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Preview

When You're Ready to Sprint But Your Team Needs to Reorient

Insights from our September Leadership Strategy Session + teaching preview đŸŽ„

🌟 While we no longer record the Q&A discussions during our Leadership Strategy Sessions, we continue to record the opening teaching. Enjoy a special preview of what I shared about managing September’s back-to-work intensity. If you want to see the complete teaching and take part in upcoming sessions, consider upgrading to join us live next month.


September is the real new year.

Kids are back in school. Summer hours end. Your team is (mostly) back and the pressure is on: finish Q3 strong, tee up Q4, and make the back half of the year count.

But here’s what most leaders miss: your team doesn’t eat, drink, and sleep organizational change like you do. Just because you spent the summer thinking about strategy doesn’t mean they did.

So how do you bridge the gap between your readiness to sprint and your team’s need to reorient? Start with reality: prepare now because Q4 is an optical illusion — when it arrives, you’ll think you have 12 work weeks but you’ll only have 9. Use this September clarity to convert organizational push goals into the pull goals that will actually motivate your people when the pressure hits.

I also shared insights from recent coaching conversations. The full recording (available to our paid subscribers) covers:

  • The three types of planning styles (top-down, bottom-up, and middle-in) and how understanding these can support your own leadership approach

  • A four-question framework for taking a “leadership beat” when you’re feeling most emotionally intense

  • The two ways we make sharing the bigger vision harder than necessary

And in our Q&A this month we covered:

  • Breaking the Trust Spiral: When everything feels like a negotiation, focus on building functional trust rather than over-communicating.

  • Navigating Toxic Servant Leadership: The difference between attending to what people need versus what they want, and why leaders shouldn't do everyone else’s jobs.

  • Managing Constant Change Fatigue: How to explain the catalyst behind changes without over-explaining, and separate productive tension from destructive conflict.

  • Communicating in Hybrid Teams: Reallocating live meeting time for strategic conversations while moving updates to async channels.

  • The Berry Bush Principle: Restoring the natural human instinct to share helpful information and warn of dangers in organizational settings.

Join us for our next Leadership Strategy Session on Wednesday, October 1, 2025, at 11:00 a.m. PDT, where we’ll explore “Protecting What Matters Most” — helping leaders maintain focus during peak execution season when everyone wants one last big push and everything feels important.

We covered a lot of ground in this session, and premium subscribers can find related resources below, including the four-question framework for taking a “leadership beat” and additional strategies for resetting your team’s pace. đŸ‘‡đŸœ

This post is for paid subscribers