Coaching Workshops, Small Group Training and One-on-one Coaching


Bold Asking® workshops and retreats are personalized, collaborative and interactive experiences designed for the entire team.  The workshops focus on learning how to effectively partner together and comfortably communicate the organization’s vision and stories and build donor relationships and giving.  Participants learn about prospect identification and cultivation, pre-solicitation conversations, partnering in making the ask and stewarding donors. Workshops are crafted specifically to support and enhance giving by all constituents. For health care and hospital clients, we focus on grateful patient and family giving.

Workshops cover: 

  • Principles of the psychology and neuroscience findings in giving

  • The role of gratitude and the power of meaningful philanthropy

  • Establishing a major gift culture

  • Effective donor conversations

  • Creating your own Signature Language and crafting the Three Most Important Questions

  • Best practices for elevating performance and engagement of your team

  • Engaging physicians and caregivers (for health care and hospital fundraising clients).

Workshops feature videotaped interviews with philanthropists and highly successful volunteer fundraisers. They candidly discuss how they approach donor conversations, what they consider when making a transformational gift, how they have gotten past their own fears of fundraising, specific donor conversations they employ, and easy, practical tips for all stages leading up to and making “the ask.”

All interactive workshops include:

  • Toolkits to support ongoing work

  • Donor Scripts

  • Role-playing to promote comfort and confidence in applying what’s learned 

Curated workshop topics may include:

  • Becoming a Philanthropy Leader

  • Introduction: Individual and Group Exercises

    • What do you value about this organization?

    • What are you grateful for?

    • Why have you chosen to join the cause?

    • What are your personal goals for your involvement?

  • Story-telling to Support Transformational Giving: Group Exercises

    • The power of passion. What’s your story?

    • Stories: How the organization has impacted your life

    • Creating Your Signature Language

  • Major Gift Philanthropy: Building Meaningful Relationships - Leaning into the Gift

    • Major Gifts 101

    • Big Vision = Big Gifts: crafting your message

    • Using your “Signature Language”

    • Rules for Active Listening

    • Connecting: The “Three Magical Questions”

    • Power Up your Story-telling with Passion: What Works and Why – Telling your Story

    • Starting the Conversation

    • Pre-solicitation Conversations

    • Staff-Volunteer Scripts for Cultivation

    • Staff-Volunteer Scripts for Closing

    • Making the Ask, Boldly!

    • Saying Thank You Abundantly: Roles in Stewardship

  • Group Exercise

    • Your three most persuasive messages for supporting transformation.

Facilitated Role-playing: Guided through small group break-out sessions to practice lessons learned and tools. Role-playing is also a time when volunteers and staff can build and practice their partnering skills. 

Follow up workshops, sometimes crafted as a Lunch ‘n Learns, provide more time for practice and role-playing.  This is a time for both volunteers and staff to try out and practice the principles, signature language and story-telling presented in previous workshops. 

Webinar Options
In some cases, webinars are utilized before the in-person workshops.  These help to convey basic information and set the stage for the in-person workshop or retreat.  We use the ZOOM communications platform which supports virtual interactive experiences.  Webinars may also be recorded for future reference.

Small Group Training

Oftentimes, learning occurs best in small group settings. Bold Asking® training may be delivered through a combination of large workshops followed by small group sessions that address special needs.  Small group sessions are designed for your development team, the C-suite, Campaign Committees or physician groups for our hospital fundraising clients.

Curated Small Group Topics include:

  • Strategies for building and sustaining board engagement in philanthropy

  • Strategies for building effective physician and caregiver partnerships and engagement (for health care and hospital clients)

  • Creating and sustaining partnerships with the CEO, executive team and board members

  • Navigating effective donor conversations:  getting the meeting, effective cultivation, pre-solicitation, and solicitation language

  • Step-by-step process for making hospital visits (for health care and hospital clients)

  • Role-playing and toolkits 

Personalized one-one-one coaching

Occasionally, virtual or in-person one-on-one coaching is needed to support staff and/or the CEO in a more personalized way.  VPG has extensive experience providing one-on-one coaching for hospital presidents, non-profit CEOs, board chairs and development staff, in consultation with development leaders.  We have deep experience in mentoring institutional leaders and major gift officers. 

During one-on-one structured coaching, we use mutually agreed upon benchmarks and metrics to guide the coaching.  Coaching may also support individual major gift officer skill development. This approach ensures that optimum results are consistently reinforced.  One-on-one coaching typically augments our workshops or small group training.  Coaching is frequently delivered in once or sometimes twice monthly virtual or personal meetings for a period of time.

Board and staff at Beth Israel Deaconess - Milton practice making “the ask” during a Bold Asking ®  workshop.

Board and staff at Beth Israel Deaconess - Milton practice making “the ask” during a Bold Asking® workshop.

Susan speaks to a workshop on hospital culture of philanthropy at the San Andres Univeristy in Buenos Aires, Argentina.

Susan speaks to a workshop on hospital culture of philanthropy at the San Andres Univeristy in Buenos Aires, Argentina.