How to handle a conversation that keeps going in circles

The topic of respectfully disagreeing has come up a lot recently.

Whether with a leader, a direct report, or a cross-functional partner, it’s one of the trickiest scenarios — knowing when to push back and explicitly disagree vs. preserve a relationship.

Good news is you can do both.

The Situation

How do I respectfully disagree in meetings? A stakeholder strongly challenged my recommendation in a meeting, and I chose not to defend my position because I didn’t want to create tension or go in circles in front of everyone. But afterward, I regretted not speaking up.

My Take

Here’s how to disagree and actually influence someone’s opinion. And…if the convo goes sideways, how to recover.

The biggest mistake to disagreeing is making it about you and your POV. Sure you want your POV to be heard, but in order to do that you need to make it about the other person.

Here’s how I approach disagreeing and what to do if you keep going in circles:

1️⃣ First Disagreement: Use PREP

POV, Reason, Evidence, Path Forward

BUT acknowledge their POV fully first.

People are much more open to your perspective when they feel heard first. Note: this is not “I hear you but…”

Example: “I understand why it seems like usability might be the issue. If adoption’s low, that’s often the first place we look. But based on the data, the main challenge actually appears to be awareness, not design. [Then follow with your evidence (e.g. an example or the most compelling data point) and a suggested path forward]”

2️⃣ Second Disagreement: Look for an in-between

If you’re still disagreeing after the first pass, stop trying to “win.” Is there anything you agree on to move the conversation forward? Is there a follow-up (that you agree with) that takes into account both POVs?

Example: “I’d like to get more data on the design from users and still do an awareness push.”

This keeps the conversation collaborative instead of oppositional.

3️⃣ 3rd disagree: Pause + what you agree on + what you disagree on + concrete next step

If you’re still going in circles, it’s time to take this offline. Nothing productive is coming from this conversation.

“Let’s pause because we are going in circles. I think we agree we need to prioritize the customer experience, but we need a solution that takes into account both the awareness and the user experience. Let’s get A, B, and C in a room tomorrow to align on a plan forward.”

Final Thought

Disagreeing respectfully is not about avoiding tension. If you don’t state your POV, you’re implicitly agreeing to the other person’s POV.

But disagreeing can be done in a way that acknowledges the other perspective, communicates your thinking clearly, and helps the group move forward productively.

That’s what builds trust. Not “winning” the argument.