Executive Search Insights & Leadership Strategies | Edgility Search

Hire Ground Podcast Episode 22: Succession, Scale, and What Young People Actually Want with Diane Tavenner

Written by Christina Greenberg | Sep 22, 2026, 3:45:45 PM

Episode 22 of Hire Ground Podcast 

"Our greatest responsibility as a leader leaving is creating the conditions for success for whoever comes next."

Diane Tavenner has done the thing most founders talk about and few do well: she built something, grew it, and handed it off cleanly. Then she started over. She co-founded Summit Public Schools, scaled it from one high school into a network across California and Washington, transitioned it to a successor, and is now CEO of Futre, a platform helping young people figure out what comes next. She joins host Christina Greenberg for a conversation that moves across all three chapters: leaving well, scaling well, and building for a generation whose expectations have shifted.

What she and host, Christina Greenberg, get into:

 

On succession:

  • Why her board set a bar instead of hunting for a unicorn, and how that avoided the internal-candidate-versus-national-search trap that poisons so many processes
  • The eight-month side-by-side onboarding and offboarding plan she built with her successor, Cady Ching
  • The outgoing leader's real last job: doing the hard, yucky things so the next CEO doesn't have to

On scale:

  • What stays non-negotiable at every size, and what has to change
  • Personalized learning plans for everyone, and why "where do you see yourself" should be a bigger question than someone's job
  • Why engineering teams and teams of teachers have more in common than she expected, and why mission comes free in education but has to be built deliberately in a company

On what young people actually want:

  • The two questions they ask first: what does it pay, and will this job still exist in ten years
  • Why they're optimizing for a good life, not a career, and Diane's invitation to leaders who find that framing uncomfortable
  • Northeastern's co-ops, Minerva, and why apprenticeships still aren't a realistic pathway at scale

Listen on your platform of choice:

Hire Ground is the essential podcast for K12 school and nonprofit leaders who are serious about hiring, retaining and developing high performing teams. This podcast brings together thought leaders, executives, and board members for honest conversations about leadership, hiring, governance, and what it really takes to build a thriving organization from the ground up.

Hire Ground is hosted by Christina Greenberg - founder and CEO of Edgility Search and 20-year veteran of executive search and nonprofit talent - and was co-created with Josh Czupryk, founder of Josh’s K12 Jobs Blast.

Follow along and join the conversation on LinkedIn.
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