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How to have deeper (and better) conversations with your coworkers

It’s easy to stick to the same old topics like the weather or your weekend plans. But making an effort to get to know your coworkers can really pay off.

How to have deeper (and better) conversations with your coworkers
[Photo: Sam Lion/Pexels]
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Workplace conversations have changed their character during the pandemic. Lots of our communication has shifted from face-to-face to something mediated by technology. We talk to people on the phone and via videoconference tools. Instead of catching up in the office kitchen, we exchange brief pleasantries via email or Slack DM.

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As a result, our conversations have become both more transactional and more superficial. When you schedule a call, you generally feel like you need to get down to business. As a result, the focus tends to be on a particular task at hand. And when you do chat or engage in a little small talk, it tends to stay small.

Good workplace relationships, though, require trust. And part of that trust comes from knowing the people around you. When you trust the people you work with, you are more likely to let them know when you’re struggling with a task or just feeling burned out. You let them know about your half-baked ideas, which might become the germ of something significant. You also are better able to learn from them.

So how can you engage in deeper conversations that will lead to greater trust and open the door to these benefits?

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Returning to nontransactional discussions

In clinical psychology, it is important for clients to be willing to disclose information that might be a source of shame or embarrassment. Most people are not willing to talk about these difficult topics on day one. Instead, there is a certain amount of relationship development that takes place first.

In the workplace, that relationship development happens (in part) during conversations that allow colleagues to get to know each other. That requires having a certain amount of discussion that is not focused on a particular agenda. Those free-form discussions allow people to get to know each other more personally, as well as having a chance to share aspects of their experience and their hopes for the future. Over time, this creates more willingness for colleagues to share information, even when it is not completely thought through.

To get there, invite your colleagues out for lunch or a cup of coffee. Go without an expectation that there is something specific you need to cover. But do have some thoughts about things you’d like to know about your colleague or to learn from them. Ask questions and follow up on things that they say.

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Listen more than you play

Having a good conversation requires understanding the other participants. Shared understanding starts with really listening to what other people have to say. Listening is a neglected art these days. In an age of multitasking and surface conversations, we often don’t pay careful attention to other people.

To have a deep conversation, you have to start by putting away all of the distractions. Park your phone somewhere else. Go somewhere that other people won’t interrupt you.

Then, change your mindset about the discussion. Often, we listen to someone else long enough to figure out what we are going to say next. Then, we stop really paying attention so we don’t forget what we wanted to say. Instead, when your conversation partner is talking, just listen. Follow up by asking for more detail or clarifying key points rather than taking things in another direction. Your aim is that by the end of the conversation, you could repeat back the central aspects of what they said accurately.

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Converse, don’t compete

Good conversations are fundamentally cooperative. One person speaks. The other builds on that initial statement. In order for speakers to understand each other, each thing they say has to connect to what was said before.

The cooperation that builds trust can be undermined when the conversation becomes competitive. This can happen in different ways. Sometimes, people spend conversations trying to impress each other, which means that each story becomes an attempt to one-up the one just told. The other is when the topic of the conversation focuses on a point of disagreement in which the discussion becomes a debate in which each side tries to convince the other that their point of view is correct.

When you try to “win” a conversation, you may feel energized by the encounter, but it doesn’t deepen your relationship with your opponent. That doesn’t mean you can’t discuss topics you disagree about. Instead, try to understand what the other person believes and why. Express your own opinion and the reasons for it. But, do it with the aim of creating mutual knowledge rather than with the aim of bringing the other person around to your way of thinking.

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Even if you’re convinced that your colleague is wrong, there is value in just understanding your point of view. In the long run at work there will be issues you’re right about and issues you’re wrong about. Your work will be enhanced when people feel free to raise concerns knowing that they will be heard. Practicing that skill in general conversation is a great way to develop that level of trust with the people at work.