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What Happens at the Retreat Doesn’t Stay at the Retreat

By Tracey Diamond & Emily Schifter on July 28, 2026
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In this episode of Hiring to Firing, hosts Tracey Diamond and Emily Schifter take a close look at the legal landscape surrounding company retreats, inspired by the workplace antics on display at Rockin’ Grandma’s Hot Sauce company retreat in the hidden camera series “Jury Duty Presents: Company Retreat.” Joined by Rachel Keene, vice president and assistant general counsel at Accolade, they discuss key considerations for employers when planning an off-site event. The conversation highlights the benefits of retreats for morale, team building, and connection, against the very real risks that emerge when professional boundaries begin to blur. They unpack how “mandatory fun” can create real legal exposure, from harassment concerns to employee injuries and wage-and-hour pitfalls that employers often overlook in the excitement of planning. Whether you are a seasoned HR professional or a manager planning your first company outing, this episode provides practical guidance on designing retreats that build culture while minimizing legal risk.

Transcript: What Happens at the Retreat Doesn’t Stay at the Retreat (PDF)


Troutman Pepper Locke’s Labor + Employment Practice Group provides comprehensive thought leadership through various channels. We regularly issue advisories that offer timely insights into the evolving employment law landscape, and maintain the HiringToFiring.Law Blog, a resource spotlighting best practices for employers. Our Hiring to Firing Podcast, hosted by Tracey Diamond and Emily Schifter, delves into pressing labor and employment law topics, drawing unique parallels from pop culture, hit shows, and movies.

Photo of Tracey Diamond Tracey Diamond

Tracey Diamond counsels clients on workplace issues, provides harassment training, conducts internal investigations, drafts policies and procedures, negotiates employment and severance agreements, advises on independent contractor, FMLA and ADA compliance issues, and partners with clients to structure their workforce in the most efficient…

Tracey Diamond counsels clients on workplace issues, provides harassment training, conducts internal investigations, drafts policies and procedures, negotiates employment and severance agreements, advises on independent contractor, FMLA and ADA compliance issues, and partners with clients to structure their workforce in the most efficient and effective way possible.

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Photo of Emily Schifter Emily Schifter

Emily is a partner in the Labor + Employment Practice Group, where she represents clients in a variety of labor and employment-related matters, including employment discrimination, leave, disability accommodation, and wage and hour litigation. Additionally, she counsels employers on many aspects of employment

…

Emily is a partner in the Labor + Employment Practice Group, where she represents clients in a variety of labor and employment-related matters, including employment discrimination, leave, disability accommodation, and wage and hour litigation. Additionally, she counsels employers on many aspects of employment law and human resources issues, including employee handbooks, policies and restrictive covenants drafted under various states’ laws for a variety of circumstances, including as part of mergers and acquisitions.

Read more about Emily SchifterEmail
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  • Posted in:
    Employment & Labor
  • Blog:
    Hiring To Firing Law Blog
  • Organization:
    Troutman Pepper Locke
  • Article: View Original Source

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