Workshops & Programs
Practical programs for consequential decisions
Some decisions are difficult because the answer is not obvious. Information may be incomplete.
People may see different parts of the situation. Priorities may compete. And the consequences may extend well beyond the immediate choice.
I lead interactive workshops that help leaders, families, boards, and advisors think more clearly in those situations. The programs are practical and case-based, with an emphasis on applying the ideas to decisions participants actually face. Several programs use carefully constructed hypothetical cases, allowing participants to practice their judgment in situations resembling their own challenges without having to disclose sensitive client or family matters.
Programs can be adapted for leadership teams, professional firms, family enterprises, family offices, boards, associations, and advisor groups.
INTERACTIVE WORKSHOP
Better Judgment in High-Stakes Decisions
Thinking clearly when priorities compete, perspectives differ, and consequences are real
The flagship program: a case worked in stages using the COImpAct framework, showing how a decision changes when the situation is framed more carefully.
TYPICALLY FOR
Leadership teams, professional
firms, boards, family enterprises,
and family offices
TYPICAL FORMAT
75-90 minutes, interactive and case-based
FAMILY OFFICE PROGRAM
High-Stakes Investment Decisions
Improving judgment when risk and family dynamics intersect
For family offices, where a sound investment recommendation can become entangled with legacy, control, liquidity, trust, and authority.
TYPICALLY FOR
Family offices, investment committees, CIOs, trustees, family members, and wealth advisors
TYPICAL FORMAT
45-90 minutes, conference session to workshop
LEADERSHIP TRANSITION WORKSHOP
Preparing Future Leaders Through Past Decisions
Retrospective Decision Mapping for Leadership Transition
Uses a completed consequential decision to make accumulated judgment visible, then turns what surfaces into requirements for the next leader.
TYPICALLY FOR
Founders, next-generation leaders, family enterprises, boards, and advisory teams
TYPICAL FORMAT
75-90 minutes, half-day, or custom in-house
FAMILY MEETING PROGRAM
Practicing Better Decisions Together
Facilitated Case Study Discussions for Enterprising Families
A self-contained case discussion for family meetings, retreats, rising-generation programs, and advisor-led client education. Participants work through a realistic situation together, practicing how to slow down complex decisions, surface competing obligations, and examine implications before moving to action.
TYPICALLY FOR
Family meetings, family retreats, rising-generation programs, family offices, family councils, boards of family enterprises, and advisor-led client programs
TYPICAL FORMAT
75-90 minutes, interactive and case-based; half-day or custom formats available
ADVISOR DEVELOPMENT WORKSHOP
Developing Advisor Judgment in Difficult Client Situations
Facilitated Case Discussions for Family Offices, Fiduciaries, and Wealth Advisors
Strengthening advisor judgment when technically sound recommendations encounter competing goals, concerns, or resistance. Through carefully constructed hypothetical cases, participants practice recognizing what clients are trying to accomplish, protect, or avoid — and how different responses may affect both the decision and the working relationship — without disclosing confidential client matters.
TYPICALLY FOR
Trust companies, family offices, wealth advisors, estate planning professionals, and multidisciplinary advisory teams
TYPICAL FORMAT
60–90 minutes, interactive and case-based; half-day or series formats available
INTERACTIVE WORKSHOP
Better Judgment in High-Stakes Decisions
Thinking clearly when priorities compete, perspectives differ, and consequences are real
High-stakes decisions often become difficult before anyone begins comparing solutions. The problem may have been framed too narrowly. Different stakeholders may be working from incomplete perspectives. Emotionally charged language can push people toward positions before the underlying concerns have been examined.
This interactive workshop introduces the COImpAct decision framework:
Context Desired Outcomes Options Implications Decision / Action
Participants work through a common case in stages, with small-group discussion and brief share-outs, and experience how the quality of a decision changes when the situation is framed more carefully, desired outcomes are made explicit, credible alternatives are compared, and downstream implications are considered. The case can be adapted to the audience while the decision process remains the same.
