Help for the Confused: Resources for Challenging Conversations


“If you can’t handle the tough conversations, you can’t handle the tough decisions.”

Greetings friends and leaders! I am not sure about you, but the last week or so has been quite taxing and stressful in my house. Many of you have expressed interest in having some tools for conversation, so I am including some tools here. There are suggestions for mostly short readings, movies and possible scripts to follow in discussing a host of different issues. These are only to get you started and you will no doubt find your own as you develop a way of conversation and engagement that makes sense for you. Most of what you find here is based on my experience in undergraduate, graduate, religious and military educational contexts with a wide variety of ages, structures and topics. As an ethicist, I teach all the hot button issues (war, race, politics, ethics, business) so I likely have a higher threshold of comfort for discomfort. To lead discussion well comfort with discomfort is very helpful.

Please feel free to reach out for more personal or tailored ideas that fit your context.

Starting Discussions 

The most important thing is to start. But that will take courage and vulnerability, as well as empathy and humility. So start small. Somethings to consider:

  1. Start small with your topic: What do you want to talk about? Why?
  2. Start small with your group: smaller groups tend to produce better discussion, as people are more willing to be vulnerable and share with a smaller group. You also have a better shot at more people and ideas getting heard and engaged in depth.
  3. What do you want to accomplish? Do you want to give people a chance to vent? Do you want to allow people to be heard? Do you want to solve a problem or come up with an action plan? Do you want to explore arguments or alternative perspectives? Do you want to build community?
  4. What preparation will you do for the discussion? What preparation do you want the participants to do? Read or view something? Ponder a question or two in advance that they come prepared to discuss?
  5. What will the ground rules be? The fewer and simpler the better. And if you can get your group to generate them, that’s even better since you will have buy in.
  6. What is your role? Will you facilitate and not participate otherwise? Will you have a note taker or someone to help with the process? (Whatever you decide, communicate this to the group, especially if you hold a leadership role.)
  7. What are the power dynamics at play and how can you address those?
  8. What are the group and personality dynamics at play? How can you keep those in mind? (A room full of introverts requires a slightly different approach than a room of most extroverts.)
  9. When you begin the discussion, it is okay, and even good, to acknowledge the discomfort and awkwardness.

I know this seems like a long list (it is), but the more you prepare and communicate to your people how the discussion will proceed and what it is for, the better your odds of a good conversation. It will also help if you model the attitudes that you want to see: humility, vulnerability, curiosity, empathy, connection, engagement. If you are asking for these things, you should be prepared to do them, at least a little.

Emotions and Analysis

Since I talk about challenging and controversial issues in my classes, I find a structured process is helpful. This process is one way to engage emotions, but in a way that is more conducive to critical thinking and deeper engagement.

But you might say, “I think we should leave emotions out of this!” Bad news: you can’t. Even if you could, you shouldn’t. Why? Because it is there under the surface influencing arguments, positions and perspectives and the sooner you get it out there, the sooner you can examine it for what it is. Emotions are part of our humanity and an important part of leadering.

  1. What is your emotional response to x? (I keep track on the board, flip chart etc where they can be seen by all.) Just brainstorm with no comment. If people see what they say visible to others, they feel seen and heard. That matters.
  2.  Then either as a writing, pair and share or larger group exercise, ask them to identify specific ideas, commitments, moral or other values, experiences, beliefs that they think produced that reaction. (Where is this emotive reaction coming from?) Again, mapping visually can help.
  3. What do they think the answer to #2 shows, especially about themselves? This is a place where these things could be examined (is this a valid, good belief) or just acknowledged (in terms of how it is influencing them.) The point is to bring them to the surface so examination and conversation around what is really going on can happen.

I have left #3 somewhat vague, because you can do different things there depending upon your group, your aim and the context. In an academic setting, we might connect #3 to our readings or class material, engage in debate or argumentation or engage in narrative to share experiences that further the discussion. Its open to you. I find having this structure makes the venting more productive and takes it deeper.


While most of what is listed here are books, I would encourage you to explore videos especially TED talks and similar kinds of shorter formats. It can be helpful to have something concrete to gather around or ground discussion in.


A first person account of the black experience of the author which is a good way to get discussion going.  Ta-Nehsi Coates, Between the World and Me.

Critical Race Theory is an academic field which looks at questions of race, white supremacy and privilege. The work of Robin di Angelo is fairly accessible to lay audiences, especially White Fragility. Her videos may also be helpful in getting some discussion going, especially on Black Lives Matter and other movements that take CTR as their starting point.

Don’t think you have privilege? Take this quiz and discuss!

Martin Luther King Jr. A Letter from Birmingham Jail is a good read and discussion starter on race, injustice and related issues.

