Becoming a Great Conversationalist

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Most of us aren't great at business conversations

In a CNN poll run a few years ago, they asked people how well they could manage a business conversation. I'm sure that the people who responded (more than 3500 in a nationwide poll) crafted their own unique spin on the scenario they were imagining. Regardless, 70% of the respondents wouldn't classify themselves as great conversationalists.

I wonder, are you in the 30% that would or the 70% that wouldn't?

Because most of us think we're not that great at business conversations, we tend to do three things:

  1. We try to limit how often we're having them.
  2. We try to keep them focused – becoming very goal-oriented.
  3. We don't follow thru and create more of them.

Does this sound right?

Let's tackle this from a different angle.

How great are you at coming up with questions in a business conversation?

  1. Do you ask open-ended questions that send people to their imaginations?
  2. Are you comfortable asking questions more than just making statements?
  3. How well do you answer a question with a question?

Have you ever been in a conversation with someone who makes statements? “We've had some great weather for this conference.” How are you going to respond? “Yes we have.”

Those kinds of conversations end quickly and the silence is painful. Right?

What does it take to become a great conversationalist?

Rule One: Stay focused on the person you're talking to

I know this should be a no brainer, but we have all been in conversations where the person we're talking to is looking over our shoulder to see if someone more important walks into the room. Don't be that person.

More importantly, you never know if the person in front of you is royalty. I once walked into my apartment in Berkeley when I was a student and my roommate had some friends over for dinner. It wasn't until the end of the evening that I found out one of them was a prince from an African country. A prince!

Can you imagine if I had just ignored him because he was a stranger who was studying something I didn't care much about?

Thankfully I didn't blow it for myself or my roommate. But it taught me a powerful lesson to focus on the person in front of me without any preconceived judgement about who they might be.

Rule Two: Ask open-ended questions the drive people into their memories

We've all be in conversations filled with close-ended questions. “Did you see this movie?” “Have you eaten at this restaurant?” “Do you like smoking cigars?” These are all yes/no questions and they don't drive conversations forward.

Instead, ask open-ended questions. My favorites are the ones that take people back into their own memories and engage them on multiple sensory levels. “What was it like when you first moved here?” “Of all the places you visited on your recent vacation, which place was your favorite, and why?” “How have you partnered with other folks for successful joint ventures?”

People have no trouble and need very little preparation to answer open-ended questions about things they've already experienced. It's also a lot less threatening than asking for an opinion when they're not sure they trust you to give you their opinion.

Rule Three: Get introduced

I can't tell you how much easier it is to have a great conversation when someone else has done the introductions. The introductions normally create a bridge between two people that set the stage for the conversation. If someone introduces me to someone and says, “Hey, this is Tom and his family is from South America, just like yours. He also works in software,” I now have two things we can talk about and I don't have to punt to weather conversation.

Don't be bashful about this.

When I want to talk to someone because I think there could be a good connection there, I'll find someone else that knows me and ask if they know them and could introduce us. I may even tell my friend why I think we might be a good fit. This allows them to set the stage in the introduction for the kind of conversation I would like to have.

Rule Four: Create a feedback loop during the conversation

Have you ever been on a phone call with someone and it's so quiet that you say, “You still there?”

That same thing can happen in conversations in real life. The person in front of you is looking at you and wondering if you're still engaged. Or they wonder where you've gone – even if you haven't moved.

My mom, at the dinner table, would be talking about something and my dad would check out. We could all see it in his eyes. They'd glaze over. And her common response was, “Where did you go?”

Don't be that person. Instead, give verbal and visual cues that tell the person you're tracking. Sometimes it's just a “sure” or a “yup” or “makes sense.” Other times it can be follow up questions. But either way, don't let them carry the conversation completely themselves. They won't be back for another one with you.

Rule Five: Have some prepared questions for strangers

While I don't try to have a lot of conversations on planes (this is where I use my noise-canceling headphones the most), I do have a lot of conversations with strangers at conferences.

Last year my friend Jennifer Bourn and I visited a conference and at one point at brunch, she asked the person next to her, “So what brings you out here?” The response she got was so painful that we laugh about it to this day. “The event, duh.”

Not a great conversationalist. But the question, “What brings you here?” is a good one. Here are some of the prepared questions I keep with me at all times:

  1. When you're not at events like this, what are you normally doing?
  2. When you're not working, what do you love doing?
  3. Do you have any upcoming vacations? Where are you headed?
  4. Your job sounds interesting. I didn't even know that was a job. How did you discover it?
  5. What's your connection to this [event | place | person]?
  6. How is automation changing your day-to-day job?
  7. How has the “thing that keeps you up at night” changed as you've been in your role all this time?

