3 kinds of questions to ask to have more meaningful conversations

Have you ever sensed that someone has more to say but isn’t able to say it? Perhaps your direct report insists that everything is “great!” despite her impossibly heavy workload, or you notice the  same few colleagues stay silent during the weekly Zoom check-in. Or you know a project needs work, but struggle to empower your colleagues to give you some much-needed feedback to improve it. Failing to understand our conversation partners is a struggle for many of us, especially in virtual settings brought on by the pandemic, but it can lead to subpar work, support, and collaboration, and weaken relationships over all. When we are unable to cut through the superficial and get to the deep stuff, we may quickly find ourselves operating on faulty or incomplete information, stuck in place, uncertain of how to proceed and make progress.

As a user researcher in Silicon Valley, I’ve faced this challenge in many conversations. My job is to understand people’s needs and motivations, and what they think and feel about the products my team builds, and research sessions—typically hour-long conversations with a group or an individual—ensure we don’t get overly attached to an idea that sounds good but won’t actually serve its intended audience. Many participants struggle to be honest and vulnerable with researchers at the beginning of a session, thanks in part to a very real and very human desire to please. Rather than be critical of our work, they may sugarcoat their responses, be overly enthusiastic, or keep things brief and vague to avoid hurting our feelings. But my job is to gain insight, not flattery, so I’ve learned how to break through and uncover what others really need to say. 

The listening skills I’ve acquired have been crucial to my development as a researcher, but also as a professional. Which is why I’ve written Listen Like You Mean It, an essential guide to improving your listening skills that is chock-full of practical tips and hands-on exercises to help you listen with empathy, humility, and understanding, and ultimately build stronger relationships.

The next time you sense someone is holding back or keeping you at arm’s length, use what I call connecting questions to navigate these moments with grace and encouragement. Connecting questions are questions, and sometimes statements, neutrally framed to elicit an open response, without suggesting or biasing toward a particular reply. They give our conversation partners the wiggle room to answer as much or as little as they’d like—without projecting our experience or assumptions onto them—and therefore help you delve into deeper territory, draw out reluctant talkers, and create meaningful conversation on and offline. 

There are three types of connecting questions you’ll want to leverage in conversation: exploratory questions, encouraging questions, and reflection questions.

Exploratory questions

Exploratory questions are the perfect starting point in a conversation. Usually beginning with “how” and “what,” exploratory questions are unbiased: they neither presume an answer upfront, nor do they suggest a binary outcome (yes or no). Their open-ended structure can lead us down many possible and unexpected paths because they allow our conversation partner to interpret the question as they see fit; when they do, they may give us more or different information than expected. They help us to see the full picture by releasing our conversation partners from expectations, assumptions, or hypotheses we may have about them. 

These types of questions are particularly effective when you need to grease the wheels in a group discussion, discuss trade-offs in a 1:1 with a direct report, get to know your colleagues better, or even make it through the mandatory “fun” that is the dreaded virtual team happy hour. In moments like these, try the following exploratory questions to open things up:

• What does “ideal” look like?
• How would you approach . . . ?
• What would you do if . . . ?
• What’s the biggest risk to . . . ?
• How do you feel about that?

Encouraging phrases

Exploratory questions can help us further a conversation, but sometimes our conversation partners need an extra nudge. For the colleague on the edge of giving her peer some much-needed feedback, these encouragements can give her permission to go there. For the direct report with an impossible workload trying to keep it all together, so, too, can these phrases provide a necessary outlet. For the coworker who was cut off mid-thought by a peer in a Zoom meeting, a little encouragement can give them the confidence to try again. Whether our conversation partner is hesitant to be forthright due to temperament (naturally reticent), circumstance (in need of time or space to process their thoughts), or emotion (deterred by shame or pride), these small nudges help us to peel back the layers and deepen a conversation, without pushing anyone too far.

If you can tell that your conversation partner wants (or even needs) to share but isn’t sure how they may need your encouragement. Sometimes all they need is to be asked to keep talking, so they can continue processing and working on things aloud. 