Military Profession

A good introduction and overview to the topic. Mick Ryan,

More in-depth discussions from current scholars, including perspectives from the different services as well as civilians. Redefining the Modern Military: The Intersection of the Profession and Ethics.

Military Ethics 

My book on obedience in both military and civilian contexts that includes a discussion question guide. 

My blog (which you are reading on) also has short reads on lots of military ethics topics including obedience, Just War, empathy, strategy and moral injury

Both Strategy Bridge and War on the Rocks have regular and short articles on matters of interest to military and other leaders. A few of mine that might be useful.

6 Questions on Leadership and Ethics


Moral Injury

Civility and Politics

Why civility matters, with a bit of history of the topic.

Movies/Popular Culture

Consider a movie night! The movie does not have to be current or good in the least to spark discussion and gathering around a common experience can be helpful. (The same applies to any pop culture artifact – television show, song, meme….)

You can work through the emotive analysis process above or have 2-3 core questions about the movie you want to discuss. Just two examples….

The Seige has great civ/mil topics, as well as questions about terrorism and whether our moral principles give way under crisis.

Tears of the Sun is good to look at race, military humanitarian intervention, obedience and Mission Command.

Scripts for possible conversations


For this topic here are a few questions to tackle and some basic points to get started:

1- What is wrong with saying All Lives Matter?

2- Don’t we want a color blind society? Why does race matter? (I don’t see color.)

3- Enslavement was a long time ago, that has nothing to do with today or me.

4- I grew up poor, I can’t have white privilege.

5- This is all PC BS. Why should I care about diversity and inclusion?

The core issue here is really the definition of racism. Racism is prejudice (prejudging on the basis of face) PLUS institutional power to enforce that prejudice. Racism is about systems of oppression and discrimination that still persist today, as well as the legacy of enslavement both on the black community and for whites. Oppression impacts both the victim and those that below to the power structure that oppresses, whether you consent to the oppression or are aware of it.  Racism isn’t just being mean, wearing a white hood or saying the N word. It involves an entire system, not a few mean people.

All Lives Matter and the color blind issue are attempts (well-meaning perhaps) to erase the acknowledgment of racism both in history and today, its impacts and also the role that race plays in a person’s identity. To say that I do not see my black son’s color, is to say that I do not see part of who he is and how he experiences the world.

Diversity and inclusion matter for organizational effectiveness, team belonging and identity as well as for other leadering qualities like humility, empathy, innovation and critical thinking. We only know what we know. We only have the experiences that we have. Broadening our horizons is a strategic and moral imperative.

What Can I Say on Social Media?

First, there are legal issues here especially for the military community (even civilians who work within that structure, like myself.)

Second, there are issues of the Profession, which involves the military being non-partisan (not apolitical as there is no such thing) because of the ideal of civilian control of the military. Why is that important? What are the dangers if the military is partisan? What has happened in other countries with a partisan military?

All that said, members of the military are also citizens and have moral obligations in that regard too. How should we think about our social media interactions given our personal and professional obligations?


Why should you obey? When should you obey? What should we do with people are being disobedient? Is it ever morally acceptable to engage in disobedience?

Where are your lines that you would not cross?

For members of the military, it might be worth thinking about how responses to the protesters, rioters and looters (who are likely different groups) are similar or different from how we think about combatants (who can be targeted and harmed) and non-combatants (who cannot, though collateral damage is permitted under limited circumstances) in warfare.  With civil unrest, who are the combatants? Are they enemy combatants when they are citizens like yourself? What are your obligations to members of your own society?

Ok! I have just dumped a ton on you. Think of this as a small plates menu that you will pick and choose a few things (or one) to try with your community. Talk to your colleagues and share the burden. Experiment to see what works for you. The most important thing is to get the conversation going and keep it going. Conversation builds connection and it should be a regular habit.

What else? What should we talk about? What do you need help with in getting your tough conversations started? 

Published by shankskaurin

Philosopher and military ethicist. Author of two books, including "On Obedience" (USNI Press, 2020) I also teach war college students for the Navy. (Views here are personal only.) Mother to two energetic young lads. Foodie, gardener and Diva with a shoe obsession.

One thought on “Help for the Confused: Resources for Challenging Conversations

  1. Just so I am clear, are endorsing Critical Race Theory and DiAngelo’s work as being legitimate tools for discussion to help with talking about issues of race? I would also like to ask if you believe that the definition you put in this article of what racism is? It does not match what traditionally has been thought of for the meaning of the term. In addition, by implying that one group has power over another simply due to the color of their skin seems to be a bit disconnected from reality, unless you are just using that as a way to start a discussion?


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