Questions that sound like interrogation, and fixes

You will be able to spot leading, stacked and loaded questions and rewrite them.

Play back a recording of one of your own meetings and listen only to your questions. Most people are surprised. Questions they remember as open and curious turn out to have an answer built in, or three questions joined together, or a tone that sounds faintly like a telling-off. The buyer answered them, so nothing seemed wrong at the time. But each one cost a little goodwill and a lot of information.

This lesson covers three question habits that make discovery feel like an interrogation, and a simple way to soften the hard questions you still need to ask. Sales foundations lesson 3.2, Open questions that get people talking, touched on stacked and why questions. Here you will learn to spot all three in your own words and rewrite them.

Leading questions

A leading question puts the answer in the buyer's mouth. It usually starts with "would it not be better if," "don't you think," "wouldn't you agree," or "surely you'd want."

"Wouldn't it be better if payroll took one day instead of three?" Of course it would. The buyer says yes, and you have learned nothing, because nobody prefers three days to one. Worse, the buyer can tell you are steering them towards a product, so they start to guard their answers.

Leading questions also creep in through assumptions. "How much is the overtime problem costing you?" assumes there is an overtime problem. If the buyer never said there was, you have told them what their problem is.

The fix is to ask about the situation and let the buyer judge it. "How long does payroll take each month?" then "How do you feel about that?" or "Is that a problem, or just how it is?" If they say it is fine, believe them for now. You have saved yourself from pitching a fix for something they do not care about.

Stacked questions

A stacked question asks two or three things at once. "How do you handle leave at the moment, and is it a problem, and who looks after it?" The buyer answers the easiest part, usually the last, and the other two disappear. You may not even notice, because you got an answer.

Stacking often comes from nerves or from wanting to be efficient. It is neither. One clear question gets a full answer, and three stacked ones get a partial answer to one of them.

To fix it, split the stack and ask the broadest part first. "How do you handle leave at the moment?" Wait. The other two questions often get answered without being asked. If not, ask them one at a time.

Watch for the softer kind of stacking, too: a question followed by an example answer. "What worries you most about the business? Like cash flow, or staff, or something else?" The buyer picks one of your options, and their own answer, which might have been better, never comes out.

Why questions that sound like blame

Why is useful in theory. In practice, "Why did you do that?" often lands as "what were you thinking?" Buyers who suspect they made a mistake hear it as criticism and start defending the choice instead of describing it.

Hafiz, the payroll software seller from lesson 1.3, Handle the buyer who wants the pitch first, used to ask, "Why are you still doing payroll in Excel?" Every time, the buyer explained at length why Excel was fine. Now he asks, "What led you to set it up in Excel originally?" and "How did that come about?" He gets the same information, plus the story, and the buyer stays relaxed.

"What led to," "how did that come about" and "what was behind" do the same job as why without the edge. A quick test: say your question in a slightly tired voice. If it sounds like a parent or a manager unhappy with someone, rephrase it.

Soften hard questions with a reason

Some questions are hard however you phrase them. Income, debts, family health, who else in the company has a say, what went wrong with the last supplier. You still need to ask them.

What softens them most is telling the buyer why you are asking. "So I don't suggest something that doesn't fit, can I ask roughly what your monthly commitments are?" "I ask because some firms need sign-off from finance and some don't. Who else would be involved in a decision like this?"

A reason turns a demand for information into a request with a purpose the buyer can see. They can also say no, which most will not, because the reason is in their interest.

Rewriting your own questions

Here are some typical before-and-after rewrites, so you can see the pattern:

"Wouldn't it help to have everything in one app?" becomes "How do staff apply for leave and claims today?" "Do you track overtime manually and is that slow?" becomes "How do you track overtime at the moment?" "Why didn't you get cover earlier?" becomes "What got in the way of sorting out cover before now?" "What's your budget?" becomes "So I don't suggest something out of range, have you set aside an amount for this?"

None of the rewrites is clever. Each one removes the built-in answer, the extra question or the edge, and in two of them adds a reason. Lesson 5.3, Ask about money without making it awkward, goes further on the last one.

Find a recording of a recent meeting, or failing that your notes from one, and have it ready before you start the activity below.

Review a recent meeting recording or your notes and rewrite five questions that were leading, stacked or blaming.

Course

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