Planning Facilitation in Chicago, IL

Strong planning can be the difference between a team that moves forward with confidence and one that stalls without direction. We provide planning facilitation services in Chicago, IL, that bring clarity, focus, and momentum to leadership teams and boards.

As a strategic planning facilitator, we help organizations align around priorities, improve decision-making, and turn strategy into action. Our role is to guide conversations that cut through distractions so leaders can transform vision into focus, build commitment, and achieve measurable outcomes.

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Facilitation That Fits Chicago’s Pace and Culture

Chicago organizations operate in a diverse, fast-moving environment where leaders need clarity, alignment, and energy to keep momentum strong. Our planning facilitation services in Chicago, Illinois, are designed to help leadership teams and boards channel their drive into focused strategies that lead to measurable progress.

Our approach is collaborative and practical, shaped by the rhythm of your organization. As a strategic planning facilitator in Chicago, we work with you to identify strengths, uncover obstacles, and build alignment on priorities. Together, we design pathways that give your team confidence, focus, and shared accountability as you move into the next stage of growth.

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Strategic Outcomes Your Team Can Trust

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  • Goals that are practical, measurable, and achievable, not just aspirational

  • Alignment that extends beyond the planning session and into daily work

  • Clear next steps tied directly to ownership and accountability

  • Less confusion, more structured progress toward shared objectives

  • A culture of open, honest dialogue that supports confident decision-making

Speak with an Expert

  • “Members of my Board of Directors are telling me that the planning retreat Shane and his team designed and facilitated for was truly a wonderful experience and the most productive RBFF gathering they have ever been to. I couldn’t agree more.”

    — Dave Chanda, President & CEO, Recreational Boating & Fishing Foundation

  • “Investing in continuous learning and up-skilling is critical for personal and organizational growth. I’ve been a CEO for many years, yet since I invested in working with Shane, I find myself scaling my own value to my business. Our executive team will climb higher mountains thanks to subtle but crucial calibrations resulting from working with Shane.”

    — Virgil Bretz, CEO, MacroHealth

  • “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

How Teams Gain Clarity Through Facilitation

Big ideas lose momentum when teams can’t align on the path forward. Facilitation bridges the gap, helping leaders focus, make clear decisions, and create commitments that last.

Through guided conversations, Shane helps teams cut through the noise, clarify priorities, and turn strategy into action. The result is clarity, confidence, and alignment that drives measurable progress.

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Speak with an Expert

  • Teams experiencing rapid growth but needing a clear roadmap to channel their energy

  • Leaders who want planning sessions to produce action instead of stalled conversations

  • Organizations that have strong ideas but struggle with consistent execution

  • Boards and cross-functional groups seeking alignment to reduce delays in decision-making

  • Nonprofits and mission-driven teams determined to expand their impact without losing focus

Who Planning Facilitation Supports Most

Here’s how we help.

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    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
  • Four hands, three with white gloves and one with a brown sleeve, stacked together in a sign of teamwork or unity.

    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
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    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
  • Illustration of three puzzle pieces in white, yellow, and white with diagonal lines, connected by arrows suggesting assembly.

    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
  • A simple line drawing of a person standing behind a podium, with a speech bubble above them indicating they are speaking.

    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
  • Hand-drawn diagram of a game plan with a blackboard showing a strategy with an X mark and an arrow.

    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
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Frequently Asked Questions

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  • Why should an organization use a facilitator instead of leading planning on their own?
    An outside facilitator brings neutrality and structure that internal leaders often can’t provide. We create a focused environment where every voice is heard and decisions are guided toward clear outcomes without the bias of internal politics.

  • What problems does planning facilitation typically solve?
    It helps resolve common challenges like unclear priorities, meetings that drift without resolution, or teams that struggle to translate ideas into action. For Chicago organizations, facilitation is especially valuable in fast-paced industries where clarity and momentum are critical.

  • Does facilitation only work for large organizations?
    No. Facilitation is useful for startups, nonprofits, mid-sized companies, and established enterprises alike. Whether it’s a growing business in Chicago or a long-standing organization, structured facilitation adapts to the size and complexity of the team.

  • When is the right time to bring in a facilitator?
    If your team is repeating the same conversations, struggling to follow through, or unclear about what matters most right now, facilitation can reset the process and provide traction when it’s most needed.

  • What happens during a facilitated planning session?
    Sessions surface the real challenges, clarify goals, and establish next steps with clear ownership. The process is collaborative, practical, and focused on alignment your team can sustain long after the meeting.

  • How long do planning facilitation engagements usually last?
    Most engagements run anywhere from a single-day workshop to a series of sessions over several months, with prep and follow-up built in to ensure accountability and results.