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2025.10 Approach Training (Nashville) October 22 & 23, 2025

Table of Contents

Overview

This training will be hosted at the headquarters of Community Foundation of Middle Tennessee.

The 21/64 Approach Training and ongoing peer network helps you acquire the personal skills, generational awareness, and technical tools to work more effectively with next-generation funders and multigenerational family enterprise clients.

In this in-person training taking place over two days, you will learn 21/64’s proven methodology for engaging individuals, families, and institutions at the intersection of values and governance. The program is specifically designed to help you more comfortably engage donors and clients in important and often complicated conversations, whether you are new to the field or a seasoned advisor adjusting to new modalities of engaging with clients.

Once you’ve completed the 21/64 Approach Training, you will become a 21/64 Certified Advisor, joining a global network of accredited professionals. You will also have the option of joining the 21/64 Learning Community with free access to continued skill building, next level trainings, the latest resources and tools, and more.

BENEFITS TO PARTICIPANTS

  • Understand assumptions around family, wealth, and philanthropy
  • Acquire fresh facilitation techniques for how to build engagement
  • Apply group dynamics and group process skills
  • Learn to facilitate 21/64 tools to have productive conversations on values, legacy, generational differences, and more
  • Personal and professional development
  • Acquire research and resources on engaging the next generation
  • Interact in small groups and expand your network

WHO SHOULD ATTEND

  • Philanthropic Advisors
  • Community Foundation Professionals
  • Investment Advisors, Private Bankers, and Estate Attorneys
  • Family Office Professionals
  • Foundation Directors
  • Trustees who also staff their family philanthropy

BENEFITS OF CERTIFICATION

The 21/64 approach is practiced worldwide and is today considered a best practice in the field of philanthropy and multifamily enterprise. As a Certified Advisor, you’re telling people that you lead with values and are equipped with the tools and methodology to teach others. Benefits of certification include:

  • Add “21/64 Certified Advisor” to your credentials (signatures, LinkedIn profile, bio, etc.)
  • Enjoy significant discounts on all tools
  • Tap into a global network of professionals on our proprietary social platform, 21/64 Connect.
  • Access to the 21/64 Learning Community (see below)
  • Complimentary post-training “Welcome to the Community” call
  • Access to our annual Certified Advisor gathering (virtual), along with “pop-up” events, and online community conversations for continued practice and skill building
  • Receive resources and the latest articles and research


Participants should plan for a combination of live learning in person, small group participant discussion, and independent work before and between sessions.

Live Learning:

Wednesday, October 22, 2025, 8:30am/9:00am – 4:30pm CT

Thursday, October 23, 2025, 8:00am/8:30am – 3:30pm CT

The training will be held at Community Foundation of Middle Tennessee, located at 3421 Belmont Blvd, Nashville, TN 37215.

Click here for a list of recommended hotels for your consideration.

Pre-work and Between Sessions:

We will share some independent work, readings, and videos to prepare for the training.

Light work will be assigned between the sessions.

Materials

You will receive pre-training details electronically and hard materials once you arrive at the training. Agenda, pre-reading, and additional logistics will be shared via email and on 21/64 Connect.

21/64 Learning Community (Optional)
The 21/64 Learning Community is a community of Certified Advisors who want to deepen their learning and develop power in their practice. As a Certified Advisor who is part of the Community, you will have free access to a full complement of virtual Workshops and advisor gatherings throughout the year. Benefits include:

  • Join all 21/64 Workshops at no additional cost
  • Access Learning Community-only events 
  • Receive 20% discounts on next level trainings
  • Receive 30% discounts on repeat 21/64 Approach trainings
  • Serve as our thought partners when beta-testing new tools and ideating future programming


You can sign up for the Learning Community when you register below. To do so, there will be an additional fee of $300. After one year, your certification and Learning Community fee will auto-renew at a rate of $365 annually (you can opt out at any time).

Get Started

Location & Hotels

The training will be held at Community Foundation of Middle Tennessee, located at 3421 Belmont Blvd, Nashville, TN 37215. 

The schedule is Wednesday, October 22, 9:00am – 4:30pm CT and Thursday, October 23, 8:30am – 3:30pm CT.

We’ll be providing a light breakfast 30 minutes before the training program begins on both days.

Pre-Training Letter from 21/64

Dear Colleagues,

On behalf of the 21/64 team and our sponsoring partner, Community Foundation of Middle Tennessee, we’re looking forward to hosting you in Nashville for the 21/64 Approach Training, October 22-23, 2025. Your two-day program will be led by 21/64 Executive Director and President Danielle Oristian York and me, Stefanie Borsari, Senior Consultant and Community Engagement Director.

