EP 59: The Transformational Power of Conversational Leadership with Daniel Stillman

Uncategorized Aug 19, 2022


How you talk to yourself often reflects how you lead and how you talk with others. 

The harshness of your inner conversations seeps through into your conversations with others.  The vice grip of judgment, resentment, and out of aligned expectations you’re holding combined with the burdens from difficult life experiences make it loud between the ears. 

We navigate our internal conversations while simultaneously engaging in conversations with others. It gets messy and the inner conversations eventually spill out to our external conversations. 

But our inner conversations of doubt, shame, and judgment are not a moral failure but a reflection of our past pain plus the world we live in and the thousands of messages we get everyday focused on questioning our health and our worth. 

The message that we are the problem when we are struggling with how we talk to ourselves leaves out the responsibility of our history, our current culture that conflates beauty, power, and confidence in a way that fosters more hubris and masking. 

We need to learn to befriend the parts of ourselves that are hyper critical and judgmental instead of exiling them or power-over them. 

My guest today specializes in conversational leadership. The tools and practices he offers help us design conversations that matter.

Daniel Stillman designs conversations for a living and insists that you do, too. He's an executive coach for leaders who want to facilitate real change. He's also the host of The Conversation Factory podcast and author of Good Talk, a handbook for changemakers and innovators.



Listen to the full episode to hear:

  • How creating the conditions for a transformational conversation opens the door to possibilities and new understanding
  • How paying attention to space, place, and time sets the stage for transformational conversations
  • How your internal conversations directly impact your ability to communicate with others
  • Why conversational leaders need to focus on intrinsically motivating others
  • The elements of a “conversation operating system” 

Learn more about Daniel Stillman:

Learn more about Rebecca:


 Scroll Down for The Full Episode Transcript:

Daniel Stillman: And most people don't realize, mostly, that they're negotiating against themselves. Before we even go into a conversion we’re like, “I don't deserve this. I’m no good.” So I think the conversation that I struggle with the most, Rebecca, (and that I think that all of us do) is my inner dialogue. It is rough in there. We address ourselves in ways that we would never address anybody that we know, like, and respect.

[Inspirational Intro Music]

Rebecca Ching: How you talk to yourself often reflects how you lead and how you talk with others. Now, I usually get a lot of pushback when I share this with folks I work with and know. So many people are well aware of their propensity for harsh conversations with themselves, and they go to great lengths to make sure they treat and care for others well, regardless of how they talk to themselves, but in practice, the harshness of your inner conversations seep through into your conversations with others because of the amount of judgment, resentment, and simply just being out of alignment with expectations your holding. This may look like faking a smile when, really, seething inside or staying silent, instead of speaking your truth (for fear of losing control) or the pressure or rush to a decision instead of listening and slowing down. 

We navigate our internal conversations while simultaneously engaging in conversations with others. It gets messy, and the inner conversations eventually spill out to our external conversations. Now, we don't need a three-step plan to cure our fear, instead, we need to learn to befriend these parts of ourselves that are hyper-critical and judgmental instead of exiling them or power-overing them.

I'm Rebecca Ching, and you're listening to The Unburdened Leader, the show that goes deep with leaders whose burdens have inspired their life's work.  Our goal is to learn how they’ve addressed these burdens, how they continue to rise from them and become better and more impactful leaders of themselves and others.


The most challenging conversion you’re having right now is probably with yourself. My conversions with myself, for most of my life, have been, well, subpar at best. I grew up on the slogans from Madison Avenue, “Just do it,” and, “No pain, no gain,” basically believing that I just needed to push through my pain, and if I can’t overcome it, then that failure is a reflection on me. These internal conversations that were hard on myself felt normal. Now, when I connected with others, I found out that they had the same toxic conversations within themselves too, but my common humanity with others who were also having harsh internal conversations helped a little, but I also started to see just how messed up the vice grip of the stories I told myself, combined with the pressure on how I should show up continually, leaving me at war with myself. Enter personal development and self-help that offered promised, logical steps to understand and re-author the conversations with myself.

Now, there are some phenomenal resources out there, some of which I use and recommend on repeat. Shoot, I’m even a part of the industry, so I do believe in it, but, over the years, I continue to see a trend from a good percentage of those in the personal and professional development spaces pressuring you to quickly fix your inner struggles and how it became a moniker of success and respect (even personal responsibility) on whether you achieved this relief or not. I remember when mental health moved to HMOs.


I was fresh out of college, navigating adulting and the echoes from my childhood showing up hard and fast, and I researched my healthcare benefits and found out my insurance covered eight mental health sessions. Eight sessions, yikes! [Laughs] Did they not know my family of origin and the impact of growing up in a John Hughes, MTV, Nuclear War, existential threat of a 1980s world? Did the insurance company really believe eight sessions would cover all I was navigating? [Chuckles] Well, yes. Post-modern theories like solution-focused therapy and strategic therapy approaches believe powerful change can happen in a short amount of time, and these approaches became a fan-favorite of insurance companies.

Having studied these theories and used them early in my clinical career, I saw the initial changes in those I worked with, along with some of the promising research around their efficacy, but often, the changes were not sustaining which led to a phenomenon I still see today - my clients turning on themselves for not feeling fixed quickly and, therefore, further amplifying the toxic, internal conversations they're having. These approaches never really change the conversing within their inner system but, instead, mask it with helpful tools and practices. These approaches also neglected to take into account the many burdens we hold, both from our story and the world we live in. They are very present-oriented approaches that are not as interested in the past. 

