Key #21. When someone is talking to you . . .

. . . make the person interesting!

It stands to reason: the more interesting we find people, the more enjoyable our conversations become, and the more connected we feel. However, I can’t ask you to manufacture interest like you can a gob of spit. We can’t manufacture emotions. If we could, all of us would be calm, dynamic, loving people, and as happy as a butcher’s dog.

We don’t choose our emotions; we struggle to even control the thoughts behind them.

The happiness gurus make that mistake. They tell us that if we want to make friends we need to show an interest in the other person. Their advice is: ‘If you want to be interesting, be interested.’ They seem to think we can choose to be interested in what the other person is saying. We can’t simply choose to be interested. If we could, we would find lousy plays and banal television interesting.

I made that mistake with a friend of mine. Tom struggles to take an interest in the concerns of other people, and only talks about his interests. One day he was complaining about having so few friends, and I suggested he try showing an interest in what other people were saying. I gave him the mantra, ‘If you want to be interesting, be interested’, and he thought that was a good idea.

‘Let’s try it,’ I said to him. ‘I’m about to tell you something about myself. All you have to do is try to be curious about what I say, and ask a few questions.’

‘Righto,’ he said, keen to experiment.

I said to him, ‘My football team, Hawthorn, lost its coach this week indefinitely. The guy has a rare disease.’

Tom is only mildly interested in Australian Rules football, but this was his chance to at least pretend to be interested. He could have asked me questions like,
‘Mark, does this concern you?’

‘Are you confident in the team’s ability to win anyway?’

‘Will the coach be alright by the time the finals come round, do you think?’

‘Could this be a blessing? Will the team freshen up under his replacement?’


His response?

‘That happened to Arsenal a few years ago. The Manager —’


We examined his response and tried again. I told him I had been on a date the night before, and suggested to him that he show interest by asking me questions about her. 
 I thought he might ask me questions like,
‘What’s her name?’
‘What is she like?’
‘Where did you go?’ 
‘How did you meet her?’

He said he remembered something else about Arsenal.

When the happiness gurus ask us to ‘be interested’ they don’t take into account that many people are not yet able to do so. Even if a person asks questions to indicate interest, they can’t sustain it. They quickly feel bored, unloved and uninterested, and revert to talking about themselves.

However, there is one thing we can do. To become interested we can make the other person interesting. The strategies below are designed for just that.

‘But Mark, I want people to like and value me. If I show interest in them, when will it ever be my turn to be the centre of attention? I’m 45 and no-one has ever truly valued me, and now you are telling me to “find other people interesting”. If I spend precious time listening to other people, at this rate I’ll never feel valued!
  ‘Besides, if those people are happy to talk about themselves, they are probably self-centred and high maintenance. To keep their friendship I’ll have to keep listening to them and keep showing interest in them. I’ll be setting myself up for a long and arduous task, just to gain their friendship. It’s just not worth it.’


That’s why it’s no good pretending to be interested. When you are genuinely interested in what the other person is saying you will prefer to stay on that subject. Unless you have a skilled questioner eliciting self-revelations from you, you won’t want to talk about yourself. You will find yourself boring, because you already know your material!

Besides, if the other person has good communication skills there will be plenty of opportunities to discuss your interests.

Further, it’s not the attention you crave, it’s the connection you crave. That connection isn’t built on one person’s stories, it is built on the bond created when two people find the conversation interesting.

Make the person interesting:

(1) Ask open questions, not closed questions.
(Closed questions are answered with a ‘yes’ or ‘no’.)
Frank meets gail at a cooking class:
Frank: ‘Gail, do you like cooking?’ It’s a poor question because it’s a closed question.
Frank: ‘Why are you learning to cook?’ Good! That is an open question and it focuses on Gail’s interests.
‘What is it like to —?’

‘How did it feel when you —?



(2) Don’t ask questions for the sake of asking them. Ask questions to which you want to know the answer.
If you find someone boring it might be that you’re not asking the right questions. Search for a question that makes you want to know the answer. For example:
Gail: ‘I’m learning to cook so that my husband and I can enjoy good food at home.’

Frank ‘What does he like to eat?’  That’s a poor question. Why would Frank ask that question? Why would he care about what Gail’s husband likes to eat? He wouldn’t, would he? The question is not only boring, it’s disingenuous. He is obviously talking for the sake of talking. When we ask a question, we need to ask one that makes us want to know the answer. Frank could try instead:
Frank: ‘For how long have you been married? I’m asking because I’m wondering why you’re learning to cook now?’ There are two questions there, and both are personal. But provided personal questions are not too intrusive, they’re the ones that matter. If Gail is reticent to answer, Frank can back off.

Insightful questions generate interest. Then we have communication and connection. If we ask questions simply to make friends, the only friends we’ll make are those who also want company. Then we end up with a friendship that succeeds only because we are company for one another, not because there is a rich closeness between us. Which type of friendship do you want?

