In this episode, I had the pleasure of speaking with Abby Flynn, Senior Manager of HR at Olympia Hospitality, a family-owned hotel management company with an impressive portfolio of properties. Their portfolio includes the exceptional Inn by the Sea, which is one of the favorite properties of our family.
What stood out most in our conversation? A simple, but often overlooked truth articulated by Abby, "You cannot deliver a great guest experience without first creating a great employee experience."
Abby shares how Olympia Hospitality navigated the post-COVID talent crisis in an industry known for long hours, limited remote flexibility, and historically lower pay. Rather than retreat, they adapted:
- Reframed hospitality roles around transferable skills
- Rebuilt talent pipelines by recruiting from adjacent industries (including daycares and customer service sectors)
- Increased pay competitiveness
- Focused on flexibility in scheduling
- Strengthened onboarding and training
But the real differentiator isn’t just recruitment, it’s Olympia Hospitality's leadership philosophy.
Abby is deeply committed to a Strengths-based approach to leadership. Instead of obsessing over weaknesses, she focuses on identifying where employees naturally excel and developing those areas from a “6 to a 10,” rather than trying to force a “2 to become an 8.”
Her perspective on leadership is rooted in:
- Servant leadership (“Home Office,” not “Corporate”)
- Self-awareness and receptivity to feedback
- Investing in long-term employee growth
- Recognizing that team members are at the core of business success
We also discussed:
- Why hospitality teaches highly transferable leadership skills
- The importance of adaptability over rigid plans
- The power of ownership culture (if you see the trash, you own it)
- How longevity within an organization reflects leadership health
- Why focusing on strengths unlocks performance at scale
One of my favorite insights from Abby, “We’re in the memory-making business. We are part of people’s stories.” That mindset changes everything.
This episode is a powerful reminder that strategy, service excellence, and performance all begin with how leaders treat their people.
If you care about leadership development, culture, Strengths-based management, or the future of hospitality, then this conversation is worth your time.