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How to Keep Your Bigger Projects From Derailing This Holiday Season

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The holidays are almost here, bringing with it the festive joy we all love and the opportunity to relax, at the very least. Yet, it is rarely the case for those working on or managing projects, especially if those projects involve multiple teams spread across global locations. After all, amidst all the merriness, it becomes extremely challenging to keep projects on track as people take time off and disrupt well-planned schedules. On the other hand, clients tend to push to get their projects, particularly the bigger ones, completed before the holiday season, despite the shortfall of resources. 

Therefore, it is small wonder that projects slow down to a crawl during the holiday season. To help you keep your bigger projects from derailing this holiday season, we talked to experts and business leaders to gain their insight. Here is what we learned.

How to Enjoy the Holidays without Derailing Projects?

As the holiday season comes around at the same time, organizations should know when to expect time off requests to pour in. With this information, it becomes easier to plan tasks and resource allocations well in advance to ensure continuity in project progress. 

Alexis Haselberger, Productivity, Time Management and Leadership Coach, notes “Companies should expect that employees will want time off around the holidays and should plan for that. If you plan in advance, and build in the time off into the project timeline, you have nothing to worry about and employees can take the time off they need without fear or stress.”

Alexis goes on to add, “So long as you set expectations with your clients to account for a slower period, it won’t be a problem.” Organizations need to contact their clients beforehand and establish expectations as to how those projects will progress during the holiday season. They need to prepare clients for any potential slowdown in progress. After all, the last thing any organization wants is an unhappy client, particularly during the festivities. Similarly, project managers, employees, and other stakeholders, must also be made aware of these plans. As Alexis says, “It’s all about planning, preparing and setting expectations with employees, clients and leadership alike.”

How Does Time Off Impact Your Projects?

It is not uncommon for sudden spikes in time off requests during the holidays. Organizations need to be proactive in ensuring these requests do not affect the project plan through intelligent resource allocation. As Alexis notes, “Planned time off doesn’t impact projects at all.” By getting all requests in early, you gain the opportunity to develop a schedule that ensures the project can continue successfully even with fewer resources. 

Of course, there is always the concern of unplanned and sudden time off requests, such as in the form of sick time off. Alexis adds, “Unexpected time off can definitely throw a project off track. One key is to ensure that you have a buffer in the timeline. While we can control for vacation time needs, you can’t control for sick time. So building in a healthy buffer ensures that projects are completed on time, even if there are delays or unforeseen events.” Managers should consider adding in those buffers well in advance while mapping out tasks and activities during the holiday season. 

Establish Time Off Expectations

It falls upon the employers to let their employees know what is expected of them with respect to time off requests during the holidays, or any time really. This is where a well-defined comprehensive time off policy helps enormously. 

Alexis agrees, “Companies should have a clear set of policies and procedures for time off and should ensure that all employees understand the policies. It doesn’t really matter what the expectations are as long as they are fair, and are communicated well in advance.”

For example, you can let your employees know that they are expected to hand in holiday time off requests two weeks before. This should give you enough time to reallocate resources and even reschedule tasks as needed, while also updating clients of the same.

Update Project Plans

For projects that haven’t started yet, organizations do have more room to maneuver in. There are a few steps that you can take to streamline project progress in these instances. 

Te Wu of PMO Advisory LLC notes, “Managing projects during major holidays are difficult, especially when there is a lack of discipline and shared understanding”. To that end, Wu advises, “If the project is starting or if time permits, start the project with an understanding of the resource availabilities. This way, project managers can plan accordingly with reasonable workload. This can also help with expectation setting with project executives and customers.” 

By accounting for the lack of resources, the work can be more evenly distributed among those who will remain at the office. This prevents bottlenecks and delays from derailing the project in the middle of the festivities. 

Te Wu also wonders, “Can the work be front-loaded (or back-loaded)? If yes, then start working on them now so you have more relaxing holidays. The same can be said of back-load too.” By shifting critical project tasks and activities to before or after the holidays, organizations can reduce employee burden during what is already a stressful time. Moreover, it also prevents organizations from having to compromise and deliver subpar work. 

Rethink How You Work

In some cases, organizations may have to rethink their approach to work to keep projects from derailing during the holiday season. 

Reschedule Projects Among Global Workforce

Redistribute the tasks among multiple teams across the world, particularly where the holiday season is different or shorter. This not only reduces the stress for your employees during the holiday but also ensures that the project remains on track. Of course, developing a schedule that works for everyone across different countries may be a challenge but it will be worth the effort.

Consider Remote or Hybrid Working

Your organization may have already experimented with remote or hybrid forms of working due to the business disruptions in 2020. With the holiday season fast approaching, it is time to consider bringing them back once more. This can help reduce time off requests while ensuring that your tasks are completed on time.

The holiday season can be a challenging time for project-based organizations and managers. However, a few proactive strategies can go a long way in minimizing the disruption to projects. Alexis remarks, “The absolute best thing companies can do to keep projects on track around the holidays (or anytime, really) is to factor in expected time off, and a generous buffer, during the planning stages. The holidays are predictable; they occur every year. And we know that employees will want time off. So plan for that in advance when you’re determining project timelines.” Employ these strategies and you can prevent your bigger projects from derailing and help everyone enjoy the festivities.

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Arpan Patra


Arpan Patra


Arpan Patra has been writing about technology for over a decade. Now, as a Senior Marketing Communications Specialist at Deltek | Replicon, he focuses on how technologies like AI/ML-powered professional services automation solutions can empower organizations to optimize and grow their business. When he’s not busy typing noisily, he enjoys sitting down with a book and a warm cup of coffee.


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