Your agency offsites aren't working

Published 3 days ago • 1 min read

In this week's AgencyHabits Podcast, Peter and Sei-Wook break down leadership offsites: what they're actually for, how to structure them, and what they learned from running them quarterly for over seven years.

The core insight: a leadership offsite isn't another meeting. It's an investment in alignment. The conversations that don't happen during the normal course of work - the hard decisions, the tensions that linger, the things everyone avoids -that's what offsites are for.

They share the structure they refined over time:

Look back. What went well, what didn't, what surprised us.

Learn together. For Peter and Sei-Wook, this meant reading books together (over 40 books across seven years.)

Build forward. What are we focusing on next quarter? What are we saying no to? What are we changing?

They also share exercises that worked: future-self writing (a visioning exercise that gets personal), drawing business flywheels (everyone has a different mental model, surfacing that is valuable), and revisiting mission and values (stress-tested over multiple iterations, not just once).

And what didn't work: overpacked agendas, no documentation, lazy exercises like SWOT or group vent sessions, and leaving with too many initiatives. The offsite that produces a 20-item to-do list has failed.

👉 Listen to the full episode here.

If your offsites feel like wasted time, this episode will help you fix them.

Who are we?

Hi, we're Peter and Sei-Wook, co-founders of Barrel Holdings, a portfolio of agency businesses. We also run AgencyHabits, a resource for agency operators featuring lessons learned from our various agency businesses.

Thanks for being a subscriber. If you or anyone you know is interested in selling their agency business, please check out what types of agencies we're looking for and email hi@barrel-holdings.com.

Also: Peter posts a lot of agency content on LinkedIn, give him a follow!

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