Most enterprise deals stall for the same reason: the seller is having a product conversation when the buyer's executives are having a business one. You don't close that gap with a better demo — you close it by asking better questions. Take these into your next strategic account and notice how the conversation changes.
1What outcome matters enough to be on the board's agenda?
If your deal isn't tied to something the leadership team is already accountable for — revenue, cost, risk, market share — it will always be a "nice to have." Find the outcome they're measured on, and attach your value to it.
2What happens to them personally if this problem isn't solved?
Executives act on consequences, not features. Understand what's at stake for the individual — reputation, targets, career — and you understand what will actually move the deal.
3Who else has to say yes, and what do they each care about?
Complex deals are won or lost in the buying group you can't see. Map every stakeholder and the specific outcome each one needs before you present anything.
4What is the cost of doing nothing?
Your real competitor is usually inertia. Quantify what standing still costs them each quarter — that number, not your price, is what justifies action.
5How will they measure whether this worked?
Agree the success metric up front. It turns a vague promise into a business case you can both defend to a CFO — and it makes you the person who thinks like they do.
6What have they already tried, and why did it fall short?
Their history tells you where the landmines are. It also lets you position your approach as different rather than "another vendor saying the same thing."
7If we did nothing else this year but fix this, would it be worth it?
This question forces prioritisation. If the answer is yes, you have a must-win transformation. If it's no, you've saved yourself a quarter chasing a deal that was never going to close.
How to use them
Don't fire all seven like a checklist. Pick the two or three that fit where the deal is stuck, ask them of the right person, and then listen. The goal isn't to interrogate — it's to be the one seller in the room thinking about their business instead of your product. That is what a Strategic Adviser does, and it's what clients pay attention to.
Want help applying this to your real deals?
Book a free 30-minute strategy session. We'll take one deal you're working on right now and find the executive conversation hiding inside it.
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