Leadership Conversations

Open to all Outward Bound staff, Leadership Conversations are virtual workshops to learn about, discuss, and apply important leadership skills, tools, and concepts.

Upcoming Sessions

All sessions will take place from 11am-12pm PT/2-3pm ET

From Chaos to Coordination:
How to Prioritize Your Work
February 19, 2026

OB is a mission-driven organization, so every project can feel mission-critical. But with limited time and resources, it's impossible to do it all. Learn practical tools to help you manage your work with confidence.

Fundamentals for a Strong Team Culture
April 16, 2026

Whether you're a team leader or an individual contributor who works collaboratively, understanding some foundational elements of a successful team culture will support you in achieving deeper alignment, growth, and impact.

Managing Up & Sideways
June 25, 2026

How can you use management skills with your boss and peers? How do you exert influence without formal authority? Learn tactical strategies to support you in working confidently and collaboartively at all levels of the organization.

Understanding Access & Belonging
at Outward Bound
March 19, 2026

Learn the basics around OB's commitment to access and belonging and how we operationalize it through our work on course in the communities we serve. Facilitated by OBUSA's Director of Equity & Access, Elyse Rylander.

Equity in Hiring
May 21 , 2026

Join us to learn strategies and tools for making OB's hiring processes more equitable. From clear job descriptions to structured interviews, this session will give you practical guidance and opportunities for peer learning.

Microagressions: Naming, Navigating, and Interrupting
July 16, 2026

Join us to gain a deeper understanding of microaggressions, identify common microaggressions, share real-life examples, and practice ways to respond as targets, bystanders, and leaders.

Meet Your Facilitators

National Talent Development Manager

Kristen Freaney

Kristen is an experienced talent and organizational development professional with expertise in program design and facilitation. She's built programming and facilitated training for a wide variety of organizations including Patagonia, National Park Service, Outdoor Industry Association, Oregon State University, and University of Colorado Boulder, and serves as a resident leadership development facilitator for Conscious Culture Co.

She's a certified administrator of the Gallup CliftonStrengths Assessment, a certified Prosci Change Management Trainer, and a qualified facilitator of the True Colors and EQ-i 2.0 assessments.

Kristen lives in Boulder, CO with her husband, John, and son, Finn. She is passionate about cheese, poetry, and pop culture.

Screen+Shot+2018-04-03+at+1.43_edited.jpg

Director of Equity, Access & Belonging

Elyse Rylander

Elyse builds the future of the outdoor industry—where equity, leadership, and risk management aren’t separate lanes, but the same operating system. She founded OUT There Adventures to expand LGBTQ+ youth access and co-founded the LGBTQ Outdoor Summit, now a flagship gathering shaping culture change across the outdoor ecosystem. Elyse serves on the Wilderness Risk Management Conference Steering Committee and the Board of Directors for the North Cascades Institute.

She is a certified Prosci Change Management Practitioner and a qualified administrator of the Intercultural Conflict Styles and Intercultural Development Inventories.

Elyse lives in Bellingham, WA with her partner and young daughter.

Join the Community

Stay up-to-date on the latest news and events by signing up for our Crew Newsletter!