5 Ways to Have Deeper Conversations
In September, my friend Shell called and said, “I had some tests run recently and I wanted to share the results with you. It’s cancer. I’m calling you because I believe you are one of the few people in my life who actually cares about me.”
While it is absolutely true that I cared about Shell, I was taken aback and saddened by her comment. Shell and I were not exactly bosom buddies. We’d worked together many years ago, hit it off, and continued to meet for lunch a couple of times per year. That’s it.
How was spending just a few hours together per year (!!!) enough to make me one of the few people who cared?
Clearly, we packed those few hours with substance. Shell typically did most of the talking—but in her defense, I asked a lot of questions. And perhaps, therein lies the answer.
How do you have conversations that strengthen connections and address real issues? Ask better questions.
Regardless of your role, you need accurate information and good working relationships in order to succeed. Asking good questions gets you both. According to a Harvard Business School study, one of the most common complaints made about conversations is that people don’t ask enough questions. So, just start asking!
But if you want to make your conversations more substantial and productive, here are five ways to ask better questions:
1) Stay mellow.
You can get away with asking all sorts of questions if you make it safe for the other person to answer. Ask questions about relevant topics. Keep your tone casual and curious. Avoid judgment like the plague.
If you need information and/or want connection, you have to make it okay for the other person to be honest. Don’t expect people to open up to you if you’re immediately going to shame or punish them for what they reveal. It’s on you to create an atmosphere of safety.
2) Go deeper.
For a conversation to have substance, go beyond facts. Whether you’re engaged in small talk or data-driven analyses, the questions you ask can keep things shallow or lead to deeper understanding of the person, the situation, the facts, everything! Usually, that’s pretty helpful.
For example, let’s say you and a new coworker are doing the classic small talk thing and discussing the weather. He says, “I hope it snows.” You could respond with a closed-ended data-driven question like, “Yeah? What does the forecast say?” Or, you could ask something more personal, like, “Yeah? What do you like about the snow?” The answer you get (I’ll get to work from home… snow reminds me of where I grew up… I just bought a new truck and it will be fun to take it out…) reveals something about what’s important to your coworker.
Sharing thought processes and values leads to better decision-making, higher productivity, and stronger relationships. But most of the time, people don’t just offer those things up. You have to ask.
3) Invite reflection.
Humans are notoriously messy. They come with emotions, bias, beliefs and values they don’t even know they have, an enormous amount of personal experience, and their own unique key for interpreting their experiences. To have deeper conversations, ask questions that invite people to share their inner workings in a non-threatening way.
There are innumerable websites with lists of potential “conversation starter” questions out there, and frankly, I hate them all. These questions only work if you have some context. It’s not a good idea to walk up to someone and ask, “Do you like yourself?” or “What impresses you?” (actual questions on some of those websites).
Sure, it can be helpful to have a few “conversation starter” questions that you keep in your back pocket. But in my experience, once you’ve established a topic, it’s more useful to consider types of questions that invite reflection. Here are a few:
- Evaluations—Ask about preferences and opinions
- Conclusions—Ask what formed those preferences and opinions
- Comparisons—Ask for examples and illustrations or fresh perspectives
- Emotions—Ask about the personal impact of your topic
- Hypothetical—Ask “What would you do if…”
- Memories—Ask about a meaningful past experience, a time something went wrong, or any other type of story
Returning to our pretend conversation about snow, an evaluation question could be, “What do you like best about the snow?” For a comparison, you might ask, “How do snowy days affect you differently than rainy days?” This topic would be great for bringing up memories, as well: “Do you have fond memories that involve snow?”
Exchanging basic facts rarely deepens a conversation—whether it’s a conversation about your organization’s strategic plan for the next five years or a chat with a client you’re hoping to build rapport with. Ask questions that get people talking about who they are, how they think, what they feel, and what is important to them.
4) Reciprocate.
This is a bit of a cheat. Reciprocity doesn’t improve your questions. But reciprocity does make it easier for others to answer your questions, keep the conversation going, and build bonds. It improves the whole process.
If you’re always be the one probing without sharing anything about yourself, your conversation will feel like an interrogation. In order for others to feel safe enough to open up, you have to open up, too. That doesn’t mean you make it all about you or presume to know what the other person is thinking and feeling. Just add some relevant commentary and then bounce it back with another question. Like, “I love the snow so long as I don’t have to drive in it. How comfortable are you driving in the snow?”
True, some people will talk the hind legs off a donkey if given an opportunity. You might not even need to ask questions at all! But if one person is doing all the talking, your conversation might go long, but it won’t go far. Meaningful conversations take at least two participants.
5) Follow-up.
One way to show you’re listening, build trust, and deepen the conversation is to ask relevant follow-up questions. A Harvard Business Review article stated that “follow-up questions seem to have a special power” when it comes to creating connection.
You can’t prepare follow-up questions in advance, but if you pay attention, you’ll find lots of ideas for asking questions. Here are a few:
- Clarify vagueness. Don’t just smile and nod, ask questions.
- Define terms. Make sure you understand the other person’s personal vocabulary.
- Pursue anything that sparks your curiosity. If a question comes to mind that doesn’t take the conversation off-topic, ask it!
- Use some version of “Tell me more” that works for you, such as “How did that go?” “What was that like?” “What happened next?” etc.
With listening skills and some curiosity, you can become an outstanding conversationalist.
Asking good questions builds knowledge, wisdom, people-skills, and relationships. You can’t help but improve the quality of both your personal and professional life by using this skill. Get to know the people around you—how they think, how they feel, what they want. It’s super useful information! And it will deepen your connections, too.
Life is short. My friend Shell died less than three months after she called me with her diagnosis. I am sad she is gone. But I am grateful for the time and conversations we did have.
If you want deeper conversations, ask better questions.