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Get OOO: Vacation Planning at Work

June 2, 2026
Getting OOO vacation planning
By Maria Negron Kneib

We hear it, see it in our data, and we get it. Unplugging is hard. Always-on work makes claiming time off more difficult. Our vacation planning at work guide identifies systemic reasons preventing you from checking out and provides tactical tips so you can disconnect without the dread. Use it and share it with your team.

PTO Matters

The research is clear. Time off improves your mind (creativity, mood, lower dementia risk), your body (lower cortisol, immune recovery, reduced heart disease risk), and your performance (an Ernst & Young analysis found year-end ratings rose 8% for every 10 extra vacation hours taken). Employees who vacation regularly also stay longer. Time off improves retention.

Why Is It So Hard?

According to a Pew study, less than half of American workers use all their vacation days despite prioritizing PTO as a benefit.

The reasons?

  • 52% said they didn’t need it
  • 49% feared falling behind
  • 43% didn’t want to add to their colleagues’ plates

Some worried it could cost them a raise or a promotion. Taken together these signal systemic issues that we can and should solve for.  

Vacation Planning: Organizational Level

Most vacation problems are system problems. Organization-wide understanding and clarity in these areas eliminates speculation:

Policies. These are your guardrails. You need a formal, current vacation policy that’s clearly understood. Eliminate assumptions about advance notice, accrual, etc. to avoid any overly cautious interpretation.

Culture. This is how your rules shape your organization. Do leaders actively encourage time off? Does HR audit PTO usage? Do leaders and staff equate “availability” with “love for the job?”

Norms. These unwritten rules can override written ones. Uncover and unpack them. Can multiple people be out at once? Are certain seasons off-limits? Is there an expectation that staff remain reachable? Address ambiguity.

Tools. Embrace your tools to work asynchronously. A well-adopted project management tool is an underrated system to keep everyone informed.

Vacation Planning: Individual Level

With a solid foundation, individual planning gets easier. We recommend:

3-4 weeks out (earlier if you know!)

  • Put vacation on every relevant calendar
  • Set expectations for your availability: unreachable, one check per day, or somewhere in between

2 weeks out

  • Identify your Point(s) of Contact(s) (POC)
  • Define “emergency” so it’s situation-based instead of feelings-based (hint: most things aren’t)
  • Authorize one person to notify you of a true emergency

The week before

  • Inform teams, clients, and external partners of your last working day
  • Set your OOO with a buffer. If you return Sunday, internal communications can wait until Tuesday, external until Wednesday or Thursday
  • Add value with your OOO. Name a POC, link to recent research, or highlight an upcoming event
  • Confirm how your team signals priority (e.g. do you flag the email, write urgent in the subject line, etc.). This should be a team norm, not a personal preference
  • Reiterate your availability and honor it

Post-Vacation Planning

Triage with your PM tool first. Five minutes covers 80% of what you missed.

Use a “while you were out” memo. Have team members alternate writing one for whoever’s returning. Include links to project status in PM tool or red/yellow/green dot system, meeting notes/recordings, deadlines, and top issues needing attention.

Triage email by priority, not chronology. Rely on your priority signals. Reviewing emails from old-to-new is a trap.

Plan Ahead So You Can Check Out

Apps ping. Emails pile up. A “quick check” can result in working half the day. It’s hard to step away when you carry your workplace with you. However, with thoughtfully crafted organizational and individual systems we can confidently set our OOO. Vacation planning at work can be tricky, but it pays back in creativity, health, productivity, and tenure.

Want help improving your systems and policies at your organization? Reach out to the Achurch team.

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