Planning Facilitation

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

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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.

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I am a certified master facilitator.

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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

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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.

Relieve the pressure so you can lead well.

Leadership Development

Lead with more purpose

Unlock executive potential with tools that stick. This isn’t about fixing what’s broken. It’s about sharpening what’s already strong.

Effective Facilitator Training

Make meetings move forward

Don’t just run the meeting. Lead the room.

Non-Profit Coaching

Clarity for mission leaders

Coaching for nonprofit execs that clarifies priorities, deepens board alignment, and restores the joy of doing meaningful work

Strategy Development

Bold strategy, built together

Vision without action is just a poster. Collaborate to define bold, grounded strategy that your leaders will believe in—and implement.

Strategic Planning Facilitator

Plans that actually stick

Great plans don’t sit in binders. They shape daily decisions. Facilitation that sparks clarity, drives ownership.

Strategy Advisory Consulting

Decide with more confidence

High-stakes decisions need a second brain. Tap into sharp, candid advisory that turns ambiguity into traction and aligns your exec team fast.

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.