"The Strategy Handoff: Where Good Plans Go Off Track" featuring Brooks Busch

Episode Summary

Strategy failure rarely starts with bad ideas. It starts with bad translation.

In this episode, Clint and Greg sit down with Brooks Busch to unpack why strategy planning and execution remain one of the most consistent failure points inside growing companies. From thousand-slide decks to disconnected OKRs, Brooks explains how most organizations confuse documenting strategy with actually running the business.

The conversation reframes AI as a management discipline, not a productivity trick. Instead of asking how AI can save time, Brooks challenges leaders to ask how AI can improve decision quality, surface hidden risks, and preserve institutional knowledge when leaders turn over.

You will hear why the best strategy leaders act as facilitators, not geniuses with answers, how different operating frameworks fit different company stages, and why execution breaks down long before the quarterly review. The episode also explores how AI can democratize world-class strategic thinking that was once only available through expensive consultants.

If you lead a team, own a number, or sit in executive meetings wondering why alignment feels fragile, this episode gives you a clearer lens on what to fix first.

Guest Introduction

Brooks Busch is the CEO and co-founder of Elate, an AI-powered platform built to help companies define strategy, pressure test decisions, and track execution across the business. Before founding Elate, Brooks led strategy and go-to-market efforts at companies ranging from early-stage startups to global enterprises. His work focuses on closing the long-standing gap between executive vision and day-to-day execution, using AI as a strategic thought partner rather than just an automation layer.

AI Challenge: Pressure Test Your Strategy

This week’s AI Challenge builds directly on the conversation with Brooks.

Your assignment: 

  1. Pick one active company priority or initiative.

  2. Use an AI tool to pressure test it against your company strategy.

  3. Rewrite that priority from the perspective of at least two other roles in your organization.

  4. Compare the outputs and look for misalignment, gaps, or hidden risks.

The goal is to see whether your strategy actually travels through the organization clearly or if it breaks down as it moves from leadership to execution.

πŸ‘‰ Full step-by-step instructions: https://www.promptthis.ai/blog/how-to-use-ai-to-check-if-your-team-is-aligned-on-priorities 

πŸ‘‰ Share your experience or results: https://www.promptthis.ai/contact

Chapter Breakdown

00:00 – Welcome to Prompt This 
Why strategy and execution are where companies stumble most.

01:55 – Meet Brooks Busch and Elate 
What drove Brooks to build an AI-first strategy platform.

03:30 – The Strategy Disconnect 
Why long slide decks and static plans fail in real organizations.

06:10 – The Real Role of a Strategy Leader 
Why asking the right questions matters more than having answers.

08:45 – Defining β€œStrategy” Across Leadership Teams 
How misaligned definitions derail planning before execution starts.

11:00 – AI as a Strategic Thought Partner 
Using AI to pressure test assumptions and expose trade-offs.

15:00 – The Strategy Vault Concept 
Preserving institutional knowledge and past decisions with AI.

19:40 – Frameworks That Actually Work 
EOS, OKRs, and why commitment matters more than methodology.

22:30 – Why Execution Fails 
The banana-phone problem and how strategy breaks down at scale.

26:00 – Clarity as a Force Multiplier 
How shared priorities help teams say no to the wrong work.

28:20 – Where Leaders Should Start with AI 
Why understanding risk comes before buying tools.

31:30 – Mining Customer Conversations with AI 
Turning calls into real strategic input.

33:00 – Favorite AI Tools in Practice 
How Brooks uses AI across product, sales, and personal work.

38:30 – One Piece of Advice for Leaders 
Why admitting uncertainty is the best starting point with AI.

39:20 – This Week’s AI Challenge 
Pressure testing priorities for alignment.