Make an offer they can't refuse

How to approach your manager to ask for a sabbatical.

Bonjour, and welcome to everyone who’s just joined!

There’s a fresh intake of people who have come from LinkedIn, now that I’m a bit more present on the platform. I recognise some names—it’s good to see you here :)

In this issue, I share a couple of things on the theme of sabbaticals.

First: an exciting little quiz I created recently and launched on Monday.

Second: some thoughts about how to approach your manager to ask for a sabbatical. I wrote this in response to questions I received from people this week, so if there are things you would like me to write about next, do let me know.

Alright—let’s dive right in!

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Discover your ideal sabbatical with the Quiz!

So many people who feel like they need a break from work never actually take one. The most common reason they give for not doing it is that they don’t have the headspace to think about it properly.

If that’s you—or if you know someone who keeps saying that they need a break and aren’t taking one—I’ve just created something that I think you’ll find useful.

It takes 3 minutes. It’s fun. It’s free.

It’s the Sabbatical Quiz!!

The quiz will help you reflect on your current situation and tell you what kind of break from work would likely do you loads of good right now. You'll also get a report with relevant stories and tips that is tailored to your results.

So—why would it make most sense for you to go on sabbatical?

• To shape the next phase of your life more meaningfully

• To reorient your career in an exciting way

• To dive into a project you’re passionate about

• To recharge your batteries fully

Take the quiz now to find out!

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Make an offer your manager can’t refuse

Many people who go on sabbatical do so after having quit their jobs or having been made redundant. For those who go on a traditional sabbatical—the kind where you’re still employed even when you’re not at work—asking your manager for extended time off can feel just as awkward as asking for a pay rise. 

I was lucky that the conversation went pretty smoothly for me.

I had a great relationship with my boss. I’d been doing good work for the company for more than five years. I was well prepared for the conversation and I was ready to quit my job if my request was refused. The only difficulty was that my manager would struggle to replace me quickly, so I knew I might have to wait a bit longer than I was hoping to before going on sabbatical.

But honestly, having the conversation is not that complicated if you prepare for it well and if the company values your work. It might even feel pleasant. After all, it’s one of those moments where you get to shape the course of your life by tuning into what you want and then saying it out loud. It’s very empowering.

To optimise your chances that the conversation goes well, you’ll have to take three perspectives into account when you prepare: the company’s, your manager’s and yours. I’ll dive into each of those in sequence and share some useful tips.

Perspective #1: your company

Before you do anything else, check your company’s sabbatical policy:

• Do they offer sabbaticals?

• How long can you go on sabbatical for?

• How long does your tenure need to be before you unlock that benefit?

• Are there any conditions attached e.g. volunteering or studying?

• Will you have to return to a different position in the business—or yours?

I was lucky to work for a big company that offered sabbaticals as a part of the employment package. All I needed to qualify for an extended sabbatical (twelve months) was to have worked for the company for more than five years—which I had— and be comfortable taking on any job they would offer me when I came back—which I trusted would be something I would want to do.

If all the boxes are ticked in the right way for you too, that’s brilliant! Just bear in mind that the policy will certainly give your manager the right to ask you to delay, shorten or give up on your request if it puts the business at risk.

So your job—before going into the conversation—is to identify those risks and find ways of managing them. We’ll have a look at that in the next section.

If the policy isn’t in your favour, don’t lose hope. At least now you know the starting point for your negotiations and you can prepare accordingly.

Either way, download the policy and keep it at hand so you can share it with your manager to support your conversation later on.

Perspective #2: your manager

Your request is likely to create some chaos for your manager, even if they’re a wonderful human who you get along with really well.

As soon as you mention the word ‘sabbatical’ they will immediately start thinking about the impact your absence will have on the business, and how the work you’re doing now will get done while you’re away. The more unique your skillset and the quicker you want to leave, the more difficult it is going to be for them to find a good answer to those questions.

Technically that’s their problem to solve.

Dealing with your request is more complicated than replacing someone who’s announcing that they are going on maternity leave in six months, but less complicated than replacing someone who’s just quit and is leaving in a month.

Regardless, your manager will be more inclined to agree to your request if you help them solve the problem you’re creating, either partially or fully.

So put yourself in their shoes. 

First, schedule the sabbatical conversation sufficiently in advance of your intended departure date so it gives them enough time to find a solution they’re comfortable with to replace you.

Second, make sure you understand the impact your absence will have on the business: what won’t get done if you’re not around? How easy is it to replace you?

—and then shape your request so you limit that impact as much as possible while still honouring your needs.

Think of the timing.

Suggest your sabbatical starts at the end of the big project you’re currently working on. Or if the team typically experiences a lull in activity at a specific time of the year, offer to go on leave at that time—and maybe to come back before the next uptake in activity.

Also think of who could cover for you while you’re away.

Offer to train them and to prepare a comprehensive handover for them. And if it’s relevant you can present your absence as an opportunity to build resilience in the company as two people would be able to do the work you’re currently doing once you’re back, instead of one.

I knew it wouldn’t be easy for my manager to find a replacement quickly, so I told him I’d be comfortable working my entire contractual notice period (three months) and a bit more if needed.

When he asked me to work another seven months, I refused and explained that I didn’t have enough energy left in me to continue delivering at my usual standards for that much time—so we settled on five months, and I chose to use that time to re-inject another round of energy into my work, to deliver a mini-project that I ended up being really proud of. Thanks to that, I left on a high.

And now last—but not least…

Perspective #3: you

Get your story straight before you share it with your manager.

Here’s how I would structure and tell my story, if I were to do this again.

Start by expressing gratitude for the opportunities the business has given you. This will help set a positive tone for the conversation and lighten up any stress you might be feeling.

And shortly after:

Ask for a sabbatical—don’t make your manager wait too long to hear the news, that’s not cool. Don’t dive into any practical details just yet either.

Explain why this is important to you—the more you bring your story to life, the more human the conversation will be. And immediately after that show how your sabbatical will benefit the company as well—maybe you’re planning to learn a valuable skill, or you expect to come back energised and full of creativity. 

Acknowledge the disruption that this is likely to cause—no need to be exhaustive, instead simply pick a couple of specific examples to show that you understand the impact of your request on your manager and your team.

Use that to inform the next part.

Be clear about what you want, practically—tell your manager when you’d like to leave, for how long, and what role you’d like to return to. The more clarity you give your manager and the more confident you are that this is what you need, the easier it will be for your manager to respond to your request.

Ultimately you need to go into the conversation with a professional tone while being as authentic and flexible as possible.

Be clear (at least with yourself) what the non-negotiable items of your request are, and what you will do if they’re not met. That way you won’t be destabilised if your manager pushes back on part of your request.

And finally, don’t make the same mistake as I did back in 2021…

I let the conversation end with my manager telling me that he ‘would have a chat with HR about it and get back to me soon’ and I didn’t ask when that would be. I’d assumed he would be quick to give me an answer but unfortunately it took weeks (and some uncomfortable pestering from me) for him to finally get back to me.

So don’t leave the conversation without being super clear on when you can expect your manager to give you their answer. Treat this like a negotiation. Put any next steps you’ve agreed with them in writing including the date they committed they’d give you an answer by. 

That’s it.

Good luck. Have fun!

And remember: requesting what you need is an empowering thing to do.