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How to Have Meaningful Conversations at Work


Earlier this week,  I wrote about the need for us to have more meaningful conversations at and about work, digging deeper into the real issues that influence us. Today I want to share some thoughts on how we can start to move in the direction of having more meaningful discussions. I'm "thinking out loud" here, so bear with me. . . 

Ask Different Questions. 

 Conversations start with questions. It can be easy to get into a "tell" mode at work, where we are talking at each other, rather than with each other. We can also get into the habit of transactional questions--questions that are strictly about the transactional nature of our work. Where's the report? Who is going to be responsible for this task?

Asking different questions can start to move us toward more meaningful discussions. You can start small with questions like:

  • Why do you think that happened?
  • How are you feeling about what happened?
  • What do you think we need to do about it? 
  • What do you need from me? 

As we develop the questioning habit, we can go deeper. We can start to practice with positive questions , with debriefing questions and with looking for important questions in our work. We can ask questions that challenge the status quo or that are the questions we usually try to avoid. 

Our questions shape our discussions, so this is the place we have to start. 

Reveal Yourself

 We all wear masks to work. We all play roles. Both of these things tend to force us to act in accordance with those masks, keeping us on the shallow side of life.

To have REAL conversations, though, we have to go beneath our masks. We have to be willing to speak our truths as we feel them and to say the things that are on our minds. 

That means that sometimes we have to show the raw, vulnerable parts of ourselves that lie just beneath the surface. We have to share when something evokes an emotional response, be it pleasure or pain. I'm not talking about being a walking wound at work. I'm talking about sharing the human side, the part of you that feels unsure about a decision you've made or that sees that people are having a difficult time getting along and calls attention to it. Or the part that feels really grateful for a few co-workers and says so. 

Several years ago, I stopped in the middle of a facilitator training session that was going off the rails and said that I needed us to break for the day. We were clearly headed into bad territory and I needed to collect my thoughts on how to proceed. This was a MAJOR removal of my mask and I was scared to death to do it, but it turned out to be the best decision I ever made. It completely transformed the rest of the course. And we ended up having a very real discussion about how people's identities were being challenged and the fears and concerns they had as a result. 

Make it Safe For Others To Reveal Themselves

Of course, one of the main reasons we don't reveal ourselves is because we don't feel safe doing it. We can't control how others behave in the workplace, but we can control our own behavior. So if someone reveals themselves to us, we can make it safe for them to do so. We can keep their confidences. We can ask questions to draw them out. We can try to put aside any of our own defensiveness that may be getting in the way. In doing this, we start to create a safe space for others to come to us have more meaningful discussions. 

One strategy I use all the time is the "Vegas Rule"--what's said in Vegas, stays in Vegas. I've found that this is an excellent way to help people feel more comfortable about getting into meatier discussions. And it helps when I'm explicit about it. "This goes no further." 

Be Intentional

One thing I realized about our retreat was the fact that there was something about the intentional nature of it that allowed us to be more open with one another. We created a space specifically for people to talk and share. We came to the space knowing that we were going to have conversations that went deeper than the norm. 

In structuring things, I drew on the ideas in Christina Baldwin and Ann Linnea's book, The Circle Way. There's a lot of great information in there on how to structure space to make it safe to have more meaningful discussions. I highly recommend it. Not only does it talk about the need to be intentional, it also has some valuable insights on the use of circles and how the physical structure of the discussion can be transformative. There's intention in having the discussion, but there's also intention in creating the right space for it to happen. 

Go with the Flow

So here's some advice that contradicts what I just said about being intentional.

Something I learned from two teenage daughters was that often the best conversations happened when I least expected it--in the car, walking through the mall, just before bedtime. I learned to pick up on the signals that told me that they wanted to talk. Often it was at a time when they didn't have to look me in the eye. Somehow it felt safer to talk without having to see my face. This has been true of work-related conversations, too. 

We have to be alert for the doorways that open up and be willing to go through them. Sometimes they don't appear when and where we expect them to or plan for them. We have to be willing to go with the flow and to ride it into something deeper than what we expected. 

Take a Chance

Ultimately, the biggest shift we have to make is in our willingness to take the risk on meaningful discussions. I'm acutely aware of the toll that anxiety and fear takes on many of us. When you're worried about your livelihood or spending your days putting out fires, it can be hard to see the space for any kind of meaningful discussion. 

But I would argue that fear and anxiety are actually clues that deeper conversations are necessary. It is precisely those emotions that tell us it's time to start getting real about what's going on. 

There are no guarantees that our first attempts, or even our second or third attempts will get us anywhere. We can keep trying, though, in small ways with a few discussions with a few trusted colleagues. And then maybe in bigger ways, speaking up in meetings or deliberately calling together a larger group of people. 

We are the only ones who can really make things happen. If we wait for someone else to do it, we could be waiting quite awhile. If we're feeling the need, then we need to take the leap, show others how to do it and bring them along with us. I know from experience that major shifts take place when we do. 

What else can we do to encourage and support meaningful conversations at and about work? 






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Thanks for this post - it is very timely for me, as I have been thinking about conversations at work. One more thing we can do to encourage meaningful conversations is to focus more on inquiry and less on advocacy. I wrote recently about this -
BTW - I love your observation about the best conversations with your daughters. My best conversations with my son are also in the car!

Jean, read your post--such great questions! Focusing on inquiry instead of advocating for your position could do so much for enhancing the safety we need to feel to go deeper. It also gets us really talking and understanding different perspectives.

And I'm glad to hear that I'm not the only one who has had the most meaningful discussions in the car. :-)

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Just read this, Michele, and so enjoyed it! Hope you don't mind that we'll be sharing the link to this later this week on our podcast. Each point you mention is so important, though I especially like the need for authenticity in our interactions. Is especially timely for me - the past several days I have been puzzling over my dwindling energy, lack of focus and general feeling of being unconnected. Recognized last night that at least some of this was because I have done little to engage meaningfully with others. Finding this article this morning seems to affirm that, so is time to make more of this happen :-)

Hi Terri--so glad you enjoyed this and I'm happy to have it reach a broader audience, so thank you for sharing it on the podcast! I think the feelings you're describing are pretty common--I've been noticing them in a lot of meetings I've been at and it's come up in a number of conversations I've been having with people. I've resolved this year to try to engage in more meaningful conversations, not only as a gift to myself, but also because I'm seeing that other people need and want the space to have them too.

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