Podcast Summary: The Ops Experts Club Podcast

Episode 78: From Overworked to Out-of-Office: Building a Real OOO Plan
Date: August 21, 2025
Hosts: The Collab Team (Aaron, Taryn, and Savannah)

Overview:

In this episode, Aaron and Taryn from The Collab Team dive deep into the art and science of taking a real vacation as an operations professional—what they call a "real OOO (Out-of-Office) plan." They explore practical frameworks, mindset shifts, and processes that allow high-achieving operators and business owners to disconnect from work without jeopardizing business continuity. Drawing from their extensive experience supporting multimillion-dollar business leaders, they share actionable strategies, behind-the-scenes stories, and the unexpected benefits of empowering your team through absence.

Key Discussion Points & Insights

1. The Mindset: Can You Really Go on Vacation?

• Aaron opens the topic by challenging listeners on whether they can—and will—allow themselves to unplug.
  • "Will you allow yourself to go on vacation? Because I think a lot of us end up shackling ourselves and creating a prison of our own design when it comes to OOO." (02:08)
• Taryn points out that everyone "can and should take time off," even if they don't travel, but highlights that true time off means truly unplugging—leaving the laptop behind.
  • Quips about different vacation approaches and how they’ve learned through practice to set up for absence.
  • "I've learned how to do it, how to set up people, get my calendar cleared, get processes in place, do it all so I can leave." (03:14)

2. The Tale of Two Vacation Styles

• Aaron describes his own struggle to fully disconnect—relating how some "vacations" (like visiting Belize) still involve work because of ongoing business interests, vs. others (like camping in Yosemite, where internet isn’t available) that force him offline.
  • "Next week, I don't think I'll take my computer because I don't know that I want my computer living in a tent..." (04:53)
• Contrast between Aaron’s ongoing journey with OOO and Taryn’s more practiced systems for a clean break.

3. Designing a Functional OOO Plan

a) OOO as a Living Document and Process

• Taryn advocates for treating out-of-office planning as a durable process—a living document that outlines emergency contacts, key recurring tasks, and escalations.
  • "It's like the emergency phone number list you leave for the babysitter... In case this happens, here's your best spot for answers." (05:54)

b) The Importance of SOPs (Standard Operating Procedures)

• Aaron underscores that SOPs are non-negotiable for critical tasks. He recommends that operators regularly document critical processes—especially those that only they know how to do.

  • "Could I create an SOP that's simple enough that a monkey could execute this thing? ...If you're too busy... you don't have to do it all... We've just gotta get it outta your brain." (08:09)

• Both agree that you don’t need to get bogged down creating the perfect SOP immediately; you can jot down steps as you do them and hand over documentation duties to someone else.

• Using delegated access judiciously (eg, via LastPass) keeps business systems secure while enabling handoff.

c) Assigning and Tracking OOO Tasks

• Use task/project management tools (like Asana, Monday, ClickUp) to track handoff, completion, and accountability.
  • "The nice thing about project management tools is visibility... I can see as they complete it and ask them at the end to comment back—'Aaron, complete'—so I know it's done." (09:18)

4. Don’t “Single-Point-of-Failure” Yourself

• Discussion on the danger of being the only person who can do a job (like running payroll), and how to gradually spread responsibility to avoid creating detours around yourself or your #2.
  • "Did you lock yourself into a position where you're the only one who can do it? If so, try to figure out how to get out of that." (10:34)
• Advocates for cross-training within the team to ensure coverage and reduce risk.

5. OOO as an Opportunity for Delegation, Growth, and Up-Leveling

• Taryn shares how going on vacation sometimes leads to permanently offloading a responsibility, freeing capacity.

  • "You hand it off while you're gone. They do such a great job, they can keep doing it when you get back." (12:34)
  • Aaron adds:
    "A lot of times the best way you can challenge your own role is by going on vacation and removing yourself from the equation..." (14:03)

• Real example: Taryn delegated duties to Ben during his honeymoon; Ben not only picked up the work but improved it ("fresh eyes, fresh processes").