Now, over the years, I saw how these brief therapy approaches to real pain were co-opted by others in both the personal and professional spaces. Some of these were combined with individuals’ personal experiences of healing with the hopes to scale their healing journey to others, and many of the quick fixes offered from the personal development industry began to clash with my two decades of experience working with those who carry the burdens of trauma, shame, and crippling self-doubt.


Change and repair take time and happen through relationship within our inner system and with those around us. Quick fixes and hacks are band-aids that do not stick forever, and I see on repeat how those marketing solutions to our pain have been and continue to be problematic. These messages play on our pain points and scarcity with three-step plans to change your life, to kill the fear, to conquer your doubt, to overcome your overwhelm - sound familiar? Let’s take a look at these words: kill, conquer, overcome. Oof, we all see these promises delivered in ways that teach us to lead ourselves and others in ways that perpetuate power-over and exiling the very parts of us that need connection and compassion.

I’ll be honest, I feel like I’m still sorting through what it means to communicate solutions to pain without doing harm or adding to the burdens people are carrying, and when it comes to the conversations we engage with ourselves, I know many of us would qualify for a restraining order from parts of us due to the violence of how we talk to ourselves. I now see how our inner conversations of doubt, shame, judgment are not a moral failure but a reflection of the world we live in and the thousands of messages we get every day focused on having us question our health and our worth. Add to that our own personal burdens we carry from our traumas and difficult life experiences, and it makes sense the conversations within can get rough, and they're not quick to resolve but so worth healing. 


Our capacity to sit with and witness the discomfort of others is in direct proportion to our relationship with our own struggles.

Now, Dr. Frank Anderson (a previous Unburdened Leader guest) teaches that the highly critical and judgmental parts of our internal system are directly connected to our experiences of betrayal and neglect, but the message that we are the problem when we’re struggling with how we talk to ourselves leaves out the responsibility of our history, our current culture that conflates beauty, power, and confidence in a way that fosters more hubris and masking. Many of us end up solely blaming ourselves for our negative self-talk and, in turn, end up doing the same to others who show up struggling with similar struggles, often, wrapped in people-pleasing and over-functioning. I see and experience the relentless messages that pressure us all to be fixed and that our struggles are solely our fault. 

These days, my internal conversations are a lot better, but it still takes a lot of work to navigate, with compassion, the parts of me that love to pile on when I make a mistake or feel vulnerable or misunderstood. When we exile our inner critics and self-doubt, we only add to the shame. Befriending these parts of us is the path to healing and relief, and that happens with practice in relationship over time. Instead of exiling them, I see the power of developing a relationship with the parts of us that always chomp at the bit to remind us that we’re not enough, and as I deepen my compassion towards myself, I see that grow exponentially in my capacity to offer that in my conversations with others.


Now, My guest today specializes in conversational leadership. The tools and practices he offers help us design conversations that matter. Daniel Stillman is the author of Good Talk: How to Design Conversations That Matter. He’s also an executive coach for leaders who want to facilitate real change, and he’s the host of The Conversation Factory podcast. Now, listen for how Daniel explains what he believes are the key ingredients to a transformational conversation, notice when he describes the steps to create the space for these transformational conversations, and, gosh, please pay attention to how Daniel connects the conversations we have with ourselves with the conversations we have with others. Now, please welcome Daniel Stillman to The Unburdened Leader podcast.

Daniel, welcome. 

Daniel Stillman: Hey, friends!

Rebecca Ching: [Laughs]

Daniel Stillman: Rebecca, thanks for having me.

Rebecca Ching: I want to start by noting this belief that you have that leadership is the art of transformative conversations. I love that. when I read that it really stood out to me, and I’d love to hear more how you define a conversation. 

Daniel Stillman: So, I would say, you can create the conditions for a transformative conversation, right? You can design the conditions. You could open the door, but somebody has to walk through it, and so, I think it really is a very, very powerful skill to create the conditions for a transformative conversation, but I don’t think you can have [Laughs] -- you can't make clean water, and so, I think that’s what we can really do is make a real invitation to a real, equal interaction that can be really transformative. I think maybe that’s the way I think about it a little bit differently. 


We can’t make anybody do anything. We’re all just free, independent human beings, and we get the best out of people by inviting it from them. [Laughs]

Rebecca Ching: You know, you’ve got me thinking because I think if we’re trying to get people to do things, we’re missing it, but it’s really a YOU-turn (the Y-O-U turn) of what am I offering? Am I offering something that’s gonna repel or am I really offering something that will draw people in genuinely. 

So I’d love for you to go a little deeper or even more granular of what is a transformative conversation? What does that mean? That’s a big word, right?

Daniel Stillman: Yeah, I mean, we’ve all been stuck, right? And so, that’s what I mean. A good conversation delivers what we expect, and there’s nothing wrong with having a good conversation like, “Hey, good talk, everybody. That was a good meeting. We got what we needed out of it.” That’s great, but what I think we need more and more is something better than we can imagine, right? That’s really stepping into a place in a space with someone expecting to or hoping to be surprised and to create the conditions for transformation because we see gridlock in The United States government. We see gridlock in our board rooms. Certainly, there’s plenty of gridlock in our personal lives from time to time, not constantly and consistently, I hope, but that’s what I mean by together. That, to me, is what a great conversation is. A truly transformational conversation is when one or more people steps into the circle and they're willing to really lean into what the possibilities are. It’s not about trying to win over someone to defeat them or to convince them. It’s exploration. I think that every time I’ve done that myself, every time I’ve seen someone willing to do that, I think that’s a really great conversation, right, where all of us leave with more than we came in with, especially with surprise and energy.


