Wednesday, August 18, 2021

How to Make Conversation

Actions to take: Put work into paying attention to others' interest level during a conversation. If they are more interested than you, stay on the topic longer than you normally would. If less, try to cut off your thoughts a little early. Make conversation flow easily using the following structure for your comments: 1) acknowledge what the other person said, 2) say whatever is on your mind, 3) ask them a question.

Note: this advice pertains to everyday conversations, spontaneous work conversations, one-on-one meetings with your direct reports, and similar situations. Be selective about applying this advice to meetings that you are running. Meetings with agendas, structure, and specific desired outcomes have a different set of social norms, and you may need to be a bit more abrupt in your communication at times.


Are you an expert conversationalist? Can you deftly engage virtually anyone in conversation, enter and exit discussions smoothly when you want, and get your points across while making the other person feel heard no matter the circumstance? If your answer is, "yes," you can safely skip this blog entry. For the rest of us, here is a very simple strategy for improving your conversational skill.

In a workplace, we have a lot of topics to cover in a relatively short period of time. This leads a lot of managers to rationalize the negative consequences of abruptly cutting from one topic to the next or ending a conversation. In almost all live communication, and in one-on-ones especially, bosses can be so caught up in "getting the conversation done" that they destroy the value of having a conversation. 

Remember, the point of having a conversation is rarely just an information dump. We might wish that communication were that simple. It is not. The world is not that simple. Humans are not that simple. We have conversation to help understand one another. That takes time and a little bit of finesse. 

When a boss, or anyone for that matter, abruptly changes topic in a conversation, it makes the other person doubt. The other person doubts that the boss cared about the last topic. Doubt that the boss heard their thoughts on that topic. Doubt that the boss cares about their thoughts on the last topic. This is a little bit melodramatic, I admit. If you are generally a thoughtful, caring person, then the other party won't think this completely. But you are still undermining yourself when you fail to engage in the finer details of making conversation. 

We've mentioned finesse, and we've mentioned the finer details, but what, exactly, are we supposed to do differently? There are two very easy strategies that will make people think of you as an excellent conversationalist. 

First and foremost, start paying attention to the other person's interest in the topic. If they are more excited about it than you are, stay on that topic longer than you want to. On the other hand, you may be the type to talk at length about things. Train yourself to watch for when others' attention fades (are they giving one word answers? Looking away a lot? Not making an effort to contribute their own thoughts?). Make it part of your job to match the other person a little bit more closely.

Second, you can make a conversation flow naturally and easily for as long as you want (2 minutes, 20 minutes, 2 hours) with the following strategy. Any time it is your "conversational turn," structure your thoughts like this:

  1. Acknowledge what the other person just said,
  2. Say whatever you have on your mind, and
  3. Ask an open-ended question. 

If you want to continue that same topic, it might look like this: "I know what you mean about the new layout of our software. [Thoughts about how it is worse in some ways, better in others, and how to get over the problems with it]. How well do you think those things would work?" 

If you need to move on to the next topic, here's how it might go: "The new layout has some problems for sure. Let's talk a little bit about the office space discussion you brought up in our last one-on-one. [Continue with your latest thoughts on subject]. What thoughts have you had about it since last week?"

This works due to a concept I mentioned earlier, the conversational turn. Conversations become stilted or awkward when it is not totally clear who should be talking, or when they are done. Have you ever witnessed someone continue add every thought as it occurs to them, seemingly without any plan to stop talking? It happens in interviews fairly often. It is because the person doesn't know how "pass the conversational turn" back to the other party (or are so nervous they forgot). Asking a question is the most common, easiest way to pass the conversational turn. 

That explains the last step. The middle step is obvious—you're saying whatever it is that you wanted to say. 

Regarding the first step, we could say "this is just good manners," and leave it at that. But let's take a moment. Etiquette has a purpose. It fulfills some necessary or useful function when dealing with others. In this case, the good etiquette accomplishes two things. First, it makes the other person feel heard. We can't very well acknowledge what the other person said without listening to it. Second, it forces us to actually listen. If you know that you'll be acknowledging their comment in some way, it pushes you to pay attention to what they are saying, rather than just waiting for your turn to speak. 


Knowing how to make conversation is a skill that is helpful to everyone everywhere. To be an effective boss, you have to develop relationships with your employees. Jolting, awkward conversation is high on the list of things that signal, "we barely understand one another." Use the tips we just discussed to make a better impression, have better conversation, and develop work relationships more easily. 

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