Drop-In: Weekly Group Coaching for Curious, Committed Leaders
30 Minutes. Every Friday. Real Conversations with Leaders Outside Your Bubble.
Leadership doesn’t have to be lonely.
Drop-In is a live, online group coaching experience designed for leaders at every level–from emerging managers to seasoned executives–who crave fresh perspective, honest dialogue, and practical growth. Every Friday at 12pm ET (excluding holidays), join a rotating community of leaders from diverse industries for 30 focused minutes of insight, reflection, and connection.
Why Drop-In Works
- Cross-Pollinate Across Domains: We learn best from unexpected places. In Drop-In, you’ll engage with leaders from outside your industry–people who face similar challenges but bring wildly different lenses. That variety fuels surprising insights and practical breakthroughs.
- Neutral Ground, Honest Dialogue: This isn’t your company’s Zoom room. Drop-In offers a confidential, non-performative environment where leaders can be candid, vulnerable, and real–without worrying about internal optics or office politics.
- Efficient and Energizing: Each session is just 30 minutes. We use a proven rhythm that balances structure with spontaneity.
What You’ll Gain
- Weekly mindset tune-ups
- Exposure to diverse leadership stories
- Practical insights to apply immediately
- A growing network of thoughtful, values-driven leaders
- A space to wrestle with hard questions without fear of judgment
Who It’s For
- Leaders in transition
- Executives seeking outside perspective
- Managers hungry for community
- Consultants, creatives, and solopreneurs
- Anyone serious about personal and professional growth
What Participants Are Saying
“Drop-in… has been such a valuable space for me to focus on my own leadership growth and step away from the nitty-gritty of daily work.”
“Being able to bounce ideas and get real feedback from people outside of your circle is awesome. Real, genuine and down-to-earth people who get ‘get it’ and don’t waste your time. The ability to ‘drop-in’ as you can is great.”
“I have participated in the Drop-In coaching program for several months and am developing into a better leader. The content, format, and connections with other attendees have been excellent!”
Logistics
- When: Fridays at 12:00pm ET (30 minutes)
- Where: Live via Zoom
- Who: A rotating, diverse group of growth-minded leaders
- Cost: $34 per month
- Replays: Core insights are recorded and shared selectively. Conversations are private.
Join the Circle
Whether you’re new to coaching or a leadership development junkie, Drop-In is a simple way to connect, stretch, and grow. Show up as you are. Leave feeling a little more clear, connected, and courageous.
👉 People Always: How Leaders Choose to Humanize or Objectify
- A quick check-in
- 5–10 minutes of insight based on our 5 Fundamentals of Leadership
- Breakouts for reflection and peer coaching
- Brief group debrief, then you’re back to your day—refreshed and refocused
“Leaders see the long game. They have a mindset of lifelong improvement for themselves and those they lead.
Outsider is an ally for your development journey.”
Jamey Gadoury
Founder of Outsider Consulting
Drop-In Previews
Do Nothing: Decisive Leadership Strategy
In this session, we explore the concept of ‘doing nothing’ as a strategic leadership decision. We discuss tactical patience, the importance of allowing others to grow, and the necessity of prioritizing key actions over diverting efforts. Sometimes the best way to take decisive action is to intentionally wait and observe.
See Clearly
How can we “see clearly” through the fog and distraction of our daily grind?
Teams are made up of individuals, with unique drivers and personality traits. If you want to build an exceptional team, Outsider gives you the knowledge, awareness and tools to expedite development and fast-track growth.
Methods Used
Leader Coaching
Examine strengths and weaknesses, compare and contrast personality, leverage a sounding board, and apply what you learn.
Data & Assessments
Optimize your team’s performance in light of critical barriers to growth & create a roadmap to discover your full potential.
Facilitation
Create & maintain a healthy culture, understand your team dynamics & cast a shared vision of success.
Teaching & Speaking
Harness the power of story and lessons learned to refine how your team works cohesively toward effective outcomes.
Download the CEO’s Express Lane to Cohesive Leader Teams eBook
Building a cohesive leader team takes time, deliberate effort, and a little bit of luck. But what if you could take the express lane?