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đź’ś Setting a PTO-Positive Precedent
#53. How to actually prepare for time off (worksheet included!)

Hello and happy Thursday!
Let me be the first to say it. I need a vacation. Maybe you do too?
If so, may I offer a new perspective? You taking time off isn’t just for you. It’s also for your team.
No, I’m not insinuating they need a break from you. What they need is the reminder (through behavior modeling) that it’s OK to take time off and really unplug. To those of you with direct reports, your willingness to actually use your PTO (or not) sets a cultural precedent.
So how do you set yourself up for success when it comes to taking vacation time this summer? That’s exactly what we’re exploring (in practical, actionable ways - of course) in this week’s issue.
To unplugging without guilt,
Jill
P.S. A BIG enthusiastic hello to the 300+ new subscribers who found us through this article that went out in Hebba Youssef’s I Hate It Here newsletter last week. I’m genuinely thrilled to welcome you to our little corner of the internet!
Reflect on this…
Do you lead by example when it comes to unplugging and recharging?
What keeps you (or your team) from taking full advantage of our time off?
If someone on your team needed to take emergency leave tomorrow, could you handle it smoothly?
You Can’t Pour from an Empty Slack
Paid time off is viewed differently outside the United States, where “grind” culture is less glorified and rest is seen as a right, not a reward. Many countries in Europe and Asia mandate that their employees take anywhere from 26 to 38 days off per year.
There is no similar requirement for U.S. employers, but many of those that do offer time off give 10-15 days per year - and a lot of people don’t even take that much!
We could very easily get on our soapbox here and present a thorough argument for why this should change–like how taking time away from work increases productivity and morale, supports retention, and reduces burnout–but we'll just send you to this article about how important it is to take PTO.
Let’s focus instead on how you can plan to actually disconnect from work.
We've put together our best tips, along with a copy/paste worksheet you can use to make your PTO-prep run like clockwork.
Let's get into it...
First Things First, Complete a PTO-Prep Worksheet
If there's one thing we love, it's a worksheet.
Mostly because, in moments of chaos, we can't trust our brains to remember every detail. That's why we continue to sing the praises of documentation. And the process of preparing for PTO should be just like any other process.
One of our WTWT team members recently recommended using a PTO-prep Worksheet and let me tell you... I was all ears! Think of this as your central dashboard for ensuring you can set that OOO email and truly log off–and your team will continue to function without you.
Your PTO prep document should include everything from getting PTO approved to handing off responsibilities to colleagues to setting up your email auto-reply. To get you started, we've broken this checklist down by things you should do 30 days, 2 weeks, 1 week, 2 days and 48 hours before your PTO begins. And we've even created a template you can copy and add to yourself!
🗓️ Get started here → Check out our PTO Prep Template and make a copy to customize for your organization.
30 Days Before PTO:
So you've decided to finally take that trip you and your partner/best friend/buddies from college have been chatting about for years! (or maybe a solo escape to an off-grid cabin with a stack of books??) Good for you!
Now it's time to document. document. document.
One reason you may be hesitant to take PTO, or that you continue to check & respond to emails while on vacation, is because there are certain tasks or responsibilities that are managed solely by you. These processes should be documented somewhere so someone else can step in and take over - while you are on vacation or in case of an emergency.
We wrote about the importance of documentation a few issues back, and as Podge Thomas shared in an episode of the Want To Work There podcast, "Nothing empowers people to truly step away like being able to easily hand over responsibilities while you’re out.”
Start by documenting the days you'll be away and notifying your team(s) using whichever process your company uses. Then, create a list of ongoing responsibilities someone else will need to cover while you're away. If you're part of a lean People Ops team, this might be things like: managing responses to job postings, conducting performance reviews, etc.
Use the 'My Responsibilities' tab of the Prep Worksheet and start a running list of responsibilities and active projects. Don't worry about capturing everything in one go. Come back and add more things as you go about your day-to-day responsibilities.
This is also a great way to catalog which activities could use a new or updated SOP. Don't feel pressure to create an SOP for everything before you take time off, but use this as a way to document what needs to be documented.
Make sure to note who on your team will take care of these responsibilities and be sure to ask them if they're able to cover this activity while you're away.

