[Vacation Series] Mastering Out of Office Messaging: Set Expectations So You Can Finally Vacation Well

⬆️ Mindset Shift with Your Out of Office Messaging Policy

Your Out of Office (OOO) message structure is an important firewall protecting you and your team’s hard-earned time off while ensuring smooth operations while away. As part of your Communication Policy, setting clear expectations and being intentional with your OOO or vacation message design will help you and those on your team unplug when on vacation. Adding to the vacation freedom is the knowledge that expectations are appropriately set while away. The Vacation Series continues next week, focusing on reentering well after returning from vacation so be on the lookout.

📋 A Better Out of Office (OOO) Template

As laser-focused Operators, we execute with excellence by paying close attention to the details, including our team’s Out of Office messaging. 

First, when should an OOO message be set? Email response expectations are 24 hours or sooner for most emails. I recommend setting an Out of Office Message if your time away is a full day or more.

In addition, we have earned our time off and should default to more fully unplugged vacations - and so should our team members. The Internet is awash in articles showing that Americans miss the mark with unplugging and vacationing well, like in this WSJ article showcasing Gartner's research titled, ‘Americans Are Vacationing More, but Staying in Work Mode.’ 

When disciplined with fully unplugging more often, we can connect with others better and return to work fully rested and ready to innovate. If we frequently feel we cannot fully unplug, this could signify that we must delegate responsibilities better while allowing others to step up and grow professionally in our absence. 

⚡ PRO TIP: It’s essential to have an agreed upon ‘Communication Channel Escalation’ approach, which should be part of your defined Communication Policy as detailed in the Com Check post. With an agreed-upon communication escalation policy, you and your team members can unplug when on vacation or out of the office because your team knows only to text or call you in an emergency. This way, you aren’t chained to your phone with an unhealthy need to constantly check in. Consider the level of freedom this brings.

Here are three common missing elements with Out of Office (OOO) messages or vacation messages:

1. There is no clear indication that the message is an automated reply.

2. There is no clear indication of whether or not email will be checked while away.

3. An alternative point person to connect with is often missing.

Next, let’s review the following Out of Office Message and the key components in the following fictional example.

***This is an automated response***

Hi!

I am out of the office and will return on Tuesday, the 21st.

As my time away will be unplugged, I will not check my email.

In my absence, please contact [email protected] for anything that is urgent. 

I look forward to connecting when I return,

Steve

Let’s break down the key template nuances in this screenshot from the OOO message above.

Part 1 - We clearly show this is an automated message, respecting the recipient.

Part 2 - The return date is clear.

⚡ PRO TIP: As I will be out for seven working days in this fictional scenario, note that I plan to use Monday the 20th as my remote email and digital communication catch-up day and will have significant parts of my day blocked out for extra Communication Sprints. Therefore, I state that I will be returning to the office on Tuesday. This approach radically reduces ‘Reentry Stress.’ 

⚠️ SAFETY ALERT: Avoid saying, ‘I am going on vacation’ or something similar, as this broadcasts that your home will be vacant and could be a target for theft. The best practice is to say you are ‘out of the office.’ Use your best judgment when using this template and consult with others for any safety issues concerning using an Out of Office message.

Part 3 - In the same sentence as the return date, how we will handle email while out is clarified. Note these other useful variations like #3, which is essential for extended time away:

1. I will check my email periodically while away.

2. I will not be checking email regularly while away. 

3. IMPORTANTLY, please resend your email when I return. As I will be away for an extended period, to avoid an overwhelming avalanche of emails when I return, all of my messages will be deleted while away so I can start with a clean inbox. Resending your email on or after my return date will ensure I see your message. 

Like many others, I have successfully leveraged the third variation, as everyone can empathize with the stress of an overwhelming number of emails resulting from time away from the office. The proven approach works great for time away that extends around two weeks or longer and is essential for taking sabbaticals. When using this approach, when I returned, I simply highlighted all of my emails and hit delete - it felt empowering and freeing. After returning, what surprised me was the number of people who, after resending their messages, commented about how they admired the approach.

⚡ PRO TIP: When away for an extended period of time, have ‘Reentry Meetings’ already scheduled when you return with key team members who will keep a simple journal or document of key events while you are away.

