By Ben Johnson
A powerful EOS tool that is often misunderstood is the Quarterly Conversation. A Quarterly Conversation isn’t about evaluating someone. It’s about aligning with someone. It’s a chance for the manager and the direct report to slow down, get out of the day-to-day swirl, and make sure they’re actually rowing in the same direction. In most cases, a Quarterly Conversation plus team L10s replace 1 on 1s.
But here’s the tricky part: The magic of a Quarterly Conversation isn’t the meeting. It’s the preparation for the meeting.
When both people show up prepared, honest, and ready to talk about what’s working and what’s not, the conversation becomes one of the most powerful tools in EOS.
And… let’s be honest… it can be difficult to know what to prepare within a reasonable amount of time. Done right, we should be able to prepare for a great quarterly conversation in 15-30 minutes.
That’s why I created two AI prompts — one for managers, one for direct reports — that walk you step-by-step through everything you should think about before a Quarterly Conversation. You can literally copy/paste the prompt into your favorite AI tool, answer the questions one at a time, and get a crisp summary of what’s working and not working to bring into the conversation.
Like Geoff Woods, author of The AI Driven Leader, I think of AI as a thought partner and myself as the thought leader when using AI. These prompts will help create that relationship and help you prepare for a great Quarterly Conversation.
I’ll link both prompts at the end of this article.
Why Quarterly Conversations Matter
Quarterly Conversations are designed to strengthen the relationship between a manager and their direct report. They keep expectations clear. They surface issues early. And they create a healthy rhythm of honest conversation without all the complexity of HR paperwork.
There’s no scoring. No forms going into a file. No performance grids.
Just two humans sitting down and making sure they’re on the same page — so they can win together in the next 90 days.
What Makes a GREAT Quarterly Conversation?
It starts with thoughtful prep.
When you show up prepared, you can focus on the actual relationship instead of trying to remember everything you meant to say.
The AI prompts walk you through:
- Your roles
- Your Rocks
- Your measurables
- Core Values alignment
- GWC role-by-role
- Measurables (on track/off track)
- Delegate & Elevate / Your 100% Tool (if applicable)
- Leadership and management practices
- And — this is key — expectations, career aspirations, and how you like to be recognized or corrected
Both prompts end with a clean summary organized into two buckets:
- What is working
- What is not working
When both people do this work separately, the Quarterly Conversation becomes honest, mutual, and productive.
A Quick Note on Format
Quarterly Conversations work best when they’re:
- Offsite
- Informal
- Unhurried
Take the pressure off. Sit somewhere comfortable. Take your time.
Nothing from this meeting goes into HR files. This is not an “evaluation.” This is a conversation — a powerful one.
How to Structure the Conversation
Once you’re sitting down together:
1. Share what is working.
Manager shares first. Direct report goes second. Celebrate wins. Acknowledge strengths. Reinforce alignment.
2. Then share what is not working.
Again, manager first. Then the direct report. This part only works when both parties are open and honest.
3. For each “not working,” decide what happens next.
There are only five possible outcomes:
- Let it go. No one can fix it and you are both willing to drop it
- Add it to the team IDS list for an upcoming L10
- Manager takes a To-Do
- Direct report takes a To-Do
- Add it to the long-term issues list
That’s it. Keep it simple. Stay in the IDS mindset.
My Experience Using the AI Prompt
Heather is my Practice Manager, and we decided to use the AI prompts to help us prepare for the Quarterly Conversations we had with each other: mine with her about her seats in the business, and hers with me about my seats.
The biggest benefit wasn’t the questions themselves (though those were helpful). It was partnering with AI for note-taking and organization. I was able to think clearly, come up with meaningful feedback and insights, and then let the AI capture, organize, and summarize everything for me. That alone saved me a significant amount of time and made the actual conversations far more focused and meaningful.
We also used the experience to improve the AI prompts linked later in this article, removing redundancy and tightening them up so the prep process is even more efficient and effective going forward.
One other note. If you’re a Visionary or Integrator and you’ve never had someone do a Quarterly Conversation with you about your seats in the business, I strongly encourage you to do it. I found it incredibly insightful to hear how Heather experiences my leadership and how she sees the work I do day to day. I gained clarity on things I’m doing well from her perspective, along with a few opportunities to be better that never would have surfaced in our normal, everyday working relationship.
Heather’s Experience Using the AI Tool
As the Practice Manager, I used the same AI prompts to prepare for my Quarterly Conversation with Ben: mine with him about his seats in the business, and his with me about my seats.
What stood out most was the clarity the preparation process created before we ever sat down together. The prompts helped me slow my thinking, move past surface-level observations, and articulate what was actually happening in the business — what was working, where friction existed, and where I felt alignment or misalignment.
Partnering with AI for note-taking and organization made a meaningful difference. I didn’t lose insights, second-guess my feedback, or struggle to find the right words in the moment. Instead, I came into the conversation grounded, confident, and prepared to share thoughtful, constructive input.
That preparation changed the quality of the conversation itself. Because my thoughts were already organized, the discussion felt focused, respectful, and productive — not emotional, reactive, or vague. We were able to talk openly about strengths and opportunities without defensiveness, which ultimately strengthened trust and alignment between us.
This experience reinforced something important for me: Quarterly Conversations aren’t just a leadership tool for managers. When done well, they create space for honest upward feedback that rarely surfaces in day-to-day work — and that perspective is invaluable for building a healthier, stronger leadership team.
When You Do Quarterly Conversations Right…
You walk away with:
- A stronger relationship
- Clearer expectations
- More alignment
- Less frustration
- More energized
- A healthier team
- And a better 90 days ahead
Quarterly Conversations are one of the simplest tools in EOS, but also one of the most transformative — when you prepare correctly.
These AI prompts make that prep 10x easier.
Want the Prompts?
I created two versions. Here are the links:
- Manager Prep Prompt
- Direct Report Prep Prompt
If you want help implementing Quarterly Conversations or strengthening your LMA skills, feel free to reach out to your implementer. If you don't have an implementer, don't hesitate to contact me. This is one of my absolute favorite parts of helping teams run on EOS.