Difficult Conversations: How to Discuss What Matters Most

Douglas Stone

Book cover

This book was assigned reading for my class on negotiation and conflict management. As I began reading it, I realized that a day-long training that I attended at work (also called “Difficult Conversations”) had essentially been based on the precepts of this book. So I read through the book fairly quickly, and didn’t get a ton of marginal benefit out of it, but that’s not the book’s fault.

I will say that I suspect that I would have been more skeptical of the book had I read it without going to the training. It is written in the classic “business self-help” style, which is generally a turn-off for me. What’s more, it would be much easier to discount the effectiveness of the prescribed approaches in the book had I not watched someone well-trained in them (our training facilitator) employ them quite effectively, even in role-plays where his counterparts (including me) were deliberately trying to portray difficult individuals and situations.

I will also say that, thankfully, I do not think I have recently had to handle any conversations that I would consider truly difficult, so I suppose it’s somewhat hard for me to judge the effectiveness of the book’s prescriptions. They have (through the training) at least somewhat influenced the ways that I’ve approached some moderately difficult topics in my own personal and professional lives, and I think they have served me well.

In brief, the authors’ prescription is to turn difficult conversations into “learning conversations,” where instead of going in with a message to deliver (usually about how the other person has done something wrong), one goes in with a message to deliver (about the impact some event has had on oneself) as well as an authentic desire to understand the other person’s view and to work together to keep a problem from arising again.

Although it is most certainly not presented in these terms, I consider the authors’ prescriptions to be a very Christian approach to handling problems and conflicts. I don’t mean to claim the approach exclusively for Christianity–I’m sure it can be used effectively by anyone, and I also bet that people from other faiths or moral traditions could interpret it through their own lenses. That said, here are a few of the aspects of the approach that I consider “Christian”:

-It ties in very well with my conception of the command to love one’s neighbor as oneself. One of the key aspects of my understanding of that command is that love for one’s neighbor does not equate to affection for one’s neighbor. After all, there are many times when we do not feel affectionate toward ourselves! Rather, it is more like caring for that neighbor’s well-being, respect for their individuality, and refusal to give up on them–all of which are integral components of a healthy “love” for oneself as well. The authors’ approach seems consonant with such a conception of the other, primarily in the sense that one must enter a difficult conversation with an authentic desire to understand the other person’s perspective on the situation, and an invitation to them to share. We are all too often willing to ascribe bad faith to others, though we would almost never ascribe bad faith to ourselves. Even in cases where the other person has done something we consider to be clearly reprehensible, such as lying, in order to move forward it is important for us to understand why they did. After all, we have all lied at one time or another, and that has not ruined our conceptions of ourselves as trustworthy people.

-It is rooted in the active recognition that none of us is “all good” or “all bad.” The role of not assuming that anyone is “all bad” is mostly what I described in the previous point. But interestingly, the authors discuss at length how the implicit assumption that oneself is “all good” can cause just as serious of problems. In an obvious sense, it can prevent us from exploring and understanding our own contributions to problems. In a less obvious sense, the authors assert that much of the difficulty of difficult conversations arises when a situation challenges one’s sense of identity. For instance, if an important part of one’s identity is “being a good son,” then an accusation of imperfect filial duty can be very threatening and cause one to react badly. Accepting that no one is uniformly a “good X” makes it easier to confront specific problems without feeling that one’s identity is at stake.

-It is fundamentally devoted to reconciliation (and here I expect someone within the Jewish tradition would employ the idea of tikkun olam, healing the world). There is a strong sense in this book that ignoring problems is a damaging approach, and that the way to be kind to someone with whom one is having a problem is not simply to give in to them, but to engage them in an honest and straightforward conversation geared toward preventing the problem from arising again. One of the authors’ prescriptions is to scrap the idea of “who is to blame” and to replace it with an exploration of the joint contribution of the two parties (understanding that this doesn’t mean that each party contributed equally, but that in nearly all cases each party contributed to some extent). I saw this approach as a compelling understanding of the idea of forgiveness. The authors give a nice illustration using a hypothetical scenario (which I actually role-played in my training class) where an assistant brings the wrong presentation to a meeting, which causes his boss to look pretty bad in front of a client. They depict two common responses to the problem. One is the response of “mean” blame, yelling at the assistant and threatening to fire them if it ever happens again. The other, of somewhat more interest, is the response of “nice” blame, where the boss says, I’m not going to yell and scream at you, and I understand that we all make mistakes, so I just need your assurance that this won’t happen again. The authors point out how, even though the latter is a pretty common and “nice” approach, it is fundamentally the same as the former. I saw an interesting parallel between this and the idea of radical forgiveness, where forgiving is not something that builds you up against the other person, makes you feel superior and like they “owe you one,” but rather is the true forgetting of blame or, even better, the dismissal of the question of blame from the start. I like this as a way of understanding Jesus’s statement that we should forgive “seventy times seven”–that to tally up forgiveness is to get the idea completely wrong.

The implicit ideal offered by this book is quite simple–a world where we understand and admit that everyone, including ourselves, is imperfect, where we love each other anyway, where we are fiercely committed to reconciliation, and where we figure out ways to make things better in spite of our imperfections. I do not think it would be wrong to call this the Kingdom of God.

My Goodreads rating: 3 stars