Note how the second variation above offers more freedom and flexibility, whereas the first one implies that you would check your email daily while out. This second variation can be useful for a busy work conference in the coming week, where you will help work the booth and engage prospective clients. Your time to realistically check all of your emails periodically will not be achievable.

Part 4 - Including one or more alternative contacts, depending on the needs of those you serve, is important. In this example, I intentionally left off Troy’s phone number as he and I would prefer people to email him. Since I will give all my key contacts a courteous heads up several days before I leave, I intentionally use ‘for anything urgent’ to keep the demands on Troy lightweight. 

Part 5 - Since I stated I would not check email while away, I wrote, ‘I look forward to connecting when I return!’ For the other two variations mentioned in Part 3, I would instead write:

I look forward to connecting soon,

Steve

To keep it simple, I typically use the same OOO message for both external and internal facing audiences, like in this Microsoft 365 example:

⚡ PRO TIP: I ensure my personal email accounts use a similar OOO message structure. 

🗨️ Finally, If you are like me, you are probably eager for an OOO option for text messages. Hopefully, we will get something soon, as this feature will allow for better vacations. 

📖 Avoiding Damage to Your Personal Brand: 

Recently, I recommended a trusted resource to another colleague for consulting services. The one I recommended was on vacation and forgot to set their Out of Office Message. After following up multiple times and with multiple communication mediums, the lack of responsiveness caused some frustration. This could all have been avoided if an OOO message was set.

⚠️ HEADS UP: Helping to ensure I don’t forget to enable my OOO messages, and being a big fan of the Paperless checklist app on my iPhone, I have a checklist item as a reminder as per this screenshot:

⚡ Take Action and Save the OOO Message:

Bookmark this page and/or copy this clean template into your Out of Office message section so it is ready to be edited and set for your next outing. Consider publishing the template and the above variations to your corporate wiki so others can benefit. 

***This is an automated response***

Hi!

I am out of the office and will return on [DATE].

While away, I will not check my email.

In my absence, please contact [PERSON/EMAIL ADDRESS] for anything that is urgent. 

I look forward to connecting when I return,

[YOUR NAME]

⚠️ HEADS UP: It is critical to test your OOO message. Right before leaving, I recommend enabling it and then sending a test message from another email account that you operate to ensure precision in your messaging. 

🔎 Ready to Go Deeper?

First, be sure to check out the important follow-on to this post titled [Vacation Series] Stop Dreading Your Return to Work! 7 Pro Moves for an Easy Reentry.

If you like tactical content like this, consider applying for the Productivity Accelerator, where I guarantee to 10x your knowledge and ability to execute with excellence. 

💡 What Do You Think About the OOO Approach?

Your thoughts? What would you change with the OOO messaging template? Consider leaving a comment or a question so others can benefit and learn. 

🛠️ Tools for OOO Messages:

The Out of Office message approach is great for Microsoft 365 and Google Workspace, allowing you to set exactly when your message will fire and stop firing. The Out of Office message works as well with almost any email program with automatic message capabilities. 

☁️ AI Content Disclaimer:

Bard offered some help with part of the subject line. Everything else is 100% original, human-created content. Grammaly Pro helped me tune the content. 

✅ Mind Break:

Since you made it this far, to wrap up, check out this super short video of a rhino calf playing with a zoo keeper. 

🗓️ What’s Coming Up Next:

We will continue the Vacation Series and dive more into Reentry Stress and Reentry Meetings next week. If you missed last week, check out 3 Ways a ‘Commander Intent’ Mindset Empowers Operators to Achieve Extraordinary Results.

Here’s to you having better vacations,

Steve Kahle |  ELITE OPERATORS

🔵 P.S.

P.S. If you find value, consider signing up for The Elite Operator Report if you haven’t already. I encourage you to share my content with others, which is a great way to help me build a growing community of elite operators. Also, check out my no-cost resources, like the Ideal Recurring Week Mini-Course. You can also apply for my next Productivity Accelerator, become a paid subscriber, or recommend me for executive coaching, operational and technology consulting, or speaking opportunities like this interview called Time Architecture, Transition from Stressed, and Distracted to Focused.

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