The Ops Experts Club Podcast

Episode 90: The Art of Delegation in Leadership

Released: November 20, 2025
Host: The Collab Team (Aaron, Taryn, Savannah)

Episode Overview

In this episode, Aaron and Taryn of The Collab Team dive deep into the operational art of delegation in leadership, centered on their own annual team planning retreat. They share insights from their recent team gathering in Montana, the practical tools they use (like the “Delegate and Elevate” exercise), and honest reflections on what it takes to foster enjoyment and effectiveness in high-performing teams. The conversation is candid and practical, offering both big-picture strategy and real-world lessons learned in developing strong, scalable operations for 7- and 8-figure businesses.

Key Discussion Points and Insights

1. The Value of In-Person Retreats for Remote Teams

• Aaron and Taryn recount bringing their mostly virtual leadership team together in Montana:

  • Shared space boosts team morale, camaraderie, and facilitates open conversation.
  • Meeting face-to-face strengthens relationships and trust, especially for new team members.
  • Simple pleasures—shared meals, walks, and movies—contribute to a “happy headspace” and sense of team value.
    • “It just starts it off right…feeling valued and important and just loved enough to get to share in your space with you.” — Taryn (04:52)

• [03:41]: “Not to take apart the etymology of the words. I’m just saying that it was great to get everybody in a common space…” — Aaron

• Leaders are encouraged to offer team members access to personal “special places” as a unique, low-cost benefit and gesture of appreciation.

2. Annual Planning—Lessons from the Trenches

• Annual planning can—and should—be done at whatever time supports the business and team schedule, not just on a strict calendar basis.
• Their process has evolved from Zoom half-days to immersive off-site experiences.
• Offers a candid look at the topics discussed, such as team development, personal growth, and operational evaluation.

3. Delegate and Elevate: A Team Self-Assessment

• The “Delegate and Elevate” (D&E) exercise—a staple from EOS (Entrepreneurial Operating System)—was used for the first time with their leadership team.

  • Purpose: Identify who enjoys and excels at which tasks and what each team member wants to stop doing.
  • Surprising discoveries: Overlapping skill sets can mask key differences in preferences, e.g., both Ben and Taryn are tech experts, but Ben prefers maintenance, while Taryn enjoys building new systems.

• [08:23]: “We had never really done that as a leadership team...And so, and we follow a really strong, you know, like, project plan anytime we roll out a new retainer for a client. So we’re operating to a plan. But within that there are going to be things that Taryn’s like, I love doing this part of that and I freaking hate doing this part.” — Aaron

• Conclusion: Leaders should not assume silent team members are satisfied—proactively uncover and delegate disliked or mismatched tasks.

4. Operationalizing Delegation for the Whole Team

• Extending the D&E exercise beyond leadership to the entire team will ensure everyone is working in their “zone of genius.”
• The goal isn’t hyper-growth, but increasing the enjoyment and fulfillment of current team members, scaling only as opportunities arise.
• “I want to 10x the enjoyment of the people that are working here and fill them up with as much work as they want…” — Aaron (12:58)

5. Personal Delegation: The Leader’s Own Blindspot

• Aaron identifies his own aversion to marketing, and how annual planning and team feedback prompted him to delegate this function by hiring a fractional CMO.

• Breakthrough: Leaders must apply “delegate and elevate” to themselves, not just their teams.

• [14:38]: “I hate marketing. Like, that’s just the truth…So we identified, well Aaron, if you hate it, let’s solve for that.”

6. Reflecting on Successes and Failures

• Annual review includes honest “done wells,” “do betters,” and “quit or cut” evaluations.

• Example: Experimenting with joint venture models didn’t work, served as a valuable lesson, and required accountability and swift course correction.

• [16:34]: “Sometimes you gotta try stuff. Sometimes you have to fail at stuff. But being able to own that in front of your team and say, hey, we’re making a decision together, we’re going to cut this thing loose. I think it was good.” — Aaron

• “Fail forward” and learning from mistakes are celebrated; delegation includes letting go of failed experiments or low-energy projects.

• [17:09]: “The best thing you can do is fail and learn from your failures. The worst thing you can do is fail and just keep repeating the idiosyncrasy of failure over and over and over again.” — Aaron

Notable Quotes & Memorable Moments

• [04:52] Taryn: “It just starts it off right…feeling valued and important and just loved enough to get to share in your space with you.”
• [08:23] Aaron: “…it was a great delineation…two guys with a very similar skill set, but they have two very different ends of the pond they like to play in.”
• [12:58] Aaron: “My goal is I want to 10x the enjoyment of the people that are working here and fill them up with as much work as they want…”
• [14:38] Aaron: “I hate marketing. Like, that’s just the truth…So we identified, well Aaron, if you hate it, let’s solve for that.”
• [17:09] Aaron: “The best thing you can do is fail and learn from your failures. The worst thing you can do is fail and just keep repeating the idiosyncrasy of failure…”

Timestamps for Key Segments

• [03:41] – Benefits of in-person retreats for virtual teams
• [07:25] – Insights from the Delegate and Elevate exercise
• [08:23] – Matching team strengths and preferences to tasks
• [12:58] – Company vision: enjoyment over hyper-growth
• [14:38] – Leaders facing up to their own delegation needs
• [16:34] – Owning experiments and learning from failure
• [17:09] – The concept of “return on failure”

Takeaways for Leaders and Operators

• Prioritize in-person connections, even for virtual teams, as a way to deepen trust and increase morale.
• Conduct regular “Delegate and Elevate” reviews for both leaders and entire teams to ensure everyone is working in their strengths and enjoys their roles.
• Be proactive about uncovering blindspots—both in team operations and in your own leadership.
• Celebrate failures as learning opportunities, not just successes.
• Design company growth around team enjoyment, not just revenue or client numbers.

This episode gives a thorough behind-the-scenes look at how real operations experts approach annual planning, honest reflection, and the critical art of delegation, with plenty of practical examples and candid leadership lessons.