Participants learn to:
-
Recognize when framing is contributing to the difficulty
-
Separate charged language from the substantive issues
-
Clarify what a good decision must accomplish, preserve, or avoid
-
Compare alternatives before narrowing prematurely
-
Examine immediate and downstream implications
Participants leave with a one-page COImpAct decision map they can apply to a live decision after the
session.
Relevant for: leadership teams, professional firms, boards, family enterprises, family offices, and organizations facing consequential decisions. Applications include strategy and capital allocation, leadership and succession, governance, philanthropy, and investment decisions.
Typical format: 75-90 minutes, interactive and case-based.
A USEFUL QUESTION
Before asking, "What should we do?" ask, "What do we need to understand first?"
“How to start the conversation was the biggest thing I took away. The example of the difference between asking, ‘Who wants to go to dinner?’ and ‘Who wants to go out and get steak?’ showed me how framing an issue too specifically can create unnecessary disagreement.”
- Stephen Gilman
Managing Director, CBIZ
FAMILY OFFICE PROGRAM
High-Stakes Investment Decisions
Improving judgment when risk and family dynamics intersect
In a family office, an investment decision is rarely only an investment decision. A recommendation
may also raise questions about legacy, control, liquidity, stewardship, trust, authority, and rising generation voice.
Technical investment analysis remains essential. But analysis alone may not settle what the family is
actually deciding.
This program helps families and investment teams make the non-technical dimensions of an
investment decision more explicit. Working from a familiar family-office case, such as concentration
risk, participants consider how the family frames the question, whose interests matter, what the
capital is meant to accomplish, what credible alternatives exist, and what would cause the decision to
be revisited.
Participants learn to:
-
Surface the non-technical factors shaping an investment decision
-
Clarify what the capital is meant to accomplish, protect, or make possible
-
Identify whose interests and time horizons matter
-
Move from advocacy to selection among credible alternatives
-
Make tradeoffs explicit and establish when the decision should be revisited
Participants leave with a practical discipline for helping families understand the decision, own the tradeoffs, and know when to revisit it.
Relevant for: family offices, investment committees, CIOs and investment teams, trustees, family members, wealth advisors, and other family-office professionals.
Typical format: 45-90 minutes, from conference presentation to interactive workshop.
CORE IDEA
Approval is not ownership.
A family can approve a recommendation without fully understanding what it has decided, what tradeoffs it has accepted, or what would cause it to reconsider.
LEADERSHIP TRANSITION WORKSHOP
Preparing Future Leaders Through Past Decisions
Retrospective decision mapping for leadership transition
Succession often transfers titles and responsibilities before it transfers judgment.
Retrospective Decision Mapping uses a consequential past decision to make some of that accumulated judgment more visible. Participants reconstruct how the decision actually unfolded: what was considered, who was involved, what information and relationships mattered, where authority sat, what remained uncertain, and where people understood the same events differently.
The mapping process is the same in every setting. The decision can be drawn from the group’s own
experience or from a case adapted to the audience.
The group then turns that history into requirements for future leadership.
Participants work to:
-
Reconstruct a consequential decision in a neutral sequence
-
Surface the judgment contributed by the current leader
-
Identify the information, experience, relationships, and authority boundaries that shaped the decision
-
Examine where participants understood the same decision differently
-
Translate those observations into requirements for the next comparable decision and the leadership
transition
The process can help clarify which decisions a future leader might begin owning now, what should
trigger consultation or escalation, and which future decisions could provide supervised practice for
building judgment. It also leaves the group with a framework that can be reused as succession
unfolds.
Succession is partly the transfer of decision capacity. The objective is to make enough of that capacity visible that it can be developed, shared, and gradually handed off.
Relevant for: founders, next-generation leaders, family enterprises, family offices, boards, and advisory teams preparing for leadership transition or changes in decision authority.
