Courageous Conversations: Stories That Foster Self-Awareness, Build Skills and Cultivate Confidence


Courageous Conversations: Stories That Foster Self-Awareness, Build Skills and Cultivate Confidence

© David Lee 2013


Fine Oronce, Map of the Austral Earth, Paris, 1536, engraved on wood.

Sharing stories about challenging conversations provides tremendous educational and therapeutic value to the listener. In this article, we will explore why Courageous Conversation Stories are so powerful, two versions you can tell, depending on your intent, and I will share with you an example.

Why Tell Courageous Conversation Stories?

Fostering Self-Acceptance

First, sharing these stories makes it more comfortable for others to acknowledge their own issues and then work through them. As anyone who has been to twelve-step groups, attended group therapy, or has friends with whom they share deeply knows, hearing someone else’s story about a challenge helps to normalize your own feeling and reactions. You realize you’re not the only person who has those feelings and issues. By sharing your struggles about whether to bring up an issue, the emotions it triggers, and your reactions, you help the listener accept their humanity, which then opens the door to them being willing to explore how they might respond more resourcefully.

Fostering Self-Awareness

Second, when you share your internal world with the listener, you help them connect up with their inner world. When you share your thoughts and feelings, it helps the listener connect with their thoughts and feelings. This is one of the most powerful and useful results of using stories that deal with interpersonal challenges. They are a gentle vehicle for stimulating self-awareness and self-reflection. So, rather than peppering a person with questions designed to turn their attention inward, you can share a story that models this inward attention and the resulting self-awareness. This allows them to participate as deeply as they feel comfortable.

They can delve deeply into their own inner world or they can simply take in the story as “only a story”, while at the unconscious level, they are making associations that can later result in epiphanies. In the story I will be sharing with you, you will notice the story focuses primarily on sharing my internal process, because this Courageous Conversation Story is more of an example of how to use a story to foster self-awareness and insight than a “Here’s what to say” story.

“New Maps” Of Effective Ways To Navigate The Territory

Third, you can use stories about challenging conversations as a “Flight Simulator”, providing the listener with a non-threatening, virtual experience in which they can imagine responding in new ways. Sometimes when using stories around challenging conversations, I go into detail about what I said, because my goal is to instruct. My goal is to provide an example of how one could bring up a difficult issue in a way that doesn’t trigger defensiveness or how one could respond to another person who is upset.

When this is your purpose, your story serves almost as a virtual training video, because the listener “plays the video in their head” as you recount the story. Because your “lesson” is embedded in a story, rather than you just giving a list of suggestions, the person is both more likely to remember the key take away messages. Also, because you show how they are used in a real life context, they can literally see how to apply them in the real world. Thus, whenever you want to teach communication skills or language pattern, if you embed them in a story, your message will be received and remembered more effectively.

Challenging Limiting Beliefs While Offering Hope

Fourth, sharing your Courageous Conversation Story can provide hope for others. By sharing examples of tough conversations you were willing to have and the fact that they turned out well, you give the listener hope that it IS possible to have a conversation that they fear having and doubt will work out and….have it work out wonderfully.

This is an important benefit Of Courageous Conversation Stories, because people won’t even try to have the conversation if they don’t believe it has any hope of working out. By sharing examples of “I really didn’t think this would work out…but it did” stories, you help them see it IS possible.

To add counterbalance, I always try to remember to say that being good at these conversations is no guarantee that they will always work out, and follow up by saying I’ve had my share of conversations that, despite my best efforts, crashed and burned. Even though it is commonsense that not every conversation will go well, I like to say “learning these skills will increase the odds that difficult discussions will go well, but they obviously guarantee every conversation will go well.

How to Use Your Experience as a Teaching Story

Before We Get Started

The story I am about to share with you is not a story I share when I’m giving Constructive Conversations in the business world, but would be a story I would share if I were still doing seminars around cultivating more deeply meaningful relationships and…healing our childhood relationship wounds.

I wanted to share this story with you, rather than some of my work-related ones, because it offers a deeper, richer example of how you can use stories to foster self-awareness as well as hope.