 Learning will take place on two levels which will be discussed in more detail when we are all together: understanding how identity and lived experiences inform our professional roles and gaining new frameworks and tools to bring back to the people with whom you work. We look forward to providing an opportunity for you to grow, both personally and professionally, in an open space where you can practice and learn with your peers. 

This email covers access to program materials and prework, logistics, and scheduling. In the meantime, please let us know if you have any questions or expectations for training that you’d like us to know about in advance. 

LOCATION

The training will take place Community Foundation of Middle Tennessee, located at 3421 Belmont Blvd, Nashville, TN 37215. 

FOOD

A light breakfast will be provided each morning, starting a half hour before the training starts, and a lunch is also included on both days. Thank you for advising us of your dietary restrictions during the registration process. We will make every effort to accommodate your various needs.  

SCHEDULE

  • Day 1 Training: Wednesday, October 22nd, 8:30 am – 4:30 pm (program starts at 9:00 am)
  • Day 2 Training: Thursday, October 23rd, 8:00 am – 3:30 pm (program starts at 8:30 am)


HAPPY HOUR

Please join us for a community convening with local 21/64 Certified Advisors and friends immediately following the training on Day 1. While this is optional, we encourage you to attend for casual fellowship and connecting with your cohort colleagues and Nashville-area 21/64 community members. We’ll gather on Wednesday, October 22 from 5:00 — 7:00 pm at The Greenhouse for drinks and light bites. I’ll send the official invitation from Paperless Post soon and request the favor of an RSVP to that when it arrives (thank you!).  

ACCESS MATERIALS AND MEET YOUR COHORT 

21/64 Connect is an interactive space where hundreds of Certified Advisors share, learn, and stay connected. We have created a dedicated (and private) space on our platform for your training cohort. First, visit this link to join your cohort and to access materials for the course. Follow these easy steps:

  • Click on the above link. Then, if this is your first visit, create your login and password.
  • Add a bio and headshot. This is important because it lets your colleagues know with whom they will be sharing space. In addition to your bio, feel free to add some personal interests and fun facts. What is a question you would want someone to ask you?
  • Be sure to add your geographic location and area of specialty when prompted.


PREWORK FOR TRAINING

Please complete before you arrive to training on Wednesday, October 22nd:

Watch/Read:

  • Changing Behavior – Peter Bregman
    • This piece sets the stage for learning on Day 1 and offers a glimpse at how we’ll be shifting our thinking. 
  • Jam Study – Sheena Iyengar
    • This brief video by researcher, Sheena Iyengar, gives us a glimpse into the complexity of choice.


Optional:

Please complete before Day 2 of training on Thursday, October 23:

  • Read the article: Action Research: The Anchor of OD Practice
    • As you read the section of the article on Entry, think about a typical or challenging Entry scenario you have encountered, within the system that you work, that you could roleplay for Day 2.


HOTELS AND PARKING

For your convenience and consideration, here’s a list of area hotels near the Community Foundation of Middle Tennessee, our training venue. 

Our time together will be interactive and jam-packed with learning and connection opportunities. As always, please don’t hesitate to reach out with any questions beforehand. See you soon!

Warmly,  
Stefanie Borsari
Community Engagement Director and Senior Consultant

Post Day 1 - Drinks and Appetizers with Colleagues

Please join us for a community convening with local 21/64 Certified Advisors and friends immediately following the training on Day 1. While this is optional, we encourage you to attend for casual fellowship and connecting with your cohort colleagues and Nashville-area 21/64 community members. We’ll gather on Wednesday, October 22 from 5:00 — 7:00 pm at The Greenhouse for drinks and light bites.

Facilitator Bio - Danielle Oristian York

Danielle Oristian York is a creative systems-thinker, a leader and fan of embracing complexity.  She has been a consistent leader in the field, spending 24 years helping families, leaders, organizations, and communities have complicated conversations about change, identity and the future. Danielle is Executive Director of President of 21/64, a nonprofit practice serving next gen and multigenerational families. She is an expert facilitator, trainer, and keynote speaker.  She brings a constant curiosity and warm presence to work with new and seasoned leaders, family enterprises, family foundations and the advisors who serve them. Among her many writings, Danielle co-authored the chapter “Values That Matter” in Tom McCullough and Keith Whitaker’s book Wealth of Wisdom: Top Practices for Wealth Families and their Advisors, published by Wiley in 2022.  Prior to joining the 21/64 team, Danielle worked at UBS and Pitcairn Family Office, this experience provided different vantage points from which to catalyze and support strategic decision making. Danielle lives in Boston with her husband and two terrific kids.

