The Missing Middle: When Strategy Doesn’t Translate to Execution

You have a clear strategy. Your teams are talented. So why do they keep slipping back into output-focused delivery instead of the outcome-led approach you’ve been pushing?

Jonathan Tari has lived this challenge. As Product Operations Principal at Planday—a 300-person subsidiary of Xero, he’s spent years trying to transform a 20+ year old organization from legacy ways of working to outcome-focused product development. In this conversation with host Becky Flint (CEO & Founder, Dragonboat), he gets honest about what worked, what didn’t, and why their first attempt at outcome-focused roadmaps completely failed.

What you’ll hear:

• The “assumptions layer” that changed everything: Creating intermediate altitude between strategy and execution so teams understand not just what to achieve, but why specific opportunity spaces matter.
• Why outcome-focused roadmaps failed year one: How prioritization conversations immediately devolved into solution-level debates, and what finally fixed it.
• Structure enables autonomy: Why teams with proper guardrails and context are “much better at unblocking themselves” than organizations expect.
• Making competing priorities visible: How putting four parallel work streams on one page transformed prioritization conversations.
• Signal vs. noise across all levels: The persistent challenge of helping everyone distinguish what actually matters from what should fade into the background.
• AI as a strategy translation layer – Using AI agents as “living personas” trained on company strategy to help teams access context without friction.

Reference

• Jonathan Tari on LinkedIn: https://www.linkedin.com/in/jtari/
• Becky Flint on LinkedIn: https://www.linkedin.com/in/beckyflint/