Most people prepare for these meetings by rehearsing what they're going to say. The better preparation is figuring out what they're going to be asked.
An executive walking into a meeting with you is almost always trying to answer one of a small number of questions: is this on track, does this need my help, or does this need my decision. Walk in with a strong narrative about your work but no read on which question they actually have, and you'll spend the meeting talking past what they came for.
Write down the single headline first, literally, on paper or in a note, the one sentence you'd give if that's all you had. If you can't compress your update into one sentence, you haven't finished preparing yet, no matter how much you know about the details.
Headline: "The migration is on track for the 15th, and I need a decision on whether we freeze new feature requests during the final two weeks."
That sentence tells the executive exactly what kind of meeting this is, a status check with one decision attached, before you've said anything else. Everything else you prepared exists to support it if they ask, not to replace it.
A director is close enough to the work to have opinions about it, the system, the team, the last few quarters of context. An executive is reading your update next to a dozen others from teams they don't know that well. They're not evaluating your process, they're deciding whether this needs their attention now or can keep running on its own.
A director wants the trade-offs. An executive wants the bottom line. Send an executive the director-level version, every option you weighed and rejected, and it reads as unfocused, like you don't know which details matter.
"We're behind on the migration by about a week. I looked at pulling in a contractor versus pushing the date, contracting adds ramp-up time we don't have, so I'm planning to push the date and backfill by deferring the dashboard. Wanted your read before I lock it in."
"The migration will land a week later than planned. No impact to the finance dashboard commitment. Handled internally, nothing needed from you."
A director is asking how are we doing this. An executive is asking are we going to be fine. Walk in ready to answer the one they're actually asking.
From there, prepare for two things specifically: the number they're most likely to ask for, and the objection they're most likely to raise. If your update touches budget, timeline, or headcount, know that number cold, not "I'll have to check," the actual figure. Think honestly about the one thing in your plan a skeptical executive would poke at, and have your answer ready before they ask, not while they're asking.
Bring less material than you think you need, not more. The instinct is to over-prepare, twelve slides, every data cut, every contingency, as insurance against being caught off guard. Executives rarely want the insurance. They want the headline, the number, and the decision they're there to make. Anything beyond that belongs in an appendix you only open if asked.
Know before you walk in whether you're asking for a decision or just informing them. If you need a decision, say that explicitly at the start, "I need a call on X by the end of this meeting," instead of hoping it emerges naturally. Executives make decisions quickly once the question is put to them directly. What slows them down is a vague update they have to reverse-engineer into a question themselves.