Outsight <> Insight

An Executive Leadership Mastermind

Transform your leadership. Elevate your organization.

Are you ready to shift perspective, spark innovation, and build a culture of excellence?

Join Outsight <> Insight, an executive-level mastermind designed for senior leaders who are ready to grow with intention.

We combine monthly group sessions, one-on-one coaching, a one-day in-person retreat in the Seattle region, strategic tools, and a trusted peer cohort to help you step OUT OF the daily grind and lead INTO impact..

Why Join?

  • Collective Wisdom, Elevated Thinking

    Your toughest leadership challenges don’t have to be faced in isolation. Tap into deep experience, candor, and insight from a carefully selected group of fellow senior leaders.

  • Tailored to Your Leadership Journey

    From January to September 2026, you’ll engage with a small, committed cohort. Our approach adapts to your unique style so that your growth feels personal — not prescribed.

  • Drive Tangible Impact

    This isn’t just about ideas. You’ll emerge with sharpened strategic thinking, strengthened influence, greater clarity under pressure, and enhanced capacity to drive meaningful change.

  • Hybrid Format, High Engagement

    We deliver virtual sessions monthly (group + 1:1 coaching), plus a one-day in-person retreat in the Seattle region. This flexible mix fosters connection without overloading your schedule.

What You’ll Experience

Audience: Senior & Executive Leaders (including Founders)

Size: Limited to 10 participants for intimacy & impact

Duration: January – September (cohort model)

Program Details

Monthly Group Meetings: 55 minutes each, including a “hot seat” deep-dive for one member

Two Guest Speakers: Learn from thought leaders and emerging voices

Six 1:1 Coaching Sessions: Dedicated 45-minute sessions targeting your personal growth

Full-Day Onsite Retreat in March 2026: Deepen relationships, reset perspective, spark collaboration

Program Highlights

What Participants Say

  • "It was so valuable to get peer feedback on what felt like an intractable, unsolvable, perplexing set of issues. The frank, but kind, feedback was refreshing and helped me move in a direction that I wouldn't have been able to divine on my own. I was too much in my own way to see a path, and the group absolutely provided much needed clarity."

  • "The most valuable aspect of the program was connection and reflection - meeting others and having the space to reflect on your grow and others within the group."

  • "Outsight <> Insight gave me an understanding the applicability of disparate industry experiences as a great leveler. "

  • "I would definitely recommend Outsight <> Insight. It provided me with both focused attention, and great peer perspectives."

Apply to Outsight <> Insight

Applications for the 2026 cohort open this fall.
Want to be among the first invited? Notify me (via form) and we’ll ensure you get early access.