For the rest of this article, imagine that you are at a seminar on Courageous Conversations, and I am facilitating. You will notice that as I tell the story, I interweave the sharing of my inner world and also commentary about its relevance to the larger context of our lives and society. This is one way I tell Courageous Conversation Stories. If my goal is to simply offer the listener an example of how to respond in a more productive way, I will typically just share a bit of the context and the share how I brought up the topic, how the other person responded, briefly what happened next, and then debrief.

Because the central feature of this story is around the issues it brought up for me and the choices we make in relationships—and their consequences, it is longer and more self-revelatory than other stories I might share. I mention this because I don’t want you to think that you have to self-disclose in very personal ways for your Courageous Conversation Story to be useful.

So again…imagine from this point forward, you are sitting in the audience, and I am talking…

Setting Up My Story

“Being willing to have courageous conversations has probably been the most transformative practice in my life…

I am just as reluctant as the next person to bring up difficult issues and face the emotional discomfort they can create. I share the fear that many have expressed in seminars I’ve lead, the fear that bringing up the issue will make the situation worse and damage the relationship irreparably.

Despite this, I continue to challenge myself to have courageous conversations because I’ve seen how they can transform a relationship and how they have transformed my life. It has been through these conversations that I have experienced some of the most important growth.

I am also a big believer in being willing to “suck it up” and have the conversation because it is perhaps through these conversations that we can make the biggest difference in the world.

“Be The Change”

When we are willing to work through our anger, blame, and fear and bring our best selves to a conversation, when we are willing to speak with both courage and kindness, when we do our work so we can model how to address difficult issues in a courageous, mature, and compassionate manner, we demonstrate to others that it can be done.

Through their experience of having the conversation with us, others can learn that it IS possible to talk about difficult issues, rather than avoid them. They can experience what it’s like to have someone courageously confront an issue without being aggressive or judging.

They can experience what happens when a person makes a different choice when feeling hurt or angry. They can see through our actions and how they are affected by our brave and open-hearted approach that icy withdrawal or angry, blaming attack are not the only options.

When we choose not to harden our heart or make the person less important to us, but instead allow ourselves to feel vulnerable and share openly, we model a healthier approach to responding to interpersonal pain. When we do this, we also give the relationship a chance to heal.

Even more wonderful, we make it possible to receive the gift that waits on the other side of the uncomfortable conversation: a deeper, more authentic, more soul-satisfying relationship.
That being said, that gift does not always come.

As we have all experienced, sometimes the other person is not willing or able to engage in such a conversation. While it’s important to acknowledge that reality, that’s not the topic of this article. I do want to acknowledge, though, that our willingness to have the conversation does not come with a guaranteed positive outcome. That’s why these are difficult conversations. If the outcome was guaranteed, they wouldn’t be difficult and we wouldn’t need courage and skills to have them.

Let me give you an example of one of these conversations I was faced with and see if you can relate to your own version. My hope is that sharing the issues that this situation brought up in me will help you get in touch with your own process and the choices you make when faced with a potentially awkward and difficult conversation.

The Courageous Conversation Story Begins

A couple of years ago, I was talking with a friend who I see for bodywork. She is amazing at what she does and has made a huge difference in my life, both in healing from injuries and keeping my body “tuned up” and at optimal health. I have deep appreciation for her and the difference she has made in my life.

In our conversation, she was sharing how she was bashful about marketing her services and knew that her unwillingness to do so had kept her practice from growing. As she talked about her work and who she most enjoyed working with, I shared my thoughts about how she might reach those people. Since I am part of the demographic, I shared how I could imagine framing her work in terms of helping people who help others for a living. More specifically, how people who are healers and helpers need a place they can go to get rejuvenated and how her work provides that place.

She seemed to resonate with that idea, but it was clear that she didn’t know how to implement it.
I started thinking about what I had learned about third party endorsement marketing. This is where someone who loves your product or service writes a letter about how wonderful your work is, and they mail it to people in their circle of influence and/or you mail it to your target market. Either way, because it is someone else praising your work rather than you doing so, the message obviously has far greater credibility.

