Prepare team for annual leave

What’s that peeping over the horizon? Could it be… sun?! Your eyes do not deceive you: the shortest day is a distant memory, the temperature has reached double digits and the rain is (almost) dried up… Summer is coming! And you know what that means?

Panic stations.

Sleepless nights running through your mental (in all senses of the word) to-do lists. Frenzied days spent refreshing the passport website. Desperate hunts for the perfect Airbnb that’s as close to the beach as it is to the town. Then your partner jokes, “You’ll need the time off after all this work!” Time off… now why is that setting off alarm bells?

Of all the stresses of planning a holiday, don’t let the one thing you forget to book be your annual leave! It would be easier to blag your way onto a plane without a passport than to get a last-minute week off out of “the gatekeeper” Gary from HR.

But that’s just the first hurdle. For many, booking time off work can feel like pulling the pin out of a grenade. Of course everything will implode while they’re away, and they’ll return just in time to have to clear up all the mess, leaving them so exhausted they’ll immediately need another holiday. Is it even worth it?!

Table of Contents

In this article, we’ll talk about how to prepare your team – and yourself – for annual leave that is exactly what it’s supposed to be: restful, enjoyable and rejuvenating.

Why aren’t we using our annual leave entitlements?

Did you know that half of adults in the UK don’t use their full annual leave allowance? It couldn’t be us, we love leave – but apparently, it’s more of us than we’d expect. The idea of all that wasted holiday is enough to bring a tear to the eye (and not just for the airline bosses).

The first step to getting the most out of annual leave is actually getting your head around taking it. Now, some people have no issue with this – filling up that leave calendar infuriatingly fast, planning out their long weekends and special trips months in advance. Others forget all about it until it’s too late. 

Some people actively avoid taking it, fearing it will make them less productive or appear less committed. This is a form of presenteeism and is to be avoided at all costs. It’s counterproductive, unhealthy and with all the efficiency-during tools and tech we now have at our disposal, it has no place in a modern workplace. It is the job of management to send this message loud and clear.

Is time off a productivity killer? Never.

Wasted annual leave is wasted potential. A short-term focus on productivity misses the bigger picture, which is life.

Also, as we should all know by now, productivity is not measured in time. The hours we put in have diminishing returns, and it serves no one to work yourself to the bone. Chaining yourself to your desk does not make you a more committed or productive employee. It shows you’re on top of your workload, managing your time and prioritising your wellbeing – smashing it on all fronts. 

This is what you should be looking for from your team - not their face in the staff room 365 days a year.

Someone who can’t risk taking a week off for fear of everything falling apart has clearly not mastered their workload, team, or mental health. 

When you’re burned out, you do the bare minimum to keep things ticking over. You have no energy to be creative or innovative. It’s no coincidence that we often have our best ideas when we’re relaxed on a walk or lying in the bath. When you’re stressed out you think only of what you need to do, not what you could do or would be fun/interesting to try. As people’s jobs shift to be increasingly creative while AI takes some of the grunt work off our hands, this ‘get through the day without collapsing’ approach is not the state we want people coming into work in. Or was it ever?

So, how do you prepare your team and yourself for annual leave?

Aside from the mindset shift of not seeing time off as time lost, the key to getting people to take (and actually enjoy) leave is preparation. The BA survey found that 42% of Brits have felt stressed about work while on holiday, and nearly half have worked when ‘away’. Email has a lot to answer for here - 48% of people have checked work emails while on annual leave, and 39% responded.

1. Use your email features

In the digital era, our phones are basically windows into our lives and minds (and for some of us, souls), and we tend to leave them open. Unless you’ve got a work phone that you can switch off and leave at home, you’ll need to put some controls in place when you go away. Because let’s face it, how many of us can resist a scroll through TikTok on a sun lounger, or posting a hot-dog legs Insta pic in front of a perfect sunset to ensure our friends and family back home are suitably envious. The last thing you need is Brenda popping up on Slack and spoiling your mojito.

It’s not enough anymore to just set an out-of-office auto reply; you’ve got to actively enforce it. In the new world of hybrid work, where ‘office’ has become a much more fluid term, there is a risk of ‘OOO’ messages being disregarded or assumed to be open to interpretation. Are you actually off or just working from home? When taking annual leave, out of office should mean ‘do not disturb’.

