OOO: Tips for preparing for a sabbatical leave

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5 mins, 54 secs read time

Greenhouse Senior Director of Talent Planning & Acquisition Ariana Moon shares advice for leaders preparing to go on a sabbatical leave.

As employers are beginning to recognize the value of prioritizing their people’s needs, and providing great benefits like paid time off, a new hero emerges – the sabbatical. With the right kind of preparation and intention, sabbaticals enhance the wellbeing of the person going out of office and provide an incredible opportunity for accelerated growth and business exposure for the coworkers stepping in and up to support them.

This combined focus on wellbeing and professional growth across the board can drive employee development, engagement and ultimately (and excitingly) retention, which positively impacts business performance. In this way, sabbatical programs can be considered a competitive business advantage. As a leader who has had a personal experience with this and recently returned to work after a restorative 7-week sabbatical in Spain, I’d like to share my reflections on how leaders can get it right.

There are many benefits of a sabbatical program, but you and your team have to prepare. The prep work will look different depending on whether you manage a team or not. For this post, I’ll be focusing on the perspective of a people manager leading a specific function.

At least 3 months before:

Socialize out-of-office dates

Start preparing your team and stakeholders for your absence at least a quarter ahead of your departure date. This gives you the opportunity to do “test runs” and “close the gaps” (more on this below) in a deliberate, unrushed way. Being the planner that I am, I started these conversations six months in advance.

Step 1) Announce that you intend to take a sabbatical

Step 2) Socialize and communicate the dates you’re considering

After setting my dates, it was important for me to remind folks about them. There’s a well-known saying that in order for someone to remember a fact, they have to hear it seven times. I took this to heart. Very quickly, my sabbatical became a known deadline to work toward, which had the extra benefit of adding pace and purpose to whatever we were working on.

Identify key relationships

Another exercise I did early on was write out my perspective of all the relationship gaps that would appear if I were to disappear from work today. For example, I asked myself – for the stakeholders who depend on me for a certain kind of information or collaboration, who would I direct them to in order to make things as painless as possible? Or – if my direct reports had challenges they needed guidance on, do they know who to go to for what?

These kinds of questions helped me think proactively through various situations, put myself in other people’s shoes and identify areas where I needed to delegate or appoint a decision-maker more clearly.

Here are some buckets of collaborators to consider in this exercise:

  • Manager/department head

  • Peer group

  • Stakeholders

  • Direct reports

  • Greater team or department

  • ERG and committee collaborators

  • Clients and customers

  • Third-party vendors, suppliers, etc.

Be clear about priorities

In any growing company, there’s never a shortage of things to do. In recognizing this, I was conscious not to kick off a bunch of new, meaty projects right before I left, especially if there was no one to pick it up in my absence. What was more important than launching shiny, new initiatives was making sure my team had the confidence to maintain operations, collaborate with each other and make sound, balanced decisions without me.

Prioritize team-building to normalize a new level of collaboration

In the month before my sabbatical, I planned a virtual “offsite” with my direct reports. This offsite spanned several full days and was focused on being vulnerable and building trust in the spirit of enhanced collaboration, as I knew they’d have to rely on each other more than ever while I was out. To help structure these conversations, I hired a skilled facilitator who provided us with a common language to talk openly about our communication and personality styles.

I later received feedback that the offsite experience was one of the most helpful things I’d done to prepare my team and help build a collaborative, cohesive culture in my absence.

Build confidence through a “test run”

About a month before my departure date, I decided to do a “test run.” This was a fun (for me) exercise where I let my team know I’d be taking a back seat on all operational tasks and escalations for an entire week. I was around for any emergencies, but unless they titled a text message or email as such, I was clear that I wouldn’t respond. If they were blocked, my guidance was for them to collaborate with each other or other colleagues that we’d identified ahead of time.

Fortunately, the test-run week progressed smoothly. But the more important thing that came out of this experience was that my team developed higher confidence in operating without me before I was even gone.

1-2 weeks before:

In the last week or so leading up to your sabbatical, you’ll start to truly experience the excitement of taking extended time off and for your team to stretch and grow in your absence. Here are a few tips on things to do during this time that future, post-sabbatical you will appreciate.

Unclutter your future inbox

Unsubscribe! Think of all the emails that would be collecting in your inbox for the many weeks you’re out that you wouldn’t consider important or worth going back and reading. This might include newsletters, scheduled reports, automated software notifications, pings on whatever messenger platform you use – as you know, the list goes on and on.

Set up a thoughtful out-of-office message

A thoughtful OOO message is key to expectation-setting with anyone looking to reach you while you’re out on vacation. When thinking about this message, I like to prioritize a few things.

1. Start by thanking the sender for their message.

2. Share your perspective on the importance of regularly unplugging from work, and a bit of what you’re doing during the time off (this can be a fun way to show how you’re prioritizing time off).

3. Let folks know to what degree they can expect a response from you (or not) upon your return.

Create a sabbatical hand-off doc

Finally, it’s worth putting together out-of-office documentation that outlines key workflows such as owners of ongoing logistics, appropriate escalation points, projects on hold and information on how to be contacted if necessary. This can be as simple as a Google Doc shared with your direct manager and your business partner team. If you’re sharing all your direct reports in this document, be mindful that it doesn’t include any personal or performance content that shouldn’t be shared with them all.

Learn about how to create a great people-first hiring strategy by watching this virtual session at Lattice Resources for Humans.

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Ariana Moon

Ariana Moon

leads the Talent Acquisition function at Greenhouse and is proud to be Greenhouse's longest-standing member of the People team. She works with all departmental leaders to hire for what’s next with the goal of modeling best-in-class, predictive recruiting. Outside of work, she is an avid yogi, rock climber and donut eater.

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