Facilitator Bio - Stefanie Borsari

Stefanie Borsari serves in a dual role that lives at the nexus of 21/64’s two major divisions, training/community and consulting, a position that draws on her diverse range of skills and professional and personal interests.

As Community Engagement Director, Stefanie sustains a vibrant global community of Certified Advisors who have chosen 21/64 as their home for professional development. She organizes workshops and convenings that enhance Certified Advisors’ experience with 21/64 while affording opportunities for peer learning. On the consulting side, Stefanie facilitates multigenerational family meetings, coaches donors and professionals of all ages, moderates and facilitates panels and trainings, and publicly represents 21/64 in the field. Her innate curiosity about people and desire to foster mutuality, combined with her natural leadership and relational communication skills all come into play with this role.

Stefanie has extensive professional experience and a deep understanding of the social sector, having worked directly with the boards, volunteer committees, staff, and advisors of more than 200 private foundations and public charities. She joined 21/64 after founding and leading a philanthropic consulting practice, where she specialized in working with private foundations and the people who govern them. Prior to establishing her practice, Stefanie spent 14 years at Foundation Source where she ultimately served as the firm’s National Director of Client Services. In this role, she supervised more than 30 private client advisors and led the engagement, service, and experience initiatives for more than 1,700 private foundations while helping to advance a consultative approach to developing relationships and providing strategic operational support to foundations of all sizes and structures. She also has intimate experience with the challenges of being both a professional and volunteer fundraiser, having worked as a development officer for an internationally renowned dance company, an academic medical center, and a private university during the first half of her career.

A native and longtime resident of Connecticut, Stefanie is a trustee for Fairfield Public Library and volunteers as a sous chef with City Seed’s Sanctuary Kitchen in New Haven. She lives with her husband and teenage daughter and a college-age son who occasionally returns home for a homecooked meal and playtime with the family’s two dogs.  She is the creator and host of Giving Voices: a podcast featuring stories told by and about philanthropists.

Email: [email protected]

Schedule Your Post Training Support Call

We invite you to schedule a complimentary 30-minute call to discuss the benefits of being a 21/64 Certified Advisor, to explore your needs coming out of the training and how you can begin integrating this work in your practice.

Schedule with Stefanie Borsari using this scheduling link.

Day 1: October 22, 2025, 9:00am - 4:30pm CT

Pre Work Before Day 1 (Plan for 30 minutes)

The below should take you approximately 30 minutes.  Please plan ahead and schedule time to complete the pre work prior to Day 1.

To Watch/Read:

  • Changing Behavior– Peter Bregman
    • This piece sets the stage for learning on Day 1 and offers a glimpse at how we’ll be shifting our thinking.
  • Jam Study – Sheena Iyengar
    • This brief video by researcher, Sheena Iyengar, gives us a glimpse into the complexity of choice.


Optional:

Tools and Materials to Bring to Day 1

  • Notepad and writing utensils. 
  • A mobile device (phone, tablet etc).

Peter Bregman's Article on Changing Behavior

Chapter Two of Generation Impact

Self & Role

Venn diagram with two overlapping circles labeled SELF and ROLE. The intersection is shaded and contains a check mark, indicating alignment between personal identity and role.

Purpose, Objectives, and Process (POP)

Screenshot of a document outlining the purpose, objectives, and process of a facilitation approach, with bullet points under each heading detailing skills, techniques, and collaborative learning goals.

Group Agreements

A slide with text outlining a meetings purpose, objectives, process, and best practice group agreements. In the bottom right corner, there is an illustration of a red bicycle.

Lay It On the Line

A document explains an activity called Lay It On the Line, outlining its purpose, objectives, and process for discussing assumptions about family, wealth, and philanthropy using a Yes-No spectrum and group participation.

Active Listening

A text-based document outlines the purpose, objectives, listening continuum, and building blocks of active listening, including steps such as ignoring, pretending, selective, attentive, and empathic listening.

Generational Profiles

A poster describes Generation X with colorful drawings and keywords like Woodstock, Cold War, and Moon landing. Beside it, text lists objectives and generational groups from Traditionalist (1928-1945) to Generation Z (1997-2012).

