Difficult conversations — How to discuss what matters most — A book review

Karthik Krishnan
5 min readJan 30, 2017

My 2017 New Year’s resolution is to read 2 books a month for a total of 24 this year. This poses 2 issues for me

  1. This is at least 3x the pace of reading that I usually am on, which is a challenge in itself, given the rest of my schedule and balancing being the dad of 3 kids between 5 and 8
  2. Given this constraint, I don’t want to compromise the quality of what I imbibe from my reading due to the suddenly increased pace

The compromise solution — A blog on Medium that captures what I learnt about each book as soon as I am done finishing it.. This is the first on this series for the first book I finished reading in 2017. Hope you find this helpful

My first book review is “Difficult Conversations: How to Discuss what matters most” by Douglas Stone. This book is about understanding the dimensions of difficult conversations, techniques to engage and finding ways to

Step 1: Any time you converse with someone, conversations are always at multiple layers a. What actually happened? b. How do we feel about what happened? c.what does it mean for our identity as a person?

Recognizing this is crucial. Too often people get stuck assuming difficult conversations are about fact based conversations when they are very often about how people felt about the issue or their sense of self worth

Step 2: When engaging folks on issues, separate impact from intention..

  1. Impact is “what was the impact of this on me or how did the other person’s action make me feel?”
  2. Intention is “what did this person intend when they did this?”

Impact is a fact. Intention is an assumption. When engaging on difficult issues, always start with impact.. Starting with intention makes the other person defensive and ends up not being very productive. Some sample opening lines here include

What you said there made me feel pretty bad. I was hurt by that (starting with how I felt)


You always boss and and act like you own me and I resented what you said (starting with intent)

Step 3: When looking for solutions, step away from the blame game to what the author calls a contribution system which is about understanding the role of both parties in getting to this position and looking forward to exploring how to get out of the mess or ensure it never happens again?

Some sample statements that can help on this regard

  1. What happened there was pretty bad? I want to talk to you about that.. Lets retrace our steps and think about what happened.. I suspect we may both have contributed to the problem. From your perspective what could I have done differently?

Contribution is always joint and interactive and just because you start off by asking about things you could have done differently doesn’t mean you are always to blame. Even if you have no blame to shoulder it is a good way to engage. Contribution allows for issues to be raised more easily and encourages learning and change

Even if you think you may share no blame, it is worth looking at 4 dimensions of blame that are often overlooked and making sure you exhaust before assuming you had no blame to share

  1. Avoiding the issue till it escalates
  2. Being unapproachable: Your subordinates or others feeling intimidated about approaching you or you not making the time to meet with them
  3. Differences in opinion: because of differences in background, preferences, communication style etc
  4. Incorrect role assumptions: False assumptions about our role in a situation

Step 4: Identifying the feelings behind the conversation

This could be our own or the ones of the person we are engaging with.. Feelings could be one of love, anger, hurt, shame, fear, self doubt, joy, sadness, jealousy, gratitude, loneliness

Do not translate feelings into attribution, judgement, characterization or problem solving as it leads to defensiveness

  1. Frame the feelings back into the problem instead of venting
  2. Express your feelings fully
  3. Don’t judge others feelings
  4. Express feelings without judging or attribution
  5. Don’t monopolize — give the other person also time to express their feelings

Step 5: The identity conversation. What concerns us most during difficult conversations are negative outcomes that may influence how we feel along the following dimensions

  1. Am I competent?
  2. Am I a good person?
  3. Am i worthy of love?

Make sure you are cognizant of these as you embark on this conversation..Also it is possible that your identity is complex for e.g. you have been loyal to the company AND you are leaving for a better job offer elsewhere .. Embrace the complexity in identity

Step 6: In each difficult conversation decide if you want to raise it as an issue and if you plan to, recognize that there are 3 purposes

  1. Learning their story
  2. Expressing views and feelings
  3. Problem solving together

When beginning , there is always a 3rd story.. the neutral story that an independent observer might begin with (vs your story or her story).. Start with that as that ensures that conversations don’t derail into judgments or defensiveness

Step 7: During conversations

  1. Inquire: Show genuine interest in learning about what the other person has to say
  2. Paraphrase so the other person knows you are getting it or for clarity
  3. Acknowledge their feelings

Step 8: When making your case

  1. Never present your conclusions as truth… Words like I believe soften the tone of delivery
  2. Share where your conclusions come from
  3. Don’t exaggerate with always or never — Give them room to change

Step 9: Problem Solving

  1. Reframe conversations to guide them in a positive direction
  2. Use the “and” to accommodate parallel views — choice between what you think and what they think and between how you feel and how they feel

When it comes to problem solving

  1. Propose tests to validate assumptions
  2. say what is still missing
  3. say what would persuade you
  4. ask what would persuade them
  5. ask their advice

Questions that come up for specific situations

  1. What is you are discussing this with your boss or you are the boss?

When you are having such a conversation with your boss, separate control from influence. You can influence your boss but not control him

Similarly if you are the boss, conversations have many flavors

  1. Commanding — I decide and I tell you my decision
  2. Consulting — I ask for input and I decide and tell you
  3. Collaborating — We decide together
  4. Delegating — You decide

When having conversations, make sure to communicate to others what you expect from them

In summary

A. Prepare for it by walking thru the 3 conversations

  1. Sort out what happened
  2. Understand emotions
  3. Ground your identity

B. Decide whether to raise the issue

C. If yes, start from the 3rd story

  1. Describe the problem as difference between stories
  2. Share your purposes
  3. Invite them to join you as a partner in sorting out the situations

D. Explore their story and yours

  1. Listen to understand
  2. Share your viewpoint, experiences, intentions, feelings
  3. Reframe, reframe, reframe to ensure a positive, productive conversation

E. Problem solving

  1. Invent options that meet each side’s concerns and interests
  2. Look to standards for what should happen for win win
  3. Talk about how to keep communications open as you go forward