Role Play with Jocelyn.
Money, roles, control, family. Practice the talks you keep putting off.
A live, small-group program for family business leaders, led by Jocelyn Greenky.
For the person in the business or family who’s ready to talk about what nobody’s saying.
In most family businesses, everyone knows the conversation that needs to happen. Nobody wants to start it. So it waits. And while it waits, it gets more expensive: in money, in trust, and at the dinner table.
You don’t need the whole family in the room to change that. You need one person who knows how to open the door. Role Play with Jocelyn is for that person.
It’s for owners, successors, and family members working in businesses doing $2M or more, who are tired of avoiding the talk and ready to have it well.
One conversation: yours.
You bring the real conversation you need to have. We work on it together, week by week, until you’re ready. You have a private advisory board with the group. It might be about any of these:
Money & Roles
Who gets paid what, and why. Who’s in charge, and who isn’t. What to do about the relative who isn’t pulling their weight. How to set roles based on the business, not birth order.
Control & the Future
The founder who won’t let go. The successor who isn’t ready, or isn’t interested. Spouses and in-laws who want a say. How to talk about what comes next without starting a war.
Conflict & Boundaries
Siblings who’ve stopped speaking. Old resentments that show up in every meeting. Keeping the business out of Thanksgiving dinner, and Thanksgiving out of the business.
…or anything else: in-laws and spouses, a buyout, a family member leaving the business, stepping back, or the conversation you haven’t found words for yet.
Knowing what to say isn’t the same as being able to say it.
You’ve probably rehearsed this talk in your head a hundred times. Then the moment comes and old patterns take over: you get defensive, they shut down, and nothing changes.
In Role Play with Jocelyn, you practice out loud, in a private setting, alongside peers who understand exactly what’s at stake. You’ll role-play your real conversation, get direct feedback from Jocelyn, and try again until it feels natural. By the time you have the real talk, you’ve already had it.
Every member signs a confidentiality agreement (NDA) before joining. Members share situations, not names, and what’s said in the room stays in the room.
The Sider Road five-step conversation framework.
- 01Name it. Get clear on what the real issue is, underneath the surface one.
- 02Know the stakes. What happens to the family, and the business, if nothing changes?
- 03Prepare. Plan your opening, your ask, and how you’ll respond when it gets hard.
- 04Practice. Role-play it live, get feedback, and do it again.
- 05Follow through. Have the real conversation, then come back to the group and debrief.
Ten weeks. One hour a week.
- NDA required: every member signs before the first session
- 10 weeks, 1 hour a week on Zoom
- A private circle of family business leaders navigating the same decisions, each from a different family
- Live role-play with direct coaching from Jocelyn
- The Hard Conversations Playbook: scripts, openers and worksheets for the conversation you’re preparing
- Every session recorded, so you never miss anything
- Start anytime: sessions run every week, so you can join whenever you’re ready
Jocelyn Greenky.
Jocelyn Greenky is the founder and CEO of Sider Road, a family business advisory firm, and co-runs it with her daughter, so she knows family business from the inside. She brings 40+ years of operating experience, including senior roles at Hachette Filipacchi and Wenner Media, and has advised and spoken for organizations including EY, PwC, KPMG, Kraft, Viacom and Bank of America.
She is the author of The Big Sister’s Guide to the World of Work (Simon & Schuster) and the forthcoming Design Your Reputation, an adjunct professor at Queens College CUNY, and a frequent voice on CNBC, CNN, FOX News, and in the WSJ, Forbes and Fortune.
Her promise is simple: the truth, with a plan attached.
Join whenever you’re ready.
Sessions run every week, all year. Your 10 weeks begin from your start date. If you miss a week, the recording is waiting for you.
- Weekly session
- Fridays
- Time
- 12:30–1:30 PM ET / 9:30–10:30 AM PT
- Where
- Zoom
- Program
- Role Play with Jocelyn
10 weeks · 90 mins 1x a week on Zoom
3000$ for 15 Sessions
Limited Number of Spots Available - Included
- The Hard Conversations Playbook
Confidential, NDA-protected group - Investment
- $3,000