Frequently Asked Questions

About the Experience

Discover what makes this journey unique, who it’s for, and what kind of transformation you can expect—professionally and personally.
What is Beyond the Leap?

Beyond the Leap offers immersive leadership development experiences in inspiring destinations. We blend executive coaching, facilitated strategy, and intentional travel to help individuals and teams pause, realign, and grow.

We offer two core tracks:

  • Executive Retreats (1–2 weeks) for leadership teams
  • 30-Day Remote Work + Leadership Experiences for individual professionals
  • Senior leaders and executive teams
  • High-performing professionals seeking clarity, growth, or reset
  • HR and Talent Leaders exploring leadership development and retention tools
  • Entrepreneurs, founders, and individuals navigating professional transitions

Whether you’re guiding a team or defining your next step, Beyond the Leap helps you lead with greater purpose and alignment.

  • 30-Day Experience: No. It’s designed as a remote work experience—you continue your job while engaging in coaching and growth.
  • Executive Retreats: These can be structured as unplugged offsites or strategy-focused team sessions—we’ll customize based on your goals.

Our current destination is Costa Rica. Each location is chosen for its natural beauty and ability to support meaningful reflection and professional growth.

Travel & Logistics

Get clarity on flights, accommodations, visas, group size, and everything else you need to know before packing your bags.
Where do these experiences take place?

Our current destination is Costa Rica, with plans to expand globally. Each location is selected for its natural beauty, infrastructure, and ability to support deep reflection and growth.

We work with trusted local property managers to offer remote work-friendly condos with strong Wi-Fi, walkable access to key areas, and flexible pricing based on your preferences. You’ll sign a rental agreement directly with the property manager to ensure full control and customization of your stay.

Yes. For the 30-day experience, companions are welcome. The leadership development content is designed for the enrolled participant, but we’ll help you plan around your personal needs.
For retreats, the focus is on team dynamics, though custom requests can be accommodated.

Coaching & Development

Understand how the coaching process works, what’s included, and how it’s tailored to support your individual and team growth.
What kind of coaching is included?

All experiences include 1:1 executive coaching before and after the program. During the experience, you’ll also receive regular check-ins and facilitated leadership development sessions.

Coaching is led by Crystal-Lee Olson, MA, PCC—or an ICF-certified coach at the PCC level or higher.

Topics vary based on your goals, but commonly include:

  • Leadership style & self-awareness
  • Communicating to build trust
  • Productive conflict & collaboration
  • Leading through change and uncertainty
  • DiSC® & Catalyst™ assessments and facilitation

Yes. Executive retreats are fully customized. We co-create each session agenda based on your leadership team’s goals, strategy, and communication needs. From strategy facilitation to agile leadership and trust-building, you’ll choose a track that moves your team forward.

Booking & Payment

Learn about pricing, what’s covered, how to reserve your spot, and what flexible options are available.
What does the program cost?

Program pricing varies based on the experience selected, accommodations, group size, and optional excursions. Full details will be shared during your discovery call after we review your application.

Yes. We ask all potential participants to complete a short application to ensure alignment. After that, we’ll schedule a connection call to answer questions and confirm next steps.

Absolutely. We regularly partner with organizations to invoice directly, support employee growth initiatives, and tailor team experiences.

Your deposit is non-refundable. However, with enough notice, you may be eligible to transfer your participation to a future cohort. Full terms will be outlined in your participant agreement.

We’re happy to help. Contact us directly at info@beyondtheleap.co or use the contact form to connect.

Get Your FREE Leadership Reset Toolkit

Ready to lead with clarity, calm, and confidence?
Download our Leadership Reset Toolkit — designed to help you pause with purpose, reflect with intention, and reignite your leadership without stepping away from your work.

Please enable JavaScript in your browser to complete this form.