Strategic Planning Facilitation

Dream Big. Plan Smart. Make it Happen.

Coach-led strategic planning that turns ambitious vision into clear decisions, alignment, and execution.

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Strategic planning facilitation session - Steve Weiss guiding executive leadership retreat in Cleveland Ohio
Free 30-min call · No obligation
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Why do strategic plans fail—and how do leadership teams make them succeed?

Strategic plans fail due to poor execution, lack of clear accountability, and insufficient leadership team alignment. Leadership teams make strategy succeed by creating measurable goals, establishing regular review cycles, maintaining focus on core vision, and developing detailed roadmaps that translate high-level strategy into actionable steps.

I work with leadership teams to bridge the gap between ambitious vision and practical execution. We focus on creating accountability structures and communication rhythms that keep everyone aligned and moving forward together.

Based in Cleveland, Ohio· In-person, virtual, or I'll travel to you

Is This For You?

Leadership teams needing alignment
Organizations at a crossroads
Teams with plans that don't stick
Leaders wanting real decisions, not discussion

Strategic Planning: Consultant vs. Coach Approach

Both can facilitate your planning retreat. The difference is WHO does the strategic thinking.

Consultant
Coach ✓

Who's Talking

Consultant presents findings—your team listens and reacts

YOUR team talks 90% of the time—I ask questions and facilitate

Team Buy-In

Recommendations often face resistance ('that won't work here')

Built-in commitment—people own what they create

The Hard Conversations

May avoid conflict to keep the client happy

Creates safe space for honest dialogue your team needs to have

Decision Making

Consultant recommends; you approve or reject

YOUR team debates, decides, and commits together

What You Pay For

Research into things your team already knows

Facilitation that unlocks what your team already knows

6 Months Later

Plan often sits in a drawer—nobody owns it

Living strategy your team keeps executing—they built it

Building Capacity

You need them again next year for fresh insights

Your team learns to think strategically together

Best For

When you need expertise you truly don't have internally

When your team has the answers but needs help finding them

Ready to see how a coach-led approach can transform your strategic planning?

What You Walk Away With

Not just a filled whiteboard or a binder that collects dust. Actual outcomes you can use to drive your business forward.

Crystal Clear Direction

No more wondering what the real priorities are or which projects actually matter. You'll walk away from your strategic planning session with absolute clarity on where you're headed and why.

Genuine Team Alignment

When your leadership team is pulling in different directions, nothing works well. Your strategy retreat will get everyone rowing in the same direction with shared understanding of the plan.

Concrete Action Plans

Vague goals and good intentions don't create results. You'll leave your leadership offsite with specific actions, clear deadlines, and assigned accountability for every major initiative.

Honest Assessment of Reality

Sometimes the hardest part of strategic planning is admitting what's not working. Your planning session will include an honest look at current reality – both strengths to leverage and problems to solve.

Strategic Planning Session Options

Every engagement is customized, but here are the common starting points for most Cleveland and Ohio organizations I work with.

Most Popular

Annual Strategic Planning Retreat

1-2 Days

Your comprehensive yearly strategy session where YOUR team tackles the big picture – vision, priorities, and major initiatives. I facilitate the process; you and your team do the strategic thinking.

  • Pre-session alignment call to clarify objectives and desired outcomes
  • Facilitated discussion on vision, mission, and strategic priorities
  • Team-driven analysis of challenges and opportunities
  • Structured decision-making on key initiatives and resource focus
  • Accountability assignments owned by your team
  • Clear documentation of YOUR decisions and commitments

Leadership Team Off-Site

1-2 Days

Focused sessions for leadership alignment on specific challenges or opportunities. I create the space for honest dialogue; your team discovers the path forward together.

  • Facilitated exploration of team dynamics and communication
  • Structured process for priority setting and tough conversations
  • Role clarity discussions led by your team
  • Collaborative problem-solving on specific challenges
  • Team-generated action plans and commitments
  • Follow-up coaching to support accountability

Strategic Planning Series

~4 Months

Not every team can block out full days for planning. This flexible format spreads your strategic work across 90-120 minute sessions every 2-3 weeks—giving time for reflection and real-world testing between sessions. Available via Zoom or in-person in Northeast Ohio.

