Tips to help leaders detox difficult conversations

One of my most recommended resources for clients is the book, Difficult Conversations: How to Discuss What Matters Most.

I often work with leaders at social impact organizations who are trained to argue and question—lawyers, policy thinkers, political strategists, social scientists, academics and the like. Their conversational style typically resembles a ping-pong match with a volley of opposing views yet little real dialogue.

As each person asserts and reasserts their points, frustration and intensity increases on all sides. This dynamic can lead executive directors and team leaders to feel baffled, frustrated and thwarted by negative responses to their expert input on complicated projects.

How can you reshape the ping-pong match of debate into more productive conversation and a better work culture? I frequently help leaders cultivate new skills for the meta conversations needed to effectively address underlying feelings, history, beliefs and power dynamics.

One of my most recommended resources for clients is the book, Difficult Conversations: How to Discuss What Matters Most, by Douglas Stone and colleagues from the Harvard Negotiation Project. Research by Stone et al revealed that dialogue often breaks down underneath a conversation at these three crucial layers: #1 what happened, #2 identity and #3 feelings. Conversations to explore these layers are foundational to emotionally intelligent leadership.

Amidst a conversation that breaks down, things can feel too intense. The leadership move is to talk again in a calmer moment and explore together where the discussion broke down. The focus needs to be not on the substance but on the interaction itself. That follow-up conversation might sound like this: “Let’s take a pause to look at what went on between us in our recent conversation.” While asking this could feel unsettling and contrived, your curiosity and openness can yield high returns in what you learn and your ongoing relationship. Raising this question is an act of leadership that extends trust.

Begin with “What Happened”

Until you can acknowledge the impact your actions and words may have had on others, the conflict may well roll on. Ask one another:

  • What intention did you have in the conversation?
  • What impact did my input have on you (that I might not have anticipated)?

Most people can’t listen until they feel heard. Listen to the other person’s perspective. Think about how the situation must have looked and felt from the other side. True listening (and feeling listened to) are necessary steps toward letting go of the hurt.

Explore “Identity”

A conversation about what happened is important yet may not lead to sufficient learning and trust needed to turn things around. If you sense an intense emotional response, that’s a clue that a staff member feels that their sense of competence is being threatened. Or that your own sense of competence feels threatened. Either of you can get triggered into a fight or flight response, what Stone et al call an “identity quake,” which can make the interaction challenging to resolve. Ask:

  • What’s at stake here for my identity as a leader?
  • Did what happened threaten my sense of competence, or my sense of myself as a good boss?
  • What is at stake here for the other person’s identity—as a colleague, as a professional?

Processing these questions together can deepen mutual understanding and trust so you can strategize together about ways to avoid similarly unproductive conflicts in the future.

Focus on Feelings

Even after this important conversation about professional identity, it can be helpful to process other potentially underlying emotions that may have spurred your ping-pong-like conflict. Listen to each other as you share what may be a relevant work context for your intense feelings (such as a conflict with your board chair or an issue your employee may face with a colleague) or factors in your respective non-work lives (such as childcare issues or a sick parent). Ask:

  • What emotions or difficult work or personal scenarios might be influencing how am I feeling about this?
  • What might be similarly happening for the other person?
  • Is there a longer, ongoing dynamic in your relationship that needs to be explored and addressed?

Sharing and acknowledging the factors that influence each other’s perspective can build human connection and deepen trust, which can avert conflicts in the future.

The power of listening well

When a conversation feels problematic, try moving the conversation to an entirely different realm. Step back from the argument. Be curious. Learn from each other. Build trust for a stronger work relationship.

Replacing the ping-pong of debate with a conversation about underlying dynamics can make you feel vulnerable. These skills make you a stronger leader; it takes practice. If you find these conversations triggering, this is a hint you have more work to do to use these techniques well.

Listening well means managing your own defensiveness and reactions during intense conversations—but that is the topic of another post.


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