Helping Nonprofit Leaders Navigate Complexity with Clarity & Confidence
For more than 45+ years, I have worked alongside nonprofit organizations as an executive leader, board volunteer, facilitator, consultant, and change agent. Through those experiences, I have learned that successful organizations rarely need more information—they need greater clarity. I serve as a trusted thinking partner to nonprofit leaders, helping boards and executive teams navigate complex challenges, make confident decisions, and strengthen their impact.
I have supported hundreds of organizations across diverse missions, sizes, and communities. Whether addressing strategic priorities, governance challenges, leadership transitions, or organizational change, I help leaders think critically about their future, align around shared goals, and move forward with purpose.
Today's nonprofit environment demands agility, focus, and intentional leadership. Every organization faces unique opportunities and challenges, which is why I do not believe in one-size-fits-all solutions. I work collaboratively with volunteer and staff leaders to design strategic processes that are both structured and flexible—grounded in your organization's current reality, responsive to your unique needs, and focused on achieving meaningful outcomes.
As part of DBD Group, I collaborate with a team of more than 40+ experienced nonprofit professionals who share a commitment to helping nonprofits and faith-based organizations strengthen their capacity, amplify their impact, and realize their vision for the future.
Who I Work With
I partner with nonprofit organizations that are committed to strengthening leadership, improving governance, and increasing community impact, including:
Community-Based Nonprofits
Human Service Organizations
YMCAs, JCCs, Boys and Girls Clubs, Scouting Organizations
Faith-Based Organizations
Foundations
Educational Organizations
Associations and Membership Organizations
What You Can Expect
Organizations that work with me can expect a collaborative and practical approach grounded in experience and focused on results.
Clarity — Helping leaders make sense of complexity and focus on what matters most.
Alignment — Building shared understanding and commitment among boards, staff, and stakeholders.
Engagement — Creating processes that encourage participation, ownership, and meaningful dialogue.
Action — Translating ideas into practical strategies, decisions, and measurable outcomes.
Confidence — Equipping leaders with the insight and direction needed to move forward successfully.
Richard Clegg
Nonprofit Consultant serving nonprofit organizations throughout the Greater Chicago area, the Midwest, and across the country
Consulting Services
Strategic Planning
I help nonprofit boards and leadership teams develop clear, actionable strategies that strengthen impact and position their organizations for long-term success. Through a collaborative planning process, we clarify your mission, identify strategic advantages, define desired outcomes, and create practical roadmaps with measurable goals. The result is a focused strategic plan that guides decision-making, aligns resources, and helps your organization adapt confidently to changing opportunities and challenges.
Board Development & Governance
As a BoardSource Certified Advanced Board Consultant, I help nonprofit boards strengthen governance, improve effectiveness, and provide stronger strategic leadership. Drawing on extensive experience as a nonprofit executive, board member, and board chair, I work with boards and executive leaders to clarify roles, enhance governance practices, and build the capacity needed to advance their mission and achieve greater impact.
CEO/Executive Director Search
A CEO or an Executive Director transition is one of the most significant decisions a nonprofit board will make. With more than 20 years of experience leading nonprofit CEO and executive director searches, I help boards navigate the process with confidence—from defining leadership needs and recruiting candidates to conducting interviews and selecting the right leader. My approach ensures a thoughtful, transparent, and strategic search that positions the organization for future success.
Retreat & Meeting Facilitation
I facilitate engaging workshops, retreats, and leadership gatherings that help nonprofit organizations build alignment, foster meaningful dialogue, and move from discussion to action. Whether in person, virtual, or hybrid, each session is customized to your goals and designed to create clarity, collaboration, and measurable results.
Let’s Start the Conversation
Share a few details about your organization and goals, and I'll provide thoughtful recommendations for how we can work together.