Private counsel for high-stakes leaders

We help CEOs, foundation leaders, and board chairs make high-stakes decisions and lead through them with clarity and confidence.

You get practical strategy, sound judgment, and a plan your organization can run with.

Who we are

Glassroot Partners is a private advisory and leadership firm for high-stakes decision makers.

We work with two kinds of clients:

Nonprofit and foundation leaders

who need clear strategy, stronger boards, and sustainable results.

Business executives

who need steady, judgment-based coaching to lead well under pressure.

And through Impact Boardroom, we make that same caliber of guidance available to a wider network of nonprofit executives, often sponsored by boards, companies, and foundations.

In short:
We advise leaders. We coach leaders. And we develop the next generation of them. We bridge vision and velocity, helping leaders turn clarity into motion.

What we do

1

Nonprofit & Foundation Advisory

Clarity, alignment, and sustainable strategy for mission-driven organizations.

We advise nonprofit and foundation leaders through complex strategic and organizational decisions.

Our role is to bring clarity to the room, align leadership and boards, and translate big goals into clear, workable plans.

  • Typical work includes:
  • Strategic planning and board alignment
  • Leadership transitions and succession planning
  • Capital campaigns, fundraising strategy, and communications clarity
  • Foundation setup and philanthropic structure
  • You'll leave with:
  • A concise written plan
  • Clear priorities and ownership
  • Confidence communicating with donors and stakeholders

2

Executive Leadership Coaching

Steady counsel and structure for leaders navigating complexity and change.

We coach CEOs, founders, and portfolio executives who lead in fast-moving or high-pressure environments.

Our coaching builds self-awareness, sharper decision-making, and the calm, consistent presence teams rely on.

  • Common Scenarios:
  • New CEO transitions and post-acquisition integration
  • Founder-to-operator shifts and culture resets
  • Board and investor alignment
  • Leadership growth, communication, and executive presence
  • You'll gain:
  • Better decisions with less friction
  • Stronger trust from boards and teams
  • Sustainable leadership habits that hold under pressure

3

Impact Boardroom

Group-based executive coaching for nonprofit leaders seeking real-time strategy, accountability, and growth.

Impact Boardroom brings our private advisory and coaching model into a small-group format, giving nonprofit leaders the same caliber of strategic guidance trusted by Fortune-level executives.

  • What it includes:
  • Group Coaching — Two live calls per month (60 minutes each).
  • Strategy Clinic — Monthly working session to refine strategy, plans, and key decisions.
  • Private Calls — Private 1:1 sessions with Matt to align goals and priorities.
  • Monthly Cohort Call — Small-group advisory session for deeper analysis and accountability.
  • Practical Tools, Short Exercises, and Peer Learning — that you can apply right away.
  • Optional Private Cohort — for boards, companies, and foundations sponsoring multiple leaders.

Impact Boardroom gives nonprofit leaders real-time coaching, structure, and accountability to lead with clarity and confidence.

How our work connects

Each of our three practices (Advisory, Coaching, and Impact Boardroom) stand alone but reinforce each other, forming a complete support system for modern leadership.

Advisory

clarifies organizational direction.

Coaching

strengthens the leader.

Impact Boardroom

scales both to more leaders.

Together, they turn strategy into motion, helping leadership teams make better decisions, move faster, and stay aligned as they grow. This shared approach runs through every engagement, whether it’s a CEO under pressure, a foundation realigning strategy, or a nonprofit scaling responsibly.

Our approach

Start with truth.

We get to the real issues fast.

Decide what matters.

We narrow to the few priorities that change outcomes.

Write it down.

Every engagement ends with clear decisions, next steps, and accountability.

Keep it human.

Mission and numbers stay in balance.

Protect the room.

Privacy enables candor; candor drives progress.

Who we serve

The Principals

Vision + Velocity. Matt defines the path. Mike builds the machine that gets you there. Together, this bridges the gap between insight and implementation, to bring calm, clarity, and momentum to high-stakes environments.

Matt George

Co-Founder

Executive Leadership Coach at Harvard Business School and trusted advisor to CEOs, board chairs, and philanthropists.

Former CEO of a 500-person nonprofit and author of Nonprofit Game Plan and The Nonprophet Prophet.

Matt has spent 30+ years guiding leaders through growth, transition, and high-visibility pressure. He’s known for calm judgment, sharp insight, and the rare ability to hold truth and empathy in the same conversation. Boards and executives rely on him to anchor difficult decisions, rebuild trust, and strengthen leadership teams without theatrics.

Clients describe him as the “steady voice in the storm,” the person they call when clarity and composure matter most.

Mike Silvestri

Co-Founder

CPA, systems architect, and former COO and Chief of Staff across multiple high-growth companies.

Two-time Emmy® Award winner with 15+ years of experience bridging finance, operations, AI, and technology.

Mike bridges finance, operations, AI, and technology to help leaders transform vision into execution. He has built hundreds of systems, workflows, and scalable solutions that connect strategic intent with measurable outcomes. His work combines pragmatic leadership, financial precision, and modern tools, including the integration of AI-driven analysis and automation to make strategy more actionable.

He’s known for practical thinking, disciplined follow-through, and helping organizations move from “idea” to “in motion” without adding complexity.

Discretion and availability

Our work is private and selective, typically by referral. You work directly with us, not a team of associates. We take on a limited number of clients each year. If timing aligns, we move quickly. References are available with client permission.