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Workshop · Flagship format

The Family Estate Readiness Workshop

The conversation most families never have, run as a guided 90-minute session. The 8 documents every adult needs, the scripts for the conversation with mom and dad, and the executor playbook — for the ~60% of American adults who don't yet have a will. Live, virtual, or co-branded for your organization.

Duration

90 minutes

Audience

Adult children of aging parents, couples, blended families

Investment

$500 – $2,000 per event

Inquire about this workshop

What participants leave with

The outcome

By the end of 90 minutes, every participant has:

  • A clear understanding of the 8 documents in a complete estate plan — what each does, what each doesn't do, and which they're missing.
  • Three scripts they can use this week to start the conversation with their aging parents (or with their own adult children).
  • A 47-point family readiness checklist they fill out in real time during the workshop, with their three highest-priority gaps identified.
  • A decision framework for the family home — sell, keep, rent, or one heir buys out the others — with the step-up basis math walked through.
  • The first-72-hours executor playbook for what to do (and what NOT to do) in the days immediately after a death.
  • An emotional reset. Most participants come in scared. They leave understanding that the work is finite, and the conversation is doable.

The arc

90-minute structured agenda

Segment 1 — Opening (0:00–0:10)
• Welcome + housekeeping (2 min) • The $50 vase story (5 min) — the emotional anchor that sets the tone. Verbatim script available below in the "Speaker Notes" section. Always told live. Never read from slides. • Three things we'll cover today (3 min)
Segment 2 — The 8 Documents (0:10–0:30)
• Will — what it actually does (and the FOUR major things it doesn't do) • Revocable Living Trust — when it's worth it, when it isn't • Durable Power of Attorney (financial) • Healthcare Power of Attorney • Living Will / Advance Directive • HIPAA Authorization (often missed — makes the POA usable) • Letter of Instruction (not legal — but most-read document your family will get) • Digital Legacy Plan (passwords, social, crypto) ACTIVITY: Participants fill out the "What I have / What I'm missing" worksheet. 5 min, individual. Most participants discover 2-4 gaps they didn't know they had.
Segment 3 — The Conversation (0:30–0:50)
Why families avoid it (5 min): • Feels morbid • Feels like giving up • Feels like inviting bad luck • What's actually worse: NOT having it Three scripts that work (10 min, read each aloud): 1. Direct but gentle: "Mom/Dad, I love you and I want to make sure we're honoring your wishes…" 2. Story-based: "A friend's parent just passed away and they're having a really hard time figuring out…" 3. Document-focused: "I'm updating my own will. Made me think — do you have everything in order?" What to cover (3 min): • The house (stay, sell, give to whom) • Healthcare (what kind of care, who decides) • Finances (who handles things if you can't) • Personal property (items with meaning) • The soft stuff (stories, values, life lessons) When emotions run high (2 min): • If someone cries: "Take your time." • If someone gets angry: "I can see this is upsetting. Let's take a break." • If someone shuts down: "It seems overwhelming. Want to talk about something else for a bit?" ACTIVITY: Pair exercise. Two participants face each other. One plays "aging parent," one plays "adult child." Use Script 1 verbatim. Then swap. 10 min total.
Segment 4 — The House (0:50–1:10)
The four options (8 min): 1. Sell — cash, clean, fast 2. Keep and rent — income, hassle, manager required 3. One heir buys out the others — needs cash or financing 4. Joint family ownership without buyout — usually fails Step-up basis explained (5 min): • Date of death → cost basis resets to FMV • Example: $200K → $600K → $620K • You only pay capital gains on the $20K • A $400-$600 date-of-death appraisal documents the basis • This is the #1 thing families miss Sibling co-ownership — the long-term failure pattern (4 min): • Why it sounds nice • Why it almost never works • The conversations to have BEFORE choosing this When to involve a realtor (3 min): • Before you list — for the family conversation • Step-up basis math • Pre-listing prep ACTIVITY: Decision-tree worksheet on a hypothetical house. 8 min, small groups of 3.
Segment 5 — The Executor (1:10–1:25)
The 72-hour list (5 min): Hour 1–24: notify immediate family, locate the original will, secure the home, contact funeral director. Hour 24–48: get 10 copies of death certificate, locate any pre-paid funeral arrangements, contact attorney if there is one. Hour 48–72: notify Social Security (if applicable), begin inventory of accounts, do NOT distribute anything. Common executor mistakes (5 min): • Commingling estate funds with personal funds • Distributing too early (before creditor period closes) • Ignoring or missing the creditor claim period • Not getting 10 copies of the death certificate • Promising more than you can deliver When to hire vs DIY (5 min): • Net estate under $50K — often DIY-able • Real estate involved — talk to a real estate attorney • Multiple states — usually requires professional help • Family conflict — get an attorney • Complex assets (business, IP, crypto) — get help
Segment 6 — Close + Q&A (1:25–1:30)
Recap (2 min): • The 8 documents • The three scripts • The 72-hour list • The house decision framework The offer (2 min): • Free 20-minute consultation (link / contact info) • Continued access to the resource portal • Workshop kit handout to take home Schedule one-on-ones (1 min): • Clipboard pass-around for follow-up calls • Or QR code to scheduling link • Or paper sign-up sheet for in-person events

