Demo or proof-of-concept language appears in 74% of these postings. The single most common failure is demonstrating before understanding — which produces a competent tour of features the customer did not ask about.

• “How are you doing this today?” The most valuable question in the set. What they do manually now is both the problem and the value ceiling.
• “What triggered this conversation?” A renewal date, a price rise, an outage, a new executive. There is always a trigger and it is rarely in the brief.
• “Who else has to agree?” Security review, procurement, the platform team who will actually operate it. Deals die on people who were never in the room.
• “What have you already tried?” Stops you proposing something that failed last year.
• “What happens if you do nothing?” Establishes real urgency, and occasionally reveals there is none — which is worth knowing in week one rather than month four.

A good demo shows their workflow, with data that resembles theirs, and stops. Every additional feature you show dilutes the one that mattered and adds surface for objections. The strongest move available is to skip something impressive because it is not relevant to them and say so — it signals that you were listening and it buys enormous credibility.

The most common failure in a technical sales call is demonstrating before understanding. It feels efficient — the customer asked to see the product — and it produces a demo that shows features rather than answers, after which the customer politely disengages.

• What are they doing today, concretely? Not their strategy — the actual workflow, who touches it, and how long it takes. Specificity here is what makes the demo land.
• What made them start looking now? There is always a trigger: an incident, an audit finding, a renewal, a new regulation, a person who left. No trigger usually means no deal, however interested they seem, and finding that out early is a gift.
• Who else has to agree, and what do they care about? The person in front of you is rarely the only decision maker, and technical enthusiasm does not survive a procurement or security review it was not prepared for.
• What have they already tried? This is the question that prevents the worst outcome — demonstrating an approach they rejected eighteen months ago for reasons you have just failed to ask about.
• What would make this a failure in six months? The best question in the set. It surfaces the real constraint, and it is one almost nobody asks.

Then the demo is not a tour. It is a demonstration that the specific thing they described is handled, in the order they described it, ideally with their vocabulary and their data shapes. Every screen that is not about their problem costs attention you cannot get back.