Identity Equation

A diagram with three blue circles: “What am I inheriting?” plus “Who am I?” equals “What do I want to do about it?”.

What Am I Inheriting?

A person writes with a red pen on a family history chart filled with names, notes, and lines. Text nearby describes the purpose and objectives of mapping family history on values and legacies.

Money Messages

A document titled money messages is shown next to a white napkin. Text above outlines a workshops purpose: exploring personal and social assumptions about money, and objectives for examining and discussing money-related behaviors.

Motivational Values

A stack of blue and white cards labeled Motivational Values and Compassion lies on a white surface. Text beside the cards explains the purpose and objectives of clarifying and understanding personal values.

Additional Resources from Day 1

Day 2: October 23, 2025, 8:30am - 3:30pm CT

Pre Work Before Day 2 (Plan for 10-15 Minutes)

The below should take you approximately 10-15 minutes. Please plan ahead and schedule time to complete the pre work prior to Day 2.

  • Read the article: Action Research: The Anchor of OD Practice

    • As you read the section of the article on Entry, think about a typical or challenging Entry scenario you have encountered within the system that you work, that you could roleplay for tomorrow.

Action Research Article

Action Research Cycle

A circular flowchart with six blue boxes: Entry, Data Collection, Feedback, Action Planning, Intervention, and Evaluation & Next Steps, connected by arrows. Text notes its inspired by Kurt Lewins work.

Entry

A document section with the heading Purpose, describing the importance of a consultative tone when engaging clients, followed by bullet-pointed objectives such as using active listening and moving from expert to consultant.

Action Research: Case Study

Data Collection

A section of a document outlining the purpose and objectives for data collection in the Action Research Cycle, emphasizing active listening, session setup, and asking open-ended questions.

Sample Data Collection Questions

A list of 18 reflective questions about philanthropy, family values, and giving, including topics like motivations, family influence, personal impact, and future legacy. A quote by David Whyte is at the top.

Feedback

Screenshot of a document section. The Purpose explains the importance of hearing family members to address generational challenges. Under Objectives, two goals are listed: distinguishing data from interpretation and hearing all voices.

Ladder of Inference

A diagram of the Ladder of Inference, showing steps from Observable Data and Experience up to Take Actions Based on Beliefs, with a reflexive loop and labeled points A and B at the base.

Action Planning & Intervention

A document section titled Purpose explains how to recommend the next best step for a client, and an Objectives list with three bullet points about being a consultative consultant, using intervention tools, and acquiring resources.

Picture Your Legacy

A stack of colorful cards titled PICTURE YOUR LEGACY stands upright on a table. Text beside it describes the purpose and objectives of using these cards for exploring legacy, values, and philanthropic vision.

Evaluation & Next Steps

Screenshot of text outlining the purpose and objectives of evaluating consultations, including assessing success, impact, feedback application, and tools for data collection and evaluation.

Additional Resources from Day 2

  • Quote: Nan Fairbrother, The House in the Country: “Most of us are experts at solving other people’s problems, but we generally solve them in terms of our own and the advice we give is seldom for other people but rather for ourselves.”


For more on Asking Hard Questions:


For more on Data Collection:


Best Practices:

  • Best Practices – Entry
    • Go Slow to Go Fast
    • Consultative, not Expert
    • Establish POP (Purpose, Objectives, Process)
  • Best Practices – Data Collection
    • Have confidence to say sensitive questions
    • Create a preamble including confidentiality and safe space. There may be some emotionality. You’re here as an objective third-party. No skin in the game.
    • Schedule these 3 weeks in advance of a family meeting/close to the family meeting.
    • Last question should be, “What else do you think I should should know?”
    • Don’t unpack what you can’t put back together in the time allowed.
    • Don’t interview people that aren’t going to have a say in the outcome.

Post Training

Evaluation

If you did not have a chance to finish the evaluation towards the end of training, here is the link: https://2164ss.typeform.com/to/qltwSSzf

Schedule Your Post Training Support Call

We invite you to schedule a complimentary 30-minute call to discuss the benefits of being a 21/64 Certified Advisor, to explore your needs coming out of the training and how you can begin integrating this work in your practice.

Schedule with Stefanie Borsari using this scheduling link.

Participant Contact Sheet

Training Slides

Pictures From Case Study Group Work (optional - decide on if you want to add a note to the LA for facilitators )

Case Study Groups - Data Collection Questions

Combined Family Giving and Business Discussion Questions

Overview

Table of Contents

Overview

This training will be hosted at the headquarters of Community Foundation of Middle Tennessee.

