• Delivering constructive feedback to your direct report about their disappointing progress on a project 
  • Sharing with your colleague that you are not going to accept their proposal that they worked so hard on.  
  • Telling your friend that you would like him to wear a COVID mask when you meet for coffee  
  • Telling your uncle that his comments aren’t inclusive of people of color. 

These are all situations that can lead to a difficult conversation. And figuring out whether or not you want to have this conversation, when to have this conversation and how to approach it can determine whether it will be a learning conversation.  

A difficult conversation is any interaction that you know you need to have but that you desperately want to avoid. Usually it involves delivering news, feedback or a suggestion that you think will be challenging to the identity of a person you care about. In our conflict-adverse culture, many of us would rather let these issues die from benign neglect and be forgotten. Sometimes we will just absorb the frustration and live with this issue withinEven worse, we will convey our opinions in an indirect, therefore, passive aggressive way. But if the issue is very important to you then it will not float away into the ether. Rather, the presenting problem will fester, and you will have abdicated your opportunity to make a positive change in a precious relationship. 

Exercising leadership is fraught with difficult conversations. Indeed, difficult conversations are actually required in exercising leadership since your role as a leader is to ensure that competing interests, opinions and values are addressed honestly and maturely so that your organization, community or partnerships can thrive. Often this means that you will be precisely the one to initiate a difficult conversation. The question for us as caring leaders is how to do that skillfully.  

You will not refine this skill by reading this short article. For that you will need to do the same as you would in order to get to Carnegie Hall – practice, practice, practice and also read, read, read (I’ve provided some of my favorites links to further reading below). You will mess it up and you will forgive yourself and you will learn. But first, you will need to clarify for yourself what you want to gain from a difficult conversation.  

Do you want to win the conversation or do you want to learn from it? Do you want to get what you want or do you want to build a relationship? Think of a difficult conversation like playing a friendly game of tennis with a young child. You can choose to serve an ace every time and you will win the point, but chances are they won’t want to play anymore. Or you can engage in a mutually supportive volley that lasts a long time leading to years of fun tennis. Sometimes winning the point is actually missing the point. Unlike competitive sports, in our precious communal projects we want partners, not opponents. Engaging in a difficult conversation with the right mindset can save a relationship. Our organizations are made up of relationships so strengthening relationships means strengthening our organizations.  

So, what is the right mindset?  

Leadership teacher (and Wexner Foundation faculty) Ann Garrido says “I don’t go into a conversation unless I have a genuine question in mind – something to ask that I don’t know the answer to. A good purpose for going into a conversation is to get more information. A second purpose is to share my own perceptions. I may not be able to persuade you to see things my way, but there’s value, for the sake of my own integrity, in saying how I see the situation. A third purpose is to invite problem solving. I can invite you to stand alongside me and ask, “Can we figure out how to work on this issue together?”  

The right mindset involves genuine curiosity, honest sharing, and a desire for problem solving.  

Disagreement and its resulting difficult conversations are important parts of what it means to be Jewish and are a characteristically Jewish exercise for learning how to exist in this world. But it is not argument for argument’s sake, it’s not about winning or getting what you want at the expense of all else. Rather it is the uniquely Jewish value of makhloket l’shem Shamayim  a disagreement (or difficult conversation) for heaven’s sake. What does it mean to have a disagreement for heaven’s sake? The Talmud answers by giving the example of the house of Hillel who approached philosophical disagreements with the house of Shammai with humility and patience by essentially asking Garrido’s question “Can we figure out how to work on this issue together?”  

A disagreement for the sake of heaven is an elegantly executed difficult conversation that preserves and enhances relationships through what leadership teacher (and also Wexner faculty) Roger Schwarz calls “mutual learning” where both or all members of a difficult conversation are set up to learn from it. According to Schwarz, not only is mutual learning a moral good, it is also strategic. For example, by approaching difficult conversations in our workplaces with genuine curiosity and mutual learning in mind, we can increase understanding (since real issues are being skillfully surfaced), increase efficiency (since we are not wasting time with emotional runarounds), and increase the quality of work life (since we are all investing in relationships with people we spend hours on end with).   

Not every difficult conversation has to happen. Shakespeare famously wrote in Henry IV Part 1 The better part of valor is discretion,” that is, choosing your battles (or difficult conversationswisely is the first step to engaging the most important ones with the right mindset. But avoiding all difficult conversations will prevent the most important kind of learning, that is, knowing what is in the hearts and minds of the people we live and work with so that we can move forward with compassion and mutual understanding 

In Pirkei Avot 2:5Hillel the Elder reminds us לֹא הַבַּיְשָׁן לָמֵדthe timid person doesn’t learn. For our purposes this can mean that the leader who avoids engaging in the right difficult conversations skillfully will not be a leader who learns. And the best leaders are learning leaders.   

For further reading, I suggest the following (short!) books: 

Difficult Conversations: How to Discuss What Matters Most by Douglass Stone, Bruce Patton and Sheila Heen 

Nonviolent Communication: A Language of Life by Marshall Rosenberg 

Smart Leaders, Smarter Teams: How You and Your Team Get Unstuck to Get Results by Roger Schwarz 

Standing in the Fire: Leading High-Heat Meetings with Clarity, Calm, and Courage by Larry Dressler 

If you have other books on this subject that you would like to recommend, please share them with me. 

Get To Know The Author

WGF Alum Or Mars (Class 6) is Vice President of The Wexner Foundation.