How To Ask Better Questions In Sales

Asking questions is one of, if not the most fundamental key to success in sales.

According to research from Gong.io, after analyzing 25,537 B2B sales conversations using artificial intelligence, they determined that the highest converting talk-to-listen ratio on B2B sales calls is approximately 43:57.

In other words, from Gong.io:

“Top closers spend the most time listening and the least time talking.”

It’s also one of Dale Carnegie’s “Twelve Ways to Win People to Your Way of Thinking.”

Carnegie says,

“Let the other person do a great deal of the talking.”

And you know what is the best way to get your prospect talking? That’s right … by asking questions.

Here are four tips for asking better questions:

  1. Ask questions that are clear and direct.
  2. Ask questions that are open-ended.
  3. Pause after you ask the question.
  4. Ask follow-up questions.

1. Ask questions that are clear and direct. 

The question needs to signal to the prospect that it’s their turn to talk.

It’s similar to how a famous person walks onto stage. They don’t even have to say anything, and the audience starts to applaud.

Your question needs to be like the famous person. It needs to be automatically deserving of a response.

In order to achieve this, the question should be clear and direct. By clear, we mean that the question is not punctuated by um’s or filler words. By direct, we mean that the question is short and to the point.

Bad question:

“Oh, interesting, well, could you maybe tell me more about that? If you don’t mind …”

Good question:

“Can you tell me more about that?”

2. Ask questions that are open-ended. 

We want to avoid asking questions that can be answered with one word, like “yes” or “no.”

To take this one step further, you can intentionally design the question to invoke a longer response.

Here are four examples of these “long-response” questions from Gong:

  • Can you help me understand …
  • Can you walk me through …
  • Can you talk to me about …
  • Can you tell me about …

So you can take a question like this:

“What’s your budget for this project?”

And turn it into a long-response question like this:

“Can you help me understand your budget for this project?”

This small shift in phrasing invites the prospect to give a more long-winded answer.

Longer answers are better because they contain more information about whether the prospect is a potential buyer.

3. Pause after you ask the question. 

When you ask a question, pause immediately afterward. Pause until your prospect responds. Sometimes this will take 3-5 seconds, maybe longer.

Let the silence add some healthy pressure to the conversation. There’s a fine line here—between being awkward and being regarded as a calm and confident professional.

Whatever you do, don’t be the first one to talk again after you’ve asked the question.

A deep exhale (e.g., ugh, hmm, hmph) or a one word response (e.g., Great, Okay, Alright, Interesting) do not qualify as a response from the prospect.

A short response like this is often a sign that the prospect feels the pressure to say something (this is good). It also means that the prospect is still thinking. And you, as the salesperson, shouldn’t interrupt that thought process.

Wait until the prospect gives you a full and direct response to your question.

Don’t worry about waiting too long. I’ve waited so long on some calls that the prospect asks,

“Are you still there?”

And my response is always the same:

“Yes, I’m here. I’m just listening.”

And then I pause again and keep waiting for their response.

4. Ask follow-up questions.

Ask a logical follow-up question that pertains to one of the last few things that your prospect mentioned.

This is the most natural way to keep the conversation going.

It’s also something that junior reps really struggle with. Because they’re often reading from their scripts and asking questions one after another like a robot, without really listening to what their prospect is saying.

A senior rep, on the other hand, will make their questions conversational, by asking follow-up questions that naturally follow from the prospect’s answers.

Prospect’s answer:

“Last time we tried this, it failed, so I’m not eager to try again.”

Follow-up question:

“Can you walk me through why it failed last time?”

A bad conversation is a shallow conversation, where both sides say what they already planned on saying, without really engaging one another, like ships that pass in the night.

On the other hand, a really good conversation is one that goes deeper. Follow-up questions are the key to a deeper conversation. 

The best question.

If you get stuck and you can’t think of a question, remember this question:

“How do you feel about that?”

One of the most cathartic experiences in all of human existence is to talk about your feelings. I can’t be sure, but this would make sense as a reason why therapy is so popular. 

If you are conversing with someone who is particularly cerebral or you get the sense that they won’t be comfortable talking in terms of their feelings, you can change the question just slightly, like this:

“What are our thoughts on that?”

Seriously, try this in your next conversation.

You’ll be amazed by how much people have to say in response to such a simple question. And you can ask it about virtually anything.

People almost always have feelings about something, even a topic that isn’t typically considered to be emotive. And even if they don’t want to share their feelings, they’ll at least tell you their thoughts. 

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