes we don’t have all the details in place, leading to deadlines that didn’t account for everything in scope.

• Poor communication: Project managers aren’t always as clear about deadlines as teams need them to be. And as a team member, “Sure, I can totally meet that deadline” is the wrong thing to say when you know beyond a shadow of a doubt that you can’t. (So is “We’ll do our best!”)

• People tend to be overly ambitious/optimistic about how much work they can do: Especially in organizations that haven’t tracked task length, people tend to over or underestimate their speed.

• Unforeseen hiccups: Every project has them, so every project manager should plan for them. Even still, some unforeseen hiccups can exceed even the buffer or margin you allotted, leading to missed deadlines.

9 essential time and deadline management tips from project management professionals

Setting realistic deadlines is hard.

And so is sticking to them.

But with a little effort and project planning, most of us could be more efficient with our time management. Consider these nine proven strategies, and see if you can put a few of them to work today.

1. Use project management software to set workflows and manage deadlines

For most people, task management isn’t easy, and the more complex your team or task grows, the greater the project management challenges become. If you’re establishing start and end dates for a project, make sure you’re using a proper project management tool to do so.

Why does this matter? Simple: Tracking the details of complex projects is just too much to do manually or using spreadsheet templates. There are too many interdependencies, exceptions, and data points to keep track of, so you need software that’s purpose-built to do this.

Teamwork keeps all your tasks, due dates, and deadlines in order in an easy-to-use interface. You can track times, create tasks and subtasks, link task dependencies, and view resource allocations all from one central platform.

If you’d like to see how Teamwork can help you set workflows and manage deadlines, you can get started for free today.

2. Create daily to-do lists (preferably the day before)

The crush and chaos of a typical day’s work can be hard to overcome. Most of us would be far better off taking some time to plan and organize each day rather than diving straight into the email backlog as soon as we fire up our devices.

One great practice in this vein is simply creating daily to-do lists.

In many office environments, it’s easy to dive into an unbroken stream of tasks and interruptions so that you end the day feeling like you did little more than respond to emails and Slack messages. Setting a to-do list is a great way to rise above the chaos and distractions.

Here’s a crucial tip, though: Don’t wait until you start working for the day to create that day’s to-do list. Instead, do it the night before.

Carve out five or 10 minutes at the end of each day to slow down and start tomorrow’s to-do list. That way, you’ll already know what to focus on when you fire up your laptop the next morning.

As a bonus, committing to this strategy gives you a clear ending point for the workday and could improve your work-life balance.

3. Start your day with the most challenging tasks first

Not everything on the docket for a given day is equally important or difficult. So even once you have a to-do list in place, you still have to make decisions about what to tackle when.

Avoid the temptation to clear out your inbox first thing in the morning: You’ll end up with more distractions and be tempted to jump into nonstrategic work.

Instead, plan to tackle your most challenging or complex tasks first. In fact, the Teamwork State of Productivity Report found client services teams tend to complete the most tasks at beginning of the week.

When we save those difficult tasks for later in the day, we increase the likelihood that they get squeezed out by other priorities — or that we won’t feel mentally capable of taking them on.

4. Add buffers for every task

Another crucial strategy is to add buffers for every task. If there’s one thing that’s certain in today’s work environment, it’s that you will be interrupted.

It always happens – someone in accounting sends you an update via Slack or the agency owner wants to catch up on a last-minute proposal. And with the challenges of working from home, someone at the door can send your dog into a frenzy when you're about to hop on a call and your earbuds are still connected so everyone hears your struggle.

OK – maybe that last one is a little personal, but try as you might, you won’t move seamlessly from task to task with no breaks or distractions. Sorry, it's not going to happen.

The smart play is to recognize this reality and add some buffers. You might do this in a blanket fashion by adding 25% to your in a perfect world task completion times. Or you can tailor this to the employee, task, office context, or whatever else makes sense for the moment.

But the key is to do it. Add that buffer and you’ll find your calendar much more manageable.

5. Build multiple visualizations (think: calendars, lists, and Gantt charts)

A bulleted list of tasks can be hard to gauge. But lay those tasks out in a project timeline or a Gantt chart, and suddenly what seemed doable is clearly overloaded. Or perhaps the opposite turns out to be true!

As you consider deadline management for a team or a more complex project, building multiple visualizations will help team members (and you!) get a more holistic sense of what’s expected.

