Reading Time: 5 minutes

If you Google the phrase “managing critical deadlines,” the results show a variety of offerings to help all kinds of businesses solve the problem of managing critical deadlines. But what makes particular deadlines more critical?

It’s my sense that many of these solutions treat all deadlines equally. But are they? Have you discovered that some deadlines just aren’t that important? And some are critical!

Traditionally trained project managers use a sophisticated technique called the critical path method (or perhaps, the PERT method) to manage deadlines and project progress. Does using that technique ensure that all critical deadlines are met? I’m not convinced. A lot depends on how many true dependencies there are in the project. And a lot depends on the availability of the people who are on your team, including any subject matter experts or others who may be partially assigned to your work. The reality is that human limitations often stop us from meeting deadlines. We simply don’t have the resource capacity when we need it. And true dependencies can restrict our ability to fast track the work when people are available.

Is there a better way to manage deadlines? What might happen if we stopped trying to manage every single project detail and focused instead on what matters most? Could we just manage critical deadlines instead of every single activity deadline? Is finishing the project as quickly as possible really the best approach? Or is it better to meet the important deadlines and drive the project to completion at a steady and reasonable rate of progress?

Some of your deadlines may be important. Some may not. If you treat them all the same, you risk a reality that human bandwidth, particularly during evolving times, often keeps teams from meeting deadlines. How do we zero in on the really important deadlines? Here are five tips for managing critical deadlines.

Treat all deadlines equally and you increase the risk that human limitations cause you to miss a really critical deadline. #projectdeadlines #projectmanagement Share on X

Plan your project so that you can achieve small wins in each sprint.

The first thing you need to do is to plan your project well. If you break the project into activities that will take months to finish, it’s hard to drive success. People may be working on something, but they won’t be finishing anything very often.

Break the project down into discreet activities that can be finished in a two-week timeframe. There’s nothing magic about two weeks, but I typically recommend that teams work in sprints, which are short blocks of time, during which the team commits to finishing a batch of work.

Business teams often have trouble breaking some larger project activities into discreet chunks that can be finished in a few weeks. It may help to divide a discreet activity into two (or three) parts and identify an interim deliverable that you can produce. As you deliver that work to your client (or to your management team] you can obtain valuable feedback. Suppose you had worked three months on something and then learned that the client didn’t like it?

Identify the critical deadlines.

If some deadlines are not critical, which ones are critical? This is a big question and one I cannot answer for you. I’d opt for only those deadlines that simply cannot be missed. By reducing the number to as few as possible, you increase the chances that they are met. And, by limiting the number to a handful, you can also understand the critical deadlines on ALL of your projects. And during times of chaos, that may come in very handy. Sometimes, you just have to let go of something. But as long as you are making progress and have a handle on what is critical, that’s okay.

Can you now determine which deadlines are critical? Designating some deadlines as target deadlines, and some as fixed deadlines ensures that you don’t miss what’s truly important. And the target deadlines give you a way to drive the project forward. I’m not a huge fan of putting a deadline on each activity, though some people prefer to work that way.

Establish a zero tolerance for missed critical deadlines.

Once you have defined your critical deadlines, you need to make it very clear to the team that these few activity deadlines are important. There can be no excuses for missing them. And this is why I’d pick my battles here. If every deadline is equally critical, then, you haven’t accomplished anything. And I’m pretty sure you’ll be missing some deadlines.

Chill out on the deadlines that don’t matter and keep the project moving forward.

When your project is moving along and people are working hard, celebrate and enjoy the ride. Deadlines that are being used to guide the project along are just there to help – not to beat people up when they miss a goal. Focus on the positive. As parents learn to do, pick your battles.

Try hard to select an activity or a group of activities at the beginning of the sprint that you are able to finish by the end of the sprint. Develop a mind-set of regularly and rapidly delivering meaningful results to the client.

When times get tough and you aren’t meeting target deadlines, examine the reason. Is it because you are regularly attempting to do more than is humanly possible? Ambitious goals are great, to a point. But people have limits and you just shouldn’t continue to push the team past their limits – week after week, for months or years on end.  I don’t care what Elon Musk says! It’s unhealthy and uncaring. It’s one thing to temporarily push a team when there is a compelling reason but it’s another to live that way.

There will be times when you aren’t meeting deadlines for another reason. Are you typically underestimating the work that is needed? Or are team members over-working activities? I have written before on estimating complex projects. Try to understand the root cause and work to improve.

Use standing meetings and checkpoint meetings to drive the project momentum.

I’ve written before about standing meetings and checkpoint meetings. I didn’t invent standing meetings. They are popular in the Agile community. I did standardize the process for what I call a checkpoint meeting, which you can think of as a bit of a blend of a planning meeting, a Sprint review, and a retrospective – held at the end of each sprint, and the beginning of the first sprint.

The Scrum Alliance has written about Scrum meetings, which might help you understand the genesis on my thoughts.

Standing meetings

Depending on the project and the speed with which you need to move, you may choose to do a standing meeting every day or just twice a week. Standing meetings are very short meetings, where three questions are answered:

  • What have you accomplished since the last meeting?
  • What do you plan to accomplish next?
  • And what problems have arisen?

Standing meetings are not a time for discussing how to solve the problems that have arisen. That’s not to say that teams can’t make exceptions when the problem involves the entire team, but you run the risk that the meetings will soon grow longer, and people will begin to resist them. Try to stay positive in these meetings.

Checkpoint meetings

Checkpoint meetings are a time when teams gather to assess accomplishments and attend to a number of project management needs.

I recommend that teams work in sprints, typically two-weeks long, and bookend their sprints with a checkpoint meeting. Two weeks is sufficient time to accomplish some level of meaningful work. Depending on your situation, you may choose to invite your client to these meetings. If not, I would encourage you to send some kind of client update at the end of the meeting.

During these meetings, you should do seven things:

  • Review your end game – what are you doing and why?
  • Celebrate your accomplishments during the recent sprint.
  • Identify and document the lessons that were learned.
  • Review what it’s costing the client. Are you on track?
  • Solve any new problems or designate someone to do so.
  • Identify and analyze the project risks.
  • Plan the work for the next sprint.

Think this might help your team? Share your comments if you have other useful tips. Interested in knowing more about managing critical deadlines or anything in this blog? Why don’t you contact me about an online class I’m working on?