I Want To Help

Because I care about her, believe in her work, and know the power of third party endorsements, I spent several hours writing a letter on her behalf, sharing my experience with her and her work and what a gift it would be for any helper or healer who wants to “keep their well filled.”

I emailed it to her.

I didn’t hear back.

Now, as you know, one never knows if email arrives, so I reminded myself that her not responding could simply be because she didn’t get my email. It didn’t mean she took this act of kindness for granted.

After about a week, I either emailed or left her a voice mail message saying I just wanted to make sure she got my email.

She emailed me back a short, “yes I got it, thank you” email.
I was both hurt and annoyed.

I thought “Boy…if someone cared enough to do this for me, I would be all over it. I would be SO appreciative and I would so let them know.”

A Moment To Reflect

Think for a moment how rarely other people shine their spotlight of attention to the degree that they offered you something later that showed they really listened to what you were saying, understood, and cared about your well-being. Think about how rare it is to have someone turn their head away from their overloaded To Do List, to notice what’s going on in your life and come up with ways they can be helpful to you.

I say this not to say “Oh look how wonderful I was”, but rather to invite you to reflect on how you might be more aware of, and attentive to, others’ journeys and how you can perhaps surprise them with simple acts of kindness.

Back To The Story…

As I explored why I felt hurt and annoyed, I asked myself “Are you upset because you didn’t get the outcome you wanted? Did you do it so you would get praise or a big outpouring of gratitude?” I found myself reflecting on admonitions about giving without expecting anything in return.
As I reflected on this, I could honestly say I didn’t do it for appreciation or praise, or getting anything back.

What I came up with was more about the personal and societal implications of people taking others for granted and not expressing appreciation. I see so much of this in the world and it troubles me.

Taking Others For Granted

When we take others for granted, when we take their acts of kindness or extra effort for granted, it communicates “What you did doesn’t matter to me.”

When you take that message to a deeper level it communicates “What you do and the fact that you care doesn’t matter to me.”


Since most of my professional focus is on the workplace, I can’t help but point out the implications for at work. I believe we see the phenomenon of people being taken for granted—and its cost—writ large in the workplace. Because people so rarely receive sincere appreciation for going the extra mile, for caring about doing a great job, for the sacrifices they make, they start feeling like what they do doesn’t matter. They believe THEY don’t matter, and start to ACT like they don’t matter.

They stop caring and they stop trying.

Whether in the workplace or in society at large, taking others for granted takes a massive toll on relationships, the human psyche, and the social fabric.

So, as I explored this and reflected on why I felt the way I did, I found myself being disturbed by yet another example of this societal phenomenon…and especially disturbed that it was coming from someone I cared about.

Personal Implications

I also found myself reflecting on the spiritual and wisdom tradition teachings around gratitude and how the best way to bring more good into your life is to feel gratitude for that which you have. The flip side is the best way to NOT attract more good in your life is to take the good that is in your life for granted.
When you think about this, gratitude and appreciation work both at the metaphysical level and the earthly, relationship level. Are you not more likely to focus your finite amount of time and energy in areas, and on people, where you believe they will make the biggest difference? If you get the message that your efforts are taken for granted, does that not let you know that putting your time and energy in that place does not matter?

And don’t you find yourself focusing your attention on places and people where you can see you make a difference…where you can see your gift is received and valued?

Implications For My Friend

So the other issue for me in this situation was how my friend’s actions had left me feeling much less interested in finding ways to be helpful to her.

I thought about my response and its implications. More specifically, I thought that if taking others’ kindness and help for granted was a common response for her, she might be causing other people to lose interest in helping her. It concerned me to think that my friend might be hurting herself in other relationships, now and in the future, if she responded to others as she did to me.


1. I was judging her. My opinion of her had diminished. Now, I could simply have worked on this by reminding myself that we all act mindlessly at times. I know I have. I could have told myself that I needed to just let it go and move on. However, being curious by nature, I wanted to understand more about where she was coming from. So simply doing the “We’re all imperfect…don’t get caught up in judgment” practice would have left me always wondering.