Speaker notes

The opening story (verbatim)

The $50 vase — stand, don't hide behind the lectern
[STAND. PAUSE FOR A BEAT.] "Before I tell you what we're going to do for the next 90 minutes, I want to tell you a quick story. A few years ago I sat down with three siblings. They hadn't spoken in six weeks. Their mother had died two months earlier. The funeral was hard. The reading of the will was harder. And then — exactly the kind of thing nobody warned them about — they started fighting. About a vase. A ceramic vase. Worth maybe fifty dollars at an estate sale. It wasn't mentioned in the will. The mother had told one daughter, years ago, 'this is for you.' She had also told the son's wife, two years later, 'this is for you.' The third sibling didn't even want the vase, but he wanted the principle. Six weeks of silence. Two cancelled Thanksgivings. One Easter that didn't happen. All over a fifty-dollar vase. [PAUSE] That fight was never about the vase. It was about a conversation that never happened. The mother loved all three of her children. She just never wrote down — or said out loud, to all three at the same time — what she wanted the vase to mean. The next 90 minutes are going to give you the conversation skills, the documents, the checklists, and the family scripts to make sure that never happens in your family. Let's start."

Pricing

What's included at each tier

Standard — $500 (small private group, up to 15 people)
• 90-minute live or Zoom delivery • Participant workbook (PDF) • "What I Have / What I'm Missing" worksheet • 47-point Family Estate Readiness Checklist • 30-minute post-workshop Q&A on the recording (Zoom) • Three follow-up emails over 10 days (sent by host or by us)
Standard+ — $1,200 (larger group, up to 50 people)
Everything in Standard, plus: • Pre-event registration page (co-branded) • Branded event materials (slides, handouts) • Recording of the session • Post-event email sequence (5 emails over 30 days) • One free 20-minute follow-up call for any attendee
Premium — $2,000 (custom enterprise format)
Everything in Standard+, plus: • Pre-event survey to tailor content to your audience • Custom branding (your logo, colors, sponsor recognition) • Sponsor table or virtual booth space for partner orgs • 60-minute speaker package (extended Q&A + executive table-talk) • Post-event referral pipeline (for partner realtors/advisors) • Recording rights for your organization • White-label workshop kit if you want to run it yourself afterward

Travel beyond the SF Bay Area is invoiced separately at cost (flights + hotel). Virtual events have no travel cost. Workshops booked alongside a white-label partner subscription get a one-time 25% discount on the workshop fee.

FAQ

What organizers ask

Do we facilitate or does Roger?

Both options. Roger facilitates Premium-tier events and select Standard+ events. For most events at the Standard tier, the host organization facilitates using our complete kit. We train your facilitator over a 30-minute call (included in all tiers) so the delivery feels professional even if it's your team's first time.

Can we record and reuse the workshop internally?

Yes for organizational use at Standard+ and Premium tiers. Recordings can be shared with your members, employees, or community on internal platforms. Public republication or commercial resale of the recording requires a separate content license (typically priced per audience size).

What if we don't have 15 people in our group?

Smaller groups (5–14 people) are fine at the Standard tier and often more effective — the pair exercise and small-group discussions get richer with fewer people in the room. We don't reduce price below the Standard tier; the value comes from the kit and the facilitator time, not the headcount.

How far in advance do we need to book?

Live in-person events typically need 4–6 weeks of lead time for travel coordination. Zoom events can be booked with 2 weeks of notice or less. If you have a date-driven event (annual member meeting, post-holiday family planning event), we'll prioritize.

Can we co-brand with our organization?

Yes at Standard+ and Premium tiers. We'll incorporate your logo and brand colors into the slides, handouts, and registration page. We retain Plan Your Passing as the underlying content provider, identified in the speaker bio and a small footer disclosure on materials.

What's the refund policy?

Full refund for cancellations more than 14 days before the event. Inside 14 days, fees are non-refundable but we'll reschedule once at no charge with at least 72 hours notice. See /refund-policy for the full policy.

Ready to book?

Let's talk dates.

Email Roger with your preferred dates, audience size, location (or Zoom), and any specific topics. We respond within 24 hours with availability and a custom quote.

Email Roger to book