Rebecca Ching: And that’s really powerful because, again, it’s not about being right or winning, and I hear you, and I’m like, “Yeah, I want an invitation!”

Daniel Stillman: [Laughs] Yeah. 

Rebecca Ching: I want an invitation, and let’s explore possibility, but there’s parts of me (and I know a lot of those that I work with) that are like, “No, bullshit! I want results. I want end game. I want bottom line.”

Daniel Stillman: Totally. Sure. 

Rebecca Ching: And so, there are these interesting polarities and, at least here in US culture, where this let’s have possibility, that’s not efficient. You need more space, you need more time, or you say no.

Daniel Stillman: That is true. Oh, totally. What’s efficient about life?

Rebecca Ching: [Laughs]

Daniel Stillman: My god. I would say -- ‘cause this is something -- and I’ve coached teams on innovation programs for years, and there’s this question of, like, “Okay, we want to streamline this. We want to do it efficiently.” You don't just put an apple seed in the ground and then get an apple tree, right? These things take time, and so, if you want great fruit, you need to grow great roots, and that stuff takes time. You have to invest in it. I don't think it’s revolutionary to say that being curious about what the other person wants and needs is going to bear fruit in a one-on-one dialogue or a multi-person conversation. We know force doesn't really work. It’s a very short-term solution to try and squeeze someone to get what we want.

My first degree was in physics, and my minor was the history of philosophy in science ‘cause I was a big nerd, and there’s this book. You’ve probably heard the term “paradigm shift.” The guy who coined that term was a guy named Tom Kuhn who wrote a book called The Structure of Scientific Revolutions.


It’s kind of a heady book, but it’s really, really interesting to see how the world changed its mind about some really big, important questions like what is space, what is time, are there elements or are there not, what is fire. So there are fundamentally different ways of looking at the universe happen, and if you're getting everything you need out of your meetings and your conversations and your negotiations and whatever, great. Hooray. I want to read your book, right, but if you're hitting a wall, if you're not getting the results you want, then the question is, well, okay, maybe slow down, maybe listen more, maybe try all the things that take a little bit more time. I don't think this is for every meeting and for every conversation. There’s nothing wrong with sitting next to somebody on a bus and being like, “Oh, what are you doing these days? Okay, cool. Great, great. Nice weather,” right? Every conversation doesn't have to be like that, but I think some conversations call for a lot more intentionality, slowing down, really feeling the substance of the thing, and putting more time and energy into it so that we can get more impactful results. 

Rebecca Ching: Yeah, and I would say the folks that are hitting that well, it’s not about maybe not being smart, per se, it’s just we don't know any different. What we’ve been taught on how to connect and how to communicate really is two-dimensional (maybe even one-dimensional), and it’s getting us in a lot of trouble. So I’d love you to bring it back down to basics again.

Daniel Stillman: Sure.

Rebecca Ching: What are the main qualities required of a conversational leader?

Daniel Stillman: Well, The Conversation Operating System in my book was my effort to try and ask what is designable? I come from the industrial design world where it’s like we have materials, and we’re gonna shape them and steel doesn't act like wood, and you can’t make plastic do what leather does, right?


There’s a materiality to it. And so, when I run workshops on conversation design, I say, “Well, what do you think conversations are made out of?” So that’s the first thing I think a conversational leader needs to have is, like, what’s my material, right? Am I sensitive to my material? What do I think I can do? What can I change in this conversation? Now, people will make a big list of what they think a conversation is made out of - vibes, emotions, words, positions, ideas. I say, “Great, these are all really cool things. Which of these can we actually see and shift? Like, if it was a knob, could we turn it?” I think emotions are one of those things that I don't know what the knob is on emotions, right? I don't know how to change how I feel. I certainly don't know how to change how somebody else feels. So we’re left with words which is a very broad category.

So I think the conversational leader needs to see these subtle distinctions. The element of The Conversation Operating System that I think are probably highest leverage are invitation, right? Just understanding what it means to design an invitation that is truly inviting to someone else. Understanding the role, the space, and place that a conversation is in, how that affects the conversation. Inviting someone to the beach for a chat versus a sterile room or going for a walk verses being on the phone - chatting, texting.

Rebecca Ching: Where is the place for a negotiation?

Daniel Stillman: It totally depends!

Rebecca Ching: Tell me more. 

Daniel Stillman: What kind of time and space does it need, right? A quick call? Does it need, like, an hour? I had somebody recently who sent me a 15-minute Calendly link, and I’m like, “I don’t do 15-minute meetings.” I don't expect that we can come to any interesting conclusions in a 15-minute meeting. Now, maybe I would ask for a 15-minute meeting if somebody who I really wanted to talk to said no to an hour and said no to 30 minutes.


I’d say, “Okay, cool, well, can we start with a five-minute meeting?” Sure, right? Space, place, and time. Like, does the space and place and time say what we want it to say about the conversation that we want to have, right?

Rebecca Ching: Space, place, and time, and do those things set us up for the conversation we want to have? I love that foundation.

Daniel Stillman: Yep.

Rebecca Ching: I love that.

Daniel Stillman: Yeah.

Rebecca Ching: Okay, this probably goes without saying, but I’m gonna say it. Conversions feel more challenging these days where a lot of people feel less interested in common ground and more interested in persuasion or, worse, even bullying and dehumanizing. So I’d love for you to, maybe, share from personal experience of a time when you struggled with having a conversation and how you were feeling in the moment, and what did you do to work through it?

