Tell me about a time you had a conflict.

On the same sale-side at the boutique, the deal analyst and I disagreed about how to model the target's recurring revenue. The company had a mix of true subscription contracts and "recurring-by-habit" repeat orders that weren't actually contracted. The analyst wanted to put 100% of repeat revenue into the recurring bucket because that's how the company presented it. I thought that was going to get torn apart in diligence.

I didn't take it to the senior associate first — that would have been ducking the conversation. I asked the analyst if we could spend 20 minutes walking through the customer-level data together. We pulled the top 50 customers by revenue, and I'd already pre-tagged which ones had master service agreements vs. POs. About 30% of what was in the "recurring" bucket was actually transactional. He saw it on the page and agreed we should split the disclosure.

The conflict was real — he'd already shown his cut to the senior associate, so reversing meant going back and saying we'd been overstating it. I offered to take that conversation if he didn't want to. He said he'd rather do it himself. We re-presented it the next morning, and the senior associate's reaction was — I'll never forget — "good, this is exactly the kind of thing buyers will ask about."

The broader point: the conflict was framed as analyst vs. intern, but the actual question was "what's defensible in diligence." The minute we shifted the frame from "who's right" to "what would a buyer challenge," the disagreement resolved on its own. I've tried to use that reframe ever since.