Helping People Meet Deadlines (Especially Creative Types)

pain points people May 10, 2024

Ah, deadlines.

In one sense, a great project manager rises above deadlines and keeps everyone focused on what meets project goals under current circumstances, even if that means original deadlines shift or fall by the wayside.

But in another sense, project schedules DO matter, and meeting a deadline can itself be an important project goal.

Thus, deadlines are an aspect of projects that project managers are always watching closely. If our projects are on track and meeting deadlines, we’re probably having a good week.

Getting other people to meet project deadlines consistently is not easy. If you’re in the midst of a project that’s missing a lot of deadlines, a human-centered exploration of the root cause is important because there can be all sorts of reasons for schedule slippage related to individual team members or to the project as a whole.

One root cause I’d like to highlight is that some people don’t naturally focus on deadlines. They are often “creative types” who are most focused on making the product, service, or result something that’s awesome…and in the process, they aren’t inclined to watch the clock. We need these people! Their passion can be the magic we need to deliver awesome project outcomes. And it’s our job as project manager to support them in their weaker areas like paying attention to the calendar.

Assessing your individual situation and team is important. But across projects and situations, when I want to go into a project proactively creating a situation where deadlines are likely to be met—even by my favorite creative types—here the top strategies I use. They can set your projects up to meet more deadlines too.

1. Have THEM set the deadline.

Creating a realistic project schedule is always a collaboration between project manager and subject matter experts. Unless we have a lot of experience with a task or function from previous projects, we can’t know how long each project task will take until we talk to the person doing the task, or their manager, or someone else who’s an expert in that function.

This may be more feasible in smaller organizations, but whenever possible, I prefer to ask the actual person assigned to the task how long they need to do it. This has so many benefits:

  • It builds trust with the team member (I’m trusting them to understand the work and how to do it best).
  • The team member will feel valued when I defend their requested timeframe to the project sponsor or other decision-makers.
  • The estimate has a good chance of being accurate…and if it’s not, me asking them to estimate timeframes repeatedly on various tasks and projects might improve their estimating skills over time.
  • Most importantly: people are more likely to go out of their way to meet a deadline they set, than to meet a deadline that was set for them.

You will have the occasional bad egg who will overestimate tasks to be lazy. But this is rare, and you will have better results overall if you start by trusting people. (But having someone else give a second opinion on estimates is also okay!)

2. Get team buy-in on deadlines.

Asking task-doers for estimates—but doing it with the whole team in the room—can have even more benefits, as long as the team dynamic is positive and collaborative:

  • Other team members can speak up to validate or improve on each other’s estimates.
  • There will be minor social pressure (or accountability) for everyone to meet the deadlines they proposed in front of the team, especially assuming some people’s tasks are dependent on other people’s tasks.
  • In an agile setting, or on a team with “generalizing specialists,” team members will be primed to jump in and help if the main person working on the task isn't on track for the deadline.

If there are creative types on your team, a team discussion about deadlines means you’re not the only one in a position to help them keep those deadlines top-of-mind.

3. Emphasize why the deadline is meaningful.

People might ignore or resent deadlines that feel arbitrary to them, even if the deadline isn’t actually arbitrary. The key—it’s simple but often forgotten—is that people need to KNOW why the deadline on their task is meaningful. How does it connect to project goals? What does it mean for the project if the deadline is met or missed? Make sure this is one of the first things you communicate when you discuss deadlines with project team members.

This is especially important when you’re not in a position to let people propose their own deadlines, but you have to simply tell them what the deadline is. When people can’t control or influence a situation they’re in, it helps a lot if they can at least understand it.

4. Repeat the deadline regularly.

This is important for most team members, but especially your creative types. They aren’t focused on deadlines, so remind them (kindly, with a smile!) on a regular basis. Also remind them of the “why” behind the deadline if they seem discouraged.

You might have dates listed in a central project information repository, and you can train your teams to reference this repository more and more over time. But reminders are an important backup strategy that usually make a worthwhile improvement to the rate at which project deadlines are met.

Stay curious about the root causes of missed deadlines, and proactively apply the strategies above, and you’ll set yourself up for more of those weeks where you can sit back and watch project tasks get marked off on time.


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