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Career and Interview Tips

What To Do The Last Day Of Work Before Taking A Vacation

4 Tips (And A Download!) To Ease Your Anxiety

Recently, I decided to take the first two-week-long vacation of my professional career, and in full transparency, I was terrified.


To be clear, I've taken plenty of vacations before, but I've always strategically taken trips on long weekends or during the holidays where the impact on my team is minimal. There's nothing I hate more than that feeling of doom that sets on the last day of work before vacation, when you start thinking about the work you'll be missing, clients relying on you, or what could go wrong in your absence.

As an individual contributor, leaving was easier. I could literally do all of my work leading up to my days off, putting in long days and even longer nights, and only when I was completely finished could I turn my Slack notifications off and leave for vacation in peace. Of course, this is not healthy behavior for anyone, but I got through it.

As a manager, my work is never "complete." Now, I have even more clients depending on me, a team who relies heavily upon me for decision making and guidance, and company initiatives that are mid-cycle.

At any other company, this scenario probably would have set my anxiety completely over the edge - but not at PowerToFly. I can testify that the process we've developed has made taking a vacation just that - a vacation. For the first time, I left for my trip without the doom cloud following me out the door and I knew my team was adequately prepped for what to do in my absence.

So, how can you implement a vacation process at your organization that actually works? Follow these easy steps, and you'll be enjoying a little R&R at the beach in no time!

1. Make the decision to stay available, or go off the grid, and stick to it.

    • It is absolutely crucial to take time off without work distractions, and if you're going off the grid, stick to it. Don't check emails, turn your notifications off, and offer proper escalation pathways for any emerging issues (see below). Many companies have policies in place where at least one week of vacation should be contact-free - that's when the creative magic happens!

    2. If you choose to stay available, set clear expectations about your communication method and schedule.

    • Decide on a time or cadence for checking in that works best for you. Whether that's one hour every morning, 30 min in the evening, or periodically throughout the day, let your team know when and how it's best to contact you. For example, if you're going out of the country, it may be easier to Slack or WhatsApp as opposed to email or text.

    3. Let the team know how to ask for help.

    • If a situation does arise that needs to be escalated, be clear with your team about how they should escalate: tell them to be direct, explain the entire situation, and include an ask and when the response is needed. Make it known that there is no need for small talk in these messages, i.e. "I don't want to bother you on your trip, but…". It doesn't hurt to note that logging into different software while away from your desk is a huge pain - if your ask requires a login, don't forget to include a screenshot!

    4. Fill out a PTO tracker (Make a copy of ours here!).

    • This tracker is your golden ticket to a stress-free vacation and should be shared org-wide. Once filled out in its entirety, everyone has the opportunity to see what's being handled while you are gone, which tasks and projects are assigned to whom, and who to reach out to in case of an escalation.

    Want to see it in action? Here's a sample of a great day-before-vacation team email:


    Sample Day-Before Vacation Email

    Hi team,

    Just sending everyone a note, as I am planning to be in Mexico for the next 2 weeks.

    Also as we support all of our team members in our work-life balance, I think it is important to share what that means for each one of us. It is OK to take time off and be fully off. It is OK to take time off and work a little to stay on top of your burning priorities. It is OK to sometimes do one and sometimes do the other.

    So for that reason, it is very important to set clear expectations with your teammates on what your PTO style is/ or will be this particular time you're going away. To demonstrate this principle, here is what my next 2 weeks off mean:

    1) Ask for help, and allow me to triage

    Even when I am on PTO, you can always reach me, you're not bugging me. I am extremely good at protecting my time, and making a judgment call whether the issue you're bringing to me needs me to get engaged while I'm away or it can wait. I am good at putting my phone on silent when I need to nap. So don't hesitate to reach out when you need me.

    2) How to Ask for Help

    For this to be effective don't say things like "Hi are you there?":) that doesn't give me enough intel on whether this can wait or not

    Phrase it more like:

    "Hi we just heard back from XClient, and their legal department is requesting something that I don't know how to answer" - obviously as much detail you can provide so I can help even without getting on a call is helpful.

    3) Don't make me log in to different softwares

    Most of the time you will be reaching me on mobile, so don't send me salesforce links - send a screengrab of the relevant info instead. If you need me to send an email to a client, draft it for me, with all the relevant attachments, etc

    4) Err on the side of over transparent

    That is kind of repeating the first point, but I much rather know about an issue you're dealing with, and have the opportunity to get involved (and perhaps decide I won't), then later hear "I didn't want to bother you while you're on PTO". Transparency and over communication always wins.

    5) My schedule

    July 1-5 - planning to be more deeply off. I will not be taking internal check-ins/ group calls

    July 8-12 planning to take customer-facing and sales-related calls. I might need to prioritize the bigger ones. Not taking internal check-ins/ group calls

    6) Escalate the medium, not the message.

    Feel free to WhatsApp me or text me for anything pending from me if you don't get a response in slack. This is true any day of the week, and some of you use it more effectively than others. Seriously, leverage the escalation points!! If you're texting me too much I will tell you (no one has texted me too much in the past. :) )

    Thats it team, you know where to find me.

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