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How to avoid the end-of-year holiday headache: why companies need an automated system

A look at the challenges of managing individual holiday at the end of the holiday year.

Magnifying glass showing a date in a calendar

It's that time of the year again – the end of your company holiday period and the Easter break is upon us, and everyone is looking forward to some well-deserved rest and relaxation. For department managers and HR departments, the end of the holiday year can also mean a lot of stress and hassle.

Holiday carry over (or roll over)

Why? Because they have to deal with the dreaded holiday balances for each individual, requiring that they use up their annual leave entitlement by the end of the holiday year, or they might lose it.

Sounds simple, right? Well, not quite. Managing holiday balances can be a nightmare for managers and HR departments, especially if they have to do it manually.

They have to collect the current holiday balances for all individuals, which can be scattered across different departments, managers, systems, spreadsheets, or even paper records. Then they have to collate and analyse the data, to see who has too much or too little holiday left. And then they have to communicate with the individuals to make sure they take the right amount of holiday, or agree on what action to take if they don't.

This can be a time-consuming, error-prone, and frustrating process, for HR, managers and individuals. And it can have serious consequences for the company. These could include:

  • Reduced productivity and morale, as individuals might feel pressured to take holiday they don't want or need, or miss out on holiday they deserve.

  • Increased costs and risks, as individuals might carry over and build up too much holiday entitlement or the company has to pay out for unused holiday, or explain why individuals will lose their company contracted entitlement.

  • Decreased compliance and visibility, as the company might not have accurate records of individual holiday balances to prove company policies have been followed.

So, what can companies do to avoid the holiday headache?

The answer is simple: use an automated system.

Benefits of an automated system

An automated system is a software solution that tracks, calculates, and manages individual holiday balances automatically.

It can integrate with other systems, such as Outlook calendars, to provide a single source of truth for individual holiday data. It can also generate reports and alerts, and allow individuals and managers to request and approve holiday online, whilst providing full visibility of conflicting time-off or individuals running excessive balances, or even trying to take off more time than they are entitled to.

A happy smiling female office worker with a laptop

By using an automated system, companies can enjoy many benefits, such as:

  • Saved time and effort, as they don't have to manually gather, collate, and analyse holiday balances, or manually communicate with individuals and managers.

  • Improved accuracy and reliability, as they can avoid human errors, inconsistencies, and discrepancies in holiday data.

  • Enhanced individual satisfaction and engagement, as they can provide individuals with more flexibility, transparency, and fairness in managing their holiday.

  • Reduced costs and risks, as they can avoid paying out or carrying over holiday balances, or dealing with disgruntled individuals.

An automated system can also help managers to plan ahead and optimise their team, by providing insights into holiday trends, patterns, and preferences. This can help them to anticipate and address any potential issues, especially understaffing due to conflicting holiday requests.

Beware the holiday system trap

So, you have decided to invest in a automated system, but there are so many to choose from - how do you decide?

Cost can be a key deciding factor. Do you just tell individuals to download the same mobile app from their favourite app store and use that, or do you sign up for a cloud-based solution that stores your company and individual’s data .. who knows where?

A female office worker having a stressful moment

These solutions might provide useful automations to replace spreadsheets, email-based processes and paper forms but they can introduce new challenges:

  • A lot of the Apps and cloud-based solutions just focus on holiday – but the challenge is wider than that as individuals have time-off for other reasons, maternity, paternity, jury service, compassionate leave, and many others. If not included in your new automated system, then this can cause department time-off conflicts to go under the radar until it is too late.

  • When individuals join or leave, HR has to remember to sign-in and update the cloud-based holiday system to reflect this.

  • HR typically takes on the role of IT support, an additional headache for them, having to deal with individuals who can never remember their username and password!

  • These apps and cloud-based systems rarely integrate to the Office apps managers and individuals use during their working day. For example, enabling Outlook work calendars to be automatically updated with approved holiday, because individuals rarely (never) remember to do this and now meetings are getting booked for periods when they are not here.

  • Decisions about where to store your HR policies and guidance. Should these be in the company intranet where they have always been stored, or in the new holiday manager system. Or both!

  • And then how do I extract my company data from these systems to feed into the end of holiday year payroll processes or individual’s appraisals?


Managing individual holiday balances at the end of the year can be a daunting task for companies and especially HR departments and managers. This is further compounded if they have to do it manually

This can cause a lot of stress and hassle and have negative impacts on the company's performance and reputation.

But it doesn't have to be this way. By using an automated system, companies can simplify and streamline the process of holiday and all time-off management, and enjoy many benefits, such as saving time and effort, improving accuracy and reliability, enhancing individual satisfaction and engagement, reducing costs and risks, and increasing compliance and visibility.

Why your automated system should run within Microsoft 365

Microsoft talks about systems and tools sitting with the individuals and managers “flow of work". What do they mean by this?

When Microsoft talks about the "flow of work," they are referring to the way work moves from one operation to another, within the tools and apps that individuals use day-to-day, with the goal of increasing efficiency and reducing costs and delays.

This is what your holiday system should deliver.

A Windows 11 laptop showing Microsoft Outlook

Most companies now use Microsoft 365.

Individuals and managers spend their working day in Microsoft Teams, or accessing the company SharePoint intranet to access policies and procedures, and not to forget that Outlook is still the de-facto work calendar.

This is where your company's flow-of-work happens, This is where your people spend their time. And this is where your new holiday system should live.

So, if you want to avoid the holiday and general time-off management headache, and make the end of the year a happy and peaceful time for everyone, why not consider investing in an automated system that avoids the typical bear traps!

It might be the best end-of-year holiday gift you can give yourself, your colleagues, and your company this year.

To find out more about how time-off management automation that is integrated into your individuals flow of work could look like, head over to our Time-off Manager solution here.



Discover more and get in touch today


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