It’s a crucial part of keeping complex projects on track because good visuals make it clear at a glance how well project teams are (or aren’t) keeping up with the schedule.

Sometimes building these visualizations reveals problems with the project and it could be early enough for you to address them. Flagging schedule conflicts and unrealistic resource allocation early can alert stakeholders to issues that threaten to blow up deadlines.

6. Tie your tasks to your teammates for added accountability

In most project management tools, users with the right privileges have the ability to set task deadlines or goals to private. This makes sense for scenarios where secrecy might be warranted, but it shouldn’t be your general practice — especially if deadline management is a struggle.

Instead, set tasks to a public view or even share them with teammates. Adding your teammates will only provide accountability and awareness. It also notifies others when you complete tasks that affect them.

Bonus tip: When you do notice that you’re not likely to meet a deadline, it’s imperative to communicate ahead of time. That way, others may be able to jump in and help or timelines can be adjusted.

7. Set aside time during the week for regular re-evaluation and reprioritizations

No matter how perfect a plan you craft for yourself or your team at the beginning of the week, understand that your day (and their days) will never go exactly according to plan.

Getting to Wednesday and realizing that aspects of your weekly plan aren’t working is normal. It’s not a failure on its own.

The real failure is failing to adjust your own deadlines and short-term plans based on the changes that have occurred so far in the week. Most of the time, small ongoing or even real-time adjustments can keep you from ending up with true missed deadlines or milestones.

Our advice here is this: Make plans to make more plans. Schedule time to look at what is and isn’t working, what hasn’t gotten done, and then reprioritize as needed.

Project milestones can make this easier by tapping into project benchmarks so you get a better idea of what's to come and if you're on time.

8. Learn how to properly break down tasks into appropriate sizes

Managing deadlines for complex projects and project deliverables means successfully completing any number of smaller tasks. When issues arise, it may be because you haven’t broken tasks down into small enough chunks yet.

The right size for tasks will vary from team to team, but most project management professionals lean on the 8/80 rule, which suggests that individual tasks should not be longer than 80 hours or shorter than eight.

Anything smaller is too granular and will gum up your project management efforts. And if things are larger, things become too complex and should be broken down into smaller steps.

Tasks lists and subtasks can make processes and project tracking much more realistic. With simple-to-create subtasks within tasks, you can add further detail to your projects for more clarity. Breaking down tasks has never been easier.

9. Time yourself actually doing tasks

Last, consider literally timing yourself as you complete tasks. If you’ve never done this, then estimating how long you need for future similar tasks becomes pure guesswork.

Getting a clearer sense of how long tasks take you — and how often you get interrupted — helps you create better plans going forward.

The Teamwork Project Time Tracker is an excellent tool within our platform that allows individuals and teams to track their time simply and effectively, assigning time to projects and tasks within the platform.

How to handle project or task prioritization when you have competing deadlines

All of this seems well and good, but what about when you have multiple projects or tasks with competing deadlines? What’s the right approach to work management, one that doesn’t devolve into putting out fires or attempting to multitask?

Balancing competing deadlines starts by gathering all the tasks assigned to you (or to the various members of your team, if you’re a team manager).

Once you’ve gathered every single task, you need to decide which ones to prioritize. A 2-by-2 matrix is one classic approach, where all tasks are categorized by both urgency and importance.

Once you’ve categorized your tasks, proceed accordingly:

• Focus on urgent and important tasks.

• Schedule the important but not urgent tasks so they can be completed before their deadline.

• Delegate urgent but unimportant tasks.

• Ignore, delete, or dismiss tasks that are neither important nor urgent (within the bounds of your company culture and level of authority or autonomy, of course).

These are just a few first steps toward effectively prioritizing tasks with competing deadlines. The good news is we’ve covered these elsewhere. For more on this crucial topic, check out How to prioritize tasks (and stop getting crushed by your workload).

Manage your projects (and your deadlines) with Teamwork

Managing deadlines can be challenging, especially on complex projects or when you’re dealing with competing priorities that overlap each other.

The tips and strategies we’ve shared here can help you or your teams with deadline management. But far and away the most powerful move you can make in this arena is implementing Teamwork.

Teamwork is a better project management tool full of powerful features that can help teams understand and meet deadlines. It helps with task tracking and time tracking, and it helps project managers and team leaders visualize project data and build better project schedules.

Ready to see Teamwork for yourself? Get started for free today.