Planning Facilitation

Shane Kinkennon designs and runs collaborative problem-solving experiences and projects.

Three puzzle pieces with arrows indicating movement, one is plain white, one is striped, and one is solid brown.
Illustrated gear icon with diagonal lines

I facilitate leadership groups seeing things clearly, leaving no stone unturned, cultivating commitment, and embracing accountability for real results.

I frequently help clients evolve traditional strategic-planning calendar into a more dynamic, timely, responsive approach to strategy-setting.

And I help management teams and boards of directors discover new ways to hold yourselves truly accountable for strategies you set, including evolving annual operating planning and budgeting accordingly to truly bring strategy to life.

Cartoon wooden gear illustration with a circular center and multiple teeth.
Illustration of a gold and black medal with a checkmark symbol.

I am a certified master facilitator.

Curved upward arrow icon

I am professionally trained to design and run productive, fun, and engaging meetings that help groups and teams prepare to achieve great results.

  • “Shane’s approach to facilitation is thorough, and his style is energetic. He can keep a tough group of busy, hard-charging people moving and really drive to consensus. He is excellent.”

    — Faryar Shirzad, Chief Policy Officer, Coinbase

  • “Shane is supremely talented at uncovering whatever might be the root problem and facilitating creative solutions. He makes remarkable use of his many gifts and has left an indelible mark on me and our entire organization.”

    — Cedric X. Bryant, PhD, FACSM, President & Chief Science Officer, American Council on Exercise

  • “This is the moment for courageous leadership in the winter outdoor industry. Working with Shane, it gets easier to both consider big ideas and make tough commitments on implementation. It’s one way to get more serious about planning to make a real difference.”

    — Nick Sargent, President, Snowsports Industries America

Signs It’s Time to Facilitate Differently

You’re growing, but decision-making feels stuck.

  • The last retreat had great vibes but fuzzy takeaways.

  • The board and staff keep talking past each other.

  • You’re facing real change—and need shared direction, not just shared air.

If any of this feels familiar, I can help your team do more than nod along.

This work creates the space where clarity and commitment finally click.

  • We dig into what’s really going on—not just what’s safe to say.

  • We make sure strategy connects to budgets, roles, and timelines.

  • We leave knowing who’s doing what—and why it matters.

When Your Strategy Needs to Get Real

Too often, planning sessions are full of ideas but short on alignment. I help groups name what matters, face what’s hard, and decide what comes next.

Strategic planning is rarely just about strategy. It’s about surfacing assumptions, challenging defaults, and getting people to show up differently. That’s what I facilitate.

Here’s how I help.

  • Executive Coaching

    For C-suites and senior managers

    Unlock new mindsets and methods to inspire teams, equip them to lead change, and actually hold them accountable for results.

    LEARN MORE

  • Management Consulting

    For nonprofit leadership teams

    Devise and lead change in response to intractable organizational challenges, aligning strategy and function for mission delivery.

    LEARN MORE

  • Board Consulting

    For nonprofit boards of directors

    Sharpen focus on those activities and areas that deliver the absolute highest value to management of the organization you govern and serve.

    LEARN MORE

  • Planning Facilitation

    For boards, coalitions, and more

    Have structured, disciplined conversations about where your organization needs to go, how it will get there, and what measurable outcomes it will achieve.

    learn more

  • Strategic Communications

    For senior teams that need to break through

    Craft and deliver messages and narratives to favorably influence staffs, policymakers, and other stakeholders, in change-leadership scenarios and far beyond.

    learn more

  • Fractional Executive

    For short-term leadership needs

    Occasional interim or fractional executive leadership for organizations that need someone to engage easily, learn quickly, and bring a facilitative-leadership touch.

    Learn more

Frequently Asked Questions

  • What kinds of planning do you facilitate?
    Everything from strategic planning to decision-making retreats, annual goal setting, and board alignment sessions.

  • Is this just about strategy documents?
    No—it's about surfacing what's real, deciding what matters, and making plans that actually move.

  • Do you work with boards or staff teams?
    Both, depending on the moment—sometimes separately, sometimes together.

  • How long is a typical engagement?
    Some are single sessions; others span several weeks with multiple touchpoints and outputs.

  • Can you help if we're mid-plan but off track?
    Absolutely—that’s often when the best work happens.

  • How do we start?
    Book a short call; I’ll ask what’s happening, and we’ll take it from there.