2 Weeks Before:
We're getting closer to time off!! Maybe you're starting to plan your outfits for the trip and make a packing list.
Next on your PTO prep checklist is to identify the one person who will serve as your team's main point of contact while you're away. Just as you did with your other responsibilities, make sure this person is able to take on this role and note their confirmation.
Once you've confirmed they're in, notify your teammates and any relevant external contacts about your time away and who they can contact with questions. If you're in a client-facing role, I can guarantee your clients will appreciate this heads up coming a few weeks in advance. This gives them some time to send over any requests they need your attention on and gives you some time to respond.
1 Week Before:
One week left! This is a great time to come back to your 'My Responsibilities' chart, document any additional responsibilities, and add SOPs.
Tip: If you don't have time to document a full SOP, record a quick Loom video walking through the highlights of the process. It might not be the most thorough set of instructions, but it will give your team something to reference back to when / if they need to complete this activity.
You might also want to schedule a quick check-in with each person who will be covering your responsibilities and make sure they know what is expected of them. Pick a day or two where you can schedule some 15-minute meetings and cover any of their questions. It's so helpful to do this a week before PTO so you have time to document anything additional before signing off for your time away.
2 Days Before:
2 days!! Are you getting giddy yet? Because I sure am and there are just a few things left to do.
First, send a quick reminder to teammates and external contacts about your time away and who they can contact if needed.
Second (and only if this applies to you), determine a check-in schedule for your time away and notify others. We're not recommending this, but we know many of you are in positions where being offline for several days might not be entirely feasible. If you do need to check-in while on PTO, pick a set time of day where you'll respond to messages. This may look like saying "I'll reserve 30 minutes each day at 4pm local time to respond to any urgent Slack messages and emails." And stick to it!! If you aren't able to fully respond to something during that time, let your team know you saw the message and will respond the following day.
24 Hours Before:
Alright, it's time... for you to go away!

In the final 48 hours before you log off:
Send your completed PTO prep worksheet to your team (especially those who are managing responsibilities while you're away)
Set up your email auto-reply. Here's a very simple option:
Thank you for your email. I am out of the office until [RETURN DATE].
If you need assistance before then, please contact [ONE CONTACT PERSON].
Otherwise I will respond to your message when I return to the office.
Thank you, [NAME, EMAIL SIGNATURE]
And a more personality-filled option:
If you are reading this message, that means I am finally using my PTO! I'm likely doing something a lot more fun than checking emails right now, and won't be back until [DATE]. Give [ONE CONTACT PERSON] a shout if you need something before then. Cheers!
Last but not least, prepare your technology for vacation mode! Silence your notifications, delete the apps, hide them from your home screen... whatever is in alignment with your time off plan.
And then get ready to enjoy your time away!
Be Okay With Imperfection
Even if you make an incredible plan for other people to manage your responsibilities while you are away, they may not be done exactly as you would do them, and that’s okay! We know that delegation is hard, but it can be a lifeline to avoiding burnout. Taking a vacation is a great opportunity to share the load and teach others how to do all the things you do, and you may find that it’s time to hand off some of your responsibilities to someone else permanently. It’s also good for leaders to step away every so often so their team learns how to function without their oversight. It can be a powerful learning experience–for both you and your team!
Preach It, then Practice It!
You probably genuinely want your team to disconnect and enjoy their time off. I’m here to tell you that repeated, unsolicited, authentically-granted permission is one of the best tools at your disposal for communicating and influencing cultural norms. Proactively reiterating stated policy information doesn’t just clarify information to your teams, it signals to them that the topic is important enough to remain consistently top of mind, and worth addressing before anyone has to ask. So remind everyone to take their PTO, give them these tools to prepare for it, and be sure to follow your own advice!
Your turn
→ Copy and customize our PTO Prep Template to make vacation planning less stressful!
→ If your PTO policy needs a refresh (or overhaul!) read our thoughts on Flex Holiday Trends or use this helpful resource: Writing a Paid Time Off Policy? Read This.
→ Determine your planned OOO time over the next few months and set calendar reminders 30 days & two weeks out to start filling in the prep document.
Things We’re Loving Right Now
1-800-PEOPLEPROBLEMS: Submit a voice memo of a problem you’re having with people (book club, friend group, work team, etc.) and get some advice from Elise Granata who runs one of our new favorite newsletters, Group Hug.
Your next leadership read. More than a year ago, my friend Cassandra Gatto connected me with her then-CEO Amanda Litman who was writing a book on what leadership will look like for the next generation. It was SO FUN to recently receive the finished book, “When We’re in Charge: The Next Generation’s Guide to Leadership.” I can already tell it will be a new favorite.
In the market for a fractional role? Speaking of Cassandra, she recently stepped into a new role as an HRBP at ActBlue - and is now looking for a counterpoint to join her! If you’re on the hunt for a new HRBP opportunity, I highly recommend giving it a look.