Rule Six: Pause and Breathe

Hopefully, you have someone in your life who can tell you that you talk too much. Or that you talk too fast. Or that you hog the whole conversation. But even if you don't, let me tell you that conversations should be 50/50. And the best way to make sure that happens is really simple.

Pause. Between sentences, take a breath.

This lets the person in front of you respond. It lets them also disengage politely. Either way, it's a life-saver.

The more you're paying attention to the person in front of you, the better you may become at reading the situation and their interest. But even then, pausing between sentences helps them either drive the conversation forward or gently excuse themselves.

Rule Seven: Stay clear of certain topics

I know. You're thinking I'm going to say politics and religion. Those are good candidates for evaluation. But no, that's not where I'm going.

I'm going to tell you to stay clear of:

Relationship Status—There's no simple way to get out of a conversation about someone who has recently broken up. But more importantly, you may be sending a signal you don't intend. And even if you intend it, don't do it. We are, after all, talking about business conversations. So leave the questions about boyfriends, girlfriends, or spouses to the things you talk about with your friends.

Physical Appearance—Unless you're going with, “Wow you look great,” and hope to end it there, this one will also not be helpful to you. Even if you say “It looks like you've lost a lot of weight,” you could be stepping into a whole new conversation about the multi-level marketing program they just joined to eat more healthy. What are you going to do now? Likely become part of their downline. Is that what you wanted?

Financial Status—Talking about how expensive your next vacation will be, or how much of a discount you got on that new (and expensive) car might end your chances to have a meaningful friendship with someone simply because you've turned them off too quickly. So leave the talk of money alone if you can.

Rule Eight: Be a “yes, and…” person

This story from Pixar about their use of the improve rule of accepting all offers (“yes, and”) is fantastic in your endeavor to become a great conversationalist.

I know people suggest that you want to stay away from debate and conflict in conversations, but here's where I disagree. I think it's not the debate or the differing ideas that makes things difficult. I think it's the fact that some people are difficult. And that's what you want to stay clear of.

But Psychology Today did a study (I can't recall the article but I will find it one day) where they evaluated the kinds of conversations people were having and how it affected their mental health (and sense of well being). In general they found that the more substantive the conversations they had, the better they felt about life.

I get that, because I'm more of a deep conversation guy than a chit chat guy.

But to do it right, I think you need to embrace this Pixar approach to enhancing an idea, rather than just rejecting it.

Even if you're a total “conflict avoidant” person, the research says certain kinds of engaged debate really helps.

Rule Nine: Read a lot

Since I was a kid I've been a reader. Several teachers over the years kept reinforcing how critical it was. And I can tell you, reading certainly has an impact on my own imagination, curiosity, and the ability of my brain to stretch out of my comfort zone to see another side of a topic.

Someone has said, pretty sure it was Lincoln (haha, just kidding), to be interesting you need to be interested. Reading has helped me develop a greater sense of interest in tons of fields of study I didn't know even existed.

Kovie Biakolo says it best,

“One of the most important aspects of being a great conversationalist is reading. Reading current events, reading fun things, reading dense things, reading things that expand your views on certain subjects, reading things you like and agree with, and reading things you don’t agree with. The latter is most important because that is fundamental to understanding different perspectives of the world. You learn nothing new from reading things you already know about or agree with. But all reading increases knowledge and improves vocabulary.”

What's your rule #10?

I like to have lists that don't end in that perfect round number, because I know there's still stuff I'm missing from whatever framework I've created to help me navigate the world. So what are the rules I'm missing? What has helped you get better at conversations?

As as I wrap up, look at the list one more time. Do you notice something?

None of it is beyond your reach. You can get better at conversations, regardless of  who you are, or what background you have.

So start today on your path of becoming a great conversationalist and let me know how it goes!

About Chris Lema

Chris Lema has been working with WordPress since 2005. Over the years he's been a blogger, a speaker at WordCamps, a coach for WordPress product companies, and the founder of the conference for WordPress business owners, called CaboPress. Today he's the VP of Products at Liquid Web, where he manages the world's first managed platform for WooCommerce stores.

Chris Lema

Chris Lema has been working with WordPress since 2005. Over the years he's been a blogger, a speaker at WordCamps, a coach for WordPress product companies, and the founder of the conference for WordPress business owners, called CaboPress. Today he's the VP of Products at Liquid Web, where he manages the world's first managed platform for WooCommerce stores.

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