The Question Asker-er: Tactics on How to Use Questions to Get What You Want/Need

At the end of my last post, I said that I planned to continue exploring how to ask and craft powerful questions. Thanks to everyone who read along (a whole lot of you!) and I hope you’ll find this second entry just as intriguing. Onward!

The first thing we must remember is why we ask questions:

To interact with people, duh.

But why do we ask questions to interact with people?

I think it’s mainly for two reasons:

  1. To get information that we need in order to do things. This information can range from learning someone’s name, to what the weather will be like in Chicago, to the purpose behind a client’s project, to why someone has lived their life in a specific manner!
  2. To prolong the interaction. This is essentially info-gathering, too, but the difference is the point of the information is for the interaction itself rather than the answer and what it will let us do. That’s how we find out all those mysterious things that make people who they are. That’s how we build relationships and connections with strangers on trains, in line, on Twitter and in real life.

So with that said, what I have for you are three question-asking tactics that I recently recorded. I’ve ranked them from easiest to hardest. Let me know what you think!

LEVEL 1: Beginners

Tactic: Be curious. If you don’t know something, just ask.

Recently, some out-of-town friends found themselves on the Queen Mary. While there, some kind of conference was happening. People were walking around in period costumes from the 1930s. They kept wondering what was happening. So they did what many people do. They speculated and kept an eye out for information. But otherwise, they didn’t talk to anyone wandering around in costume. Then I came into the picture.

Most of the people in my life know I’m the question-asker. If I need something or don’t know something, I will definitely ask the question to whoever might answer. When I picked them up for an afternoon out, they told me about the event as we walked back to the parking lot.

“Do you want me to ask?” I asked them. And they agreed. Sure enough, a woman in a period, hat, gloves and dress walked by us.
“Excuse me,” I asked. “We’re really intrigued by all the costumes. What’s happening?”
“It’s the annual Art Deco Festival!” She explained. We chatted pleasantly for a few moments, then went our separate ways. Mystery solved!

Now that I’m writing this, I wonder if this is a more advanced tactic. Because it’s not so much about the question itself as it is about the mind-set. People usually don’t ask questions — and I mean questions as simple as “Excuse me, is this your seat?” — because they’re afraid about how others’ will perceive them. They don’t want to seem intrusive, uncertain or vulnerable. Added to that, the question usually needs to be asked in an uncertain environment. We’re always more comfortable asking people who we know rather than people we don’t. But when you make the mental shift …. When you get more confident in approaching people in general, you actually open yourself up to being perceived as assertive, a risk-taker, bold, curious and a leader. Then you can get yourself into such advanced just-ask-the-question levels like:

  1. Asking people for their names again when you’ve forgotten them
  2. Asking co-workers and bosses for clarity on instructions that they’ve given you in multiple mediums
  3. Never worrying about what to do in a new location because you’ll just ask a local. (I did this recently with a friend on a roadtrip. No prior research needed because we just conversed our way through our itinerary.)

So how do you practice this tactic? It’s very simple and yet perhaps the hardest thing in the world. When you think to yourself: I’m not certain what I need or what I should do. Then you locate the best person, known or unknown quantity that they are, and you ask!

LEVEL 2: Intermediate

Tactic: How to find the missing piece a.k.a ask the same question to two different people.

On my recent roadtrip, the Q-person (the question-asker) and I were enjoying some New Mexican cuisine when a flavor in a coleslaw caught her attention. The Q-person, by the way, is like Sherlock Holmes when it comes to flavors and usually amazes people with this talent.

“What was in this again?” She asked. But I didn’t know, and we didn’t have the menu anymore. So when the waitress came over to check on us, she asked.

“What’s in this?” My friend asked.
“Red cabbage, vinegar, jalapeño, carrots and olive oil.” The waitress replied.
“Are you sure?” The Q-person asked again. The waitress demurred she didn’t and offered to ask the kitchen staff.

After a few moments, the waitress returned.

“It’s salt!” She announced. But my friend didn’t look convinced.
“Are you sure?” She asked again, but the waitress nodded with conviction and went on with her life.

However, my friend was still not convinced she had her answer. So when another of the waitstaff came around to check on us, my friend asked her the same question AS IF she’d never asked it before.

“What’s in this?”
“Red cabbage, vinegar, jalapeño, carrots and olive oil,” waitress #2 replied.
“Are you sure?” Waitress #2 wasn’t sure, so she went back to ask the kitchen staff. A few minutes later, both waitresses returned.

“It’s oregano!” They announced. They explained how after the first question had been asked, the kitchen staff had talked among themselves. They recalled that a different person had made the slaw that day, and this particular person always used fresh oregano when they made it. We all had a good laugh about the mystery.

Now imagine this tactic in professional settings — you’re interviewing customers, you’re profiling a subject for a feature, you’re pitching a client, you’re questioning team members. When people are asked the same question twice, invariably they answer it differently. The first question primes them with their instinctual answer. But the second one makes them think about that answer. Often, you use this tactic when you know information is hiding from you — whether consciously or unconsciously.

LEVEL 3: Advanced

Tactic: Ask unexpected questions in a charming way a.k.a. be witty.

I went to a birthday party alone, and I met lots of new people. In such situations, there’s a formula for conversation: Who are you? How do you know the birthday person? What do you do? I think of these conversations as close-ended for the most part. You are not asking for anything beyond the obvious answer. And this is especially dangerous when you’re a new person alone at an event. Especially if you’re the ONLY person at the event who doesn’t know anybody. You need to work harder to interact with others because unlike them, you have no fall-back friend with whom to converse. And if you’re like me, you like to have fun and witty conversations anyway! So if you’re going to have to meet a bunch of strangers, you might as well make it fun and interesting. And if you’re going to put effort into making it fun and interesting, you might as well make new friends!

This is where questions can help you create banter with strangers. Because most people stick to formulaic dialogue conventions with new people, breaking those patterns can invoke some wittiness. Here’s one that stuck out to me that night:

“How do you know the birthday girl?” I asked three new potential friends (NPF).
“I work with her,” NPF #1 said of NPF #2.
“I work with her,” NPF # 2 said of NPF #1.
“I’m her roommate,” NPF# 3 said of NPF #2.
“By choice?” I asked.
This stunned them into silence.
“Well,” I said, “I didn’t want to assume.”
They started laughing.
“Yes, yes,” they laughed. “By choice. How do you know the birthday girl?”
“We were on a panel together,” I said, “Then I decided to keep her.”
“So she didn’t have a choice?”
“Well, I did,” I said. And everyone laughed.

The conversation continued for a long time after that.


What do you think of these tactics? Do you have anymore? Feel free to share them in the comments, and stay tuned for my continued exploration of questions.