Executive Director Mastermind

The Executive Director Mastermind is designed to provide a confidential, peer-driven, and facilitated space for EDs to overcome shared organizational challenges, accelerate personal and professional growth, and strategically plan for their personal development.

The cohort will be curated for maximum diversity and relevance, ensuring one person per sector and similar budget scales to foster a rich cross-pollination of ideas and experiences.

⭐️ The program is structured around three critical areas of executive leadership:

  1. Organizational Mastery: Scaling operations, funding, and impact.

  2. Leadership & Team Dynamics: Developing self and others for sustainable success.

  3. Strategic Career Development: Preparing for the next level of executive leadership.

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Program Term
January - December 2026


Cohort Size
7 - 10 Executive Directors


Commitment
Monthly virtual mastermind sessions, dedicated time for peer-to-peer connection, and two in-person retreats.


Participants
Executive Directors of with organizational operating budgets of $500,000 to $3 Million.


Cost:
$1000 per person

$650 per person for the first cohort

  • Approximately 90 minutes each

    • Mild Facilitation: A professional facilitator guides the agenda, but the peer group leads the discussion and accountability.

    • Guiding Questions: Sessions will always be launched by a reflective question for the group

    • Hot Seats: One ED presents a live, immediate executive-level challenge for the group to deploy their collective expertise and brainstorm solutions, and offer accountability.

    • Mini-Talks: Short, 10-15-minute presentations by an expert on a targeted skill, followed by a Q&A. Topics align with the Key Skill Development Areas.  

    • Retreat 1: Launch & Vision (January 2026): The Community Builder. A day-long session focused on deep relationship building, establishing trust, defining personal and professional goals for the year, and an initial mini-institute focused on Strategic Career Development.

    • Retreat 2: Strategy & Closure (Fall 2026):The Growth Accelerator. A day-long session focused on evaluating progress, long-term succession planning, developing concrete action plans for achieving the next organizational and career milestones, and creating a framework for post-mastermind peer accountability.

  • Community Platform: A dedicated space for cohort members to share resources, ask real-time questions, and schedule one-on-one connections to create community and sustained support throughout the year.

Program Structure & Format

Key Development Areas & Focus Topics

Drawing from the most critical needs identified by EDs, monthly sessions and mini-talks will center on the following high-priority competencies:

Organizational Mastery

  • Financial Scenario Planning & Cash Flow Optimization: Analyzing financial metrics to drive mission-critical Values-Aligned Decision Making and scenario planning, moving beyond basic budgeting. 

  • Advanced Major Donor Strategy: Implementing a tiered Relationship Cultivation pipeline, mastering high-stakes ask scenarios, and effectively positioning the ED as the strategic face of a scaling organization. 

  • Scaling Operations and Efficiency: Creating robust, repeatable processes across departments and leveraging data management and evaluation systems to transition from reactive to predictive organizational management. 

  • Strategic Board Partnership: How and when to work with a board or advisory group on strategy (not tactics), focusing on high-level fiduciary duties, fundraising engagement, and refining the Board/ED partnership model.

Leadership & Team Dynamics

  • Building Executive Capacity & Delegation: Advanced methods of Delegating and Succession Planning by recognizing and cultivating executive skillsets within the team. Shifting from task assignment to empowering direct reports to own and drive outcomes. 

  • Strategic Staffing Structure: Designing innovative Staffing Structure and Hiring models (including contract/full-time mix) that optimize resource allocation and sustain long-term fundraising capacity. 

  • Managing Executive Expectations: Proactively managing the expectations of board, staff, and external stakeholders, focusing on communication frameworks for navigating the complexity of scaling and growth. 

  • Mastering Difficult Conversations: Utilizing executive presence and emotional intelligence to lead difficult conversations with impact (board governance, high-level performance issues, etc.).

Strategic Career Development

  • Competency Gap Analysis: Rigorously assessing current executive competencies against the requirements for organizations in the next budget tier ($3M - $10M+). 

  • The Executive Search Deep Dive: How to package and prepare for your own career growth, including advanced resume positioning, utilizing professional networks, and negotiating total compensation packages that reflect executive value. 

  • Executive Storytelling: Developing a sophisticated Storytelling framework to communicate mission impact strategy designed for major donors, executive recruiters, and peer CEOs, moving beyond anecdotal sharing to communicating systemic impact.