How to Create Questions to Connect with People

Updated: Jun 13, 2021

Have you ever wanted to connect with someone but they were just so different from you that you couldn’t come up with any questions? Many people do, but it doesn’t have to be that way.

Creating good questions to keep a conversation going requires practice, experimentation, vulnerability, and imagination.

In this article I’ll first briefly share some of the most obvious question tips and then I’ll explore some more ideas that will help you create questions.

*** Listen to audio here ***

First, some of the basics:

5 Ws and 1 H. (Who? What? When? Where? Why? How?) These are the basic foundation questions to always return to. In addition, ask open-ended questions instead of only yes-no questions, and ask follow-up questions.

In my opinion, three of the best follow-up questions are: Why? How? Can you explain?

Keep on searching for more explanations, information, and details. The key is to follow your curiosity through questions but also to share your own ideas and experiences so that it’s a two-way conversation. Just be sure to always bring the conversation focus back to them.

Now let’s look a little deeper at a few simple question strategies.

Past, present, and future time perspectives

Talking about the present is often a good place to start, but if we stay there our conversation will be limited. Consider shifting your questions to also focus on the past or the future. This way you can understand more of their journey and also what their hopes, dreams, or predictions are for the future. Even if you stay on the exact same topic, simply shifting the direction in time can open up a whole new perspective.

Past examples: What made you want to work in advertising? Have you worked for other companies besides your current one? How has advertising changed since you started working in advertising?

Future examples: Do you think you will always work for your current company? How do you think advertising will change in the future? How would you feel if your company transferred you to a different department or country?

View them as your teacher

Asking for someone’s advice, knowledge, or opinion is one of the best ways to connect. It shows that you value their experience or expertise. If you don’t know too much about their professional field or ideas, consider it as the perfect opportunity to learn something new while also making deeper connection.

Don’t worry about sounding ignorant. Sometimes people with niche expertise or knowledge need practice explaining their knowledge in a way that normal people can understand. In fact, you will not only learn new ideas, but also help them articulate their ideas better. Also, when we ask about someone’s field, they usually feel smart, important, and respected. In the end, it will most likely make you smarter and more connected.

Asking for advice about a problem you are facing can also help the other person feel that you value their perspective. Particularly if they are very different from you, they may give you advice that you would never think of on your own. Sharing a problem also makes you seem more relatable and trustworthy, which could lead to more mutuality and commonality. In fact, psychological studies have suggested that when someone helps another person in a small way, it also makes them like the other person more.

You don't need to be perfect

If English is not your first language, you may feel self conscious about your grammar, pronunciation, or ability to ask questions easily. But remember that most people don’t care if you make a mistake.

Instead of aiming for perfection, focus on connection.

Improving your question-asking skills will only happen if you experiment and take risks, which means that of course sometimes you will make mistakes or ask strange questions. But it’s the only way to improve. And sometimes the riskiest questions prove to make the deepest connection.

Return to a previous topic

After you have been talking a while and you run out of questions, consider returning to a previous topic that seemed positive. You can easily just return to it by saying: “You mentioned earlier that __________. I was wondering if you could tell me more about that.” Or, “Oh, so I was meaning to ask you more about Italy. Have you been to other European countries too?”

Include everyone

When you’re in a group, there are often certain people who do more of the talking compared with others. If someone seems shy, quiet, or not involved in the discussion, they will probably be very grateful if you bring them into the discussion. All you have to do is say, “How about you?” and gesture toward them. You can simply reflect the same question or topic in their direction.

If you find it difficult to reflect the question because other people are talking non-stop, try interrupting them by agreeing with what they said and adding a short comment. Then, immediately ask the shy person, "How about you? What do you think?" before the other person continues talking again.

There are millions of possible questions depending on the setting, relationship, and combination of people. It can be easy to feel stuck or confused with too many options. In the end, don’t overthink how to create the perfect question because there is no perfect question. Instead of worrying about how you sound, just focus your attention on the other person. Use your curiosity and questions to help them feel valuable, respected, and understood. The connection you create with them will be well worth the effort.

*** Listen to audio here ***