Why Your Team Isn’t Using Their Holidays (And What to do About It)

Here we go again.

You hoped things would be different this year, but it’s October and a load of people in your team still have at least 10 days of holiday left to take. And in the last quarter as well… 

You wanted to be easy going. Putting rules in place seemed unnecessary (everyone wants a holiday, right?), but you’re back to where you were last year, realising that easy going’s just not going to cut it. 

Until you’ve experienced it, it’s hard to imagine the challenges that come with people not using their holiday. But we’ve been there, so we know exactly where you’re at. 

At Charlie, we rely on specific times of the year where there are more opportunities for new business, so we had to find a way of ensuring there were enough hands on deck without risking anyone burning out. 

This guide contains everything we’ve learned, and will show you how to make holidays work for both your business and your employees.

Why your team doesn’t take holidays

There’s no one reason why your team isn’t using their holiday:

• Taking time off can feel pointless if it just creates a backlog of work
• High performers may skip leave due to ambition, perfectionism, or feeling indispensable
• People who view holidays as "big trips" often delay time off until they have something planned
• Vague or complicated holiday policies discourage people from using their leave
• Fear of layoffs or job instability makes employees hesitant to take time off
• People feel guilty about leaving teammates to cover their workload
• A culture that glorifies overwork can make rest feel undeserved or frowned upon
• If managers don’t take or encourage time off, teams are unlikely to either
• Poor handover processes make holidays stressful to plan and return from
• Remote work blurs work-life boundaries, making people feel less entitled to disconnect

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8 ways to show your team that holidays matter

So much about showing your team that holidays matter is about common sense, communication and culture:

1. Remind your team holidays aren’t a perk — they’re a legal right 

This is something that people can forget, but taking a break from work is set down in UK law — this is known as statutory leave entitlement. This is a good reminder for people who have a tendency to just skip their holidays, just to nudge them in the right direction. 

2. Make annual leave policies clear and accessible 

Having an annual leave policy is one thing, but making sure everyone in your company knows where it is and is familiar with it is another. We recommend including your policy in your employee handbook, as then everyone knows where it is. 

3. Model good holiday habits by taking time off yourself

Lead by example and show your team that it’s okay to go on holiday. If they don’t see you regularly taking leave, how can you expect them to feel like they can? First model that behaviour for yourself, and allow yourself some time off. 

4. Champion flexibility, but set rules around it

Being flexible doesn’t mean being unclear. In fact, wishy-washy processes will just make your team feel less sure of what they can and can’t do. 

If your business has critical periods where you need all hands on deck, make sure everyone knows the dates and reason well in advance, and request that your employees book their leave at other times.

5. Get managers to schedule regular check ins with their team

Managers naturally have a closer working relationship with their line reports, so they should be regularly checking in and reminding their team members about their holiday allowance.  

6. Scratch off holiday carryover

Carrying over holiday makes sense when there’s a legitimate and unavoidable reason to not use all of a leave allowance. But some people make it a habit — which means they're consistently not having enough of a break from work. Removing carryover as an automatic option means that every member of your team will have to request it, which may be more of a hassle than just taking the leave in the first place.

7. Communicate, communicate, communicate

Burnout isn’t just a buzz word. Never underestimate the power of talking about taking regular breaks from work – by preventing your team from it, you’re also protecting the business from being understaffed. Remember, you have responsibilities toward your employees. 

8. Be curious, ask questions! 

As with most things, talking helps. So if someone in your team isn’t booking and taking their holiday then talk to them about it – maybe there’s some specific reason why they feel like they can’t take time off or don’t want to book a holiday. That way you might be able to work through it together. 

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Why is it difficult to spot team members who are not taking holidays?

As a small business owner, you already have a lot going on, so it might not be immediately obvious that someone in your team is not using their holiday allowance. And that’s because manually managing holiday takes a lot of time and effort:

• You have to track everyone’s allowance and check it’s up to date
• This means setting calendar reminders and regularly reviewing booked and used leave
• You have to check individual allowances one by one in order to process every request.

So it’s really easy to fall behind and lose visibility over who’s taken what.

As a fellow small business, we recognised this early on at Charlie, which is why time off is a primary feature in our HR software. Using Charlie for managing your team’s time off means that you can stop jumping between different platforms to see everyone’s time off – all of it is visible at a glance. 

With effortless visibility like this, it’s much easier to spot trends and make informed decisions about what’s going on in the business. 

By law, can you force people to take holidays?

Yes, you can. 

As an employer, you are legally allowed to require your employees to take holiday — provided they give at least twice the amount of notice as the leave to be taken (e.g. two weeks' notice for one week of holiday). 

While this is legally permitted, it’s much better for engagement and culture to encourage your team to go on holiday rather than enforce it.

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Should I really put rules around taking holiday?

Setting clear guidelines for your team is always a smart move. 

When it comes to holidays, clear guidance helps to avoid confusion, ensures fairness and keeps your business ticking along smoothly, especially as you grow.

Your employee handbook is an obvious place for guidelines around booking and taking leave, as is HR software like Charlie. You can:

• Outline any restricted dates (e.g. for business closures or peak periods)
• Define any holiday carryover rules or a “use it or lose it” policy
• Automate reminders to encourage regular holidays (one of the great things about using software like Charlie)

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What happens if an employee refuses to take holidays?

This can be a tough one to navigate, especially if you’ve never dealt with it before (particularly common in startups and small businesses).

First, try to understand why they’re not taking time off — it could be workload, guilt, feeling like they’re not “allowed”, or another reason altogether. Be open and friendly, and encourage them to take a break for wellbeing as well as performance.

If they continue to avoid it and holiday is building up, you can require them to go on leave. Legally, you must give notice that’s at least double the holiday you want them to take (e.g. two weeks’ notice for one week’s leave). This should always be a last resort — it’s much better to create a business culture where taking time off is both normal and encouraged.

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Our take — how we deal with holidays at Charlie

At Charlie, we started out with a very different approach to holidays: offering our team unlimited time off. 

Surprisingly, they didn’t like it (our unlimited holiday is available here), so we switched to a fixed leave allowance: 25 days + bank holidays + two additional days at Christmas. And this is the structure we still use today. 

When it came to the holiday year, we learned a couple of useful lessons: 

• We set our holiday year from April–March, to align with the financial year
• But this caused a spike in time off during the first quarter, which is one of our busiest periods
• So we reverted back to a January–December holiday year, and this has worked well for us.

But your leave year isn’t the only thing to factor in. Better internal processes are essential for bringing about real change: 

• Holidays are now discussed and planned in advance between managers and their teams
• Everyone is expected to give enough notice when booking time off.

Getting your team to use their holidays more isn’t rocket science, but it is consistency, communication and common sense. Plus, there are tools out there like Charlie that will make it easier for you — why not give us a try?

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