Your Meeting Superpower: Replacing Good Questions with Great Questions

Whether it’s a sales call, a performance review, or a client meeting, the quality of the outcome is only as good as the conversation you have. And your conversation will only be as good as the questions you ask.

Questions are your superpower in communication. They are the tool you use to get to the heart of the matter, to prompt real reflection, and to induce candor. 

But despite their power, we often squander our chances to ask great questions, instead reverting to the default, useless questions we’re used to.

Every day, millions of professionals mess this up — and ruin their chances of having more productive conversations. 

Enough.

It’s time to replace ho-hum, run-of-the-mill questions with super-power, stop-on-a-dime questions that do what they’re designed to do.

Let’s explore how. 

The epidemic of useless questions

The comedian Steve Martin once said that “How’s everybody doing tonight?” is the worst line in the history of stand-up comedy — and a gigantic wasted opportunity every time it’s used.

He explains it like this: You’re a comedian coming out on stage with a blank slate. You can do anything. Anything. 

That first line is a chance to take the audience by surprise, to completely change the narrative. But that chance gets wasted. Most of the time comics phone it in and do the same old tired opening — and get the same old tired response from the audience. 

And the opportunity is gone.

But as businesses, we fall into the same trap.

Walk into a store. Someone comes up to you and says, “Can I help you?” 

It’s the most obvious, rote question imaginable. We’ve all heard it hundreds of times before and so we almost always respond with our default answer: “No. Just looking. Thanks.”

What a wasted opportunity. 

What a lost chance for a brand to build a connection with a potential buyer.

Now, think about the same situation as a business owner. You’ve got a potential new customer walking into your store. Don’t let their experience start with the same useless question they hear everywhere else.

Even something as simple as “Have you been in our store before?” snaps the visitors out of their autopilot response and creates the start of a conversation. 

Useless questions exist in every business

The professional world is filled with useless placeholder questions that we use out of habit. 

We need to retrain ourselves (and the people we manage) to recognize opportunities to insert better questions into their interactions so the conversation becomes richer and more meaningful. 

Now keep in mind, better questions don’t have to be more complex. In fact, they’re usually simple — but they’re intentional and specific, making them succeed in the ways the other questions fail.

Below, I’m going to focus on three common business scenarios and explain the ways that obvious, useless questions have snuck in and diminished our chances for rich conversation. 

Better questions in sales meetings

Sales meetings are the frontline of your business’s future. Like the greeter when someone walks into a store, your salespeople are often the first people your buyers interact with, which means they have the responsibility of the first impression.

Bad questions

Too often, we cloud meetings with the same useless questions that sound more like a checklist than honest conversation starters. 

You know what I mean. Questions like these:

• What do you do? / What does your company do?
• What’s your budget?
• What’s your timeline?
• What are you looking for?

These are obvious and unhelpful because they don't spark meaningful conversation. They’re superficial, answered with half a sentence. 

Better questions

Instead, ask simple, clear, specific questions that prompt real thought and real dialogue:

• What’s the single greatest challenge you are having with your __________ right now?
• Tell me about your last experience buying a similar product? What about that experience was disappointing?
• Why are you looking to make this purchase now? 
• If you go ahead with this purchase, how does your life look different in six months?

Think about what makes these questions better. Yes, they’re specific and clear. But the biggest thing is this: They don’t prompt an automatic answer. When questions can be answered without much thought or reflection, they lose their power.

When you prompt self-reflection in your potential customers, you help them start to understand their own challenges in a way they might not have before. In doing so, they build a trusting relationship with you. 

Now, let’s think about performance reviews. 

Better questions in performance reviews

For the sake of this example, I’m considering a performance review a regular (but infrequent) meeting between a superior and a worker in which evaluative feedback is given. 

Just like a sales conversation, this is a meeting between two people, but performance reviews have two major differences from sales meetings: 

1. There is an already-established relationship between the manager and the worker. In a company with a healthy culture, there should be rapport and radical candor that create a feeling of psychological safety.
2. There are likely feelings of anxiety. Even in the most supportive workplace, a performance review can be uncomfortable — and we know that many workplaces are not very supportive at all.

All the more reason to be sure to not waste the opportunity to ask great questions.

Bad questions

There are plenty of well-intended-but-not-totally-helpful questions that we use in these situations. They often sound like this:

• What initiatives did/didn’t you complete this quarter?
• Why didn’t you accomplish everything you set out to?
• What are your top priorities for next quarter?

There’s nothing wrong with them, per se, but they don’t really prompt dialogue. They’re formulaic and obvious. Like in our sales meeting example, a better tactic is to be more pointed to prompt someone to think deeper.

Better questions

• What’s one impediment you struggled with this quarter?
• If you’re saying yes to X, what are you saying no to?
• What’s one thing that you aren’t doing right now that if you focused on it you feel would bring about dramatic positive results for you? 

Notice the move toward specificity.

When we can break people out of their tendency to generalize, we get richer answers. And that’s the first step toward a conversation that’s beneficial for both parties. 

Better questions in client meetings

In a service-based business, we meet with clients to set course, determine priorities, and chart progress.

To do this well, you’ll need to lead candid conversations that can sometimes touch on sensitive topics. 

While the nature of these conversations can vary widely, the questions you ask should all employ the same tactics: specificity and objectivity.

Bad questions

Unhelpful questions include:

• How’s it going?
• What are you going to talk about today?
• This most recent initiative is going great, right?

Better questions

Great questions in this context include:

• What is your single greatest challenge with _____ currently?
• What has to be true for us to achieve ______?
• What’s one thing that you aren’t doing right now that if you focused on it you feel would bring about dramatic positive results for you? 

Once again, we see that great questions are open-ended but specific — and they avoid pressuring the person to respond in a certain way.

Great questions cheat sheet

Asking great questions is as much about what you say as it is about how you say it. Your tone of voice, body language, and timing are vital to asking great questions. 

There are times when silence will do more than any question. There are other times when a great question posed at the wrong time can easily become the wrong question. 

And like everything else in the modern workplace, it all comes back to relationships.

Imagine the same question posed by your best friend or posed by the worst boss you ever had. In one case, you’d be open and honest. In the other, guarded. Maybe even offended by the intrusion. 

With all that in mind, here’s a quick cheat sheet for how to ask great questions no matter what situation you’re in:

Great questions are:

• Specific
• Intentional (not habitual)
• Not ignorant
• Based on a “read-the room” approach
• Simple
• Clear
• Disarming
• Efficient and effective
• Open-ended

Keep those in mind and fight against your default tendencies and you’ll turn great questions into your everyday superpower.