  • 6-8 focused sessions over approximately 4 months
  • Time between sessions to test ideas and gather input
  • Builds strategic thinking as an ongoing practice
  • Easier to schedule around busy calendars
  • Same depth of strategic work, different pace
  • Zoom or in-person in Cleveland/NEO area

Strategy Refresh Session

Half Day

Quick but thorough review of your current strategic plan with adjustments based on new realities. Your team assesses progress and recalibrates as needed.

  • Team-led progress review and honest assessment
  • Facilitated discussion on what's changed
  • Collaborative priority adjustment
  • Resource reallocation decisions by your team
  • Updated commitments and timeline
  • Clear next steps owned by team members

Not sure which format fits your situation? Let's talk. We'll figure out what works best together based on what you're trying to accomplish.

Why Leaders Choose Steve

What it's like working with a coach who genuinely cares about your success

Rahim Buford - Executive Director of Unheard Voices Outreach
Testimonial: “I feel that this is one of the first workshops I've done to actually have an impact. Tomorrow I have staff meetings and I'm going to implement some of the things I learned today.”
Brandon Chrostowski - Founder and CEO of Edwins Leadership & Restaurant Institute
Testimonial: “Steve's training and coaching are a powerful model... He quickly builds trust and enables students to face triggers and challenges that once held them back.”

Common Questions About Strategic Planning Facilitation

What is strategic planning facilitation?

Strategic planning facilitation is when a trained facilitator guides your leadership team through a structured process to set direction and make decisions. Unlike a consultant who tells you what to do, a coach-facilitator asks powerful questions that help YOUR team discover their own answers—answers they'll actually own and execute.

Why hire an outside facilitator instead of running it ourselves?

When you're inside the business every day, it's tough to see the forest for the trees. As your facilitator, I bring an outside perspective and ask the powerful questions that unlock YOUR team's insights. Plus, when the CEO or business owner tries to facilitate their own planning retreat, they end up doing all the talking instead of getting input from their team. As a trained coach, I create the space for every voice to be heard and guide your team to discover their own answers—answers they'll actually own and execute.

How is coach-led facilitation different from hiring a consultant?

A consultant researches your company, analyzes your market, and tells you what to do. I don't do that. As an ICF-credentialed coach, I believe YOUR team has the insights, expertise, and wisdom to chart your own course. My role is to ask powerful questions, facilitate honest dialogue, keep you focused on decisions (not just discussion), and hold you accountable. You leave owning a plan YOU created—not implementing someone else's recommendations.

How long should our strategic planning session be?

It depends on what you're trying to accomplish, but most effective annual planning retreats need at least a full day, often two. You can't rush good strategic thinking. Half-day sessions work well for strategy refreshes or focused problem-solving, but if you're doing comprehensive strategic planning for the year, give yourself enough time to dig deep. I'd rather do it right in two days than rush through it in four hours and miss the important stuff.

Do you help with implementation after our leadership offsite?

Absolutely. The strategic planning session is just the beginning – the real work happens in implementation. I provide follow-up coaching sessions to keep your team accountable, help you navigate obstacles, and support you in making adjustments as you learn what's working. Many of my Cleveland-area clients do quarterly check-ins to review progress and refine their approach. Virtual follow-up support is available for teams anywhere in the country.

Will you travel to our location for in-person facilitation?

Absolutely. For Northeast Ohio companies, I'm local and readily available for in-person sessions. For organizations elsewhere, I regularly travel for retreats and offsites—we'll discuss travel arrangements as part of the planning process. I also offer virtual strategic planning facilitation that serves teams globally—it's proven highly effective and eliminates travel time while maintaining all the interactive elements that make strategy sessions productive.

Ready to Turn Strategic Planning Into Strategic Results?

Stop wasting time on planning sessions that don't lead to real decisions or meaningful change. Whether you need comprehensive annual strategic planning or focused leadership team alignment, let's create a strategy session that actually drives your business forward. Available for in-person facilitation throughout Ohio or virtual sessions nationwide.

Learn About Team Coaching

Inspiring Quote: “The best strategic plan is useless if it sits in a drawer. Real strategy happens when your leadership team owns the process, commits to the outcome, and has clear accountability for execution.”

— Steve WeissFounder, Catalis Leadership

Strategic Planning Success Factors

  • Involve your leadership team in creating the plan—ownership drives execution
  • Set clear, measurable goals with specific timelines and accountability
  • Build in quarterly review checkpoints to maintain momentum
  • Align strategy with organizational values and culture
  • Communicate the plan clearly to all stakeholders at every level