Conversation Skills that Connect? Here’s the Secret

by | Jan 9, 2022

Years ago, I had a consulting assignment in New Jersey where my office was directly across from a tool crib. Every morning when I walked by, I would greet the guy working the crib and he and I would put our conversation skills to the test with the following interaction:

“How you doin’?”

“I’m doin’ good. How you doin’?”

“I’m doin’ good.”

I then would proceed to listen to that exact conversation for hours. Every time someone walked up to the tool crib, exact same conversation.

That is called a “scripted interaction” and it’s probably the most comfortable of all conversations. It is called scripted because it follows a script. When I say, “How you doin’?” you automatically know the right answer. And if you answer off-script (“Oh man, I’m glad you asked, I’ve got this terrible rash, can you take a look at it and tell me if you think it’s something I should be concerned about…”) that conversation can quickly turn awkward because you went off the script.

I think of scripted interactions as kind of a social lubricant. They let you go throughout your day interacting with strangers in almost any situation and feel sociable but comfortable at the same time. But scripted interactions are a crutch, and they definitely don’t lead to connection or good conversations. They are really designed to avoid connection.

We all have scripted interactions throughout our day. But when you are talking with your team (or anyone else in your life who you want to feel connection with) you should avoid scripted conversations. And this is where some leaders get uncomfortable, because it requires some good conversation skills. Some people are naturally comfortable conversationalists, but many are not.

Building Your Conversation Skills

You know how critical good communication is to building connection with your team. And the primary tool in a leader’s toolbox for strong communication is conversation skills. It’s why so many of the experiential exercises we do during our approachable leadership workshop center around conversation skills.

But many of us aren’t naturally comfortable with a conversation. And if a conversation is getting awkward one of two things happens. Option one is silence, which for most feels super awkward. Many conversations just end when the talking stops. Others default to option two, filling any empty space talking about our favorite subject: ourselves. After all, this is a topic we know a lot about, and can talk about at length when given the chance or a willing participant.

Talking about yourself, especially if your partner isn’t also talking about themself, reduces connection even more than a scripted interaction. At least in a scripted conversation both sides know connection isn’t the goal. This is especially true when power distance is wide.

One way to build great conversation skills is asking good questions. At the end of our workshop we ask participants to name their top takeaway from the day. One of the most common is our 3 questions of approachable leaders (Do you have what you need? What would make work better? What’s next?) While those are great questions, only asking those questions would quickly get old. But I recently ran across an article by Jeff Haden that offers a great, science-backed way to ensure your everyday conversations with teammates are comfortable and grow connection.

Haden reviews a 2017 Harvard study published in the Journal of Personality and Social Psychology. This study looked at the likeability of people after different types of conversations. The study concludes that asking questions, especially follow-up questions, as the key to connection during these conversations.

The study concludes:

“People spend most of their time during conversations talking about their own viewpoints and tend to self-promote when meeting people for the first time. In contrast, high question-askers—those that probe for information from others—are perceived as more responsive and are better liked. Although most people do not anticipate the benefits of question-asking and do not ask enough questions, people would do well to learn that it doesn’t hurt to ask.”

The Harvard researchers conducted 4 different experiments in a variety of settings. They asked participants of the conversations as well as outside observers to rate the likeability of participants. Note that one of these conversations was speed-dating. We’ve talked before about the importance of approachability not only at work, but in all the relationships in your life – including the romantic kind. Once again, that is supported by research.

The reason questions – especially follow-up questions – are so important is that they increase the perceived responsiveness of the questioner. The study states:

“…we identify follow-up questions as an important behavioral indicator of responsiveness, and we find that asking a higher rate of follow-up questions reliably predicts partner liking.”

How to Ask the Three Questions

It’s probably no surprise to you that good conversationalists are good at asking questions. Haden in his article offers some good practical tips to get better at follow up questions. I encourage you to start there. Haden’s suggestions relate more to a conversation you might have with someone at a party or networking event. Here are some tips for applying the “3 question” strategy at work.

After starting with your version of “How ya doin’?” you start with an icebreaker question. You can start with some simple icebreakers like:

  • What are you working on today?
  • How’s the schedule looking today?
  • Anything crazy happening today?

These initial questions are just meant to get a conversation started and are still somewhat scripted interactions. You can also ask some non-scripted questions right up front to get the person to open up. Some of my favorites include:

  • Anything exciting going on in your life right now?
  • You going anywhere fun this year?
  • What are you looking forward to these days?

These questions are open-ended and forward looking, so they are likely to begin a good conversation. But you may be talking to someone who you know might not be looking forward to much (that’s especially true during a pandemic). You can always adjust questions like these:

  • How is your family doing?
  • What’s the best thing going on in your world these days?
  • Have you had a chance to [name of activity they enjoy] lately?
  • Are you watching/listening/reading anything new?

Once you’ve asked the icebreaker now is the time to take advantage of what you learned in the Harvard study – ask some follow up questions. Sometimes the answer will have some obvious follow up questions. But if the follow up is not obvious it is good to have some backup questions just in case. Hader suggests a good one: “That sounds hard – how do you do that?” Here are a few others to add to your toolbox:

  • How are you dealing with that?
  • What are you doing to get ready?
  • How did you come up with that?
  • How did you learn to do that?
  • What got you interested in that?
  • Is that hard to do?

You can also use the simple phrase, “tell me more.” The good news is that the Harvard study found there’s no certain number or type of questions that increase likability. It appears that simply asking questions shows others that you are taking an interest in them and give them a chance to talk about their favorite subject: themselves.

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