Do not confuse people by not abiding by your own OOO, or allowing others to do this. Build a culture that respects absence. Make it clear that employees on leave are not to be contacted. Require an OOO that clearly states that no response should be expected until a specified date and provides an alternative point of contact if the matter is urgent. Encourage a pre-OOO warning signature in the run up so that people know the person is going to be off. This will minimise the number of emails they return to and hopefully allow them to switch their mind off from work when they switch their computer off.

2. Book your leave early

Actually booking your annual leave is the most essential item on your holiday to-do list and the one you should tick off nice and early. You can take a break without a passport, but you’d be hard-pushed to get that much-needed R&R staring at pictures of the beach on Google while still sitting behind your desk.

Managing annual leave can seem like a logistical nightmare. If you have a large team, it can be easy to lose track of who’s taken what. If you have a small team, there’s the risk of leaving yourself short-staffed if too many people are off at once.

Use leave management software to provide an easy-to-use system for booking and approving leave. Then, encourage people to get requests in early, communicating that you genuinely want and expect people to take leave. This will enable you to spot any conflicts early and arrange cover. Easy!

3. Communication and handover

One of the biggest concerns managers have related to leave is projects stalling or tasks piling up. Things need not ground to a halt when someone is away. To make it easy for someone to pick up where someone else left off, handovers are key. These should outline all ongoing tasks and responsibilities and provide clear instructions to avoid confusion, duplication or mistakes. They should contain everything that the cover will need – email folders, shared docs and folders – and clients/team members must be alerted to the absence and know who to contact instead.

Managers should not leave this up to the individual to organise – require handover meetings so that responsibility is clearly delegated and expectations communicated and documented. This also avoids last-minute scrambles. Have a handover meeting on return, too. To catch the person up on what’s happened in their absence, any outstanding issues, and let them know what’s urgent and what’s not.

4. Don’t be indispensable

This one is linked to the productivity myth and requires a mental shift at the individual level.

The need to prove our worth in some quantifiable way is so ingrained that we’re terrified of appearing too easily replaceable. We want to be missed. We want things to fall apart without us because that means we’re essential and our job is safe. But again, this is short-term thinking.

While no one ever wants to feel like they could be easily replaced, in the short term you should be. Don’t gatekeep your knowledge or resources so that only you can do your job – this doesn’t serve you in the long term, and only makes it difficult to take leave and more stressful when you do. Knowledge sharing reduces dependence on a single person – and this is a good thing. A confident employee should know that they won’t be valued less if their disappearance for a week doesn’t mean the company spirals into disaster – it means they’ve done their job well.

Well-functioning companies are about teams, not individuals. Even armed with all of your knowledge, tools, tips and tricks – your carefully curated macros and templates – your cover won’t be you. They won’t think like you, approach tasks like you or engage with the role like you. You were hired for a reason.

From an employer perspective, it’s on you to build a culture where people feel safe enough to be (temporarily) replaceable. Which is linked to the last, and perhaps most important tip…

5. Set a good example

A key part of driving home the message that the need for time off isn’t just respected but truly embraced is to live by that value yourself. This is especially important at management level and above. Take all of your annual leave, and shout about it. Never respond to emails when you have an OOO on. If people see their line managers or bosses chipping in when they’re supposed to be on holiday, they’ll think that’s what they should be doing. And that’s what aspiring leaders will think is expected of them if they’re to climb the ladder at the company.

Culture needs to come from the top down. You are setting the tone for everyone else, so lead by example. If you’re telling people to enjoy their holiday then joining a Zoom link from the beach when you’re supposed to be off, you’re not sending the message that you genuinely value rest.

Key takeaways

Annual leave is supposed to be a pleasure, not a headache. And there’s no reason it shouldn’t be. We have so many tools and tricks up our sleeves these days to make life easier and more efficient, and there’s really no reason for anyone to miss out on rest time because they think it will be too much hassle.

We already have all the means to prepare for annual leave. The main barrier is a cultural one, so managers should focus on rejecting ‘hustle culture’ and showing that they value rest by visibly prioritising it in their own lives and encouraging cross-training and knowledge sharing.

So book your leave, set your OOO, and unplug. Make sure your team does the same. You’ll all return refreshed and energised, relieved to see that the world did not end, but everyone is happy to see you back (even if only because it’s their turn next!).

Happy holidays!

Abi Angus Leave Dates


Abi is a freelance writer based in Brighton & Hove, UK, writing for businesses about work, life and everything in between.