Why Anything? Why Now? The Two Questions That Rescue Stalled Deals
Most stalled enterprise deals share the same hidden flaw: the buying team cannot confidently defend why change is necessary and why timing is urgent. If those two points are fuzzy, your opportunity sits in “interesting” mode forever.
The two questions every serious deal needs
- Why Anything? Why should the buyer change from the current state at all?
- Why Now? Why must they act in this quarter, not “sometime later”?
Peeling the onion: how to go deeper than surface pain
Surface answer: “Reporting is manual.”
Deeper layer: “Manual reporting delays leadership decisions by 10 days.”
Deeper layer: “Delayed decisions are causing forecast misses and reallocation mistakes.”
Core business risk: “If this continues through Q3, operating plan credibility drops with the board.”
That is a real Why Anything statement.
Practical interview sequence you can run in discovery
- Problem: What is broken in the current process?
- Impact: What measurable cost does this create (time, risk, revenue, compliance)?
- Consequence: What happens if nothing changes this quarter?
- Owner: Who is accountable for this outcome internally?
- Deadline: What date/event makes this urgent?
Example: translating discovery into buyer language
Weak: “Our platform has better automation.”
Strong: “You currently lose 8–10 days per cycle due to manual validation handoffs. That delay is now colliding with your Q2 board timeline. This workflow removes those handoffs and gives leadership visibility in real time.”
How to test if “Why Now” is real
- Can they point to a date?
- Can they name who gets exposed if this slips?
- Can they quantify what one-quarter delay costs?
If all three are missing, urgency is probably performative, not real.
Use this in every follow-up
Every deal update should reinforce both anchors:
- Why Anything anchor: the business risk/outcome being solved
- Why Now anchor: the deadline + consequence of delay
When follow-ups drift into generic check-ins, momentum dies. When they reinforce risk + timing, decision velocity increases.
If you can’t clearly defend Why Anything and Why Now, the deal is still curiosity — not commitment.