Daniel Stillman: When I started writing my book, I was starting with this idea that group conversations is what I really knew and cared about, right, ‘cause groups of people make decisions about what gets made and what gets put out into the world, and then I realized there’s this whole spectrum of conversations, right? There’s communities and there’s culture and there’s organizations - those are big conversations. Then, there’s, what most people would think of as conversations which is a one-on-one conversation. I think the hardest conversation (and the one that I did not really, really think about at all at the start of writing my book) is the conversation with yourself -- with myself, right?

Rebecca Ching: Mm.

Daniel Stillman: And so, one of the things that I learned at the Harvard Negotiation Institute is that when you go into a negotiation, there’s this idea that they call your aspiration value (what you aspire to, what you are willing to ask for), and that’s the first conversation, and most people don't realize, mostly, that they're negotiating against themselves before we even go into a conversation. We’re like, “I don't deserve this. I’m no good. I’m, essentially, an unlovable pile of person,” to put it how they might put it.


So I think the conversation that I struggle with the most, Rebecca, and that I think all of us do is my inner dialogue. It is rough in there, and I think I -- yeah, just breathe that in, everybody. Rebecca and I can feel it, and I feel it in my chest, right? We address ourselves in ways that we would never address anybody that we know, like, and respect. 

Rebecca Ching: It just has me thinking. It’s, like, the physics -- ‘cause in my clinical psychotherapy training, it’s The Systems approach that I was trained in, we’re trying to differentiate between content and process, right -- the content but the process and the inner process, right? How can I -- I’m just thinking about what you're saying with the time and the place and what I want from that. How can I even set that up externally if my internal dialogue, if my internal conversations with myself are for shit? And so, if I’m turning on myself or not owning my worthiness, that type of stuff, or have capacity for that discomfort, it’s gonna -- entering into an external conversation, I feel like, is already -- not that it’s necessarily set up for failure, but it’s gonna be a lot harder.

Daniel Stillman: Totally. Totally. So, a personal example: last week, I was supposed to have therapy, and my therapist, we miscommunicated. He was on vacation, and so, I was just sitting on my couch being like, “Well, fuck.” [Laughs] I’d had my journal with me anyway, and I was like, “Well, I’ve got this time anyway, so either I can go clean out my inbox or just sit with myself. 

Now, we talked about some conversations taking a little bit more time and space, and our willingness, like, are we willing to put that time and energy into those conversations, we are bad (and I include myself in the “we”) with slowing down, right?


Rebecca Ching: Mm-hmm.

Daniel Stillman: Our senses generally go outwards, right? Interoception and knowing what we are thinking and feeling and sensing is harder to sit with especially with negative emotions. Although, also positive emotions, myself, was as effective as using an actual therapist. It was what was available to me, and that was me having a conversation with myself, and I think that a pretty hard conversation to have. 

Rebecca Ching: Well, I think it’s really effective because what you did there was help your nervous system kind of -- you did reps. Kind of doing, again, what we call in the Internal Family Systems world, the YOU-turn, and, again, we say slower is faster. That’s one of our mantras in that space.

Daniel Stillman: Yeah. 

Rebecca Ching: And so, you did the YOU-turn. You checked in. Was it effective or felt like there was as much flow as with someone else there? Maybe not, but you did the reps and you helped your nervous system build up more capacity to sit with that discomfort, and you didn't go numb or comfort with work. You sat with the conversation that was coming up internally.

And so, I keep thinking about transformational conversations, and with what you're sharing about your -- and I think this is for all of us (at least most of us) that the most difficult conversation is with ourselves, often. How do you see those two connected, ‘cause I’m starting to -- and this is probably obvious, but to have a transformational conversation or create space for that externally means that I have to be doing that internally to really hold space for that. That’s not gonna be possible unless my, you know, conversation with myself and my inner system, I’m able to hold that space.

Daniel Stillman: Correct, yeah.

Rebecca Ching: Yeah, I’d love for you to elaborate on that.

Daniel Stillman: So this is why I think the ability of conversational leaders to have that conversation with themselves, to have that ability to self-regulate and ask, “Well, what do I really want?” 


Rebecca Ching: Or what do I believe, even, too, right?

Daniel Stillman: Yeah, what do I really believe? I had a coach years ago. I was in a business partnership that was really, really struggling, and I would come to our breakfasts, and I would just complain and rail, “What I deserve -- they're jerks,” you know, listing the slings and arrows of outrageous fortune that I was dealing with. He was like, “Well, what do you really want?” I was like, “Well, what do you mean?” He’s like, “Well, do you want to work through this with it or do you want to win?”

Rebecca Ching: [Laughs]

Daniel Stillman: “Or do you want to walk away?”

Rebecca Ching: All of the above? [Laughs]

Daniel Stillman: All of the above, right? And so, this is the thing. This is why I think the internal conversation is the most important one because if what I really wanted was to grind them into the pulp and stand on a pile of their bodies -- that we have, we visualize the kind of victory we want. I worked with a school leader. There’s a program called The Better Arguments Project, and you can look this up. They have a wonderful website, and they do all sorts of school programs. The first rule of The Better Arguments Project is to take winning off the table.

Rebecca Ching: Oh! Stop it. Daniel, No!

Daniel Stillman: Yeah.

Rebecca Ching: Just stop it!

Daniel Stillman: It’s not on the table. It’s not about winning, right? 

Rebecca Ching: So what is it about? The relationship?

Daniel Stillman: Yeah, I don't know.

Rebecca Ching: The relationship, yes?

Daniel Stillman: Yeah, well, it’s about understanding and empathy.

Rebecca Ching: Ugh, yes.

