From 33 Years in Education to 30+ Clients in Year One
Harry Hastings spent 33 years in education, rising to head teacher. When he left to build The Sherpa — his coaching practice — he didn’t just survive the transition. He thrived, landing over 30 clients in his first year.
Key Takeaways
- 30+ clients in year one is possible — with the right approach. Harry didn’t wait for clients to find him. He built relationships, leveraged his network, and showed up consistently.
- Education leaders make excellent coaches. The skills you develop managing schools — empathy, strategic thinking, conflict resolution — translate directly to coaching.
- The Sherpa model is about guiding, not fixing. Harry’s approach mirrors the Sherpa philosophy: he walks alongside clients, helping them navigate their own path to the summit.
Questions Explored
- How did you land 30+ coaching clients in your first year?
- What translates from education leadership to coaching, and what doesn’t?
- How do you price and position yourself when you’re brand new?
About Harry Hastings
Harry is the founder of The Sherpa, a coaching practice that helps leaders navigate career transitions and organizational change. After 33 years in education, he built a thriving practice by combining deep leadership experience with genuine care for his clients’ success.