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10 Ways to Have Better Conversations

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Josie Copeland
Ten Thousand Coffees Team -
July 12, 2019

Do a quick Google search on how to have better conversations and you will find a wealth of information on how to show people you are listening: “smile!”, “make eye contact!” and “nod whilst the person is speaking!”.

As writer and radio host Celeste Headlee argues, “there is no reason to learn to show that you’re paying attention if you are, in fact, paying attention.” Simply put, we need to spend less time learning how to show people that we are listening and spend more time learning how to actually listen to each other and converse effectively.

Here we look at how to apply her 10 rules to having better conversations with work connections:

1. Don’t multitask

“Be present. Be in that moment,” Celeste explains. “Don’t think about your argument you had with your boss. Don’t think about what you’re going to have for dinner. If you want to get out of the conversation, get out of the conversation but don’t be half in it and half out of it.”

To help yourself, try putting your phone away and make sure you allow enough time buffer on either end of your coffee chat so you can properly relax. If you do notice yourself drifting off during the conversation, gently re-direct your attention without judgement. Above all else, breathe and relax! You are exactly where you need to be!

2. Don’t pontificate

Pontificate verb To speak or write and give your opinion about something as if you knew everything about it and as if only your opinion was correct.

“You need to enter every conversation assuming that you have something to learn”, Celeste highlights, “sometimes that means setting aside your personal opinion.”

We’re all only human, so it’s easy to come across as arrogant and superior in conversation every now and again. To keep yourself in check, try to pause before you speak and notice whether you are putting too much of your own feelings into this situation. Are you feeling insecure? threatened? defensive? hurt? Oftentimes we pontificate because of our own internal fears and insecurities, recognizing this can be the first step to change.

3. Use open-ended questions

Celeste recommends avoiding very closed-ended questions which could be answered with a simple “yes” or “no”. Instead, “Try asking them things like, ‘What was that like?’ ‘How did that feel?’ Because then they might have to stop for a moment and think about it, and you’re going to get a much more interesting response.”

4. Go with the flow

Almost everyone is guilty of thinking of a really interesting point whilst someone is speaking, and then waiting impatiently for the person to finish to jump in!

As Celeste suggests, “thoughts will come into your mind and you need to let them go out of your mind.” By learning to let your thoughts go and go with the flow, you will be much better at adapting to how the conversation is going. Are they engaged? Are they itching for a new topic? Is it time to lighten the mood with some humour?

5. If you don’t know, say you don’t know

One of the biggest mistakes you can make on your coffee chat is to lie, it makes you look unreliable and untrustworthy. Celeste notes, “Talk should not be cheap”.

People appreciate vulnerability and honesty and it should always be the foundation of a good conversation. Understand it’s perfectly fine not to know something, and people do not expect you to know everything.

6. Don’t equate your experience with theirs

“If they’re talking about the trouble they’re having at work, don’t tell them about how much you hate your job,” Celeste says. “It’s not the same. It is never the same. All experiences are individual. And more importantly, it is not about you. Conversations are not a promotional opportunity.”

Whilst your attempts to show empathy are admirable, you shouldn’t always be the hero of every story. The best thing you can do is give the other person the space they need to tell their story. Listen and lend support if needed.

7. Try not to repeat yourself

Put simply: it’s boring. “Especially in work conversations”, Celeste points out “we have a point to make, so we just keep rephrasing it over and over.”

If you do feel like you have a tendency to ramble, try to turn the conversation back to the other person. Open the door for them to speak about their experiences in more detail. When put into practice, you should feel that the conversation becomes more even and you are dominating it less.

8. Stay out of the weeds

“Frankly, people don’t care about the years, the names, the dates, all those details that you’re struggling to come up with in your mind,” Celeste says. “They don’t care. What they care about is you.”

When recounting experiences or stories try to focus more on what happened rather than the specifics. You are not being tested on this, the other person just wants to learn more about you.

9. Listen

The most important thing to remember is you are listening to understand, not just to reply. Since the brain can process what we hear far quicker than how fast someone speaks, our mind fills in the blank space in-between what the other person is saying.

Our job is to focus on the other person’s responses, ask insightful questions, and not wait for the conversational trigger to transition talk back to us.

10. Be brief

Just get to the point. Don’t over-explain. Are you giving them too much information that they don’t need to know? Say what you need to say, then stop talking and listen to what the other person has to say.

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