The 21/64 Approach Training and ongoing peer network helps you acquire the personal skills, generational awareness, and technical tools to work more effectively with next-generation funders and multigenerational family enterprise clients.

In this in-person training taking place over two days, you will learn 21/64’s proven methodology for engaging individuals, families, and institutions at the intersection of values and governance. The program is specifically designed to help you more comfortably engage donors and clients in important and often complicated conversations, whether you are new to the field or a seasoned advisor adjusting to new modalities of engaging with clients.

Once you’ve completed the 21/64 Approach Training, you will become a 21/64 Certified Advisor, joining a global network of accredited professionals. You will also have the option of joining the 21/64 Learning Community with free access to continued skill building, next level trainings, the latest resources and tools, and more.

BENEFITS TO PARTICIPANTS

  • Understand assumptions around family, wealth, and philanthropy
  • Acquire fresh facilitation techniques for how to build engagement
  • Apply group dynamics and group process skills
  • Learn to facilitate 21/64 tools to have productive conversations on values, legacy, generational differences, and more
  • Personal and professional development
  • Acquire research and resources on engaging the next generation
  • Interact in small groups and expand your network

WHO SHOULD ATTEND

  • Philanthropic Advisors
  • Community Foundation Professionals
  • Investment Advisors, Private Bankers, and Estate Attorneys
  • Family Office Professionals
  • Foundation Directors
  • Trustees who also staff their family philanthropy

BENEFITS OF CERTIFICATION

The 21/64 approach is practiced worldwide and is today considered a best practice in the field of philanthropy and multifamily enterprise. As a Certified Advisor, you’re telling people that you lead with values and are equipped with the tools and methodology to teach others. Benefits of certification include:

  • Add “21/64 Certified Advisor” to your credentials (signatures, LinkedIn profile, bio, etc.)
  • Enjoy significant discounts on all tools
  • Tap into a global network of professionals on our proprietary social platform, 21/64 Connect.
  • Access to the 21/64 Learning Community (see below)
  • Complimentary post-training “Welcome to the Community” call
  • Access to our annual Certified Advisor gathering (virtual), along with “pop-up” events, and online community conversations for continued practice and skill building
  • Receive resources and the latest articles and research


Participants should plan for a combination of live learning in person, small group participant discussion, and independent work before and between sessions.

Live Learning:

Wednesday, October 22, 2025, 8:30am/9:00am – 4:30pm CT

Thursday, October 23, 2025, 8:00am/8:30am – 3:30pm CT

The training will be held at Community Foundation of Middle Tennessee, located at 3421 Belmont Blvd, Nashville, TN 37215.

Click here for a list of recommended hotels for your consideration.

Pre-work and Between Sessions:

We will share some independent work, readings, and videos to prepare for the training.

Light work will be assigned between the sessions.

Materials

You will receive pre-training details electronically and hard materials once you arrive at the training. Agenda, pre-reading, and additional logistics will be shared via email and on 21/64 Connect.

21/64 Learning Community (Optional)
The 21/64 Learning Community is a community of Certified Advisors who want to deepen their learning and develop power in their practice. As a Certified Advisor who is part of the Community, you will have free access to a full complement of virtual Workshops and advisor gatherings throughout the year. Benefits include:

  • Join all 21/64 Workshops at no additional cost
  • Access Learning Community-only events 
  • Receive 20% discounts on next level trainings
  • Receive 30% discounts on repeat 21/64 Approach trainings
  • Serve as our thought partners when beta-testing new tools and ideating future programming


You can sign up for the Learning Community when you register below. To do so, there will be an additional fee of $300. After one year, your certification and Learning Community fee will auto-renew at a rate of $365 annually (you can opt out at any time).

Get Started

Location & Hotels

The training will be held at Community Foundation of Middle Tennessee, located at 3421 Belmont Blvd, Nashville, TN 37215. 

The schedule is Wednesday, October 22, 9:00am – 4:30pm CT and Thursday, October 23, 8:30am – 3:30pm CT.

We’ll be providing a light breakfast 30 minutes before the training program begins on both days.

Pre-Training Letter from 21/64

Dear Colleagues,

On behalf of the 21/64 team and our sponsoring partner, Community Foundation of Middle Tennessee, we’re looking forward to hosting you in Nashville for the 21/64 Approach Training, October 22-23, 2025. Your two-day program will be led by 21/64 Executive Director and President Danielle Oristian York and me, Stefanie Borsari, Senior Consultant and Community Engagement Director.