Daniel Stillman: Well, so that’s the thing, and so, maybe it’s about the relationship.

Rebecca Ching: Mm.

Daniel Stillman: Again, the Harvard Negotiation Institute, I learned a lot at. I highly recommend as one of the nerdiest, most fun, week-long work vacations at Harvard. One of the things they talk about is, like, this concept of the BATNA, and this is all in Getting To Yes. You can read this. It’s a great book. What’s your BATNA? What’s your best alternative to a negotiated agreement? Like, well, what if you walk? What if you win? You can't force someone else. This is the thing. This is why invitation is so core to the Conversation Operating System is that you cannot force anyone to do anything long-term and get the best out of them.


That is something I think conversational leaders know at their core. That’s why coaching, conversation, empowerment, and understanding what is intrinsically motivating to others is the best way to get the best out of other people. Trying to squeeze it out of other people works about as well as trying to squeeze things out of ourselves.

Rebecca Ching: And I’m just thinking about just the news cycle, how we communicate in shorter blips right now, too, and we’re really hurting, and we’re diminishing the opportunity for transformational conversations if we don't step out of this pull that’s almost like a current pulling us to what’s expedient and what’s gonna get the hits, the likes, the clicks, the reaction, the outrage, you name it.

Okay, I want to shift to your book. You break down the elements needed to design a good conversation. You've touched on this a little bit already. Each of these elements offers a way of looking at a conversation. What you referenced already is, “An operating system for good conversations.” I love this. So can you just, do very high level, what are the elements of an operating system for a good conversation?

Daniel Stillman: Well, keep in mind, this is my Conversation Operating System. [Laughs] I wrote this book, and I spent maybe two, two-and-a-half years on my podcast interviewing people and trying to get a sense of what I thought were the smallest number of actually addressable elements, and I’ve been teaching with this operating system for a while. Some people have a hard time with some of them, right? Some people can't see invitation the way I can see invitation. I see invitation the way Neo sees the code in The Matrix now, right, ‘cause I’ve taken that red pill, and that’s the code I see in my operating system.


Rebecca Ching: You can't unsee it. You can’t unsee it.

Daniel Stillman: I can't unsee it, and so, I would just say for everyone, if you are stuck in a conversation, you need to make a decision for yourself. List out everything you think you have control over, everything you think you can change, right? I would invite everyone to do that who’s listening to this. If you have a stuck conversation, what is available? What can you unstick? Invitation is one of those things, right? You can change the invitation and try and make it more intrinsically motivating for the other person. The interface of the conversation is happening. Every conversation happens in a place, right? It can be a digital place. Here we are. Rebecca and I are in this digital place here. There’s lots of ways to send the message and to have and host the conversation. The space says something. The place says something about the conversation. The place and space allow certain types of things that other places don't. The place, the interface, has something to say. It is not neutral. It has something to say about it and it affects the conversation. Just those two is a lot. I think there’s a whole life in just invitation and interface, but we also have goals like what are the goals of the conversation? What are we gonna agree to as part of? What are the rules and restrictions of the conversation, right? Turn-taking - I think this was the easiest thing I realized. Certainly, in my mens’ groups realizing, like, oh, we’re all gonna go around the circle once to say something about something, and are we gonna go, “It sucks being last in that circle”?


So that’s a way to design the turn-taking structures of a group. Are we gonna have popcorn where everyone just shares when they want to share but you only pop once? Are we gonna have a round robin where everyone goes around once? Do we have a talking stick? Do we pass the mic? These are just very, very basic things, but they can really shift the conversation if for no other reason than whoever speaks first really sets the tone, anchors the entire conversation, right? Turn-taking is just maybe the most noticeable feature of conversations. I talk. You talk. Someone else talks. We all talk. 

A talking stick - that is a design for turn-taking, right? And so, just being aware of that. Something else to be aware of is cadence (the tempo of the conversation). That can be inside of a conversation. Like you said, political conversations, they get hot. There’s no conversation thermometer that I’ve ever seen, but we all have one, right? We all know is this conversation getting hot? Is it getting cool? And that’s okay. It’s okay to cool down a conversation. It’s okay to get it heated up. Some of us, in our operating system, like it hot (that’s the bar), right? Some people only want it hot and fast and other people just only like it slow and steady.

And so, what I say with conversational leadership is it’s about range. Can you step into the ring and can you go at the pace it needs to? Can you slow it down when it needs to? Having that sensitivity to the cadence of and inside of a conversation, I think, is something that you can control once you can name it. The people in the conversation, right? Who do we invite into the room? Are the right people in the room? I don't think I’ve ever had a high-level meeting, ever, where everyone said that everyone who should be in the room was, and so, who’s not in this room, and how do we get them in this room? In user experience design where I cut my teeth, we did that through personas and user research, and we would put that on the wall, and everyone would be like, “So these people are part of this process. They're in this conversation, but they are not here in this room.” I think people is one of the biggest issues.


There’s a team I’m coaching right now, and it’s like they are just in one of these cultures where everybody is supposed to be at every meeting. How is that possible, Rebecca? Like, how can you have a culture where everyone feels like they are supposed to be in every meeting and still get work done.

Rebecca Ching: Ugh.

Daniel Stillman: And who’s supposed to make the decisions if everybody’s in every meeting, and everyone has FOMO, and you're like, “Oh, you're optional, but you should totally listen in if you can.” It’s a conversation like, “Well, why should I go if I don't feel I have anything to contribute,” right? Do I have the power to say no to an invitation?

Rebecca Ching: Oof. 

