Your Guide To Asking Better Questions with Siddharth Anantharam

‘I’m sorry.’, ‘I forgive you.’, ‘I love you.’

If I asked you who are the most important people in your life, most of you would name a member of your family, gave me the name of your best friend or immediately thought of your romantic partner. Would you be so quick with your answer if I asked you to remember when was the last time you looked them in the eye and shared with them your regret, admiration or forgiveness?

Do you struggle with these conversations? Do you feel like you talk all the time but rarely say something that matters? Do you feel like you didn’t have enough time to ask the most important questions to someone who is no longer with you?

There is no
better time
to build

conversations that make life meaningful.

So how do we have more of those conversations?

How is it possible that we feel fearful to speak to the people we just called the most important people in our lives? We often feel like no-one understands us, like we have no-one to talk to at the end of a bad day. And yet, our moms are a phone call away. Our partners are just in the next room. And our friends are a WhatsApp message away. So what’s the gap between ‘These are the most important people in my life’ and ‘I am ashamed to tell you about the mistake I made at work.’ or ‘I think you will not accept that I am in love with someone who doesn’t reflect your expectations.’

It is fear that prevents us from sharing those stories. So we layer them, one of top of the other, we hide them deep inside ourselves and we let them grow heavier for so long that we cannot bear it anymore. Our secrets overpower us so much that we feel more comfortable speaking to a stranger rather than our own family or a friend.

But think about this: It’s not really the length of our relationships but the depth of our

This was Siddharth’s focus for the past few years. He brings together intimate groups of friends, strangers or family members and crafts spaces for them to explore meaningful conversations. He hosts dinners and residential retreats for those who feel the need for a safe space to go deeper beyond the day to day conversations; to discuss the things that really matter; to see things from each other’s perspective; to be really invested in the combined success of our friendships. You can join one of Siddhart’s LifeCircles by clicking here.




Here is what he found out are the key ingredients that make a conversation meaningful:

  • They happen when two or more people are willing to be vulnerable with their thoughts and emotions with each other
  • People come together with two intentions: to understand and to be understood
  • All participants of the conversation are willing to be bluntly honest with each other
  • There must be a shared willingness to step into the other person’s shoes and see it from their perspective

Siddhart shared with us 6 ideas to make your next conversation more meaningful:

  1. Check-in. Express your intentions and be fully present for the conversation. You could start with: ‘So, what’s on your mind?’
  2. Ask open-ended questions. Those are the ones that start with ‘What, When, How, Why…’ and don’t let you answer with a simple ‘Yes’ or ‘No’.
  3. ‘When was the last time…?’ Open your conversation partner’s mind with a question that allows them to tell a story.
  4. Silence is a part of a conversation. You can express so much by not speaking a word and you become a powerful listener by staying silent
  5. Be a mirror. Say things like ‘What I’m hearing you say is…’ and give the person across from you a chance feel understood and elaborate deeper on their thoughts.
  6. Check out. Ask yourself and the others: ‘What’s the most valuable thing you are taking out of this conversation?’

Invite more meaningful conversations into your life by starting them. Give yourself the opportunity to learn and gain more clarity about the people you love the most.

If you’d like to learn more about conversations, connect with Siddharth and his LifeCircles via social media or the upcoming residential retreat in Goa, 26.-30. March.

So…what’s on your mind?


Siddharth Anantharam Master Coach | Founder, The Breakthrough Weekend

He is the founder of ‘The Breakthrough Weekend’ and the card game ‘Let’s Talk’,aimed at providing spaces, tools, and methodologies that are designed to help people have conversations that matter

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