MAD Conversations ! (Mastering the Art of Deep/ Difficult Conversations)

We live so that we may learn to love.

We love so that we may learn to live.

-Mikhail Naimy

At the heart of living, learning & loving are human Relationships.

It would not be an exaggeration to say that human relationships are the cause of the deepest human challenge, pain and joy.  Whether it is in the professional, personal or the social worlds we inhabit.

  • Leadership, Collaboration & High Performance Teams (Business, Social or Education)
  • Family Relationships & well being
  • Physical & Emotional Health and even,
  • Financial Well being for people & organisations
  • Our passion & purpose and what gives meaning apart from work-  in terms of art, sports – also known as Ikigai, Heartsong, Genius etc.

Conversations – difficult and deep, intense and profound, intimate & professional, at home & at work, in love and in conflict.

Conversations are at the heart of human Relationships.

And therefore essential in the Professional world for

Leadership, Facilitation, Coaching, Teaching, Learning, building healthy cultures & developing organisations and more.

And in the Personal & Social world for Parenting, Partnering – between couples, co-creating a happy family, building Community and more.

Mastering the Art of Deep/ Difficult Conversations is undoubtedly one of the most vital (maybe The Most essential) heart- skills and mindsets (attitudes, values) that a human being needs to navigate a happy & healthy life & create a great  livelihood

In August last year (2022), I reconnected with Info Edge (,,, I had worked with them in 2006 and at a few points after that. And in the conversation exploring their Learning & Development needs, they felt a good fit in what I brought and their need for developing their senior leaders in the skill and practice of “Effective Conversations.”

Arvind, their L&D head and I got into a conversation to find a more spicy title for this need. After going back and forth with words like Collaborative, the Art & Science, Mastering, Deep & Difficult, Vulnerable etc, I asked him to pause and breathe. The penny was not dropping. Then some more interaction. We did not find the right word. He was looking for acronym. So I said let us give it a break. And then we continued on WhatsApp Chat. Back & forth. And then the bulb was aglow. Arvind said, I think I have got it.

MAD Conversations. It was a home run. Sharmeen, the Chief HR Officer and Ajjayy, the Exec VP, HR both loved it also. We had arrived at the title of the initiative through a deep conversation and applying the art.

My deepest gift and my deepest pain has been human relationships.

This deep challenge for me personally has also shaped not only my life but also my work and lifework.

I have had many, many very beautiful & deep friendships and yet, there has been a deep challenge in the field of intimate relationships. Also due to ADHD and being neuro divergent, it’s been crazy. 🙂

Last night I was drinking with some dear friends and Sangeeta reminded me that she had once told me,

Kiran, if you could only teach Deep Listening to the world, your life would have been worthwhile”

In the early days when I used to conduct Tao of facilitation programs (inspired by the book, Tao of Leadership- John Heider, I would teach 3 essential Conversation, Relationship Skills or Capabilities.

  1. Deep Listening
  2. Authentic Speaking
  3. Questioning from Wonder

I was conducting the Tao program in 2005 I think at the Taj Kuteeram in the outskirts of Bangalore.

I had unraveled these 3 core skills and a participant, Ashish Rajpal, founder iDiscoveri said,

“Kiran, what about Silence?”

I stopped in my tracks and said, “Wow, yes.. that’s true. Silence is such a vital piece of conversations. And the 4th Skill got added.

4. Spacious Silence. (Pausing)

In 2019, Rohit, Arjun & I (Ark) were developing Coaches at Bosch. Debashish, the L&D head had seen me speaking at the ICF Conference and invited me to democratize coaching in Bosch. And I realized that human beings are mostly focusing on whats missing and wrong.

Kahlil Gibran says, “The worst fault of human beings is the preoccupation with others faults.”

And I said, there is another fault, perhaps deeper, the preoccupation with our own faults.

What Adyashanti calls the human core wound of unworthiness.

One more powerful skill of Conversation became clear. I had also seen the Hendricks focus on it.

5. Generous Appreciation

Now, when we did the first Workshop for Infoedge in Nov 2021, one more skill emerged. This again was a learning I had had from travelling to the US and learning from Gay & Katie Hendricks. Our relationships, conversations and indeed, our life gets derailed because we tend to suppress, deny, avoid feeling our difficult feelings of anger, sadness, fear, sexual feelings and even happiness.