Daniel Stillman: So power is another element of conversation. We have power-over and power-with and power-for other people. Some people just don't understand that power effects, morphs, molds, mushes, deforms conversational spaces. I’ve definitely talked to leaders who just don't understand the fact that people need a lot more help from them to say what they really think around them. Them being there, there’s this idea like, “Oh, I can't really say what I’m supposed to say ‘cause they’re there. Do they really want to know what I think? They have more power than me so I’m gonna say what I think they think they want to hear.”

Rebecca Ching: What I’m supposed to say.

Daniel Stillman: Yeah, what I’m supposed to say. 

Rebecca Ching: So you just said, too -- do you work with leaders who don't understand why those around them, those in leadership, have a hard time understanding why those don't say or are you talking about those who, in the presence of power, have a hard time speaking truth?

Daniel Stillman: I’ve had both types of conversations, for sure. I think both are important. For somebody to say, “Speak truth to power,” and, power, who needs to make a safe space for everyone to speak truth. 

Rebecca Ching: Yeah, ‘cause I think it’s definitely someone who has power however that shows up. Depending on their social location, it’s really important to be aware of that even if they don't feel it, [Laughs] it’s felt by others. 

Daniel Stillman: Yeah.

Rebecca Ching: The cadence piece is sticking with me, but I want to make sure, did you get all of the elements?


Daniel Stillman: There are two more. Threading, this is something that came up in Conversational Theory. Conversations have threads, and we’ve lost the thread, and we pick up the thread. The thread is just the story of what is happening in a conversation -- what happened. Narrative is the ability to weave a conversation deftly both before, during, and after a dialogue is just absolutely critical. I think, of all the conversational leadership skills, narrative-framing is, maybe, one of the most impactful. The ability to help people see the arc of the whole story, the whole conversation. We’re here. We’re gonna be here, and we’re gonna get there, but we’re here right now so come along with me for phase one,” and people go, [Breath in and out] “Oh, thank you. Great, I am oriented in this incredibly disorienting time that is 2022.”

The last element is error, right? Mistakes happen in conversations all the time. The easiest one to see is always when we speak at the same time. We did this once where we spoke at the same time. We literally collided in mid-air, and you go, “Oh, no, no. Oh, no, no. You, you, you, you. Oh, okay. Sure,” and then someone yields a turn, right? Most often, errors are poorly defined and highly reacted to. “Ooh, what did you just say?! What did you mean?” We already have jumped four steps down of what they actually meant, right? We don't say, “So, what I heard you say was this, and I’m a little uncomfortable saying this, but it felt like you were implying this, and I just wanted to check in with you and make sure. Is this what you actually meant?” and actually self-regulating and giving the other person the opportunity to be like, “Oh, wow, no, no, no, no. I did not mean that at all. I ‘m terribly sorry. Please, can we go back to step one and start over and actually go forward with it?” That is a huge conversational skill.


Rebecca Ching: Mm, I think that’s epic because I think that’s one of the conversations that I’m hearing from the leaders I work with those most is the fear of that error, the fear of being misunderstood, the fear of doing harm even their intent and impact are different, and they feel overwhelmed when they realize their intent was so different than the impact, and so, if we normalize those errors and not normalize doing harm, then we have to just say, “We’re gonna mess up. How do we want to show up when we mess up 'cause this is not about perfection?”

Daniel Stillman: Yeah.

Rebecca Ching: If we come from a place of perfection is more what I’m talking about. Not to say, “Oh, F it. Whatever. It was what it was.” That’s not what I mean, but to really just say, “Okay, here’s my humanity. This did not land the way I meant or I didn't respond. I didn't hear this correctly. I think that’s the art is, like, whoa, this is how that landed with me. This feels a little awkward and vulnerable and tender to say, but I just want to pause and a lot of people just suck it up and kind of nod their head and don't speak to how something impacted them.

Daniel Stillman: Yeah, so this is, like, are we going to design the conditions for transformative conversation about a screw up, right? Are we gonna actually go all the way into it and say, “This hurt me”? Are we gonna go all the way into this and say, “That crossed a boundary for me”? Are we gonna go all the way down and say, “I really don't want that to happen again”? If you were to Google or go on Twitter and listen to a person of color talk about how they handle microaggressions, you would have a really, really interesting picture of a ladder of escalation of error and repair management. Well, you know, the first time, I kind of just let it go. The second time, I might actually email them afterwards, right? The third time, I mean, that’s a lot of work, and this is one of the challenges with conversational leadership is that when you're doing it from the middle up, it looks a lot like emotional labor which it is.


Rebecca Ching: It is. It is, yeah. 

Daniel Stillman: It’s 100% work. There was a Twitter thread this morning about the linguistic -- I’ll say this. Women are seven to eleven times more likely to be described as bossy or over-ambitious in their performance reviews.

Rebecca Ching: Mm-hmm.

Daniel Stillman: And so, I’m actually coaching a woman who is dealing with this. She’s getting negative feedback from her leaders about her brusk-ness or her know-it-all-y attitude. She’s really smart. I’m like, well, okay, we don't know. I haven't met your boss. [Laughs]

Rebecca Ching: Okay, can we pause here? I’m having -- I hear you.

Daniel Stillman: Are you having a reaction to this example?

Rebecca Ching: I am because I’m like if it looks like a duck, if it sounds like a duck, it’s a dang duck. I don't have to know this client of yours or her bosses to know that it’s highly likely that that is at play here. I mean, that’s my generous assumption.

Daniel Stillman: Yes, totally, but is it useful to lead with that in the conversation?

