Difficult Conversations: A Resource Guide
I read the books. Here’s what I found.
Books mentioned in this article: Difficult Conversations: How to Discuss What Matters Most, Getting to Yes: Negotiating Agreement Without Giving In, Thanks for the Feedback: The Science and Art of Receiving Feedback Well, Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity, Crucial Conversations: Tools for Talking When Stakes Are High
If you dread difficult conversations in professional settings, you’d probably love a single cookbook with easy-to-follow recipes for various scenarios. The truth is that good cooks collect recipes from a variety of sources, eventually crafting an individual approach to cooking that borrows from many of them.
The same holds true for mastering difficult conversations. Like cooking, it is a skill developed over a lifetime, and with tools, practice, and reflection, you can get better at it.
Before diving into books, start with one of the best free resources out there. If you want to get better at difficult conversations, the first and most important step is to prepare for them. Judy Ringer, an author and coach whose approach is informed by the practice of aikido, has published a checklist of questions to ask yourself before diving into the deep end with someone. Some of the questions may seem like common sense, but others are less obvious:
“What assumptions are you making about this person’s intentions?”
“How is your attitude toward the conversation influencing your perception of it?”
Both of these demand reflection and self-awareness that can help you identify blind spots in advance. This checklist is a great resource to clarify what you’re trying to accomplish in a difficult conversation. Ringer also offers a reading list (scroll down this page for it) that includes a couple of the books previewed here.
If you’re only going to read one book on this topic, Difficult Conversations: How to Discuss What Matters Most, by Douglas Stone, Bruce Patton, and Sheila Heen, has a broad set of tools that are useful in a variety of settings. Difficult Conversations is particularly strong on establishing a shared sense of “what happened.” Any disagreement between two people starts with two stories. Setting those stories side by side and looking for gaps between them can help identify a third story that clarifies misunderstandings. “Listening to learn” is a core principle throughout, and Difficult Conversations offers helpful prompts to put this idea into action.
Difficult Conversations also emphasizes the importance of addressing emotions through the “feelings conversation.” As pop-psych as that may sound, it offers constructive advice for talking about feelings in a way that can keep a conversation emotionally honest and grounded at the same time.
Difficult Conversations has the same intellectual DNA as Getting to Yes: Negotiating Agreement Without Giving In, by Roger Fisher, William Ury, and Bruce Patton. This isn’t surprising since both books share co-author Patton and a connection to the Harvard Negotiation Project. As its title suggests, Getting to Yes focuses on negotiations, but many of the concepts and skills it covers are applicable in a wide range of challenging scenarios. It is filled with portable tidbits such as “Separate the people from the problem” and “Be hard on the problem, soft on the people.” (This is often useful advice, but sometimes the person is the problem. Please keep reading.) The point I remember from this book before picking up the phone or firing off an email is that in any situation you have two kinds of interests: the issue at hand, and the relationship. Never lose sight of the relationship. Getting to Yes runs about 100 pages, and the lucid writing makes it seem even shorter. There’s a reason this one is a classic.
If you are interested specifically in learning more about effective feedback, Difficult Conversations co-authors Stone and Heen’s Thanks for the Feedback: The Science and Art of Receiving Feedback Well is a must-read. The emphasis here is on receiving feedback, which is a nice twist. This book makes an important point about learning to identify your own biases and triggers when getting feedback. Does the feedback strike you as wrong or unfair? Is the problem the messenger and not the message? Have your emotions flooded your ability to hear the message? Stone and Heen also distinguish three different kinds of feedback conversations:
Appreciation: “Hey, nice job on…”
Coaching: Conversation focusing on growth, change, improvement, or a relationship imbalance
Evaluation: Assessment of performance relative to a standard
Stone and Heen’s recommendation is to separate evaluation conversations from coaching and appreciation, which is useful advice for managers approaching performance review season. It’s hard to hear advice right after being told that your performance in a certain area doesn’t meet expectations.
I’ve taken their idea a step further and made a point of separating appreciation (“Nice job facilitating the meeting today.”) from coaching conversations (“Let’s talk about what happened yesterday with Charles.”). This helps to avoid the so-called compliment sandwich, which can sound passive-aggressive and utterly insincere: “You’re a great part of our team. But you never show up on time for meetings or meet your deadlines. But really, you’re awesome and everybody loves you.” There’s a solid justification for delivering appreciation in isolation — negative sticks more than positive. One study found a nearly 6:1 ratio of praise to criticism among members of its highest-performing teams. This insight has led me to approach appreciation conversations as short and sweet interactions that happen as frequently as merited. The positive-to-negative ratio matters.
Overcoming the compliment sandwich conundrum brings us to Kim Scott’s Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity. This book caught fire a couple years ago because it addresses a fundamental tension many people experience about difficult conversations: can you be honest without being a jerk? Her approach sounds like tough love, and it’s the juxtaposition of the two qualities captured in that phrase — directness and caring — that results in what she calls radical candor. (I am no doubt biased favorably toward this because it aligns with insights about strength and warmth that John Neffinger and I explored in Compelling People.) The underlying formulation that leads to Scott’s golden mean is, “Because I care about you, I am going to be very direct.” My favorite takeaway from Radical Candor is when she turns the lens toward self-reflection and encourages readers to adopt this question: “Is there one thing I could do differently that would make it easier to work with me?”
Crucial Conversations: Tools for Talking When Stakes Are High, by Kerry Patterson, et al., has many disciples. If you like pure how-to books with checklists and acronyms designed to serve as mnemonic devices (e.g., STATE), this is the book for you. It’s not the book for me, but two things I do appreciate are its emphasis on: 1) psychological safety, which is critical to honest, direct dialogue in a workplace, and 2) awareness of your body’s physical signals during a difficult conversation.
The underlying concern about tough conversations that motivates advice-seeking from books is, “What can I do when shit goes sideways?” A few of the resources above offer suggestions and tools for handling worst-case situations, but the real learning takes place in the practice and reflection. The fear of conflict can be so overwhelming that anything may seem preferable to the discomfort of uncontrolled negative feelings or emotions. As Seneca wrote two thousand years ago, “It is not because things are difficult that we do not dare, but because we do not dare, things are difficult.”