Encouraging phrases sound like:

• Say more about that.
• Tell me what this means to you.
• Walk me through . . . 
• Tell me more.
• What else?

Other encouraging phrases are even more subtle. With a well-timed pause, these statements can serve as a small encouragement for our conversation partner to keep going. Because they invite our conversation partner to expand on an idea or feeling, I call these types of encouraging phrases expansion prompts. For instance:

• It sounds like that was difficult for you. [pause] 
• It seems like that was very exciting for you. [pause]
• You feel that way because . . . [pause]

Reflection questions

Though encouraging questions can pack a punch, from time to time our conversation partners may need room for additional contemplation. It’s not always easy for us to share our thoughts on the spot, even when we want to. 

Reflection questions work by directly prompting our conversation partner to think through the topic at hand, typically through comparison. When we put options in front of our conversation partner, we invite them to reflect on which, if any, are closest to the sentiment they are trying to express—whether your direct report is struggling to think through their immediate projects or future career goals, your manager is spinning on how to celebrate a team milestone, or your work wife can’t decide if she wants to leave the company or not. This can be very helpful, since oftentimes, even if we can’t articulate what we want, we know with certainty what we don’t want. Having a few options to choose from can help bring those feelings, preferences, and opinions to light.

When using reflection questions, you’ll want to be careful not to offer more than one either‑or pairing at a time. If we offer more than that (is it A, B, C, or D?), we may inadvertently send our conversation partner into indecision paralysis and leave them spinning more than before. 

The questions below provide a starting point for reflection without overwhelming our conversation partner.

• Are you looking for something action-packed or low-key?
• Would you call this feedback a must-have or a nice‑to‑have?
• Would you say you feel more frustrated or disappointed?
• Is it more about wanting a raise or wanting to be recognized?
• Is it more like Mussolini or a tree? (This last one is a great word-guessing game for long car rides. You have to think about it, a lot.)

Each of these questions provides a possible path forward for our conversation partner. Though they use a close-ended structure, they are the exception that can further open—rather than close—a conversation. They are designed to extend a line of inquiry rather than to confirm and conclude it. They are a particularly helpful tool to furthering a conversation when others begin to feel Zoomed-out and video call fatigue and monotone responses set in. Most people will naturally provide more than a one-word response to these kinds of questions.

In today’s increasingly virtual environment, you can make connecting questions even more effective with a few simple changes, such as reminding yourself to look at your webcam (not at yourself!) in a video call, or even minimizing your own image on screen to help keep your focus on your conversation partner. (Add a sticky note next to your webcam as a friendly reminder to build the habit.) You might even forgo a video call altogether, and opt for that oh-so-old school and ever-effective phone call instead—on the phone, everyone is free to move about, rest their eyes, and simply listen instead. Being in motion and skipping screen eye contact can be remarkably freeing from time to time, and especially in difficult conversations, and equally effective—you can still hear the emotion, like a smile, over the phone. These small steps go a long way in creating the necessary space for others to fully step into conversation, especially in remote settings. 

Whether your conversations are virtual, in-person, or over the phone, with the right questions, you can learn to break through to your conversation partner, get to the bottom of what they are feeling, and build better, stronger, more collaborative working relationships as a result.

Adapted from LISTEN LIKE YOU MEAN IT: Reclaiming the Lost Art of True Connection by Ximena Vengoechea, in agreement with Portfolio, an imprint of Penguin Publishing Group, a division of Penguin Random House LLC. Copyright © Ximena Vengoechea, 2021.

Ximena Vengoechea is the author of Listen Like You Mean it: Reclaiming the Lost Art of True Connection. Her writing on personal and professional development, productivity, creativity, and work relationships has appeared in Fast Company, The Muse, The Washington Post, Huffington Post, and Inc., among other publications. An experienced manager and user researcher, she previously worked at Pinterest, LinkedIn, and Twitter. Follow her on Twitter or check out her website.