The Ultimate Guide to Deadline Management

We’ve all been there. It’s the night before a major project is due. You’re burning the midnight oil to meet the deadline. With minutes to spare, you manage to pull it all together. There’s a huge sigh of relief...until the next project rolls around, kicking off a fresh cycle of deadline-induced anxiety and dread.

If this scenario sounds familiar, you’re not alone.

Deadlines are among the most common types of workplace stress. Even worse, studies show staff who scramble to meet deadlines at the last-minute often turn in low-quality work.

Now, we know why there’s often a mad dash towards the deadline. Missed deadlines are costly and can even compromise cash flow.

Fortunately, you can eliminate a lot of the drama with effective deadline management. We present tried and tested strategies to help you meet deadlines confidently, producing high-quality work on time - every time.

Set Realistic Deadlines

In 1920, the Second Avenue Subway - a New York City subway line - was proposed to expand the transit system in New York.

After postponements, delays and proposal revisions, work on the line finally began in 2007. Freakonomics calls the story of the Second Avenue Subway a “grotesque example of a blown deadline”.

But it’s a situation many of us can identify with, albeit on a smaller scale.

How many times have you agreed to a deadline only to realize midway that the project was taking much longer than expected?

Even mega projects backed by governments - like the Second Avenue Subway - and large corporations are hindered by expensive overruns.

The real reason we struggle to meet deadlines is that we’re bad at estimating how long projects will take.

And that’s thanks to a phenomenon called the planning fallacy.

The planning fallacy is a concept introduced by psychologists Daniel Kahneman and Amos Tversky in 1979. It’s our tendency to underestimate how long projects will take, even when we know similar projects have taken longer in the past.

To deal with the planning fallacy, researchers suggest looking at data from your “reference class”, i.e. how long has it taken you to complete similar projects in the past?

As part of this process, do a detailed breakdown of what the task requires. Identify the team members that need to be involved and evaluate what each person needs to do. If you’re a team manager, work with staff to set estimations for how long they’ll need to complete the task.

One way to get more accurate estimates is to use time tracking software. Once you know exactly how long you typically take to complete tasks, your schedules are more reliable.

Team members should take into account the other work they need to do, too. You may realize that certain employees are only available after completing another major project. This will inform whether longer lead times are required.

Plan for Emergencies

Even if you set manageable deadlines, emergencies may pop up along the way that can derail the best laid plans.

To combat this, pad your deadline. So, if you need to deliver a project in six weeks, agree to an internal delivery of four weeks. If challenges arise, you have a reasonable buffer period. This may help you hit your deadline even if you encounter unforeseen circumstances.

Fortunately, there are a few measures companies can put in place to better deal with unexpected issues. The team at Hygger, a project management software platform, provides these practical tips:

Develop an issue path - designate specific team members to deal with certain issues. For instance, your team may be working towards a product launch when you realise your positioning is too broad. The problem should be escalated to marketing, so teams can reevaluate audience targeting immediately.
Define the issue - clearly articulate the problem so the right people start working on the solution. Going back to our example above, marketing might need to consult with the data science team to gain deeper insights into target consumers.
Determine the impact of the problem - quickly work to evaluate the scope of potential delays so you can keep everyone informed.
Ring the alarm - if there’s a major, and unavoidable delay, it’s time to inform everyone involved. This should be used sparingly.

Use Mini Goals for Daily Deadline Management

Are you prioritizing your company’s most important work? Or does it feel like you’re always rushing around, keeping busy with less important tasks that have tighter timeframes?

If so, you may be sabotaging your own productivity with something called the urgency bias.

According to a study published in the Association for Consumer Research, the urgency bias is our tendency to choose easier tasks that appear more urgent over more important tasks with longer deadlines.

From the abstract:

Employing simplified games and real-life consequential choices, we provide evidence for “urgency bias”, showing that people prefer working on urgent (vs. important) tasks that have shorter (vs. longer) completion window however involving smaller (vs. bigger) outcomes, even when task difficulty, goal gradient, outcome scarcity and task interdependence are held constant.

We pick the easy “urgent” task because our brains get an immediate dopamine hit when we finish it. Projects with a longer time frame don’t provide the instant payoff we crave.

To help team leaders deal with the urgency bias when managing projects, QZ suggests:

...there are hacks that can put the urgency bias to work in your favor. For example, managers can break large projects down into smaller tasks with several urgent deadlines to keep the team motivated, Zhu suggests.

Use daily to-do lists and checklists to order these mini-deadlines. But there’s a caveat, though: long, unmanageable to-do lists will do more harm than good. Psychologists call it the Zeigarnik effect - we’re prone to dwell on unfinished tasks. Develop short, focussed to-do lists and checklists with a limited number of tasks, so you can fully focus on the work at hand.

Even better, research shows these bite-sized goals improve motivation. Large projects and looming deadlines are immediately less menacing, and you have the extra push you need to finish on time.

Here’s an example from Zapier:

“To use an example from product management, "ship product by February 15" sounds like a monumental task that can freeze you up. But "sketch ideas by January 1; do a mockup by January 15; build a rough prototype by January 31" is much more approachable because you have specific and concrete tasks you can tackle.”

Automate Paper Processes and Workflows

There’s nothing worse than being held up by inefficient workflows. In fact, employees waste 3.5 hours each week, waiting for team members to provide information.

Setting up document workflows, for instance, eliminates a lot of this uncertainty. On top of that, improved workflows removes the friction that comes along with signing processes, making it easier for prospects to close the deal.

Here’s an example of how an efficient workflow keeps projects moving along:

Email documents, e.g., contract or payment terms
Recipient digitally signs using a tool like Xodo Sign
Automatic reminders sent to get signature before deadline
Managers review documents

Automate workflows at the start of the project. Doing so will free up a lot of time. You won’t have to do manual follow-ups or deal with clunky paper-based processes like printing and scanning documents.

Begin by assessing the types of documents you’ll need frequently throughout the project. Create templates and store them in a central location, so they’re for team members to find. This can include things like emails and invoices.

Communicate Progress

The level of communication during a project can make or break your ability to meet the deadline.

Frequent communication holds team members accountable, provides early warnings for potential delays, and keeps everyone on the same page.

If you’re a team lead, keep staff motivated and informed on project progress, with regular check-ins. Use these gatherings to discuss daily or weekly agendas. Encourage employees to raise problems that may block them from hitting the deadline.

This research paper discusses items that may require ongoing communication to all parties involved:

Routine status reports
Timelines and milestones
Key project information
Details of team members assigned to projects
Forum to log questions or concerns

Consider project management software to simplify communication. Project management software helps track, organize, and manage projects easily. Teams benefit from real-time status updates and centralized feedback. This may eliminate the need for back and forth emailing. That means you can make any changes or updates faster.

At a glance, everyone can assess whether the most pressing priorities are being addressed. A project management tool also improves collaboration - all key documents and details are easily accessible in one central location.

Simple, Stress-Free Deadline Management

Deadlines don’t need to be stressful. Imagine how much more effective you could be if you weren’t always frazzled, frantically rushing to get work done on time.

When you use the right deadline management techniques, you can increase your productivity and confidently commit to deadlines.

Which tried and tested deadline management tactics do you use to stay on track?