Asking for a sabbatical policy without feeling judged

The Overlap #59

In our last newsletter, we learned about how to help your company offer a sabbatical policy.

Davide left a really good question that I’m sure others experience:

I'm not sure how a request for a sabbatical might be perceived by a company and the managers: in my experience there's a high risk of compromising yourself, the request being seen just as a paid vacation before checking out mentally or quitting right after the sabbatical.

You focused a lot on the nuts and bolts of building a proposal — which is great and helpful — but I'm curious about how you navigated the touchy-feely side of it, and how others might prepare themselves better for the inevitable clash of different expectations and suspicions that might arise from a request for a sabbatical.

He graciously permitted me to respond to his question in the next newsletter. So, here goes!

I know that for most people, asking their boss for a sabbatical can come off negatively. Of the two places I worked at as a full-time employee, I’ve never felt like I’d be judged for asking for a sabbatical. So I’ll own that I don’t have direct experience here. If you have experience proposing a sabbatical policy and not everyone took it positively, please share your experience in the comments!

My first employer valued work-life balance. And always used integrative decision-making (IDM) to make changes to any policy. One of my colleagues proposed a “honeybattical” to take extended time off for her honeymoon. We passed this using IDM. After I left The Ready, I noticed that my friend Sam proposed a sabbatical policy that passed too.

And before I joined garden3D, I learned that we had a 6-tweek sabbatical in place for employees of three years. In 2020, we started using IDM to make changes to any policy. One policy that came out of IDM was our 16-week paid parental leave (shoutouts Isabel).

This brings me to my first idea. First, introduce a way people can make changes to policy. Then, propose a sabbatical policy. 

When I used to introduce IDM to leaders, I’d help them understand that IDM was a tool to help them quickly make informed, safe decisions. Their organization usually struggled with one of two things:

1. Making decisions too slowly. Which happens in more consensus-oriented organizations.

2. Making decisions without input from teams that the decision most impacts. Like the CEO deciding on what the prices of a local franchise’s avocado toast should be. 

The leaders who liked IDM loved that they didn’t have to have every decision escalated to them. And, they had a tool to make quick decisions, with the right input.

Anyway. Derrick Bradley has a solid essay on how IDM works.

Let’s counter my suggestion above, though. Most people who want a sabbatical aren’t willing to introduce a new decision-making framework to their leaders. And ensure its adoption. 

You just want a sabbatical without having to change the way your company makes decisions. 

So, my second idea is to find the others who also want a sabbatical.

Specifically, find a sponsor who

1. also wants a sabbatical, and

2. has the authority or influence to make this decision. 

Squad up! Your sponsor (or team, if you work with multiple people on this) will be your refuge. In this refuge, psychological safety is high. You can’t change the psych safety of your entire org, but you can create a psychologically safe team. 

Having a sponsor with influence or team might alleviate some anxiety around coming across negatively to others. If Jasper, the Head of HR, also wants a sabbatical and has sound reasons for why a sabbatical is good for the business (reduces burnout, which increases retention and saves the business $ in the long run), then maybe others won’t be as judgmental towards you.

Okay, so we’ve gone over two ideas: introduce a decision-making framework or find the others.

My last idea is more about inner work.

Reflect on these three questions:

• Are others actually going to be suspicious if you request a sabbatical?

  • This might depend on things like how long you’ve been at the company, whether people truly take time off, and how much trust you’ve built with your coworkers

• If yes, why will people be suspicious? Is there a general vibe of low trust? Or is this suspicious specific to you?

• Are you okay with going for it, knowing that others will be suspicious/judgmental? 

• If no, what can you personally do to be okay with others feeling suspicious of you? Who can you seek support from here?

In certain cases, there are real social/political consequences for asking for a sabbatical. Like you work at Twitter 80 hours a week because that’s what Elon wants. Or you work at a startup where everyone’s been grinding hard before the big launch. A sabbatical before the launch probably isn’t the right time. 

Get clear on those consequences. Then ask yourself if you want to make that tradeoff. If yes, go for it (strategically!). If not, then figure out how to de-risk those consequences. Or consider if where you work is the right workplace for you.

In other cases, people will judge, but there’s little to no consequence in asking. In these cases, don’t worry too much about judgy people. You can’t control them. You are unfazed. 

In other cases, people won’t be suspicious of you. Be objective — this may be the case! Have other coworkers taken parental leave? (If yes, that’s a good sign!) Have you made an impact? (Most likely!) Do any of your other close colleagues want a sabbatical too? (If you don’t know, find out!)

Suspicion. Distrust. Judgment. Potential clashing. To what extent is this caused by your organization’s dynamics? To what extent is this coming from you? Sometimes it’s more one than the other. Or both. Get clear on what’s mostly driving this — this will prepare you to take the best path forward.

I hope this helps, Davide!

If others have any experience with this, I’d love to hear it in the comments.

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What I’m Reading

1. Official myths by Mandy Brown. “Ultimately the real problem with the argument that we need offices to support junior staff isn’t about those junior staff at all—most of whom, I think, can see right through those claims. It’s that by constantly comparing remote work to an office straw man, we’re not engaging seriously with the challenges of remote work.”

2. “High Standards” by John Cutler. High standards are good, as long as it leaves room for different ways to achieve those standards. 

3. Five Org Design Things by CPJ is good! He’s been consistent with writing lately. Awesome to see.

See you in two weeks (or next week if you’re a subscriber), 
–tim