 Learning will take place on two levels which will be discussed in more detail when we are all together: understanding how identity and lived experiences inform our professional roles and gaining new frameworks and tools to bring back to the people with whom you work. We look forward to providing an opportunity for you to grow, both personally and professionally, in an open space where you can practice and learn with your peers. 

This email covers access to program materials and prework, logistics, and scheduling. In the meantime, please let us know if you have any questions or expectations for training that you’d like us to know about in advance. 

LOCATION

The training will take place Community Foundation of Middle Tennessee, located at 3421 Belmont Blvd, Nashville, TN 37215. 

FOOD

A light breakfast will be provided each morning, starting a half hour before the training starts, and a lunch is also included on both days. Thank you for advising us of your dietary restrictions during the registration process. We will make every effort to accommodate your various needs.  

SCHEDULE

  • Day 1 Training: Wednesday, October 22nd, 8:30 am – 4:30 pm (program starts at 9:00 am)
  • Day 2 Training: Thursday, October 23rd, 8:00 am – 3:30 pm (program starts at 8:30 am)


HAPPY HOUR

Please join us for a community convening with local 21/64 Certified Advisors and friends immediately following the training on Day 1. While this is optional, we encourage you to attend for casual fellowship and connecting with your cohort colleagues and Nashville-area 21/64 community members. We’ll gather on Wednesday, October 22 from 5:00 — 7:00 pm at The Greenhouse for drinks and light bites. I’ll send the official invitation from Paperless Post soon and request the favor of an RSVP to that when it arrives (thank you!).  

ACCESS MATERIALS AND MEET YOUR COHORT 

21/64 Connect is an interactive space where hundreds of Certified Advisors share, learn, and stay connected. We have created a dedicated (and private) space on our platform for your training cohort. First, visit this link to join your cohort and to access materials for the course. Follow these easy steps:

  • Click on the above link. Then, if this is your first visit, create your login and password.
  • Add a bio and headshot. This is important because it lets your colleagues know with whom they will be sharing space. In addition to your bio, feel free to add some personal interests and fun facts. What is a question you would want someone to ask you?
  • Be sure to add your geographic location and area of specialty when prompted.


PREWORK FOR TRAINING

Please complete before you arrive to training on Wednesday, October 22nd:

Watch/Read:

  • Changing Behavior – Peter Bregman
    • This piece sets the stage for learning on Day 1 and offers a glimpse at how we’ll be shifting our thinking. 
  • Jam Study – Sheena Iyengar
    • This brief video by researcher, Sheena Iyengar, gives us a glimpse into the complexity of choice.


Optional:

Please complete before Day 2 of training on Thursday, October 23:

  • Read the article: Action Research: The Anchor of OD Practice
    • As you read the section of the article on Entry, think about a typical or challenging Entry scenario you have encountered, within the system that you work, that you could roleplay for Day 2.


HOTELS AND PARKING

For your convenience and consideration, here’s a list of area hotels near the Community Foundation of Middle Tennessee, our training venue. 

Our time together will be interactive and jam-packed with learning and connection opportunities. As always, please don’t hesitate to reach out with any questions beforehand. See you soon!

Warmly,  
Stefanie Borsari
Community Engagement Director and Senior Consultant

Post Day 1 - Drinks and Appetizers with Colleagues

Please join us for a community convening with local 21/64 Certified Advisors and friends immediately following the training on Day 1. While this is optional, we encourage you to attend for casual fellowship and connecting with your cohort colleagues and Nashville-area 21/64 community members. We’ll gather on Wednesday, October 22 from 5:00 — 7:00 pm at The Greenhouse for drinks and light bites.

Facilitator Bio - Danielle Oristian York

Danielle Oristian York is a creative systems-thinker, a leader and fan of embracing complexity.  She has been a consistent leader in the field, spending 24 years helping families, leaders, organizations, and communities have complicated conversations about change, identity and the future. Danielle is Executive Director of President of 21/64, a nonprofit practice serving next gen and multigenerational families. She is an expert facilitator, trainer, and keynote speaker.  She brings a constant curiosity and warm presence to work with new and seasoned leaders, family enterprises, family foundations and the advisors who serve them. Among her many writings, Danielle co-authored the chapter “Values That Matter” in Tom McCullough and Keith Whitaker’s book Wealth of Wisdom: Top Practices for Wealth Families and their Advisors, published by Wiley in 2022.  Prior to joining the 21/64 team, Danielle worked at UBS and Pitcairn Family Office, this experience provided different vantage points from which to catalyze and support strategic decision making. Danielle lives in Boston with her husband and two terrific kids.

