Extended engagements
What this work
actually looks like
Extended engagements are design-build projects. They're structured enough to make real progress, and flexible enough to follow what actually surfaces. Here's what that means in practice.
The honest starting point
No engagement can be fully scoped at intake. That's not a limitation — it's the nature of the work.
Every family arrives with a presenting problem. But under it, almost always, is a network of unresolved questions, undocumented structures, unspoken fears, and unmade decisions that have been accumulating for years. The presenting problem is the check engine light. The engine is what an extended engagement addresses.
What can be scoped at intake: the opening phase, in reasonably concrete terms — and estimated ranges for what follows. What cannot be scoped: how long the full engagement will run, what it will ultimately cost, or the exact path from where you are to where you want to be. All of those depend on what we find, and how the family moves through it.
This is worth saying plainly at the front of the relationship, not discovering together at month three.
A distinction worth understanding
The Discovery Phase and the Discovery Process are not the same thing.
Both words come up in this work. They mean different things, and knowing the difference helps explain why extended engagements evolve the way they do.
The phase
Discovery Phase
The formal opening chapter of an engagement. Its purpose is to establish a shared baseline — individual goals, family and system goals, prioritization, and identification of what information will be needed to build a roadmap. It's substantially complete when everyone has been heard, the initial assessment has been shared and agreed upon, and there's at least preliminary alignment on direction.
The activity
Discovery Process
The ongoing practice of gathering, verifying, and updating information throughout the entire engagement. A trust document arrives in month six and changes the succession structure. Something surfaces in an individual session that reframes what was said two months earlier. Discovery-as-activity never fully closes. It's woven through every phase of the work.
The Discovery Phase creates the foundation. The Discovery Process keeps the foundation current. Both are necessary. Neither is a discrete box that opens and closes cleanly.
How the work unfolds
Three phases — which is not to say three stages.
These phases describe what each part of the engagement is for. They overlap, recur, and run in parallel. Multiple workstreams within the same engagement will often be in different phases simultaneously — one thread actively coached while another is still in early discovery. That's not disorganization. That's what complex family systems actually look like.
Phase one
Discovery — building a shared, accurate picture
Before any strategic work can happen, the family needs a map of what's actually going on. Not what each person thinks is going on — what's actually there, surfaced individually and then verified together. This is the purpose of the Discovery Phase.
For most families, an Intensive serves as the launch pad for this phase — compressing the early discovery work into a high-traction opening format that produces a diagnostic and a preliminary action plan within days rather than weeks. Not every engagement begins with an Intensive, but most do, and most find it significantly easier to scope what comes next once they have one under their belts.
- Individual interviews with each key participant, conducted separately before any joint sessions
- Document review: trusts, entity structures, financials, buy-sell agreements, org charts, valuations — whatever is load-bearing for the decisions that need to be made
- An initial diagnostic assessment, shared and verified with the family
- Identification of information gaps that must be resolved before strategic decisions can be made
- The Synopsis: a joint presentation where findings are shared, often described by families as one of the most clarifying experiences of the whole engagement
- A draft roadmap outlining phases, options, and the questions that must be answered before each decision can be made
Phase two
Strategic vision and roadmap — from diagnosis to direction
Once the family has a shared diagnostic, the work shifts toward decision-making: what are the options, what does each one actually require, and which direction is the family willing to commit to together? This phase is not complete until there is a signed, written agreement on direction. Alignment is a prerequisite for proceeding — not an assumption built into the timeline.
- Structured presentation of options — succession vs. exit, governance approaches, ownership transfer structures, and so on
- Facilitated family discussions to evaluate options, surface concerns, and narrow the field
- Conversations about fairness, roles, and what each person actually needs in order to say yes
- A formal roadmap: milestones, timelines, roles, and responsibilities — in writing
- Coordination with other advisors (estate attorney, CPA, financial planner, business broker) as the decisions require it
Phase three
Coaching the process — where plans meet reality
Implementation is where most plans unravel — not because the plan was wrong, but because the human side of execution is harder than the plan accounted for. This phase is less about project management and more about the work of actually changing: navigating friction, building new habits, holding the line when someone wants to backslide, and developing the governance practices that allow the family to function well without a consultant in the room.
- Coaching principals through implementation — the relational and character-building side, not project tracking
- Facilitated family conversations, sometimes instigated, sometimes responsive to what's surfacing
- Tracking against milestones; naming stagnation when it appears
- Governance habit-building: how decisions get made, how disagreements stay productive, how the family holds itself accountable
- Scope and duration of this phase defined during Phase 2, once the roadmap is in place
The part no one warns you about
Why this work is hard to price — and what that means for you.
Extended engagements typically run anywhere from six months to three years. Total investment commonly falls in the range of $30,000 to well over $100,000, depending on scope, the number of people involved, and the pace the family sets. Ongoing coaching phases generally run on a monthly retainer basis, priced by estimated hours.
These are substantial numbers. They're worth naming clearly, because the alternative — discovering the real scope together at month three — is worse for everyone.
Worth understanding
You're not just paying for hours in a room.
You're paying for a specialist who knows your family system deeply enough to intervene when things get complicated, coach implementation over time, and hold the full picture while each family member is only seeing their corner of it. That depth has a real cost — and it also limits how many engagements can be carried well at any given time.
Schema actively holds roughly two to four extended engagements simultaneously. Beyond that, the scheduling constraints of each family system begin to drag timelines, stall traction, and dilute the quality of the work. This is a feature, not a limitation.
If the scope or the timeline gives you pause, that's a reasonable response. An Intensive remains a complete, standalone engagement — and if all you need is a clear diagnostic and a roadmap, it may be exactly right. There's no pressure to take on more than fits.
One more thing to know
Not all delays are the same. Knowing the difference matters.
This work rarely moves in a straight line. There are four distinct reasons engagements slow down, and each one is handled differently.
Health, crisis, or force majeure
If someone's health, a business emergency, or an unforeseen life event requires a pause, we pause. Billing suspends, the phase timeline holds, and a clear resumption plan is established together. No penalties.
Clinical or strategic necessity
Sometimes I call the pause — because a participant needs outside support before they can engage productively, because the business needs stability before the family can think clearly, or because the system needs time to integrate something difficult. This is part of the work, not a failure.
Legitimate depth
Sometimes what looks like slow progress is the work. A conversation surfaces something from thirty years ago that has quietly been running the show. We stay with it. Scope may expand; the agreement is revised proactively before proceeding. We do not rush past what actually needs to be addressed.
Client-elected avoidance
This is the one I take seriously. Avoidance is expensive — not just financially, but relationally. Stagnation breeds confusion, anxiety, resentment, and compounding risk. When I see it, I name it. If a participant's disengagement is impeding the system's progress, that's addressed directly — and if necessary, the scope adjusts accordingly.
"What I ask of every family I work with is a shared commitment to forward motion — not perfection, not speed, just a genuine willingness to keep showing up. The one thing I won't do is pretend we're moving when we're not."
Ready to explore what this might look like for your family?
A free 30-minute call is the right starting point. You'll leave with a clear picture of what makes sense — and whether now is the right time.
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