Once you play with the big kahunas, your prospects will be tightly controlled and briefed by their procurement teams. Which means most of the question techniques outlined in the post will fall flat as the proc guys have read the same playbook.
This is where the side chats during coffee breaks, etc become the core. Be ready to show your software to anyone, anytime. The literal elevator pitch. Anything to outmaneuver the proc team.
Good luck :)
If there's anything doing demos has taught me over the years, it's that clients really hate answering the same questions over and over. If you have any of that information ahead of time, don't ask them again. But also like the article says, don't assume their answer is still the same. Say "what I understand you're looking for is X, has that changed?" It shows you're paying attention and have read the information they sent you.
On the other hand, the level of upper management that tends to make the decision is exactly the sort of person this demo advice applies most for: the people who really don't care about the flexibility of your search function or UX (because they're probably not using it themselves) but are quite impressed when you use it to highlight a solution to a problem unique to their company/sector, and don't actually have time to watch a walkthrough of Feature X but do remember the story about how it saved a company facing similar issues $100k
For example, when I hear this bit from the article:
Sales rep: “So, currently your company is losing out on
sales opportunities because leads are falling through
the cracks. [...] how much revenue do you think you’re
missing out on just because of ineffective lead
Sales rep: “So we’re talking hundreds of thousands of
dollars in lost deals every year.
Revealing this strikes me as an unconventional approach to price negotiation.
I would imagine senior executives at major companies would know such things - be it from their procurement teams, their education, or elsewhere.
Though it can be much easier if you're asking the more sensitive questions as a plausible part of a demo rather than grilling them at the beginning.
"So this is how you track your lost deals from each month, and we allow you to use different ways of handling bulk leads and smaller volumes of high value leads. So what sort of number do you think might be falling through the cracks in a typical month?"
"that definitely sounds like something you'd want the ability to monitor individually. Particularly as earlier you mentioned your typical deal size was at least $10k, so that's over $50k each month that our better lead management system could help you with accurately tracking and following up"