Book Review: Difficult Conversations – How to discuss what matters most
I can’t remember how I came across this book. In fact, most of the books that I end up getting as gifts have this provenance. I come across books from a variety of sources: sometimes I see book reviews pop-up in my RSS reader, other times friends will mention them in passing. Sometimes I’ll overhear someone talking about a book they thought was really good when I’m taking the bus or the sky train and I make a note of it. However I first hear about the book, when I get home I add the book to my Amazon wishlist and forget about it.
Before getting into the book itself, I think this is a pretty good system. Part of what makes it great is that I end up getting a lot of books for gifts that I had long since forgotten about. Sometimes the book turns out to be poor, or on a topic that I’m no longer interested in (though this latter one generally doesn’t end up being much of a problem). Most of the time, I end up getting to have my cake (requesting gifts) and eat it too (being surprised and excited when I open a present that’s shaped like a book).
The only maintenance that this system requires is a quick run through the list before I send it out to someone that has asked if there’s anything I’m looking for. Generally I scour the list to see if it has any books left on it that I received recently. Remove those, and send off the list. Easy!
Okay, enough about how awesome my many systems of organization are. Let’s talk about this book.
Difficult conversations is one of the best book’s I have ever read on the following topics:
- Project Management
- Relationships
- Maintaining a happy marriage
- Winning friends (and influencing people!)
- Arguing
- Getting ahead in business
- Human Resources
And a bunch of other subjects too. The reason for that is that this is a book that tackles one of the most fundamental causes of strife in most of our relationships. If you look at all of the above topics I’ve listed, they are ultimately all about developing or maintaining relationships, and communicating well.
But if that was really all that this book talked about, it wouldn’t be that interesting. There are a billion books out there that talk about communicating. The thing that this book does better than any other that I’ve read on the subject (and I’ve read quite a few) is that it focuses on what really underlies most communication – feelings.
Wait, is that something unique? I don’t know anymore; the more I type, the less I convince myself that this book is bringing something unique to the table. Poor articulation notwithstanding, you’ll have to take my word for it: this book really does bring something unique.
Perhaps it’s the voice that the authors use, or their method of articulating what underlies many difficult conversations that we find ourselves having. Take this anecdote that they use in the book (paraphrased with my names for the protagonists):
Buck Lightning has a lot of work on his plate for his consulting business, but he’s just gotten a last minute request from his friend, Donjulio, to push through some extra publishing work. Buck accepts the task, even though it’s last minute. If nothing else, he feels good about doing his friend a favour. However, when Donjulio gets the work Buck delivers, he’s not happy at all. Instead, he chastises Buck for making a layout mistake on one of the graphs. Buck looks at the mistake but feels that it’s really not something that is going to be noticeable to anyone but he and DonnyJ, and can’t believe how ingrateful his friend is being. Buck calls up Donjulio to discuss, and mentions that he really doesn’t think this is a big deal. Donjulio says “Look Buck, you made a mistake – just own up to it and resolve the problem”. Buck can’t believe what he’s hearing! He took on the project as a special favour to a friend, and although this may be a mistake on his part, if nothing else it’s certainly partially attributable to Donjulio’s last minute request.
You may not have had this exact conversation, but I’m sure that you can relate to the situation. The advice and insight that the book offers is always wise and insightful, and at times astounding. The authors do an excellent job articulating how much of our feelings and identity are wrapped up in our communication, and elaborating on ways to confront these facts head on. Understanding what parts of our selves we may really have at stake in a conversation like this one is the first step toward approaching them with a humble confidence and addressing the situation, rather than trying to avoid them.
I was reading this book on the bus, and someone across from me asked me what it was about. I showed him the cover and said that that’s really the crux of the book, but our conversation kept coming back to him trying to rationalize the book as a way to win arguments, or get ahead in business, or win a negotiation. None of these are really what the book is about, and that’s what I appreciate the most about it. Ultimately, the authors are espousing for empathy in all of these conversations.
When presented with a difficult conversation, the key is to not only be aware of what parts of ourselves may be invested in the conversation, but that of the person sitting across from us. Difficult conversations are typically those that arise where regardless of what circumstances may or may not have lead to this point, both participants believe that they are correct.
The key to having difficult conversations isn’t winning them, getting the upper hand, or figuring out what’s wrong with the person you’re talking to. It’s about understanding why they hold an opinion different from yours, in spite of the fact that you’re both talking about the same thing.
This final point might be a challenge for many people. We aren’t usually interested in figuring out and understanding what the person sitting across from us holds in their heads that have lead them to their own conclusion. We’re interested in getting our point across to them in such a way as to have them agree with us. As compelling as that result may be, it’s not a realistic one. We all have our own preconceived notions, judgments, backgrounds, and baggage that we bring to bear on any discussion. Learning how to empathize with someone and appreciate their perspective will not “win” an argument for you; but it will help you bring resolution and closure to those difficult conversations, and perhaps more importantly, the feelings that underlie them.
Without a doubt one of the better books I’ve read in the last year or so. If you’ve ever found yourself avoiding conversations because you feel like you already know how they’ll go, want to change the ongoing dynamic between you and someone else, or just want to get better at communicating how you feel, this is a book you should read.




The basis of this book sounds very much like what Please Read This For Me was about, which I learned about from the March 2003 episode of This American Life (the episode was called “Say Anything” – http://www.thisamericanlife.org/radio-archives/episode/234/say-anything – the most intense episode of TAL I’ve ever heard).
The mistake that Please Read This For Me made was that it scripted various scenarios – regardless of where the other person was coming from. Sounds like Difficult Conversations may have a bit more depth in relationships than the very transactional approach of Please Read This For Me. It was interesting to listen to the author of PRTFM talk about the reception and effect it ultimately had on his readership – which can be heard (and is very interesting) in the beginning of that podcast.
People are not robots that must be fed a special coded manuscript in order to live harmoniously with those around them. They’re complex and sometimes even principle based thinkers, seers, and feelers – amongst other things.
Mmm. Well, there’s certainly many different scenarios that Difficult Conversations raises and addresses, but that to me felt more like simply providing analogies and examples of the most common kinds of problems. Making the abstract concrete.
However, throughout each of these scenarios are always the common threads that make up the main narrative of the book.
This is a great read (my copy has about 50 markers throughout, indicating pages that contain points that I found particularly resonant!)