  • "He even took what I did and up-leveled it from there." (14:54)

• Encouragement for leaders to see OOO as a way to empower upcoming talent and create space for self-elevation, as well as giving others a path to justifying raises through extra responsibility (as per the Collab Team’s “toolbox” approach to promotions).

6. Checking Assumptions and Generating Team Buy-In

• Challenge the mindset that things you dislike will also be disliked by others—someone might be eager to take these tasks and see them as an opportunity to shine and grow.

  • "Don't get stuck in your own head thinking everybody feels the same way as you about things." (16:44)

• Encourage open calls for volunteers within your team, not just defaulting everything to a single deputy.

  • "Maybe ask in group chat, 'Hey, I'm out next week, who wants to do this thing?' You might be surprised." (19:41)

• Case study: Lindsay from Outsider Coffee handing off disliked tasks to Faith, leading to better outcomes and more satisfaction for both.

7. The Role of the Leadership Team in OOO Logistics

• Don’t just rely on your immediate #2 or ops manager; leverage your broader leadership team for better task distribution and more precise fits based on skills.
  • "Figure out what your job descriptions are, the key 3 to 5 duties, and help people work from their lane... It makes handoff make sense." (22:20)

Notable Quotes & Memorable Moments

• Aaron:

  • “We end up shackling ourselves and creating a prison of our own design when it comes to OOO.” (02:08)
  • “Be generous with yourself, go on vacation, enjoy your time, let somebody else handle your stuff, let them level up...” (18:15)

• Taryn:

  • “You hand it off to somebody else while you’re gone. They do such a great job, they can keep doing it when you get back.” (12:36)
  • “I definitely worked myself out of a client on my honeymoon when I gave some duties to Ben... and he’s been doing it ever since.” (14:44)

• Lighthearted Closing:

  • The episode ends with playful back-and-forth about Aaron’s lettuce wraps versus Taryn’s tortillas, with a hint that more on that might come next week.
    • “Maybe I’ll try to make a quesadilla this week with lettuce and see how it turns out.” (23:34)

Episode Timeline (Timestamps)

• 02:08 — The problem: Self-imposed limits on taking a true vacation
• 03:14 — Practicing and setting up for true OOO
• 05:54 — The “emergency phone number list” approach to OOO planning
• 08:09 — Creating bulletproof SOPs for core responsibilities
• 09:18 — Leveraging task management tools for transparency and peace of mind
• 10:34 — The risk of being a single point of failure
• 12:34 — How a good OOO plan frees you to permanently delegate tasks
• 14:44 — Working yourself out of a job (and letting rising talent shine)
• 16:44 — Not everyone hates the tasks you do—open up opportunity
• 19:41 — Don’t just default handoffs to your #2; open it up to others
• 22:20 — Using leadership teams and clear job descriptions to streamline handoffs
• 23:34 — Playful wrap up—lettuce wraps and future food experiments

Takeaways & Action Steps

• OOO time is vital for operator and business health: it’s possible with the right processes.
• Define and document your critical roles (SOPs)—start simple, refine over time.
• Use project management tools for accountability and visibility.
• Treat OOO periods as a test for your org: where does responsibility need to be cross-trained or more broadly shared?
• Don't be afraid to delegate up: empower your team and let others shine—it can lead to permanent improvements and uncover new leaders.
• Involve your whole team in OOO planning; open up opportunities and shift away from overburdening a single deputy.

In Short:
A true out-of-office plan is about more than vacation—it's a test (and a proof) of team resilience, a developer of talent, a way to expose brittle parts of your business processes, and an avenue for personal and team growth. Delegating with intention and structure makes vacations not just possible, but productive.

Next Episode Tease:
Will Aaron figure out how to make a quesadilla with lettuce? Stay tuned for more operational wisdom—and food experiments—from the team!