How to carry a conversation and comfort others?

Jeraldine Phneah
July 30, 2023
I shared about dealing with difficult conversations in my previous post.
This week, we’d focus on how to effectively carry a conversation and how to comfort others.
1. The art of asking questions
My close friend was sharing with me that on dating apps, the guys that she meet do not ask her questions about herself.
The dates are usually either about general topics or a sales pitch about their accomplishments; their goals and their wealth.
I personally had a sad experience a few years back where the guy was talking about his Rolex for 30 minutes.
When meeting new people in a personal or professional setting, many do not bother to ask questions about others.
We all like people who are interested in what we do and us. The best way to appear charismatic is to master the art of follow-up questions.
Here are three super actionable steps you can take.
i. Pick one point in their sentence and get them to elaborate
For example, if the other person says he did his exchange in Hong Kong. You can ask so many questions: What were the key differences he noticed between Hong Kong and Singapore? Does he speak Cantonese and if not, how did he assimilate? What are some things people get wrong about Hong Kong?
By doing this, you do not even need to know much about Hong Kong to carry on a conversation.
ii. Share your own story then ask questions
I like to bring up stories like how I used to go Ronchor Road Beancurd with my then boyfriend who was in National Service (NS).
From this topic, one can branch out into so many other questions:
Teenage romance: Where was your paktor spot in your childhood?
You can then add on with more stories. For example, I like to credit my then-boyfriend for influencing my perspective on inequality.
NS: What did you do for NS? Do you feel NS should be abolished? What will you change about NS if you could?
iii. Start with a compliment
There are so many things to compliment people about. I will use three examples here: Their choice of perfume/colonge; their success or their build.
Choice of perfume: Which scent they use? Was there something else they were using before that? Our scent choices are typically personal and people have their own unique reasons
Success: They went to some good university or just landed a new job. Wow, so smart! What were the entrance exams like? How did they prepare? What was the interview process like? How did they feel when they got the news? What was their backup plan if they failed?
Build: How do they train? Where did they learn? What is their routine like? Which muscle group is their strongest and weakest? What drives them to work out?
All these skills require practice.
Candidly, I am a more introverted person who prefers to stick with the same few close friends rather than interact with new people. I have been told to be careful about coming off as cliquish.
However, my job requires me to do networking. Hence, I had to pick these up over time.
2. How to comfort someone

Just sharing a recent and great example from my friend who helped me out
Facing problems can be an isolating experience. Our presence and support can do a lot to help people feel validated
I recently reached out to my friend for comfort and I thought his response was perfect.
Firstly, he expressed gratitude and that made me feel like I was not imposing on him
Next, he asked about what I needed and it prompted me to specify exactly what I needed from him.
I shall remember the above response and use it for future situations.
One mistake I use to make was to tell people “Let me know how I can be helpful.”
Instead, it is better to be specific and proactive: “Take the rest of the week off, I will hold the fort” or “Shall we meet go for a walk?”
Alternatively, you can just ask “What is one thing I can do to make you feel better”
3. How to validate people’s emotions
Everyone wants their feelings to be understood and accepted. Validation helps a person feel cared for and supported.
Yet, many do not know how to validate others. Too often, a person can feel that their inner experiences are judged and denied.
Effective validation has two components: It identifies a specific emotion. It offers justification for feeling that emotion.
For example, your friend complains to you that her colleagues left her out by not inviting her to KTV.
Instead of saying “She probably didn’t mean to do that” or the classic “Haiya, don’t think so much”
Validation looks like this: “You must feel left out to not be invited to KTV because it gives the impression they forgot about you. I would feel the same if I were you because being part of a group is important to you.”
Do I care if my own colleagues go for KTV and do not include me? No. I don’t like big groups. I don’t like going for KTV.
Empathy does not mean you agree with someone, it means you can see the world through their view for one moment.
Here is a snippet of a video that explains how you can do this.
Personal Updates
I need to focus on my new job and ramping up as quickly as possible. These are a few changes I’d be making:
Double down on good sleep, good diet and regular exercise. I need my body and mind to be in top form so I have the energy and focus for high performance.
Reduce my LinkedIn post frequency to only once a week
Instagram updates will be as per normal, follow my journey on Instagram.
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