Rebecca Ching: Ah, I think this is a conundrum for me. In this culture and day and age I understand that if I want change, I know that I don't want to shut down those who are in power, especially those in positions of power over me or with those I work with, but I also have parts of me that are really curious about walking sound something and saying, “Hey, I just want you to know this is how it lands and this is my experience and this is in the room.” Not you're sexist but sexism is here.

Daniel Stillman: Totally. 

Rebecca Ching: I think that nuance is important, but there’s parts of me, Daniel, that are just tired of walking around it, but we can throw names and identities and labels at people and everyone just shuts down, and that doesn't go -- I get that, but with these issues, there’s almost a point of why do we have to walk around it? Ugh, it’s just tiring.


Daniel Stillman: People who talk about microaggressions talk about, well, so is it calling someone out or do you call someone in? Do you call someone in first before you call them out or do you just fuckin’ call them out?

Rebecca Ching: I agree. I agree.

Daniel Stillman: So this is what I hear, Rebecca. It’s a conversation that you get to design the conversations in your life.

Rebecca Ching: Ah.

Daniel Stillman: Now, a woman of color who is experiencing microaggressions --

Rebecca Ching: Yes. 

Daniel Stillman: I’m a Jewish man. I present as one. I am not here to tell anybody how to design their conversations. I’m here to tell them that they have a choice. There’s nothing wrong with coming in hot and saying, “I think you're fucking sexist.” Now, he can, then, do whatever he wants with that information, right? What’s her BATNA? Maybe she should do some job searching before she does that. If I was coaching her, I would say, “Look, if that’s what you want to do, I would say do it, but have your best alternative to negotiate an agreement.”

Rebecca Ching: I hear you.

Daniel Stillman: I don't think it’s actually a very welcoming conversation. Nobody likes being told that they're sexist or racist, so she has to design that conversation. She’s got to. 

Rebecca Ching: Yeah, I just would like for folks to be able to name what’s in the room. Maybe we don't have to say “you are” but this is showing up in this exchange, and I need to name it, and that’s different than saying “you are.” I get that.

Daniel Stillman: Yeah, so I think, again, we’re talking about it’s better to notice and name our own experience and our own feelings than it is to try and push it. 

Rebecca Ching: Yeah.

Daniel Stillman: Now, here’s what we’re normally doing in a conversation. Conversations have direction, right? I’m gonna push blame onto you, you’ll try and push blame onto me, and we’re gonna push and pull back and forth, and then we’re in a struggle.


This is a classic -- if we look at that dynamic, then the question is, well, how do we get on the same side and look at it together, right?

Rebecca Ching: Yeah. 

Daniel Stillman: Not me versus you but us versus the challenge. That requires tons and tons of self-management, as we said earlier. There are a lot of approaches to these conversations, as you said. Like, “I’m not gonna tiptoe around this. I think your feedback is bullshit,” right? “You can't even give me any specifics. It’s just a general sense,” right? Okay, or I’m gonna call you in, and there’s a huge discussion about this on microaggressions and, again, I’m not authority on this of, like, calling people out versus calling people in. There is, like, zero tolerance on calling people out. The first time you see it say, “Tom, that’s racist.” I tried to, in my Care Bear heart, just focus on invitation, right? So that was, “We just don't say that anymore. I’m just assuming you didn't get the memo, and I don't want you to look bad in front of somebody else who would judge you,” and that’s just me in the moment trying to call someone out and call them in at the same time. 

Rebecca Ching: You’ve gotta name it. 

Daniel Stillman: I don't know if it was effective or not. 

Rebecca Ching: Well, yeah. 

Daniel Stillman: You have to name it.

Rebecca Ching: Yeah. 

Daniel Stillman: The question is what will be inviting for someone to want to continue to participate in a dialogue with you if that’s your interest. Now, here’s the thing. There is nothing wrong with -- as my old friend Carl used to say: let the bridges I burn light my way. Sometimes there’s no air there, and that’s what error and repair is all about. If you're like, look, if this person just does not get it when I tell them, “Hey, I don't know if you know this, but there’s this report, and there’s a better-than-even chance that this feedback is based on sexist norms in people’s heads, and I’d like that to be considered,” and to be able to say it that straight so that someone can really hear it, say it! 


There’s nothing wrong with it, but I think it comes from -- oh, boy, this is tough. I mean, the last thing I would want is being told -- I can't tell someone, “Well, you can’t say it like that 'cause they won't hear you.” 

Rebecca Ching: Hello. Yeah, I agree. 

Daniel Stillman: Yet, if I was coaching them, I would say, “What can you do so that they can come along with you in the conversation?” 

Rebecca Ching: And what do you want? What do you want? 

Daniel Stillman: And what do you really want?

Rebecca Ching: You know what I’m thinking, too -- and I want to move onto another question, but before I do, I just even think some of these call-ins and conversations, they require a structure that’s not hierarchical. How are we even setting up our conversations, setting up our teams and our workspaces, all of that? 

Daniel Stillman: Yes. 

Rebecca Ching: I‘ve been thinking a lot about that.

Daniel Stillman: Yeah, saving space, building a container. All these things are really important skills.

Rebecca Ching: It’s ground zero, and Glennon Doyle, I love how she talks about, “Stop building circles; we need to have more horseshoes,” you know, and the space to come in and out. It’s not also super rigid and super closed, too, even in that collaborative space.

So, yeah, no, I just feel that in my system ‘cause there are parts of me, but that’s the conversation. I had to kinda do my own YOU-turn as I’m hearing you talk going you're not -- you know, I was just feeling with this coaching client of yours. [Laughs] You know, at 50 years old. I mean, how many conversations of, “You're strong. You're ambitious. You're intense, and that’s in a bad way.” I hear that from so many people I work with too. 

