Start Here
What This Workshop Is About and Who It’s For
Watch this short video to hear directly from Courtney on what to expect at the workshop and whether it’s the right fit for you.
Most Strategic Plans End Up Back With You
They don’t fail because leaders lack ambition. They fail because there isn’t a system the team can actually follow. Priorities blur, complexity increases, and the team stops moving the plan forward.
You don’t need another big idea. You already have a clear vision for where your organization is headed.
What you need is a planning process your team can actually use. One that connects vision to execution and survives the year.
Most Strategic Plans End Up Back With You
They don’t fail because leaders lack ambition. They fail because there isn’t a system the team can actually follow. Priorities blur, complexity increases, and the team stops moving the plan forward.
You don’t need another big idea. You already have a clear vision for where your organization is headed.
What you need is a planning process your team can actually use. One that connects vision to execution and survives the year.
What You’ll Work Through
What You’ll Work Through
Scaling your organization requires three essential types of planning. Most leaders are only doing one. This workshop walks you through all three.
Long-Term Planning
Zoom out to create your three-year vision and assess your current reality. Get clear on where your business is headed, get honest about where things stand today, and define the strategies that will guide your growth.
You’ll use:
- Vision Brainstorm Worksheet
- After-Action Review
- Current Reality Snapshot
Long-Term
Planning
Zoom out to create your three-year vision and assess your current reality. Get clear on where your business is headed, get honest about where things stand today, and define the strategies that will guide your growth.
You’ll use:
- Vision Brainstorm Worksheet
- After-Action Review
- Current Reality Snapshot
Annual
Planning
Translate your vision into a focused, realistic roadmap for the year ahead. Define the right outcomes, map the right projects, and match them to your team’s true capacity.
You’ll use:
- Annual Roadmap
- Project Brief Template
Implementation Planning
Build the systems and rhythms that keep your plan alive. Assign ownership, build realistic timelines, and create a culture of follow-through. So you don’t just start strong. You stay strong.
You’ll use:
- Strategic Plan Rollout Checklist
- Meeting & Communication Cadence Builder
Annual Planning
Translate your vision into a focused, realistic roadmap for the year ahead. Define the right outcomes, map the right projects, and match them to your team’s true capacity.
You’ll use:
- Annual Roadmap
- Project Brief Template
Implementation Planning
Build the systems and rhythms that keep your plan alive. Assign ownership, build realistic timelines, and create a culture of follow-through. So you don’t just start strong. You stay strong.
You’ll use:
- Strategic Plan Rollout Checklist
- Meeting & Communication Cadence Builder
What Leaders Say About Scaling Leader
Hear From Scaling Leaders
“It is an effective, high-value experience and the people were great. I loved everything: the teaching, the structured exercises, and especially the time allotted. I have new clarity about what really matters and what doesn’t. I have an annual roadmap!”
– Lisa Bobby, Founder & CEO at Growing Self Counseling and Coaching
“The workshop struck the perfect balance of inspiration and practicality. Having my coach there helped me connect my vision to a clear, actionable plan.”
– Rose Ryan, President at Voyager Access
AUGUST 25-27, 2026
Ready? Here’s How to Join Us.
1
Register Now
Secure your seat for the workshop by registering for yourself or yourself and your leadership team.
2
Attend the Workshop
Spend three days in Vail working through your plan with your guides, Courtney and Kevin, and fellow leaders.
3
Bring Your Vision to Life
Leave with a clear plan your team can carry, and the structure to keep it moving forward.
1
Register
Now
Secure your seat for the workshop by registering for yourself or yourself and your leadership team.
2
Attend the
Workshop
Spend three days in Vail working through your plan with your guides, Courtney and Kevin, and fellow leaders.
3
Bring Your
Vision to Life
Leave with a clear plan your team can carry, and the structure to keep it moving forward.
What Past Attendees Are Saying
“It was nice to have my whole leadership team with me so we could discuss and plan in real time. This is a great program to get ahead of the curve and create a plan to scale and grow your business.”
Founder, Online Education Company
“The 3-day time period and format of blocked times were game changers. I also appreciated the flex when we needed more time to complete.”
Founder, Coaching Company
“My experience was incredibly valuable, and I would come again in a heartbeat. Having the time to brainstorm and work through our ideas was essential. We’re walking away with a focused vision for what we want to accomplish both next year and over the next three. I also really appreciated the professionalism of the staff and how easy it was to work hard. Even as someone who isn’t an owner, it was deeply valuable to go through the process.”
COO, Services Company
“It was nice to have my whole leadership team with me so we could discuss and plan in real time. This is a great program to get ahead of the curve and create a plan to scale and grow your business.”
Founder, Online Education Company
“The 3-day time period and format of blocked times were game changers. I also appreciated the flex when we needed more time to complete.”
Founder, Coaching Company
“My experience was incredibly valuable, and I would come again in a heartbeat. Having the time to brainstorm and work through our ideas was essential. We’re walking away with a focused vision for what we want to accomplish both next year and over the next three. I also really appreciated the professionalism of the staff and how easy it was to work hard. Even as someone who isn’t an owner, it was deeply valuable to go through the process.”
COO, Services Company
Guided by Courtney De Ronde and Kevin B. Jennings
Scaling Leader workshops are facilitated by Courtney De Ronde and Kevin B. Jennings, who lead the room together throughout the experience.
Courtney teaches the core frameworks and tools behind the Simple ScaleUp System™, drawing on stories and examples from her own experience leading and advising growing organizations. Kevin helps guide the working sessions that follow, coaching leaders as they apply the concepts to their own teams and organizations.
Together, they create a workshop environment that is practical, interactive, and supportive. Leaders learn the concepts, work through the tools, and receive real-time coaching as they think through their own organizations.
Courtney De Ronde
Courtney De Ronde is the Co-Founder and CEO of Forge Financial & Management Consulting and the creator of the Simple ScaleUp System™ and Scaling Leader™.
After more than two decades leading and advising growing organizations, Courtney has seen firsthand how success creates new complexity. As companies expand, leadership capacity, systems, and operating structure must evolve alongside them.
Through Scaling Leader workshops, Courtney helps founders and leadership teams build the clarity, structure, and leadership capacity required to scale their organizations without the weight of growth falling back on the leader.
Kevin B. Jennings
Kevin B. Jennings is a business coach and personal brand strategist. He helps ambitious creatives and leaders get unstuck with the credibility, clarity, and courage they need to turn their ideas into income and impact.
He is also the CEO of Junction 32, which offers marketing services and products to help small businesses grow their brands and increase revenue so they can impact people.
For more than a decade, Kevin has worked with high-profile leaders, best-selling authors, and successful small business owners, including Tony Robbins, Dave Ramsey, and Michael Hyatt
The Program Behind This Workshop
To bring your vision to life, your leadership has to grow ahead of your business.
This strategic planning workshop is one of four in-person Scaling Leader workshops hosted throughout the year, each focused on a different stage of the work scaling leaders need to do.
Annual passholders attend all four workshops, plus get access to virtual training for their teams, coaching, tools, and a community of leaders doing the same work.
The Program Behind This Workshop
To bring your vision to life, your leadership has to grow ahead of your business.
This strategic planning workshop is one of four in-person Scaling Leader workshops hosted throughout the year, each focused on a different stage of the work scaling leaders need to do.
Annual passholders attend all four workshops, plus get access to virtual training for their teams, coaching, tools, and a community of leaders doing the same work.