Format options: 75-90 minute workshop, half-day facilitated session, or customized in-house program for leadership teams, boards, or family groups.
CORE IDEA
Titles transfer faster than judgment.
A successor can hold the role without knowing which decisions are now theirs, which still require
consultation, and what the last leader was actually weighing.
FAMILY MEETING ROOM
Practicing Better Decisions Together
Facilitated Case Study Discussions for Enterprising Families
Family meetings provide opportunities to strengthen relationships, share information, and address important family and enterprise matters. Yet even well-designed meetings can begin to feel familiar, with recurring presentations, updates, and discussions of current issues.
A facilitated case study discussion offers something different: an engaging, structured learning experience that helps family members practice thinking through complex decisions together.
Rather than beginning with the family's own sensitive issues, participants explore a carefully selected case involving recognizable challenges such as succession, ownership, governance, philanthropy, leadership readiness, or shared responsibility.
The case creates enough distance for participants to consider different perspectives, examine competing obligations, and explore alternative courses of action without the pressure of an immediate family decision.
Participants learn to:
-
Distinguish the presenting issue from the underlying decision
-
Recognize how different perspectives shape the same situation
-
Clarify competing interests, responsibilities, and desired outcomes
-
Compare credible alternatives and examine their implications
-
Practice constructive dialogue and collaboration across generations
-
Develop a shared language for approaching future decisions
Participants leave with a shared learning experience, a practical framework for thinking through complex situations, and a stronger foundation for approaching future family and enterprise decisions together.
Relevant for: family meetings and retreats, family offices, rising-generation education programs, family councils, owner groups, family enterprise boards, and advisor-led client education programs.
Format options: 75-90 minute workshop, half-day facilitated session, or customized in-house program for leadership teams, boards, or family groups.
CORE IDEA
A good case lets families practice decision-making before the stakes become personal.
By examining situations outside their immediate circumstances, family members can explore difficult questions, challenge assumptions, and consider different perspectives without feeling personally exposed. The experience builds capacity for more thoughtful conversations when consequential decisions arise.
Adapting a Program for Your Group
Each program can be adapted to the audience and setting. A conference session may use a common case and focus on a small number of practical ideas. An internal workshop can allow more time for discussion, application, and connection to decisions the group is actually facing.
If one of these programs seems relevant to your organization, I would be glad to discuss the audience, the situation, and what would make the session useful.
Paul Edelman, PhD, PCC
Executive Coach & Family Enterprise Advisor
508-947-5300
ADVISOR DEVELOPMENT WORKSHOP
Developing Advisor Judgment in Difficult Client Situations
Facilitated Case Discussions for Family Offices, Fiduciaries, and Wealth Advisors
Experienced advisors sometimes encounter situations in which technically sound recommendations fail to produce movement. Family members may understand their options but see the implications differently. A beneficiary may experience a trustee's exercise of discretion as mistrust. A business founder may recognize the need for succession while continuing to exercise control.
These situations call for professional judgment that extends beyond technical expertise.
Through carefully constructed hypothetical cases, participants explore what the people involved are trying to accomplish, protect, or avoid, and consider how different advisor responses might affect both the immediate problem and the working relationship.
Because the cases are hypothetical, advisors can examine challenging situations without disclosing confidential client matters or exposing their own professional difficulties.
Participants practice:
-
Recognizing factors that may be interfering with a client's ability or willingness to move forward
-
Considering alternative explanations before drawing conclusions
-
Clarifying competing interests, concerns, and desired outcomes
-
Anticipating how different interventions might be experienced
-
Recognizing when to adjust their approach, seek consultation, or involve additional expertise
Relevant for: Trust companies, multifamily offices, wealth advisors, estate planning professionals, and multidisciplinary advisory teams.
Typical format: 60-90 minutes, with cases tailored to the professional audience.
CORE IDEA
Effective advising requires judgment about what to say, when to say it, and what may happen as a result.