Facilitation

Why work with a facilitator?

Most meetings are boring and fail to generate meaningful action. And, as a leader, having to plan and lead a session takes you away from fully participating in the discussion. I work with leaders to design engaging, creative gatherings and skillfully facilitate groups to generate insights, make decisions, and craft feasible action plans. I have designed and facilitated a wide range of convenings for business and community leaders, including strategy sessions with 5-15 executives, interactive workshops for ~50 participants, and content for conferences with 150-300 attendees.

Areas of expertise:

  • Strategic planning

  • Leadership development

  • Community engagement and participatory design

  • Board governance

“Alessandra’s superpower is the complex meeting where she has to understand and manage many different personalities. She is diplomatic and never defensive when put on the spot.”

— Wendy, Nonprofit Chief Strategy Officer

Example projects

  • Board Facilitation

    Supported the Executive Director and board of a $35M community partnership through a 1+ year strategic planning effort. Conducted a series of interviews with collective impact leaders across the country to understand best practices and inform the strategic plan. Designed and facilitated board meetings to develop of the new vision for the organization and successfully renew its primary source of funding.

  • Strategic Planning

    Facilitated the executive leadership team and key members of the board through the development of a 3-year strategic plan for an $20M community organization focused on homelessness and unemployment. The participatory process included a series of meetings, interviews, and group working sessions across the organization and also incorporated client perspectives.

  • Leadership Development

    Designed and delivered a series of new professional development courses for managers at a high-growth organization including: Understanding Your Leadership Style and Strengths, Personal Mastery, Productivity & Time Management, Managing Up & Across, Difficult Conversations, The Coaching Approach to Leadership, Building Effective Teams, and Goal Setting.

  • Community Engagement

    Launched and led a year-long series of meetings with civic leaders focused on improving democratic participation among underrepresented communities. The effort included cataloguing existing efforts across the region to identify strengths and gaps, using a new tool to map out barriers to voting, and facilitating a community-based research project to understand perspectives on civic engagement.