2. Because I believe the old adage “We teach people to treat us the way they treat us by our actions” I often wrestle with how to respond to what I perceive as ungrateful, entitled behavior. Do I simply accept that’s how they are and continue to act in generous, thoughtful ways simply because that’s “the right thing to do” or is my doing that implicitly teaching the other person that ungrateful, unappreciative responses to others are acceptable ways of treating people? If I continue to do what I enjoy doing—being generous and helpful—and they continue to take it for granted, am I simply reinforcing the kind of behavior that I see so rampant in society and which I find so troubling?

3. Do I stop being generous and giving with her? While doing so would make sure I am not reinforcing unappreciative, entitled behavior, it is also not who I am and…it would feel like active withholding. How can I be an open-hearted, loving friend and actively withholding at the same time?

4. Do I bring up the issue and feel like I am asking for accolades and effusive praise, which I wasn’t, and feel silly? I mean, it’s a bit awkward saying “Hey…I wish you had shown a little more gratitude over what I did for you.” Who has that conversation? Well, I think the very reason we don’t have those conversations is why we often harden our heart to others.

What To Do?

I shared my dilemma with my two “go to” friends from whom I seek advice when I’m wrestling with an interpersonal issue and need an outside perspective.

One friend said something like “I know how much her work means to you, and how much you care about her. I could see how sad it would be for you to put a wall up or to stop being generous with her, because being generous is who you are.”

I’ll Have The Conversation

As soon as she said that, I knew I had to have the conversation. I had to have the conversation because I care deeply about this person and I don’t want to sit idly by and not say anything about something that might be pushing others away, too… without them ever letting her know why they left.

I care about our relationship, and didn’t want to pull away emotionally. I also want to do my part to make society more kind and thoughtful. Also, on a personal note, I realized I need to have the conversation so I would not be repeating my old wounded pattern of making someone less important to me as a way to not feel hurt by their actions. So I called her up to talk.

I obviously can’t remember the exact words I used, but it was something like “I wanted to talk with you about the letter I wrote for you. I was kind of bummed that I didn’t hear back from you about it until I checked in to see if you had gotten it.”

In planning what I was going to say, I was conscious of wanting to simply share my experience and not get into judging, blaming, or lecturing.

She apologized and said that she was embarrassed that she hadn’t let me know she really appreciated that I had taken the time to do that for her. She also said that she had been going through a hard time and had been preoccupied. I asked her if she wanted to get together for lunch and talk about what’s going on with her.

She did.

Brief Conversation, Lasting Effects

I’ll be honest with you. After I wrote and rewrote this article several times, I found myself thinking “Wait a minute…will this story be anticlimactic for the reader? I mean, there’s no juicy details about what was said, no fascinating dialogue that will give people practical ‘how to have the conversation’ tips.” The conversation was over in just a couple of minutes and was very simple, without any drama or need for amazingly sophisticated communication skills.

But as I reflected on this fact, I found myself thinking how in some ways, it’s a perfect example of what can happen when we do our work ahead of time, when we work on getting our head and heart right before the conversation.

It’s also a reminder to us, when we are imagining that a conversation will be hard, that it might end up being very easy. The drama and pain we anticipate are simply a creation of our imagination, not a foregone conclusion. So, despite our fears and the emotional turmoil we create in ourselves—and I’m a master at this—if we do our work ahead of time so that we come from a warm and open-hearted place, the actual conversation often ends up being very short and sweet. So, the fact that the conversation was so easy and unremarkable is a nice reminder of this.

It’s also a nice reminder that if we get our heart right before the conversation—if we go into the conversation with good intentions and a warm heart—we are over half way home. The person senses this, responds in kind, and what seemed so complex and fraught with peril ends up being a bit anticlimactic, leading us to wonder “You mean I spent all that time worrying about this?”

What About Feedback?

After the conversation, I reflected on her explanation for why she didn’t respond. There was part of me that thought “If it were me, I would have still said ‘thank you’. If I were going through a hard time, I would be especially thankful that I had friends who cared deeply about me.”

