Navigating Challenging Dialogues: A Thoughtful Review of 'Difficult Conversations'

Last updated Jun 30, 2023 Published Jan 20, 2023

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Difficult Conversations is a book that anyone at any stage of their life could read, this is not just a book about leadership or management, it goes a step further into the relationships that we have. Relationships that require difficult conversations, be it with your children, your boss, your parents and even yourself. You should be the most interested in the feelings you might go through when a challenging idea is put in place and when disagreements occur. In that case, what should we do?

The book has three main parts, the first one depicts the problem and what a difficult conversation looks like, the kind of difficult conversations and the last part focuses on what to do when such difficult conversations take place. In the end, the authors also reserved a big chunk of the book to answer questions from readers.

The problem

If you are well prepared, the chances of getting well from a difficult conversion are higher. Therefore, most of us aren’t. There is a lack of understanding of ourselves before understand others.

The authors also argue that the conflicts take place because people are not capable of switching to a learning instance, instead, the default approach is to hold on one side of the story as the only one. The difficult conversations approach is through using cases from people who have been there and shared their history so that we can learn from and analyze what could have been better.

The three conversations

The first chapter talks about the three conversations that are playing around when we are talking with someone. In this case, the use case used was from a presentation that didn’t go well due to an error in the slides presented.

The authors then use that as a segway to the three types of conversations. The what happened conversation goes in the direction of “who is right”, “assuming that they meant it” and blame - Chapters 2 through 4 explore the types of conversations.

The bottom line from the book on whatever type of conversation is to shift the difficult conversation into a learning conversation.

The “what happened?” conversation

Difficult conversations usually involve disagreements - this is the classical behavior to start a difficult conversation. In this section, the authors presented a dialog between two parties that work together to deliver a presentation.

It turns out that the slides for the presentation had an error on them, which was the root cause for what is the starting point of “difficult conversations”.

The feelings conversation

Difficult conversations bring questions about our feelings, should I share them? What about the other person’s feelings?

The identity conversation

This is our internal conversation, what our feelings have to say and what to do to deal with them.

Ten questions

The authors also added a list of ten questions at the end of the book to mitigate some reader’s questions on specific subjects. There were a few questions I thought myself while reading the book. As a review of this book, I won’t share all of the questions here, but I will peek at least three that I found interesting.

Isn’t this a very American approach?

Fundamentally the authors agree with this statement, therefore, what the authors highlight and argue that are the same across cultures is the internal voice that one has. They recommend that listening to the internal voice and shifting from difficult conversation to learning conversation can be used as a tool regardless of the culture one is from.

What about conversations that aren’t face-to-face?

Especially in the world post-COVID-19 and still fearing its variants, the questions asked by the reader apply to today’s purpose. The author of the book argues that the main communications in the digital world have shifted to email. When that is the case, extra care should be taken when reading and writing.

When reading:

  • Remind yourself that you don’t know their intentions, hit a pause and then come back later
  • If you cannot resolve conflict email with another conflict email, pick up the phone and or talk in person if needed.

When writing:

  • Be extra explicit with your intentions.
  • Let them know if there will be delays - if you are not answering at the moment, let them know that it will take some time.
  • Don´t make assumptions, instead write a short note to check before you respond.
  • Ask for reactions, thoughts, and what you are missing.

The authors also elaborate on what to do when the conversation is on the phone which is not shared here.