4 Tips to Keep Projects on Track

As a project manager, the most important aspect of your job is to make sure that projects stay on track. However, with important projects often involving several moving parts with several dependencies, obstacles will inevitably pop up that will cause your team to miss crucial deadlines. To help project managers and teams avoid these uncomfortable situations, we put together these tips to help keep your projects on track.

1. Give reasonable estimates in the first place

To avoid missing deadlines, or unnecessarily stressful sprints to the finish line, it's important to make sure that you give reasonable estimates for completing the project in the first place. Many project managers will work backwards from a deadline, and then create a Gantt chart using their project management software to see when particular deliverables must land in order to meet the deadline. Though this may sound like a reasonable approach, if your team finds itself negotiating timelines at this stage, it often means that shortcuts will have to be taken in order to hit these timelines.

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Rather than working backwards from an expected delivery date, try to work forwards from the start date. This means that you'll start with the first dependency, and then plan a reasonable due date (with some buffer to account for unexpected roadblocks that might pop up). Then, you'll estimate when all subsequent tasks can be completed and handed off. This process of working forwards often results in more accurate estimates, since the estimates won't be crammed for the sake of hitting the deadline.

Sometimes it's unavoidable to work backwards instead of forwards, typically due to external constraints. In this case, you're best off starting this planning process as soon as possible. You'll also need to have the understanding that if the timelines already look tight during the planning stage, your team will likely need to take shortcuts, or work overtime in order to hit their deadlines. Though this can be acceptable as a one-off, it should be avoided in the long-run, since such stressful projects will ultimately result in team burnout, and lower employee satisfaction.

2. Write clear specifications for each task

As the project manager, it's your responsibility to make sure that each task has a clear specification of exactly what needs to be done, and by when. This will help avoid any confusion by team members, which can result in delays of projects, and can also result in team members simply executing on the wrong task.

To avoid these scenarios, you'll have to take the time to write out detailed specs of each task. Many project managers make the mistake of glossing over these written specs, since they're often discussed verbally with team members during meetings. It's easy to overestimate how much people will remember from conversations, and to assume that everyone is on the same page. However, the only way to really be sure is to take the time to explicitly write out descriptions of each task, and ensure that they're documented on your project management system. This way, if there are any misunderstandings or disagreements, the team will have a way to address them.

In addition, by having concrete specs written out, you'll also be able to assign clear owners for each task, so that everyone knows exactly what they're responsible for. You can assign owners for each task through your project management software, which is also convenient for team members, since they can see exactly what they need to work on over the coming weeks.

Since it's difficult to foresee every question that may arise, you'll want to make sure that you have an easy way for team members to ask any follow-up questions on specs, either through your project management software (with most systems enabling users to tag each other with questions), or through your collaboration software (such as Slack).

3. Have frequent check-ins

Though it's a bad idea to micromanage projects, being completely hands-off and not having an understanding of the project's status is just as bad. A good project manager must always know where things stand, so that if a team member is stuck, they can identify ways to help the team member overcome any roadblocks. In addition, if you find out too close to the deadline that the project is going to slip, it's already too late—the project will be doomed.

To avoid this, it's important to have frequent check-ins with the relevant teams. For teams you work with directly, you can have daily meetings. Tech companies regularly have daily standups where each team member discusses what they're working on, and any issues that they've come across. This helps the team understand the status of various tasks, but also helps project managers identify tasks that appear to be falling behind schedule, and that have an obstacle that needs to be unblocked.

For projects that involve several different teams, a daily cross-team meeting is probably too frequent, since each team should be able to operate fairly independently. In these scenarios, it's a good idea to have a daily meeting with your direct team, but a weekly or bi-weekly cross-team meeting to surface any issues that may impact other teams. There may be times where your team works closely with another team (especially during complex integrations), in which case it can make sense to have more frequent meetings between your team and the partnering team.

4. Notify stakeholders as soon as it becomes clear that a project is slipping

Even the best project managers will have projects that fall behind schedule. When this happens, it's best to notify key stakeholders sooner than later, so that expectations can be managed. This is always an uncomfortable situation, but notifying stakeholders at the last second, when it was obvious for months that the project would miss its deadlines, is an even more uncomfortable conversation.

When having this conversation, be honest and upfront about why the project is behind schedule, what the team is doing to remedy the situation, and give new delivery estimates. Not only will the stakeholders appreciate this, but your team will as well, since it resets the expectations and will allow them to accomplish their work within reasonable timeframes.

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