The Most Important Question to Ask Prospective Customers

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If you don’t like the answer, it’s time to walk away.

The fast-talking salesman is a convention of popular culture. But selling is more like taking confession or practicing psychology: It is a listening profession. The entrepreneur’s job is not to pitch his product. Rather, it is to get the potential buyer to clearly articulate her needs, budget, time frame, and desired outcomes. Only by truly listening can the entrepreneur match what his startup offers to what the client specifically seeks.

There are two elements to making the match: determining fit and proposing. Determining fit means understanding the prospect’s circumstances and judging whether the company’s value proposition aligns with them. This is the heart of the selling process, where both parties agree that it’s worth having a conversation. As with qualifying, determining fit requires asking great questions that make the prospect think hard about how this product will be used and why that’s important for him now. They frame the engagement, pinning down scope, timing, deliverables, and risks. Are the economics right? Can the requirements be fulfilled? Is the promised value attainable? Perhaps the most important question to ask is, “What exactly do you expect from this relationship?”

Entrepreneurs are often tempted to promise the moon because, in the flush of a sales conversation, the moon seems eminently deliverable. If the customer’s expectations are beyond what the relatively untested startup can deliver, it’s better to cut bait than to risk disappointing. Proposing applies everything the entrepreneur has learned from qualifying and determining fit to the specifics of the engagement. For most entrepreneurs, writing proposals is the most comfortable part of selling. Back in their caves, they are tempted to reiterate the wonder of their features and benefits when that does nothing but add pages and complexity. The best proposal is a concise document that captures the key points already established in the selling conversation. That’s it. The proposal should use the customer’s own language, emphasize her priorities, and review the specifics of her environment. Reading the proposal, she will know she has been heard and understood.


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