How to Help Your Team Meet Project Deadlines

September 22, 2015 Heather Hurst

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If you think about it, the term "deadline" is a pretty horrific word. Most etymologists agree that the term originated during the American Civil War, in the Andersonville, GA prison camp. Federal prisoners of war were confined within a stockade of roughly hewn pine logs measuring 540 by 260 yards, inside of which was a line prisoners were forbidden to cross. According to an 1864 inspection report from Confederate Captain Walter Bowie:

On the inside of the stockade and twenty feet from it there is a dead-line established, over which no prisoner is allowed to go, day or night, under penalty of being shot.

Apparently the term lost this more literal definition by the 1920s, when it was co-opted by the newspaper industry and became a synonym for "time limit."

Luckily, you're unlikely to be fired upon when you cross beyond a modern work deadline—but frequent transgressions from you and your team could lead to firings of another kind.

If you work in an environment where deadlines are treated more like suggestions, resulting in unnecessary chaos and unpredictability that undermine both team productivity and individual job satisfaction, there is hope. Review the seven common deadline problems that follow to pinpoint your team's biggest areas for improvement, and then try a few of the provided solutions to increase your on-time delivery rate.

Problem #1: Unclear Deadlines

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The deadline for a project may be perfectly distinct in your mind, but that doesn't mean you're communicating it clearly to other members of your team. The first question to ask yourself is about the method you use to delegate tasks and projects. Are you assigning work verbally, via email, during planning meetings, using a project brief or template, or perhaps through an online work management system? Perhaps a little bit of each? The more different methods you use for assigning work, the more likely it is that tasks and projects will slip through the cracks and deadlines will be misconstrued.

The second question to ask is how you are phrasing the time limit. Is the deadline expressed in vague "It would be great to see this back by Thursday" language—or in more concrete terms? Unless you really do mean that it would be "great" to see it by Thursday but also good enough to see it by Friday or Monday, then be more clear.

The Solution:

Include an actual date-based deadline with every single work request, and "ASAP" doesn't count, unless you want team members to end up with a work queue full of ASAP requests, with no idea how to prioritize them. For best results, assign every task and project in the same way, every time, preferably using a repeatable template or an online system, where the deadline is in a predictable, easy-to-spot location.

Problem #2: Deadlines That Aren't Taken Seriously

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If you or the manager before you has a history of glossing over, excusing, or failing to confront missed due dates, you may be working with people who have been inadvertently trained to think of deadlines in very flexible terms. Or worse, they may consider the deadline as the day to start thinking of the project, rather than the day to be wrapping up the loose ends and delivering polished work.

Dave Stachowiak of coachingforleaders.com described a manager who was frustrated that an employee would consistently come to her a couple of days before a deadline to ask for an extension. Her response? She'd always grant the extra time. He told the manager, "If I can walk into your office and get an extension whenever I want, haven't you essentially taught me that your original deadlines are meaningless?"

The Solution:

Stachowiak suggests three ways to hold people accountable to their commitments: 1. Communicate expectations in advance of the assignment. 2. Connect at regular intervals to discuss progress and provide coaching. 3. Give praise, support, or feedback once the work is complete.

It also helps to set reasonable, non-arbitrary deadlines in the first place. If there's a driver behind a particular due date, then communicate that clearly up front, so the employee understands the consequences to other team members or projects if they fall behind in their work. It's also important to be willing to say "no" to deadline extensions, provide extra coaching to employees who are perpetually behind (and put them on a performance improvement plan if necessary), and let the natural consequences of deadline failure happen now and then. You'll find your team starts seeing deadlines in a new light.

Problem #3: Not Enough Wiggle Room

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If more than a few of your team members are struggling to meet project deadlines, the problem could be with the deadlines themselves (or, for another explanation, see #5). If you fail to build in an adequate buffer, your project will suffer from the inevitable changes and problems that are bound to arise. There are several reasons that managers fail to include enough wiggle room, including:

  • Lack of visibility into team workload. If you don't know what your team is working on now or what they have due next week, how will you predict the amount of time they need for your next project?
  • No historical data. Unless you can refer to data from past projects, you don't know how long each individual step really took, and your timelines for your next project will be based mostly on guesses.
  • Optimism. Sure, your last three projects were delivered a week late and everyone's been working overtime since February, but this project might be on time, if you hope hard enough. Yeah, right.

