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Family Business Intensive — Private On-Site Advisory | Sider Road
Family Business Intensive — Jocelyn Greenky
An Exclusive Private Engagement

Your family has the business.
Now make sure it survives the family.

Jocelyn comes to you — privately, discreetly, at your home, estate, or wherever your family gathers — to have the conversations that have been waiting years to happen.

1+
Days On-Site
1
Family. Private.
100%
Custom Agenda
The Intensive
The real legacy isn't the house by the beach. It's a family business built to last beyond it.

This isn't a workshop. It isn't group coaching. It's Jocelyn — embedded with your family, on your terms, in your space — creating the conditions for conversations that boardroom walls never allow.

Succession. Governance. Conflict. Compensation. The questions that live in the hallways and never make it to the agenda. In a private, unhurried setting, they finally surface — and get resolved.

Families who do this work don't just leave with a plan. They leave with each other.

Who This Is For

Is this your family?

  • 01
    The succession conversation keeps getting postponed.Everyone knows it needs to happen. No one wants to start it. Years pass. The gap between generations quietly widens.
  • 02
    Family dynamics are bleeding into business decisions.Old roles, old wounds, and old assumptions are running the company more than anyone will admit — and it's affecting both performance and relationships.
  • 03
    The next generation is ready — but the current generation isn't letting go.There's capable leadership waiting in the wings. The transition just needs a neutral hand to guide it.
  • 04
    You're preparing for a sale, merger, or outside investment.Before outside parties arrive at the table, the family needs to be unified, aligned, and ready. That work happens here.
  • 05
    Nobody in the family can be truly neutral.Every conversation has a history. Every opinion has a stake. You need someone who can hear everyone — and be trusted by all of them.

"Away from offices and agendas, the conversations that have been deferred for years finally happen — and the agreements that come from them actually stick."

This engagement is not for every family. It is for families who are ready to stop managing the tension and start resolving it — with the privacy, the time, and the guidance to do it well.

See If This Is a Fit
What Changes When You Leave

Not just clarity. Real resolution.

Families who do this work leave with more than a plan. They leave with agreements everyone actually made — and the trust to hold them.

01
Conflicts Resolved
Tension cleared — not managed, not deferred. Real resolution that holds when daily life resumes.
02
Roles & Compensation Agreed
Roles, responsibilities, and compensation agreements that everyone has actually agreed to — not assumed.
03
A Succession Roadmap
A succession and governance roadmap the family built together — and will follow because they own it.
04
Decision-Making Structures
Frameworks that hold up long after Jocelyn leaves — built for your family's specific dynamics.
05
Stronger Relationships
Family relationships that are stronger for having done this — not strained by it.
+
Documented
Every agreement and commitment captured in a clear written summary — so nothing evaporates when you return to daily life.
How It Works

How the Family Business Intensive works.

Every family is different. Every engagement is custom-designed around your specific situation, dynamics, and goals — following a consistent arc from honest assessment through deep work to durable outcomes. There are no generic agendas. Jocelyn arrives prepared with the questions your family hasn't known how to ask.

Step 01
Before You Arrive

Private Pre-Work

Before the family convenes, Jocelyn speaks individually with each member — privately and confidentially. What people say one-on-one is almost always the map for what the group needs to address together.

Step 02
The Intensive Itself

Immersive Work Together

Working sessions woven into your family's natural rhythm — meals, walks, downtime. The agenda is purposeful but never forced. Hard conversations happen when the moment is right, not when the clock says so.

Step 03
What You Take Home

Documented Outcomes

Every agreement, decision, and commitment is captured in a clear written summary. Roles, plans, and next steps are documented so nothing evaporates once you're back to daily life.

Families Who Have Done This Work

What this looks like in practice.

Every situation is different. Every engagement is private. These are composite accounts — no names, no identifying details — reflecting the patterns we see most often.

Family-Owned Retail / Distribution

The Founder Who Wouldn't Let Go

A founder who had built his company over 35 years knew it was time to hand the reins to his daughter — a capable, experienced leader who had worked alongside him for over a decade. The problem wasn't capability. It was identity. He didn't know who he was without the company. Over three days at the family's primary residence, we worked through what the transition actually meant for him personally, rebuilt the relationship between father and daughter that had quietly eroded under years of professional tension, and left with a 12-month succession plan they had both written — and both meant. Six months later, the transition was complete. The founder told us he hadn't expected to feel relieved. He did.

Second-Generation Family Real Estate

Three Siblings, One Company, No Agreement

Three adult siblings had inherited equal ownership of a significant family real estate portfolio. On paper, everything was structured correctly. In practice, no decision had been made in 18 months without a fight — and two of the three hadn't spoken outside of business calls in over a year. We spent four days working through the governance vacuum at the center of their conflict: no agreed decision-making structures, no defined roles, no framework for disagreement. What looked like a personality conflict was actually a structural problem. We fixed the structure. The relationships followed. They left with a formal governance agreement, defined roles, and a decision-making process that didn't require unanimity on everything. The fights didn't disappear. But they became manageable — and less personal.