But she is not me and there is no way I could truly understand what was going on with her and how overwhelmed she was. So, I could either choose to hold onto my judgment or accept that she was doing the best she could in that moment and be spacious enough to let her be who she was and how she was, in that moment.

However, I felt conflicted. I wondered if I was not being a true friend if I didn’t share my reaction to her non-response. As I mentioned above, I feel like if we never share how other people’s actions affect us, they never get the feedback they could use—if they choose to use it—that could make a difference in their life.

So in this case, I debated on whether to share how my initial reaction was to not want to be helpful to her in the future, but because I cared about her, I didn’t want to do that…which is why I chose to have the conversation. I also found myself imagining sharing my belief about how that sort of careless behavior leads others to care less.

Now…true confession. The teacher archetype in me struggles with the question of “What is appropriate sharing of one’s belief or observation when you believe it could be important to another person’s growth?”

So, in this case, I’m not her therapist or life coach. I am a friend. She didn’t hire me for my perspective and feedback. That being said, I find myself thinking about the line “Am I not my brother’s keeper?” and thinking “Are we not all on the journey together and isn’t it kind to offer a hand?”

When we don’t speak up, are we not like the people who avoid the person who has body odor and doesn’t realize it…and never say anything to that person because it feels so awkward? Is that doing that person any favors? Which is kinder, remaining silent to avoid awkwardness or giving them the opportunity to address something that is bringing them negative consequences?

I still wonder about what is crossing over the line between helpful, frank feedback, and perspective-sharing and presumptuous, unasked for coaching or worse yet… lecturing. For the upcoming conversation, I wasn’t sure if I would go there or not.

Face to Face

When she arrived, I asked her how she was doing and she said that she was feeling “fragile.” For me, that was my cue to not pursue any further discussion about the letter. It would have felt self-indulgent and insensitive to engage her in a conversation that could easily result in her feeling exposed and even more vulnerable. In her already vulnerable state, the likely result would simply be her feeling shame—i.e. inherently flawed with that flawed nature on display.

So, I didn’t delve into it more deeply with her. I decided that I had made my point. She shared where she was coming from and that would be enough. I would take this as my cue that the Universe had not signed me up to give her this “valuable” feedback and that the lesson of the day was for me to listen to my intuition when to keep quiet and not try to be “helpful”.


I am thankful I made the choice to have the courageous conversation, rather than to engage in the unproductive, alternative responses that I would have chosen years ago and that still emerges as an automatic response today.

This is just one example of why I am a believer in having the difficult conversations, especially with people who are important to you. When we don’t have the honest conversation, but instead withdraw a part of ourselves from the other, we both suffer.

When we are willing to face our fear that the conversation will be excruciatingly uncomfortable, and the relationship might be damaged irreparably, we open the door for tremendous growth.

When we are willing to have the conversation, we open the door to growth, for us, for them, and for the relationship. That’s why, despite my reluctance, I continue to have the courageous conversation.


Ironically, as I was writing this article, something new came up with me and this friend. I thought I was getting the feeling that she did not have interest in cultivating our friendship given some of the responses or non-responses I had gotten from her. I felt reluctant to bring this up, but thought “You’ve got to be kidding… how can you write this article about how being willing to be vulnerable and have the conversation helps a relationship grow and use this relationship as an example… and then not have the conversation with her!”

So we talked today. She thanked me for being willing to bring it up. I learned that that the message I thought I was receiving was not accurate, that she in fact very much enjoys our friendship. Also, from our conversation and previous conversations where she’s shared about how depleted emotionally she feels from her very “human interaction-intensive” work, it became clearer to me that we have different ways of being in friendship.

I asked her a few questions about what works for her in a friendship and got some clarity around that. As we closed, she thanked me for being willing to bring up the issue and commented on how when we do that, it brings a relationship to a deeper level. Yes it does.

DAVID LEE is the founder of,, and He is a consultant, speaker, communications coach, and performance facilitator. Much of his work focuses on helping people communicate in ways the bring them the results they want, whether those results are in business or their personal life. For more of his work on how to engage people in constructive conversations, check out the article section of

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