How to get past shallow small talk and have more vulnerable conversations

“Are you okay?”

I just came to the office early in the morning when I saw my ex-colleague, a 50-year old lady, sitting behind her desk with a blank expression.

When she heard my voice, she looked at me, totally surprised by my candid question.

“Thank you for asking that. Working on multiple jobs does not make me feel okay.”

This was an unexpected answer for what I thought was just a casual morning greeting.

What followed was a lengthy conversation where she slowly started to open up and tell me about her real-life situation.

Starting a vulnerable conversation is not an easy task, especially with people who come from high-context culture countries like Singapore or Japan. Within these cultures, it might not feel appropriate to express feelings or discuss emotions with someone other than close friends or family (Think Cultural Health, n.d.).

That said, here are a few tips to start a vulnerable conversation with someone:

1. Build a good rapport

Having a good rapport with someone is important in order to understand their feelings, gain their trust, and figure out their communication preferences.

There are a few simple things you can do, such as: being friendly and genuine, asking questions about the person’s work, life or interests, using positive body language, and actively listening to their stories (Julia, 2024; Hanne, 2023).

By having a good rapport with someone, we will develop mutual trust and friendship with them.

2. Give to get

In order to get people talking, sometimes we need to give some information about ourselves first that can make them comfortable to share their own stories (Christina, 2021).

Ideally, try to set up a conversation by telling them something similar in our life that might encourage them to share and open up about themselves.

For example, if both of us are married, we can share our own problems in marriage or family.

  • “I’ve been working till midnight lately and I didn’t even get a chance to talk to my wife and kids. They seem unhappy with this situation. What about your communication with your family?”

Or else, we can share our own thoughts and feelings towards our work or employer.

  • “I don’t know why, but I feel my manager is giving me a lot of pressure to finish up this project sooner than it’s supposed to be. He keeps nagging me even outside of working hours. What about your manager?” 

3. Ask open-ended questions

Open-ended questions will encourage someone to share more about themselves. Encourage them to engage with questions that focus on them and their well-being (Julia, 2024; Mind, n.d).

Also try not to ask them too many questions, especially close questions which require a “yes” or “no” answer and those that begin with the word “Why?”.

For example:

  • “I heard you just moved into a new apartment by yourself. How do you look after yourself?”

  • “You look very tired lately. How well do you sleep at night?”

4. Ask them straight

Once we have built a good rapport, we can ask them straight questions that might encourage them to open up about their struggles or mental health.

Here are a few examples which can work as conversation starters (Mental Health First Aid, 2022):

  • “Are you okay?” – Ask them with genuine interest. With an open body posture and gestures, show them that you are interested and ready to listen to their answer attentively.

  • “I’ve noticed that…” – Open the conversation by explaining any behaviour changes you have noticed.

  • “How are you, really?” – If someone gives you a one-word answer like “fine,” but you have a hunch there’s more to their answer, you can gently probe to show them that you genuinely want to know how they are doing.

  • “Do you want to take a walk or go outside for a while?” – Getting out of the office and doing a little walk will take them out of nerves and discomfort. This will be one of the best ways to have a meaningful conversation.

If they feel secure and trust you enough, they will slowly open up and share more about their problems.

While getting into a vulnerable conversation might be difficult, it is a powerful way to help people who are struggling to get through difficult times.

It is one of the most handy tools in dealing with mental health problems as it encourages people to speak up, seek help or simply to be aware that there is still hope and support from other people. After all, humans need other human beings. By having a vulnerable conversation talk and being actively listening to others, you’ll never know that could be a ‘life changer’ to the other person.

Got someone to open up, but wondering how to hold space for them without internalising their struggles? Read this article.


References:

Hillsberg, C. (2021) 5 Techniques to Build Rapport with Your Colleagues. Harvard Business Review. Accessed 9 March 2024. https://hbr.org/2021/09/5-techniques-to-build-rapport-with-your-colleagues

Keiling, H. (2023) How to Build Rapport in a Professional Setting (With Examples). Indeed. Accessed 9 March 2024. https://www.indeed.com/career-advice/starting-new-job/building-rapport

Martins, J. (2024) 6 Ways to Build Rapport and Develop Meaningful Relationships. Asana. Accessed 9 March 2024. https://asana.com/resources/building-rapport

Mental Health First Aid USA (2022). 5 Tips for Starting a Conversation About Mental Health. Accessed 9 March 2024. https://www.mentalhealthfirstaid.org/2018/06/5-tips-conversation-mental-health/

Mind (n.d.). How to Have Conversations Around Mental Health. Accessed 9 March 2024. https://www.mind.org.uk/media-a/6085/annex-f.pdf

Think Cultural Health (n.d.) Communication Styles. U.S. Department of Human & Health Services. Accessed 9 March 2024. https://thinkculturalhealth.hhs.gov/assets/pdfs/resource-library/communication-styles.pdf

Wikipedia, The Free Encyclopedia (n.d.) High-context and Low-context Cultures. Accessed 9 March 2024. https://en.wikipedia.org/wiki/High-context_and_low-context_cultures

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