Facilitator Bio - Stefanie Borsari

Stefanie Borsari serves in a dual role that lives at the nexus of 21/64’s two major divisions, training/community and consulting, a position that draws on her diverse range of skills and professional and personal interests.

As Community Engagement Director, Stefanie sustains a vibrant global community of Certified Advisors who have chosen 21/64 as their home for professional development. She organizes workshops and convenings that enhance Certified Advisors’ experience with 21/64 while affording opportunities for peer learning. On the consulting side, Stefanie facilitates multigenerational family meetings, coaches donors and professionals of all ages, moderates and facilitates panels and trainings, and publicly represents 21/64 in the field. Her innate curiosity about people and desire to foster mutuality, combined with her natural leadership and relational communication skills all come into play with this role.

Stefanie has extensive professional experience and a deep understanding of the social sector, having worked directly with the boards, volunteer committees, staff, and advisors of more than 200 private foundations and public charities. She joined 21/64 after founding and leading a philanthropic consulting practice, where she specialized in working with private foundations and the people who govern them. Prior to establishing her practice, Stefanie spent 14 years at Foundation Source where she ultimately served as the firm’s National Director of Client Services. In this role, she supervised more than 30 private client advisors and led the engagement, service, and experience initiatives for more than 1,700 private foundations while helping to advance a consultative approach to developing relationships and providing strategic operational support to foundations of all sizes and structures. She also has intimate experience with the challenges of being both a professional and volunteer fundraiser, having worked as a development officer for an internationally renowned dance company, an academic medical center, and a private university during the first half of her career.

A native and longtime resident of Connecticut, Stefanie is a trustee for Fairfield Public Library and volunteers as a sous chef with City Seed’s Sanctuary Kitchen in New Haven. She lives with her husband and teenage daughter and a college-age son who occasionally returns home for a homecooked meal and playtime with the family’s two dogs.  She is the creator and host of Giving Voices: a podcast featuring stories told by and about philanthropists.

Email: [email protected]

Schedule Your Post Training Support Call

We invite you to schedule a complimentary 30-minute call to discuss the benefits of being a 21/64 Certified Advisor, to explore your needs coming out of the training and how you can begin integrating this work in your practice.

Schedule with Stefanie Borsari using this scheduling link.

Day 1: October 22, 2025, 9:00am - 4:30pm CT

Pre Work Before Day 1 (Plan for 30 minutes)

The below should take you approximately 30 minutes.  Please plan ahead and schedule time to complete the pre work prior to Day 1.

To Watch/Read:

  • Changing Behavior– Peter Bregman
    • This piece sets the stage for learning on Day 1 and offers a glimpse at how we’ll be shifting our thinking.
  • Jam Study – Sheena Iyengar
    • This brief video by researcher, Sheena Iyengar, gives us a glimpse into the complexity of choice.


Optional:

Tools and Materials to Bring to Day 1

  • Notepad and writing utensils. 
  • A mobile device (phone, tablet etc).

Peter Bregman's Article on Changing Behavior

Chapter Two of Generation Impact

Self & Role

Venn diagram with two overlapping circles labeled SELF and ROLE. The intersection is shaded and contains a check mark, indicating alignment between personal identity and role.

Purpose, Objectives, and Process (POP)

Screenshot of a document outlining the purpose, objectives, and process of a facilitation approach, with bullet points under each heading detailing skills, techniques, and collaborative learning goals.

Group Agreements

A slide with text outlining a meetings purpose, objectives, process, and best practice group agreements. In the bottom right corner, there is an illustration of a red bicycle.

Lay It On the Line

A document explains an activity called Lay It On the Line, outlining its purpose, objectives, and process for discussing assumptions about family, wealth, and philanthropy using a Yes-No spectrum and group participation.

Active Listening

A text-based document outlines the purpose, objectives, listening continuum, and building blocks of active listening, including steps such as ignoring, pretending, selective, attentive, and empathic listening.

Generational Profiles

A poster describes Generation X with colorful drawings and keywords like Woodstock, Cold War, and Moon landing. Beside it, text lists objectives and generational groups from Traditionalist (1928-1945) to Generation Z (1997-2012).