And while it was part of the repertoire, it became clear to add it as the 6th skill of Conversation.

6. Feeling our feelings.

Sanjay Salooja invited me to anchor a workshop for Hindalco High Potential leaders to do a workshop so that they could sharpen their capability to Lead Others, Influence, Develop & Inspire people. We called the workshop, The Art of Inspiring Leadership. In this workshop, I introduced one more skill, more like a deeper capability. Again it was a part of what I would always bring awareness to but it helped to put it as the 7th skill (hopefully the last). Born out of the fact that leaders and all human beings need to learn to develop a Detached Engagement in conversations and relationships. So we said,

7. Helicoptering

Hopefully the 7th is the last one. 7 habits of highly effective people. The number 7 is interesting. 7 colors of the rainbow. 7 notes of music. The 7 Chakras, levels of Consciousness.

The 7 heart skills of MAD Conversations.

(Maybe it will be a book, someday soon!)

In the sequence they are taught..

  1. Helicoptering
  • 2.Deep Listening
  • 3. Feeling the feelings
  • 4. Authentic Speaking
  • 5. Generous Appreciation
  • 6. Questioning from Wonder
  • 7. Pausing, Spacious Silence

These 7 heart-skills are the foundational skills. Conversation is so foundational to human life and relationships that these can be seen as the

7 pillars of living a healthy & fulfilling life.

And then there are the more Complex skills which require the combined use, an orchestration of each of these. These 4 skills are essential aspects of the MAD Conversations capability building.

I don’t like to call them advanced because the foundational skills also can be quite “advanced” to implement.

I found that ultimately the new world requires us to be Frentors to each other. A word I love that my Abhishek coined. Whether as a leader, a parent, a coach, a facilitator or a teacher.

Apart from the 7 Foundational skills and the 4 Frentoring Skills, we also bring 7 healthy mindflips to our workshops on Collaborative Leadership, Facilitation, Coaching or simply, MAD Conversations

The 7 Healthy Mind-flips:

  1. Slowing Down : Discovering the Speed of Life
  2. All behavior has a positive intention
  • 3. Vulnerability
  • 4. Healthy Responsibility (Blaming to Claiming)
  • 5. Learning Together
  • 6. Owning the Mirror (Judging to wonder /deep Acceptance )
  • 7. Outer to Inner to Beyond (the unknown)

The orchestration of the 7 foundational heart-skills & 7 mind-flips can help us to practice the

7 Collaboration Capabilities :

  1. Coaching & Learning Together
  2. Inspiring Together
  3. Carefrontation (Caring enough to Confront)
  4. Feedback (Feed forward & Feed Inward)
  5. Conflict to Co-creation
  6. Facilitation
  7. Certainty to Curiosity (Exploring the Unknown)

In the 2 day workshop we also introduce

The invisible is powering the visible.

The Outer Skills are complemented in MAD Conversations & Inspiring Leadership with what I call Heartistry – unraveling your heartsong what brings people alive. And here we have 3 triads

The 3 Triangles of Heartistry (Alone) & Heartistree (Together)

  1. How to enable your heartsong : A connection with
    1. Body- Health, Sexuality
    1. Nature – the 5 elements
    1. Passion (Art/ Sport)
  • 2. What areas to bring alive
    • Work
    • Home
  • Relationships & Community
  • 3. What derails Aliveness – our Relationship with
    • Time & Space
    • Power & Money
    • Pain & Pleasure

In conclusion, over the 25 plus years of developing leaders, facilitators, coaches, heartists, people who want to live a life of passion and purpose, I have found that what I have given the outline of in this note is vital to Professional, Personal, Social, Spiritual life.

And ultimately in our journey beyond- connected with God that I discovered in Oct 2021 through God’s Freedom Technique. The most beautiful, radical revelation in my life.

We now offer MAD Mornings (7am-730am) & MAD Evenings (830-9pm) from Monday-Thurs in the first 3 weeks of every month. 12 sessions (Morning or Evening) @ Indian Rs. 999 (May 2023) & 24 sessions (Morning & Evening) @ Rs. 1222

And now also a one-month MAD Facilitator-Coach journey. This is for Rs. 5310 (including GST) – details in that link.

Feel free to send me (Kiran Gulrajani) a Whatsapp message at +919823969473 to join/ know more. Looking forward to connecting with you if this calls you.

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