Small Business Leadership Retreat
Real challenges.
Practical tools.
Lasting impact.
RockRed offers leadership development experiences for people who want to make sense of what’s happening, navigate complexity with intention, and shape healthier systems where people can thrive.
Leading a small business means navigating more than strategy. You’re making decisions, building culture, responding to change, and often carrying more of the organization than anyone realizes. RockRed’s small business leadership experiences help owners engage with other small businesses; step back from the day-to-day, understand what’s happening in their business, and lead their organization and systems more intentionally.
Build a business that doesn’t depend on you for everything.
In Person Sessions
The retreat will be hosted for two 3 hour sessions in January 2027.
January 5th and 12th from 1pm-4pm in La Grande Oregon
Who this is for
This experience is designed for small business owners and founders who are carrying a lot and want the space to step back and lead more intentionally.
It may be a good fit if you:
Have an idea or several about where to go next but need time and space to engage with it
Feel like too much of the business still depends on you
Have grown your business and realize your systems need to grow with it
Are constantly responding to what’s urgent and rarely have time to think strategically
Have a challenge you keep trying to solve, but the same patterns continue to show up
Value learning alongside other business owners who understand the realities of leading a small business
You don’t need to have everything figured out before you come. Bring the real challenge you’re navigating. We’ll create the space and structure to work on it.
Key Outcomes
01 / Strategic Clarity You Can Actually Use
This experience is built for entrepreneurs who want real direction, not inspiration without action. You’ll work through strategic planning, systems, and workflow clarity; so you leave knowing what to focus on, what to simplify, and what to stop doing. Expect guided conversations that help you map growth, structure your business sustainably, and create a clear path forward you can implement immediately.
02 / Honest Leadership & Team Conversations
You’ll explore your leadership strengths, how they serve you and how they may be holding you back, alongside practical tools for building, managing, and retaining teams and contractors. Through small-group discussions and round tables, you’ll have candid conversations about real challenges, not polished success stories. This is a space for thoughtful reflection, problem-solving, and learning from peers at a similar stage.
03 / A Private, Grounded Space to Reset & Reconnect
The environment is intentionally comfortable, relaxed, and private—not corporate and not performative. You’ll experience meaningful connection with others who understand the weight of entrepreneurship, supported by optional wellness elements designed to help you reset and refocus. The goal is to leave feeling renewed, supported, and less alone, with energy to continue the work ahead
About your Facilitator
Mollie Rockafellow, Ed.D. — Strategy, Leadership & Systems
Dr. Mollie Rockafellow believes that leadership is about more than managing people and projects; it's about understanding the systems, relationships, and cultures that shape how organizations function. As Vice President for Student Affairs at Eastern Oregon University and founder of RockRed LLC, she has spent her career helping individuals and teams navigate complexity, build stronger workplaces, and create meaningful change.
Through her work in higher education, leadership development, organizational culture, and systems thinking, Mollie has seen a common challenge emerge across industries: talented leaders are often expected to solve complex problems without being taught how to understand the systems creating them. This cohort experience brings the practical lessons she has learned leading through enrollment pressures, retention initiatives, organizational change, crisis response, and team development. Participants can expect an engaging, supportive learning environment focused on practical application, reflection, and real-world leadership growth.