• Priya Venkatesan

Difficult Conversations



Sometimes, the most important conversations are the most difficult to engage in ~ Jeanne Phillips
I need to tell some of my team members that they have been laid off.

I need to tell my customer to back off to help us serve them better.

I need to tell my boss that I am capable enough to understand what she says without her having to be rude.

The above are all difficult conversations.

The need for difficult conversations arise through-out one’s leadership journey.

A leader’s peace of mind is contingent on having the courage to make them happen. To have a difficult conversation with grace and authenticity is something we can all learn to do better.

The parts that constitute a difficult conversation have been aptly summarised in the book - ‘Difficult Conversations’ by Douglas Stone, Bruce Patton & Shiela Heen, written about a decade back. These parts help us to see where we need to build courage and where we need to build skill.


The parts are:

  1. “What happened” conversation - This involves the fundamental disagreement on “W”s - Who did What to Whom, When and Whether it is right?

  2. The “Feelings” Conversation - Sometimes unsaid, sometimes half said, feelings summarise what ‘emotions’ the parties to the conversation are going through.

  3. The “Identity” Conversation - This is slightly deep - What does the conversation mean to me, does it makes me an incompetent or bad leader/person, does this align to the self image I have of myself, does it hit my self esteem?

In each part, our mental models (sum total of our experience, perceptions, beliefs, values, assumptions) have the ability to derail us.



The “what happened” conversations seems to be factual at first and we may think it will have one right view. However, in reality it does not. We interpret facts using our values, beliefs and sensory perception and call it “our fact”. This leads us to the conclusion - 'I am right'. Worse still - 'the other party is wrong' (the blame game). On top of this, we make an “intelligent” guess of the other’s intention which has even probability of being wrong.





If our “facts” are not “white” enough, its no surprise that we are taken for a ride with our feelings which are most likely ‘inferred’. To understand another’s feeling, suspending ones’s own is important and it requires high emotional intelligence (EQ). The starting point of EQ is Self Awareness.








The role of identity cannot be stressed enough (Read More on one of my earlier blogs.)

Its the highest logical level and many leaders hold this dear. The very fear of how one will be perceived makes a lot of leaders defer difficult conversations. Most of us started our leadership journey in the belief that we will strive to give a better work place for the people around us. Anything to affect this bubble places us in un-resourceful states.



While the book explains elaborately on how to navigate difficult conversation (that I highly recommend to read), the following are things that worked for me personally and also what my clients got most benefit from.


If you are new to difficult conversations, it pays to do adequate preparation before going into one. A difficult conversation requires management of content as well as state as you can see below:

  1. Clarity: To manage content, one need to know one’s view and one’s blind spots with clarity.

  2. Hold multiple views: Every party has his or her own views of the situation. To empathise with another is to park our own judgement and embrace multiple view points. Perceptual positioning helps a lot in this process. An observer’s view ( if you are a fly on the wall, what would you think about the situation?) in perceptual positioning especially helps to be more objective and prevents hijack by emotions.

  3. Listening - A difficult conversation is more about 'active listening' than speaking. Deeply listen to the other - what are they really trying to say?

  4. Silence - Most of us find it difficult to sit in silence with someone else. Sometimes, the best we can offer the other is to sit with them when they lack words to speak and hold space.

  5. Vulnerability - Acknowledging that one doesn’t know all answers gives space for the other to feel safe in your company. It also gives one permission to not live up to one’s image and always be perfect or popular.

  6. Letting go of outcome - While we all imagine that having the difficult conversation will lead to better outcomes, this very attachment derails our conversation. So letting go of what we think should happen and letting in what emerges on its own can build trust.

  7. Differentiate role Vs person - Some of us don’t like to be the cause of other’s suffering. While the sense of agency is to the role you are playing, it is not wise to attribute it to the person who you are. Knowing this difference, helps one handle it gracefully.

What has worked for your in difficult conversations? What new learning will you take away to the next one?


#coaching #leadershipcoaching #executivecoaching #difficultconversations




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