Family Business retreat
in Residence Program
I meet you wherever the real conversations need to happen. On-site, private, and fully immersed — we resolve conflict, align leadership, and protect your family’s legacy.
Whether you work best around a boardroom table or at the beach house kitchen island, I’ll be there to help you make the decisions everyone’s been avoiding.
Your Vacation, Reimagined: Sun, Sea… and Solutions
Because the real legacy isn’t the house by the beach — it’s a family business built to last.
Why Bring Jocelyn
Confidential Counsel, Seamlessly Delivered
Operations Without Overwhelm
Neutral Perspective, Trusted Voice
Agreements That Stick
Succession in Focus
Balance Without Bias
A neutral presence who ensures decisions respect both family relationships and business realities.
Clarity Over Cocktails
The Smartest Souvenir
Where Business Meets Real Life
Read about our Masterminds we offer for Family-run Businesses
For women who work with—or simply want to better support—their husbands or life partners in running a family business. Whether you’re a co-founder, informal advisor, or the “chief of everything officer,” this mastermind is for you.
- Setting and maintaining boundaries
- Effective communication strategies
- Navigating influence power dynamics
- Preserving your relationship and marriage as the business grows
- Building your own leadership and confidence with the business and at home
For men whose partners work in or support the family business, men who are tired of the business feeling like the third person in their relationship, and men smart enough to listen when their partner says, “You need this.” It is also for men whose partners are entrepreneurs or leaders in a family business, men who want to be supportive without dominating, and men who see the vision but need a smarter playbook to help.
- Sanity-saving boundaries between business and home
- Smarter communication with fewer fights
- A sharper, more strategic business partner
- Fewer 11pm arguments about QuickBooks
- Operational knowledge to offer support where it’s truly needed
- World strategies to strengthen communication and reduce tension
- Mentorship from men navigating the same dynamic
For family businesses preparing for potential sale, leadership transitions, succession planning, and generational power shifts; family business drama meets its match. It’s a no-BS roundtable for families ready to fix power struggles, awkward silences, and “we’ll talk about it later” leadership handoffs. Bring your best intentions—and your thick skin.
- Listening deeply to family members you may work with daily, but haven’t really heard in years.
- Being brave enough to have conversations that are overdue, uncomfortable, or emotionally charged—but essential for moving forward.
- Choosing growth over grudges, clarity over comfort, and the long game over short-term avoidance.
- Being honest about the unspoken tension, old wounds, or elephant-in-the-boardroom no one wants to address.
- Letting go of assumptions, roles, and control that no longer serve the business—or the people in it.
About Jocelyn
Imagine bringing Jocelyn Greenky, MBA —renowned family business whisperer, business transformation expert, Author, Professor and interim CEO with more than 40 years of experience advising CEOs, Fortune 500 leaders, and founder-led families transforming a vacation from indulgence into purposeful restoration for families.
As the founder of Sider Road, a consultancy specializing in family-run and founder-led businesses and for over 40 years, I’ve guided global leaders, entrepreneurs, and multigenerational families through the complexities of succession, governance, and communication.
I’ve spoken for organizations including Simon & Schuster, Kraft General Foods, Columbia University, Syracuse University, and the Exit Planning Institute, and I teach business leadership and communications at the university level. My specialty lies in combining discretion with results — aligning family vision with business performance so both endure across generations.
With six children, one grandchild, three dogs and various family businesses within the families, there is plenty of action to keep our family on their toes at all times!
Differentiation vs. Competitors
Bluestone Families (New Zealand):
Miraval (Berkshires, U.S.):
Sider Road Advantage:
Ready to Elevate Your Next Family vacation or retreat? Let’s Customize Your Experience.
Jocelyn Greenky, MBA
Business Transformation Expert
& Advisor to Family-Run Businesses
