How to Handle Difficult Conversations


Bowdon, T. (2007). 50 psychology classics who we are, how we think, what we do: Insight and inspiration from 50 key books. London: Nicholas Brealey Pub.

Stone, D., & Patton, B. (1999). Difficult conversations: How to discuss what matters most. New York, N.Y.: Viking.

Handling Difficult Conversations

Whether in the context of interpersonal relationships, professional work environments or family, at one time or another we must engage in a difficult conversation. Perhaps at work, you feel that you have been working hard and deserve a raise. What is the best approach to asking your supervisor for more money? Or perhaps you are in a stressed relationship and you believe it may be time to end it. How should you approach your partner?

The abovementioned situations can surely be called “difficult conversations,” and in 1999, researchers from the Harvard Negotiation Project—notably authors Douglas Stone, Bruce Patton, and Shelia Heen—published, “Difficult Conversations: How to Discuss What Matters Most,” which had been the result of 15 years of intense research. According to the “Difficult Conversations” authors, handling difficult conversations is more about finding common ground than winning the argument.

Multiple Conversations in One

According to Stone, Patton, and Heen, “. . . each difficult conversation is really three conversations.” Author Tom Butler describes it this way: “Above and beyond the actual words that are spoken, these other conversations are mostly internal and involve our perception of the encounter and what it means to us.” In other words, meaning exists above and below the words that are spoken.

In a sense, difficult conversations reveal the possibility for conflict—conflict of interpretations, values, and ideas. The authors stress, however, that this does not have to be the case. Rather, engaging in difficult conversations contain the possibility of obtaining a deeper understanding of ourselves and others. We tend to the move the conversation further, the authors suggest, by not presenting our position as “the truth” but by offering our position as a perception. This strategy tends to “disarm” the other person. Framing our position in this way allows for flexibility and does not allow the conversation to degenerate into a “me vs. you” scenario.


Throughout “Difficult Conversations,” Stone, Patton, and Heen stress the idea of listening as a way of understanding. As Butler describes it: “One of the authors’ rule is: People never change without first feeling understood.” That is to say, by beginning a difficult conversation—whether it be about relationships, finances, or whatever—by immediately “point the finger,” instantly turns off the other person. It remains better, as the authors suggest, to “shift the focus.” Make the conversation less about who is right or wrong, and this will create a positive climate.

To take this strategy one step further, Stone, Patton, and Heen suggest that, when confronted with a difficult conversation, an individual remains better off “expressing feelings” and “not getting emotional.” Although emotions are a natural part of human existence, sometimes they may cloud our judgement, especially in the context of difficult conversations. Moreover, expressing our emotions in a productive manner opens the communicative possibilities.

A Final Look at ‘Difficult Conversations’

Although it has been more than 15 years since “Difficult Conversations” was first published, the work remains influential—and useful—to this day. In the worlds of business, work, school, friendships, and relations, at one time or another, we may be forced to engage in a difficult conversation. Possessing the proper tools and strategies arm an individual with the possibility of greater success.

To summarize, it remains important to:

• Avoid “either/or” solutions

• Remain aware of how you say something . . . not just what you say

• Actively listen

• Express empathy

• Carefully “frame” your position

Again, following the steps laid out by Stone, Patton, and Heen does not guarantee success, yet it may increase the chances of proper outcome. At our core, we want to feel needed and relevant. That said, the tools offered by the authors are not psychological steps on how to manipulate another person. Rather, they are approaches toward empathy and understanding within the context of human communication. Moreover, the authors’ research reveals a larger truth: that many difficult conversation do not have to be difficult. They can, in fact, proceed without degenerating into an argument or a direct confrontation. Finally, many successful professional and personal relationships stem from good communication.

Brooke Lamberti

Brooke Lamberti is a content writer based out of Scranton, Pennsylvania. She received a Bachelor of Science in Psychology from Marywood University, and has prior career experience working in social work and domestic violence advocacy. She has a passion for writing and helping others.

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