High Table Mastermind by Venture Seed

CEO Leadership Training Program (12-Month Outline)

Program Overview

The High Table Mastermind is an intensive, invitation-only program for CEOs seeking to elevate their leadership capabilities. The program integrates:

The program is designed to fit busy schedules, with virtual sessions (2–3 hours monthly) and one in-person retreat. Participants are expected to commit to active engagement, accountability, and implementing action plans.

Month-by-Month Plan

Month 1: Onboarding and Leadership Assessment

Objective: Establish program foundations and baseline leadership capabilities.

  • Kickoff Session (Virtual, 2 hours): Introduction to the mastermind group, program structure, and GPS framework. Define leadership goals.
  • 360-Degree Assessment: Evaluate strengths and gaps with input from direct reports, peers, and board members.
  • One-on-One Coaching (1 hour): Review assessment and set goals.
  • Action Item: Complete a self-reflection journal.
  • Key Deliverable: Individual Leadership Development Plan (ILDP).

Month 2: Building Self-Awareness and Emotional Intelligence

Objective: Enhance self-awareness and emotional intelligence to lead authentically.

  • Peer Mastermind Session (Virtual, 2 hours): Discuss emotional intelligence and share challenges.
  • Workshop (Virtual, 2 hours): Led by an executive coach on self-regulation and empathy.
  • One-on-One Coaching (1 hour): Apply workshop insights to ILDP.
  • Action Item: Implement an emotional intelligence strategy (e.g., active listening).
  • Key Deliverable: Emotional Intelligence Action Plan.

Month 3: Strategic Thinking and Vision Setting

Objective: Develop skills to craft and communicate a compelling vision.

  • Peer Mastermind Session (Virtual, 2 hours): Discuss vision-setting challenges.
  • One-on-One Coaching (1 hour): Refine vision statement.
  • Action Item: Draft or revise company vision statement.
  • Key Deliverable: Refined Organizational Vision Statement.

Month 4: Building High-Performance Teams

Objective: Master team-building and delegation.

  • Peer Mastermind Session (Virtual, 2 hours): Discuss trust and accountability.
  • Workshop (Virtual, 2 hours): Led by a team dynamics expert on high-performance teams.
  • One-on-One Coaching (1 hour): Develop a delegation plan.
  • Action Item: Delegate a high-priority project.
  • Key Deliverable: Team Delegation Plan.

Month 5: Financial Acumen for CEOs

Objective: Strengthen financial leadership.

  • Peer Mastermind Session (Virtual, 2 hours): Discuss financial decision-making.
  • One-on-One Coaching (1 hour): Review financials and improve oversight.
  • Action Item: Create a financial dashboard.
  • Key Deliverable: Financial Oversight Framework.

Month 6: Midpoint Review and In-Person Retreat

Objective: Reflect on progress and deepen connections.

  • In-Person Retreat (2 days, Location: TBD): Leadership simulations, peer advisory, and scaling workshop.
  • One-on-One Coaching (1 hour, virtual): Update ILDP.
  • Action Item: Implement a scaling strategy.
  • Key Deliverable: Updated ILDP and Scaling Action Plan.

Month 7: Communication and Influence

Objective: Enhance communication to inspire stakeholders.

  • Peer Mastermind Session (Virtual, 2 hours): Discuss influential communication.
  • Workshop (Virtual, 2 hours): Led by a communications expert on storytelling.
  • One-on-One Coaching (1 hour): Practice a high-stakes presentation.
  • Action Item: Deliver a refined presentation.
  • Key Deliverable: Communication Strategy Plan.

Month 8: Navigating Change and Transformation

Objective: Build resilience to lead through change.

  • Peer Mastermind Session (Virtual, 2 hours): Discuss organizational change.
  • One-on-One Coaching (1 hour): Develop a change management plan.
  • Action Item: Initiate a change management process.
  • Key Deliverable: Change Management Plan.

Month 9: Innovation and Digital Transformation

Objective: Foster innovation and leverage technology.

  • Peer Mastermind Session (Virtual, 2 hours): Discuss driving innovation.
  • Workshop (Virtual, 2 hours): Led by a tech strategist on digital trends.
  • One-on-One Coaching (1 hour): Identify a digital initiative.
  • Action Item: Launch a digital transformation pilot.
  • Key Deliverable: Digital Transformation Pilot Plan.

Month 10: Crisis Management and Decision-Making

Objective: Prepare for high-stakes decisions and crises.

  • Peer Mastermind Session (Virtual, 2 hours): Discuss crisis leadership.
  • One-on-One Coaching (1 hour): Develop a crisis response framework.
  • Action Item: Conduct a crisis simulation.
  • Key DeliverableKey Deliverable: Crisis Response Framework.

Month 11: Scaling Leadership and Succession Planning

Objective: Prepare for long-term leadership and growth.

  • Peer Mastermind Session (Virtual, 2 hours): Discuss succession planning.
  • One-on-One Coaching (1 hour): Outline a succession plan.
  • Action Item: Identify and mentor a successor.
  • Key Deliverable: Succession Plan Outline.

Month 12: Final Assessment and Graduation

Objective: Evaluate progress and plan ongoing growth.

  • Peer Mastermind Session (Virtual, 2 hours): Reflect on leadership growth.
  • Final 360-Degree Assessment: Measure growth against initial assessment.
  • One-on-One Coaching (1 hour): Create a post-program roadmap.
  • Graduation Event (Virtual, 2 hours): Celebrate achievements.
  • Action Item: Implement a strategy from the roadmap.
  • Key Deliverable: Post-Program Leadership Roadmap.

Program Features

  • Facilitator: A seasoned CEO coach with 20+ years of experience.
  • Community: Access to a private online platform for peer discussions.
  • Accountability: Monthly check-ins to track progress.
  • Metrics: Progress tracked via assessments, confidence, and organizational outcomes.

Expected Outcomes

  • Enhanced self-awareness and emotional intelligence.
  • Clearer strategic vision and execution capabilities.
  • Stronger team leadership and delegation skills.
  • Improved financial acumen and stakeholder communication.
  • Increased resilience in navigating change and crises.
  • A robust network of peer CEOs for ongoing support.

Notes

  • Scheduling: Virtual sessions on the first Tuesday of each month at 10 AM EST. Retreat in Month 6.
  • Cost: Invitation-only; contact Venture Seed for pricing (ventureseed.com).
  • Eligibility: CEOs of companies with 10–500 employees and $1M–$50M in revenue.

This program draws inspiration from successful mastermind models like Vistage and Tandem Coaching, emphasizing peer support, measurable progress, and tailored coaching.