Questions to Ask to Have More Meaningful Conversations at Work
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 overall. 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. So, how do you have Meaningful Conversations at Work?
Ximena Vengoechea is a user researcher in Silicon Valley, they’ve faced this challenge in many conversations. Their 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 Vengoechea's job is to gain insight, not flattery, so they’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 Vengoechea wrote 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 Vengoechea calls 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.