Who's Really the BOSS?
Who's Really the BOSS?
Marcus Dillon, Rachel Dillon
Planning Team Retreats That Actually Drive Results
58 minutes Posted Dec 22, 2025 at 12:00 pm.
Rachel and Marcus break down their year-end team retreat planning process, from the leadership framework they used to set 2026 goals to the logistics of bringing 25+ remote team members together. They share what they celebrate with their team, why financial transparency has built trust, and how they structure two days to focus on relationships rather than technical content. After doubling revenue through two acquisitions and organic growth, they explain why their 2026 focus shifts from "growth, not comfort" to "lead change, create impact."Introducing Collective by DBAhttps://collective.cpahttps://www.linkedin.com/company/collectivebydbaLearn More About Dillon Business Advisorshttps://www.dillonadvisors.comhttps://www.linkedin.com/company/dillonbusinessadvisorsSign up to get free CPE for listening to this podcasthttps://earmarkcpe.comDownload the Earmark CPE AppApple: https://apps.apple.com/us/app/earmark-cpe/id1562599728Android: https://play.google.com/store/apps/details?id=com.earmarkcpe.app
Welcome to Who's Really the Boss
Team Retreat Overview
Leadership Planning Framework
Retreat Logistics and Preparation
Additional Retreat Activitiesy
Spouses and Team Bonding
Cost-Effective Team Events
Leadership Team Goals and Transparency
Retreats and Team Structure
Team Changes and Vision Alignment
Future Direction and Goals
Wrapping Up and Looking Ahead
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Rachel and Marcus break down their year-end team retreat planning process, from the leadership framework they used to set 2026 goals to the logistics of bringing 25+ remote team members together. They share what they celebrate with their team, why financial transparency has built trust, and how they structure two days to focus on relationships rather than technical content. After doubling revenue through two acquisitions and organic growth, they explain why their 2026 focus shifts from "growth, not comfort" to "lead change, create impact."Introducing Collective by DBAhttps://collective.cpahttps://www.linkedin.com/company/collectivebydbaLearn More About Dillon Business Advisorshttps://www.dillonadvisors.comhttps://www.linkedin.com/company/dillonbusinessadvisorsSign up to get free CPE for listening to this podcasthttps://earmarkcpe.comDownload the Earmark CPE AppApple: https://apps.apple.com/us/app/earmark-cpe/id1562599728Android: https://play.google.com/store/apps/details?id=com.earmarkcpe.app(00:00) - Welcome to Who's Really the Boss
(
00:58) - Team Retreat Overview
(
04:15) - Leadership Planning Framework
(
13:08) - Retreat Logistics and Preparation
(
22:45) - Additional Retreat Activitiesy
(
32:31) - Spouses and Team Bonding
(
35:02) - Cost-Effective Team Events
(
35:53) - Leadership Team Goals and Transparency
(
39:01) - Retreats and Team Structure
(
40:16) - Team Changes and Vision Alignment
(
42:14) - Future Direction and Goals
(
54:06) - Wrapping Up and Looking Ahead