The "Why Now" Question
Ask what changed to make this a priority today, exposing the real urgency or the lack of it.
How it sounds
- You You've probably lived with this a while. Why is it worth sorting now?
- Buyer Names a real trigger, a new boss, a lost client, a contract ending.
- You Listens for a concrete driver, not a vague we've been meaning to line
- Result You learn whether this is a live deal or just browsing
The full entry
The “why now” question asks what has changed to put this problem on the buyer’s desk today rather than last year or next. “You’ve probably lived with this a while. Why is it worth sorting now?” The answer reveals the trigger event driving the deal, or reveals that there isn’t one.
To use it, ask once the problem is established and listen for a real driver: a new boss, a lost client, a contract ending, a target they are missing. A concrete trigger means a live deal with a timeline. A vague “we’ve been meaning to look into it” means low urgency, which tells you to either build the urgency or spend your time elsewhere.
It works because deals close on urgency, not just fit, and this question tests for it directly. The mistake is skipping it and pouring effort into a buyer who was only browsing. This is a widely taught qualifying question with no single documented originator.