Family-Owned Professional Services

Preparing for a Sale

A husband-and-wife founding team had built a highly successful professional services firm and were preparing for a potential sale within 24 months. Their adult son was the firm's COO and expected to play a central role in whatever came next. The problem: none of the three had ever explicitly discussed what they each wanted from a sale — financially, professionally, or personally. The assumptions each of them was carrying were completely different, and no one knew it. We spent two days surfacing those assumptions, building alignment on what the family actually wanted from an exit, and establishing a shared position they could take into any external conversation. They went to market unified. They closed on terms that worked for all three of them.

What We Work Through Together

The conversations that have been waiting.

Every engagement is tailored. These are the areas most families need to address — and the ones that most often go unaddressed until it's too late.

01
Succession & Leadership Transition
Who leads next, when, and how. Ownership transfer, governance structure, and the handoff plan that protects both the business and the family relationships around it.
02
Roles, Compensation & Expectations
Clarifying who does what, what it's worth, and what's expected — before assumptions become resentments. Family agreements that hold up under pressure.
03
Conflict Resolution & Family Dynamics
The tension that lives between business decisions and family relationships. Old grievances, communication patterns, and the unspoken rules that shape how your family operates.
04
Governance & Decision-Making
How decisions get made, who has authority, and what structures ensure the business doesn't stall when the family disagrees. Clear governance built to last generations.
05
Vision, Legacy & Long-Term Direction
What the family wants the business to become — and why. Aligning personal values with business strategy so the company serves the family's larger purpose.
06
Exit, Sale & Ownership Planning
For families preparing for external investment, acquisition, or ownership changes. Ensuring the family is unified, prepared, and protected before outside parties arrive at the table.
Your Advisor

Jocelyn Greenky, MBA.
The person in the room when it matters most.

For over 40 years, Jocelyn has advised CEOs, Fortune 500 leaders, and multigenerational family businesses through succession, governance, conflict, and transformation. She has been in every seat at the table — founder, advisor, board member, interim CEO.

She has spoken for Simon & Schuster, Kraft General Foods, Columbia University, and the Exit Planning Institute — and brings that breadth of experience to every family she works with. She teaches business leadership and communications at the university level, with the directness and care that makes hard conversations feel like progress.

"With six children, one grandchild, three dogs, and various family businesses woven through our lives — I don't just understand this work academically. I live it."
  • MBA — strategic advisory, leadership, and organizational dynamics
  • Author — leadership, generational dynamics, and influence
  • University professor — business leadership and communications
  • Interim CEO and Fractional COO across industries
  • 40+ years advisory experience — Fortune 500 to family enterprise
Jocelyn Greenky
What to Expect

Everything is built around your family.

There is no standard agenda. No cohort. No shared curriculum. Every detail — from the pre-work to the final documented outcome — is designed around your family's specific situation.

Fully Private & Confidential

Everything discussed remains within the family. Jocelyn operates under full discretion — no case studies, no references, no visibility unless you choose it.

Wherever You Gather

Your home, vacation property, family estate, private venue. Domestic or international. Jocelyn comes to you — the environment is part of the work.

Duration

Typically 2 to 5 days depending on the complexity of your situation. Some families benefit from a focused weekend; others need a full week to do the work well.

The Agenda

No generic workshop. The sessions are designed around your family's specific dynamics, goals, and what the pre-work reveals. Every hour has purpose.

The First Conversation Is Free

No pitch, no pressure. Jocelyn will listen to your situation and tell you honestly whether this is the right fit — and what it would look like if it is.

Investment

Shared privately during your first conversation. The scope and duration of each engagement varies — pricing reflects that.

This is not an off-the-shelf program. There is no standard agenda, no cohort, no shared curriculum. It is built — from the first private conversation to the final documented outcome — entirely around your family.

Jocelyn's approach begins with listening. Deeply, privately, one person at a time. What she hears before the family convenes shapes everything that happens after.

The result is an engagement that feels less like a workshop and more like a turning point.

Start a Private Conversation
Two Ways to Work With Jocelyn

Not sure which is right for your family?

The Intensive is Jocelyn's most private, most immersive offering. But if a structured peer group might be the better fit, the Mastermind is worth exploring.

You are here

Family Business Intensive

Jocelyn comes to you — privately, on-site — for an immersive 2 to 5 day engagement built entirely around your family. No cohort. No shared agenda. Complete privacy and Jocelyn's undivided attention.

Best for families who need complete privacy, an immersive on-site experience, and a fully custom engagement.
Also from Sider Road

Family Leadership & Legacy Mastermind

A 3-month peer cohort for family businesses navigating succession, power shifts, and generational transitions. Eight to ten people, every other week, facilitated by Jocelyn. Structure, peer perspective, and accountability in a confidential group setting.

Best for those who want peer insight, structured sessions, and expert facilitation alongside others navigating the same terrain.
Explore the Mastermind →
The Next Step

Some conversations can't wait another year.

The first conversation is private, free, and without obligation. Tell Jocelyn what's going on — she'll tell you honestly what she sees, and whether this is the right fit.

Confidential. No pressure. No pitch.  ·  [email protected]

Schedule a Private Call

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