Preparing for Contentious Conversations

1. Delivering a less-than-excellent performance rating to a strong-willed, vocal individual—a decision that could end their shot at promotion.

2. Confronting a boss about behavior undermining your team’s effectiveness.

3. Negotiating with a key leader in a partner organization whose conflicting priorities jeopardize your mission.

4. Participating in an organizational After Action Review (AAR) to examine and learn from a failure stemming from a decision you made.

5. Meeting with your boss and peers to develop a strategy to address significant budget cuts, knowing your unit’s priorities are on the chopping block.

6. Reorganizing a unit in ways that combines sub-elements, prioritizes certain elements over others, and/or requires physically moving people to a new location.

Before reading further, pause to clarify a contentious conversation pending in your near future. Put the rest of this article to work by applying the insights that follow to the conversation you need to address. We believe that the potential for contentious conversations to be productive depends in large measure on what happens before the conversation. Your preparation is key.

1. Go to the Balcony.[1] Pause and consider the larger purpose—bigger than your personal interests or the individual interests of those involved. Shift your perspective to focus on shared, higher-order goals. Reflect on:

  • Q1.1: What is the larger mission I share with those I’ll engage with?
  • Q1.2: What higher-order commitment requires me to be firm yet open to possibilities?
  • Q1.3: What outcomes would best serve the organization, mission, and Nation over the long-term?

This broader perspective moves your mindset from “down-and-in” (personal concerns) to “up-and-out” (collective interests).

2. Put Yourself in Their Shoes. Understand the perspectives of all stakeholders involved—even those not present in the conversation. Ask yourself:

  • Q2.1: What matters to them, and why?
  • Q2.2: What would need to be true for their current behavior to make sense?
  • Q2.3: What pressures are they under, what is at stake for them?

This exercise isn’t about agreeing with others but about fostering understanding, which lays the groundwork for collaboration.

3. Check your attitude. Your emotions and mindset will set the tone for the conversation. Regulate them to create a productive atmosphere. Consider:

  • Q3.1: What emotions am I feeling? What is their source?
  • Q3.2: What fears and doubts do I have about the conversation?
  • Q3.3: What attitude or mindset will help achieve the best outcome?

Mutual respect is critical. As the authors of Crucial Conversations: Tools for Talking When Stakes Are High remind us:

(1) Seek Wise Counsel: Share your thoughts with a trusted mentor or friend. Get their candid feedback on your preparation and approach.

(2) Build Resilience: Develop thick skin. Don’t take slights personally and encourage your teammates to do the same.

(3) Design the Environment Thoughtfully: If possible, choose a location and setup that is welcoming and relaxing. As William Ury notes:

Navigating contentious conversations with humility, maturity, and a commitment to the greater good is one of the most important contributions you can make as a leader. When done well, these discussions become catalysts for growth and advancement toward excellence. Preparation is your secret weapon. By investing time to reflect on the bigger picture, understand perspectives, and regulate your attitude, you’ll be better equipped to transform conflict into meaningful progress.

What contentious conversation—ripe for disagreement or argument—have you been avoiding or need to prepare for? Spend a few minutes reflecting on the three-step framework above and set the stage for a productive dialogue.

1. Conflict Communication: A New Paradigm in Conscious Communication

Interesting insights about our “monkey” and “lizard” brain and the unconscious scripts that drive our behavior. Quote: “The shadow community we have in our heads, the voices telling us what other people believe and think, aren’t accurate.” And: “Once you trigger the other person’s limbic system, he or she cannot process your facts.” This book has excellent practical applications for military and LE leaders.

2. Possible: How We Survive (and Thrive) in an Age of Conflict

We referenced this book in the article. The author, William Ury, is renowned in the field of negotiation and conflict mediation.

3. Difficult Conversations: How to Discuss What Matters Most

This is a classic in the field. Quote: “Focusing on blame is a bad idea because it inhibits our ability to learn what’s really causing the problem and to do anything meaningful to correct it.” And: “Rather than assuming we already know everything we need to, we should assume that there is important information we don’t have access to” [yet].

4. Crucial Conversations: Tools for Talking When Stakes Are High

We referenced this book in the article. It pairs nicely with Difficult Conversations, covering some of the same ground but different enough to be useful. We find that with both books you can flip through to parts that strike you and read those to great benefit; you don’t need to read them all.

Live your mission. Lead well.


[1] We learned of the “go to the balcony” terminology from William Ury and Ronald Heifetz. The idea is to get off the dance floor (or field of play) to be able to see the bigger picture.