Ask More Questions, Make Fewer Assumptions, Sell More

Ask More Questions, Make Fewer Assumptions, Sell More


People buy workflows; therefore sales is a discovery process that reveals the challenges in their workflows that you might be in a position to solve. You have to ask more question and make fewer assumptions.


The number one mistake made in sales is thinking you must have quick answers. What happens when you are in the “rapid fie solutions” mindset? You quickly answer everything almost as if you’re on a game show and the fastest answer wins. Sales is not a game show and quick answers are rarely the best solutions. In fact, most quick answers have one thing in common – they are loaded with assumptions. When you answer quick, it means you weren’t really listening to the customer, you were formulating your answer based on partial understanding while they were talking!

A new customer of mine said this very important statement as we were walking out of a complex sales call – “people buy workflows.” I can’t stop thinking about this because most of our industry is trying to sell print when what people really want is a workflow. You can’t sell a workflow with rapid-fire solutions based on little knowledge of the workflow, you have to ask more questions.

My favorite quick answer example is:

Can your system generate a custom report that shows usability by user and user group?

The customer barely gets the last word out and sales people jump across the table and list every feature of custom reporting. What’s wrong with this example? I hate custom reports. The #1 thing asked for after you deliver a custom report, is for another custom report. They are a snap shot of what happened in the past, good if you’re a CPA, not ideal if you’re in operations. The question is not a question at all, it’s a proposed solution to an undefined problem. Your quick answer assumed you know the problem they are trying to solve and that a custom report is the right solution to that problem.

The answer to this question is a clarifying question; what do you need to learn from that report? Who needs that information? What do they do with that information? How often do they need it?

What if the answers to those questions are we need to closely monitor the users because we have a lot of turnover in the field, so we need to turn users off as soon as they leave the company? If that’s the problem, a custom report is a terrible solution. The real solution is SSO (single sign-on) which would actually solve the problem rather than provide more work for a human. With SSO, when IT cuts the employee off from their user management/HR solution, they would be automatically removed from the web-to-print system. This is why assumptions are so dangerous in the sales cycle.

Many people in sales are uncomfortable when the conversation moves anywhere outside the quick answer during the sales process. Again, they think they are playing a game show where the fastest answer wins. I’ve personally been berated by sales people for “asking too many questions” during a sales meeting. This hasn’t changed my behavior in the slightest because the most powerful tool in sales is the question.

People like to be listened to, people like to be understood. People like to be respected for their unique knowledge. When you demonstrate genuine curiosity, you will always come out ahead. If you are pitching a company in the financial sector, why would you assume you know what they need? Have you spent your entire career in the financial sector? This goes for virtually every company you pitch. When you spew rapid fire solutions you base them on assumptions, you jump to conclusions based on partial information, then you look foolish because it’s so easy for the customer to think “they don’t know shit about my workflow.”

What’s the alternative? Questions. Well formed, open ended questions based on you listening to what the prospect said, because you want to build your knowledge of their problem. Asking questions doesn’t make you look dumb or slow, it makes you look curious and respectful of their unique knowledge. Asking questions shows you care. Often in a sales call, the customer will ask “can your software do this or that?” I almost always ask a couple clarifying questions and it always reveals more details about the business process challenge they are trying to solve. Sometimes my answer is, “it’s just not clear how we would solve that particular problem but I would sure appreciate learning more about it so we could come back with a holistic solution.” This is when rapid-fire sales resources are squirming under the table – yes, I just said “I don’t know” in a sales call. And, the other thing I just did was create immediate trust. I don’t know takes you out of the bucket “everything they say should be discounted because I’m being sold to” into a bucket – she can be trusted.

I’ve had prospects (who are not doing any business with the printer I’m representing ask us back in to learn more for several hours!) This is from a prospect who the sales people had a hard time landing a thirty-minute meeting. People don’t want to be sold. They want their lives to be better and the only way we can make their lives better is if we take the time to understand their challenges.

Sales is not a game show. Pause, listen, ask clarifying questions and then restate your understanding in your own words back to the customer to show that you actually got it. Do this only if you want to develop trust and build a long-term relationship – if you just want them to buy your stuff so you can cash your commission check; stick with the rapid fire half-baked solutions.

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