As an introvert, I used to dread taking part in conversations. I was the guy who stood there looking dumb, not knowing what to say. Still, I couldn’t avoid engagement, not after seeing friends exploit their gift of gab to win friendships, expand connections, and find romance.

Those two dueling fears, looking dumb and missing out, nudged me into sales decades ago. I thought it would make me a better communicator, buying into the myth that the one who says the most, speaks the loudest, and pushes the hardest wins all the spoils.

That belief evaporated after spending months observing the top producers. They spoke as little as possible, I discovered. Instead, they kept their prospects talking by asking lots of open-ended questions and playing off the responses.

As I soon learned, asking questions not only enhances your sales chops, it makes you a more skilled and likable conversationalist. But not all questions advance the cause.

There’s a difference between people who query effectively and those who don’t. The true superstars excel because they refrain from asking questions that create awkwardness, tension, and resentment.

As my old mentor used to say, asking lots of questions will either make you super-likable or super-foolish. It’s these six that result in the latter.

Serial Rhetorical Questions

A rhetorical question is posed for dramatic, comedic, or satirical effect. The person who uses this device never expects an answer, or do they? I never know how to respond to these conversational enigmas. Should I supply the obvious answer, pretend to laugh, nod, grunt, or remain silent?

Besides the challenge of trying to answer them, rhetorical questions can come across as biting sarcasm, self-centeredness, and even insulting. When delivered at the right time, in the right way, they can add a comedic effect. If you use it this way, do so sparingly.

An occasional rhetorical jab won’t destroy your credibility but beware of becoming a serial rhetorical abuser. They’re more annoying than people who refer to themselves in the third person.

Orphan Close-Ended Questions

A close-ended question requires a yes or no answer from the person to whom you direct the question. An orphan close-ended question has no obvious follow up. They’re conversational dead-ends.

If you must ask a close-ended question, don’t rely on someone else to keep the conversation going. Either follow up with an open-ended question or put the focus back on you. “Here’s why I’m asking…”

If you’re on the receiving end, it’s best to respond with a reversal — a short phrase that forces the questioner to elaborate or clarify. Examples include:

• Yes. That’s interesting. Can you share why you asked?
• No, but I see what you mean. What do you think?
• I’m not sure. Can you elaborate?
• Yes, but curious. Why is that?

Dark Alley Leading Questions

A leading question is framed so that the questioner controls the answer or limits the range of possibilities. The query often contains information that suggests the answers.

How upset were you when Sharon declined your invitation?

In the above example, the questioner assumed you were upset. Sure, you can say you weren’t upset at all, but see how it leads you down a dark alley, almost daring you into a confrontation?

Leading questions are powerful tools in courtrooms and debate competitions, but in everyday conversation, they add tension by leading your partner down a path they may not want to go. If you seek to create tension, then sure, they work. But if you’re aiming to enhance your conversational chops, it’s best to avoid these devices.

Gotcha Questions

Nothing will anger someone more in a discussion than questions framed to catch someone in a contradiction. Those who use this strategy have little regard for winning praise as a conversationalist. They’re in it merely to exact a measure of personal satisfaction.

Even so, it’s easy to fall into this trap yourself when engaged in confrontational subjects like politics, religion, and other deeply held beliefs. We often resort to this tactic without consciously realizing it.

It normally requires two or more questions. The first few involve a setup. The last one serves as the gotcha zinger. It might look something like this:

Them: Hey, can you put in a good word for me with Kate?
You: I’m not really comfortable with that.
Them: Do you consider me a good friend?
You: Of course.
Them: If I’m such a good friend, why won’t you vouch for me?

It’s a simplistic example, but you can see how putting someone in that position can not only kill a conversation but also strain a relationship.

Belittling Questions

You’ll see this tactic in movies and television shows. It’s cliché, but it’s also common in everyday talk.

Two or more people engage in a discussion. One becomes jealous of the other(s). The jealous one brags about his superiority in wealth, position, title, family, or another valued metric, knowing their counterpart cannot match their status. When the jealous one finishes, they ask their target about their credentials, knowing it will reveal the questioner’s superiority.

Here’s an example:

Them: I was just promoted to senior VP at ABC investment bank. Hey, you work in banking. What’s your position there?
You: I’m still a loan officer, but you knew that.

The questioner knows you can’t match his title but asks the question to accentuate his superiority in status.

People often adopt this tactic to impress a third party, but I’ve been on the receiving end of this transparent ploy in one-on-one conversations. It’s an ugly move and not only ends a conversation but also puts an end to any future ones.

Backdoor Disparaging Questions

The cowardly way to insult someone. It happens when someone plays off a mundane question to make a point about someone, their beliefs, their family, or any other point of contention. Here’s how it works.

You: Let’s go hang out at Eddie’s tomorrow night.
Them: So, I guess tomorrow night is asshole night?

Here’s where it gets tricky. If everyone present in the conversation despises Eddie, then the question garners a good laugh. Still, you never know what people really think when you take this tack. When you paint yourself as that guy or gal — the one who talks shit about everyone behind their back, you’ll find yourself with a scant selection of people to converse with.

Great conversationalists go out of their way to make everyone else look like champions. They ask open-ended questions, making it easy to keep the discussion moving forward. They show interest in people, recognizing that if everyone else walks away feeling great, it makes them look good.