Identity Equation

A diagram with three blue circles: “What am I inheriting?” plus “Who am I?” equals “What do I want to do about it?”.

What Am I Inheriting?

A person writes with a red pen on a family history chart filled with names, notes, and lines. Text nearby describes the purpose and objectives of mapping family history on values and legacies.

Money Messages

A document titled money messages is shown next to a white napkin. Text above outlines a workshops purpose: exploring personal and social assumptions about money, and objectives for examining and discussing money-related behaviors.

Motivational Values

A stack of blue and white cards labeled Motivational Values and Compassion lies on a white surface. Text beside the cards explains the purpose and objectives of clarifying and understanding personal values.

Additional Resources from Day 1

Day 2: October 23, 2025, 8:30am - 3:30pm CT

Pre Work Before Day 2 (Plan for 10-15 Minutes)

The below should take you approximately 10-15 minutes. Please plan ahead and schedule time to complete the pre work prior to Day 2.

  • Read the article: Action Research: The Anchor of OD Practice

    • As you read the section of the article on Entry, think about a typical or challenging Entry scenario you have encountered within the system that you work, that you could roleplay for tomorrow.

Action Research Article

Action Research Cycle

A circular flowchart with six blue boxes: Entry, Data Collection, Feedback, Action Planning, Intervention, and Evaluation & Next Steps, connected by arrows. Text notes its inspired by Kurt Lewins work.

Entry

A document section with the heading Purpose, describing the importance of a consultative tone when engaging clients, followed by bullet-pointed objectives such as using active listening and moving from expert to consultant.

Action Research: Case Study

Data Collection

A section of a document outlining the purpose and objectives for data collection in the Action Research Cycle, emphasizing active listening, session setup, and asking open-ended questions.

Sample Data Collection Questions

A list of 18 reflective questions about philanthropy, family values, and giving, including topics like motivations, family influence, personal impact, and future legacy. A quote by David Whyte is at the top.

Feedback

Screenshot of a document section. The Purpose explains the importance of hearing family members to address generational challenges. Under Objectives, two goals are listed: distinguishing data from interpretation and hearing all voices.

Ladder of Inference

A diagram of the Ladder of Inference, showing steps from Observable Data and Experience up to Take Actions Based on Beliefs, with a reflexive loop and labeled points A and B at the base.

Action Planning & Intervention

A document section titled Purpose explains how to recommend the next best step for a client, and an Objectives list with three bullet points about being a consultative consultant, using intervention tools, and acquiring resources.

Picture Your Legacy

A stack of colorful cards titled PICTURE YOUR LEGACY stands upright on a table. Text beside it describes the purpose and objectives of using these cards for exploring legacy, values, and philanthropic vision.

Evaluation & Next Steps

Screenshot of text outlining the purpose and objectives of evaluating consultations, including assessing success, impact, feedback application, and tools for data collection and evaluation.

Additional Resources from Day 2

  • Quote: Nan Fairbrother, The House in the Country: “Most of us are experts at solving other people’s problems, but we generally solve them in terms of our own and the advice we give is seldom for other people but rather for ourselves.”


For more on Asking Hard Questions:


For more on Data Collection:


Best Practices:

  • Best Practices – Entry
    • Go Slow to Go Fast
    • Consultative, not Expert
    • Establish POP (Purpose, Objectives, Process)
  • Best Practices – Data Collection
    • Have confidence to say sensitive questions
    • Create a preamble including confidentiality and safe space. There may be some emotionality. You’re here as an objective third-party. No skin in the game.
    • Schedule these 3 weeks in advance of a family meeting/close to the family meeting.
    • Last question should be, “What else do you think I should should know?”
    • Don’t unpack what you can’t put back together in the time allowed.
    • Don’t interview people that aren’t going to have a say in the outcome.

Post Training

Evaluation

If you did not have a chance to finish the evaluation towards the end of training, here is the link: https://2164ss.typeform.com/to/qltwSSzf

Schedule Your Post Training Support Call

We invite you to schedule a complimentary 30-minute call to discuss the benefits of being a 21/64 Certified Advisor, to explore your needs coming out of the training and how you can begin integrating this work in your practice.

Schedule with Stefanie Borsari using this scheduling link.

Participant Contact Sheet

Training Slides

Pictures From Case Study Group Work (optional - decide on if you want to add a note to the LA for facilitators )

Case Study Groups - Data Collection Questions

Combined Family Giving and Business Discussion Questions

Pre-Training Letter from 21/64
Agenda