The Solution:

Utilize technology to gain visibility into team bandwidth and historical data from past projects. Cloud-based project management software makes it easy to achieve both goals, although you can also see similar results via shared spreadsheets, as long as all team members are diligent about keeping them updated. Once you know what everyone's working on and how long a similar project took last time, you can be more realistic about future deadlines, building in a bit of a buffer for unexpected developments.

Problem #4: Poor Tracking System

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How are you managing and tracking all of your work? Does everyone on your team have his or her own personal system, ranging from the read/unread features of an email inbox to a clipboard containing a handwritten to-do list? Does it take an in-person meeting to synch up about what is due when? How are one-off projects or ad-hoc requests treated? Without a centralized system that provides real-time visibility to everyone in the organization, team members have no other choice than to march to the beat of their own drums, making it nearly impossible to play in synch.

The Solution:

Save time for everyone by centralizing and streamlining task management, so there's one process and protocol used by every member of the team. Look for a solution that enables each team member to: * manage their own tasks * easily delegate work to each other * collaborate within the tool * follow up on progress * provide real-time status updates.

If a comprehensive software solution isn't in the budget—and there are hundreds to choose from at all price levels—look for free solutions that will accomplish individual items from the above list. Or you can assign a single team member to be a traffic controller of sorts—and then hope that person never gets sick, goes on vacation, or finds a new job.

Problem #5: Inadequate Staffing

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If more than a few of your team members are struggling to meet project deadlines, the problem could be that you're understaffed (or, for another explanation, see #3). It doesn't matter how clear you are about deadlines, how much of a buffer you build in to your process, or how well you track everything if you simply don't have enough warm bodies to handle all of the work in a standard work week.

The Solution:

In the absence of serious performance issues with your team, you basically have two choices: either reassess the amount of work your team can manage (and say a justified "no" as needed), or hire more staff. For help with the latter, read Marcus Varner's blog post, "Your Hiring Forecast: Sunny with a Chance of Headcount," which offers 5 tips to help you hire the talent you need, when you need it.

Problem #6: Performance Issues

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Is there an individual on your team who is causing a bottleneck due to poor performance? Even if you do everything else right, if you fail to isolate and address performance issues, individual and team deadlines—not to mention morale—can suffer.

The Solution:

It all starts with visibility. You can't solve problems that you can't see. Don't just oversee the process, become a part of it. Utilize technology wherever possible to automate progress and status reports, so you have easy access to the objective data you need to make decisions—and intervene as needed. And once you've identified the roadblocks that are affecting productivity, you must be willing to solve them, whether that means extra coaching, performance plans, reassigning tasks, or eventual termination. It does tend to boost the morale of top performers when they see that unproductive behavior is addressed rather than allowed to continue.

Problem #7: Your Process Needs an Overhaul

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Do you have a repeatable process outlined, divided into individual steps, and documented? If not, start there. If yes, you may need to review your process and update it to reflect changes in your industry, your company, your staff, or even technology. A cumbersome, overly complex or antiquated process can cause just as many deadline problems as having no repeatable process at all.

The Solution:

Consult our recent series of interviews with project management experts to brush up on the foundational principles that lead to project success:

What's Your Problem?

If missed due dates are a persistent problem for your organization, count your lucky stars that "deadline" no longer means what it meant in 1864. And also realize that there's probably more than one contributing factor to your endemic tardiness. From unclear deadlines to inadequate staffing to an outdated process, all seven of these potential pitfalls is likely to cross your path at some time in your career. The key is to be vigilant about watching for issues as they arise, be willing to address them quickly and thoroughly, and always be on the lookout for advances in technology that can provide the ongoing visibility and objective data you need to meet project deadlines more consistently.

About the Author

Heather Hurst

Heather has enjoyed playing the game of marketing for the past 15 years, at the agency and corporate level, in both B2C and B2B companies. She's run PR campaigns that took her from the MTV Beach House to NASDAQ and many media outlets and content channels in between. She is currently the Corporate Marketing Director at Workfront.

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