There are exceptions: boy meets girl. Boy and girl have to ask questions to get a conversation going, and the questions can be trite. That’s understood. But for their relationship to grow, they will have to start asking insightful questions.


(3) Don’t settle for glib.

Let’s say you learn that your friend goes to kickboxing classes.

You: ‘Ali, why do you go to kickboxing classes?
Ali: ‘To keep fit.’
If you accept that answer it shows you aren’t interested. Ali hasn’t explained why he chose to do kickboxing classes instead of aerobic classes or jogging, for example. By accepting his answer you have missed a chance to connect with him. Only by genuinely wanting to know the answer, and pushing for it, will you get the answer that connects you both. And beautifully, the answer becomes interesting.

Don’t ask question after question though, going deeper and deeper. It might sound like an interrogation. Or just plain creepy. Stop when your curiosity is sated.

(4) Give the person your full attention.

(i) If you are on the phone to the person, ignore your computer.
(ii) When face to face with the person, don’t read or text.
(iii) Don’t let yourself daydream. Focus. A good way to focus is to look for the person’s underlying message.

(5) Listen for the message behind what is being said. 

Look for the big picture. For example, if a neighbour talks endlessly about his cats, remind yourself that his deeper message may be ‘I don’t feel connected with anyone, so by telling you my problems I am hoping I create a connection with you.’ Or, the message might be that he fears for his cats’ health and wants reassurance from you. It’s your job to figure which one it is.

Let’s say a friend talks about her daughter’s wedding plans. On the surface it might appear to be a conversation about trite things of little interest to you. but by listening for the real message you might discover that she believes her daughter isn’t yet ready for marriage. Direct your questions there. Your friend will benefit because she gets to talk about her real concerns, and you both benefit because the conversation becomes more interesting, and you both experience a stronger connection.

If John is telling you about his great idea, understand the idea as best you can, so that you want to ask questions.

Also, by listening for the message behind what is being said, we don’t start constructing our own response (a big no-no).

‘Most people do not listen with the intent to understand; they listen with the intent to reply.’
Stephen R. Covey, from his book, ‘The 7 habits of Highly Effective People’



(6) Interrupt the person if you don’t understand something, or need clarification. That makes the conversation more enjoyable for you, and it lets the person know you are listening.

But don’t finish a person’s sentence for them. It’s not just the sentence they’re trying to figure out, it’s the thought behind it.



(7) Imagine yourself in the other person’s situation, and what that person might be feeling.
This could make it more interesting for you, and easier to understand their message.



(8) Refrain from adding to their story.

Remember Tom? The guy who ignored my story and talked about Arsenal? Don’t be like him. When a person tells you their story, keep it their story.

(9) Make a mental note of at least one thing the person tells you.

The next time you see that person, ask them about it. For example, if Max says he is going trout fishing tomorrow, when you see him again ask him how it went.

If you hear something interesting about trout fishing, remember it, and the next time you see Max, tell him.
‘But I’m not interested in trout fishing. Didn’t you ask us to be genuine? Why ask us to fake an interest?’

I’m not asking you to pretend to be interested, I’m asking you to make a mental note, and then later, ask how it went. That does two things:
(1) It gives him a gift; he feels acknowledged, and therefore, valued.
(2) Having that habit – of making a mental note – increases your ability to listen and build an actual interest.

(10) Let the person know you are listening. 

Ask questions. Even better, let the person know that you understand their deeper message by paraphrasing what they have said.
‘Let me get this right: your idea is to . . . is that correct?’
‘From what you have been saying, I understand that your daughter . . .’

Though Celeste Headlee makes a good point:
‘There is no reason to learn how to show you’re paying attention if you are in fact paying attention.’

Celeste in her TED Talk, ‘10 Ways to Have a Better Conversation.’


(11) Notice your judgments and leave them aside.
Notice when you make your judgments. ‘This guy is a fool. Oh, I’m judging him.’ 
 But don’t criticise yourself for thinking those things. Instead, say to yourself something like, ‘Ah, I’m being judgmental. I can let that thought go.’ Then let it go.

(If you like, after the conversation has concluded, ask yourself, ‘Why was I judgmental? Why did I make the judgment? What does that say about me and my values? Do I really need to impose my values on her?’) Do that and you will learn heaps about yourself.

(12) End the conversation on your terms.

If you want the conversation to end, do it honestly. End it respectfully. Look the person in the eye, smile, and say, ‘I’m going now. Goodbye.’
‘Goodbye Noddy!’
‘Goodbye, Golliwog!’

An exercise:
Which do you think is the better response, and why?

Damien: ’I have a new girlfriend.’

Geoff: ‘Good for you! Tell me about her.’ 

Geoff: ‘Lucky you. I haven’t had a girlfriend for a while.’



Elka: ’I am pregnant. At long last I’m going to have a child.’

Elka’s mother: ‘Lovely! Tell me what you know!’ 

Elka’s mother: ‘At last, I’m going to be a grandmother!’


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