Daniel Stillman: Because men haven't been trained to handle strong women, and that’s mens’ work. I think what’s liberating is to realize that we have choices, right? Calling out versus calling in is just a choice, right? Then, the question is which one will get you more of what you want in your life long term?

Rebecca Ching: Yeah. 

Daniel Stillman: That’s a question everyone has to answer for themselves. I can't answer that. That’s an internal dialogue thing.


Rebecca Ching: Yeah, and it’s a bigger conversation 'cause some people may feel like their choices are limited because they have to keep the job for their livelihood so there’s a lot here. There’s a lot here.

Daniel Stillman: Yes.

Rebecca Ching: So I want to shift to what brought me to inviting you to this podcast. You wrote an email, and I immediately replied. I was like, “Can you come on the podcast?” I don't know if it was in this email but somewhere in my research for this interview you said you believe how we talk is how we work and do life, and I was like, [Gasp] oh, my gosh, yes. You’ve been an advocate for those who identify as male to do their own work so they don't default into the common pitfalls of mansplaining or manspreading, right? So I’d love for you to walk me through how leaders and facilitators can use your elements of a good conversation to respond to these common power-over dynamics.

Daniel Stillman: I’ll take a big step back, first, and say, yes, men have to do their own work. I mean, just in the larger cultural conversation I think it’s kind of a trope that men don't have friends. SNL did a whole bit about it. There was, like, a man-playground that women could take their men to, and it’s funny 'cause it’s true and it’s sad.

Rebecca Ching: It’s so sad and funny, yeah. 

Daniel Stillman: Yeah, it’s sad and funny, and I get the sense that there’s a loneliness epidemic, period. Full stop. There’s research that showed -- I had Casper ter Kuile on my podcast. He wrote a book called The Power of Ritual, and he quoted some research that showed that, like, between the ‘80s and the 2000s, if you asked a random person in America, “How many people do you have who you can really talk to about what’s really going on in your life,” people would say, “Oh, you know, I have, like, two or three, or three or four people.” In the 2000s, people were like, “Yeah, I’ve got, like, one or two.” It’s like all of America lost one or two friends which is, like -- and that’s not even with the pandemic. Like, if that doesn't make you want to cry just to think about the whole country losing half of its best friends, that’s really sad.


Now, the question becomes women, or people who identify as women, have this characterization or stereotype that women talk to each other. You may have experienced this trope. I think it’s slightly true, right? There’s actually no evidence that shows that men or women talk more of an amount than one or another, but it does feel like the man box is real. The man box is like what you’d call traditional masculinity. It’s certainly in The United States of America. You just have to watch a Ford truck commercial or a cigarette ad, and so, yeah, there are ways that men are supposed to be: strong, certain, steady, powerful. There’s this sort of 1950s vision. I think when we’re talking about new modes of working and new modes of collaboration and new modes of leadership, they don't look like traditional patriarchal forms of leadership and relating. The father-knows-best approach doesn't really work anymore, and I think men are in a decades-, maybe even centuries-long transition.

On one hand, Rebecca, I think it’s sad. I think every decade or so masculinity is taken out, dusted off, and is deemed wanting in some way, shape, or form and needs to be revised or reimagined or fixed. I think what I’m saying is range. So there’s evidence that shows that women are punished (as we were just talking about) for taking on so-called masculine characteristics: being too certain about themselves.


Rebecca Ching: Confident. Imagine the -- 

Daniel Stillman: Right? The audacity.

Rebecca Ching: How dare you. 

Daniel Stillman: Right? So women use hedges and tags. “Well, you know, you might have thought of this spot,” or, “Well, you know, I’m not sure. This might be helpful. I hope to. I could. I might be able to.” There’s all these hedges and tags that women use in their speech to try and lessen the appearance of taking power. Power, as you may remember, is, I think, a very, very fundamental element in a conversation. That evidence that women are seven to eleven times more likely to be judged as being over-achieving -- but the flipside is also true. So if we think about what are, quote unquote, “female characteristics” like empathy and collaboration and listening and nurturing and warmth and compassion, if a man does that too much, he is a wuss. He’s a sissy. He’s weak, and I think those characterizations of the extreme are absurd.

We know that women can be strong and decisive and also compassionate, and we also know that men can be those things too, but I think men have a bit of a crisis of confidence. Like, we don't actually know how to navigate both sides of that spectrum. I think, largely, because we’re aware of how -- I think there’s a lot of white men out there who know, yeah, this is not my time. I’m supposed to step back. I need to be more this, and I can't be, then, decisive or firm or angry because, then, I’m gonna come across as a fill-in-the-blank, and so, it can be a lot of second-, or third-, or fifth-guessing, and actually saying, “Yeah, okay, I’m gonna be decisive about this but also warm and compassionate at the same time.”


I don't think I’m answering your question anymore, but I think what does it mean to be a good leader solves gender identity. Do I feel comfortable to just --

Rebecca Ching: Be.

Daniel Stillman: Be, right!

Rebecca Ching: And get out of the binary.

Daniel Stillman: To bring what I think is needed and to get out of the binary.

Rebecca Ching: Yeah. 

Daniel Stillman: But we are stuck in this binary. Stay in the man box. It doesn't really serve anybody at all. Men have [Deep breath] -- a lot of people say, “The patriarchy works for you.” I’m like, yes, and we go to war. We die sooner. We kill ourselves more often. It’s hard to say how much men are suffering in silence. I definitely work with several men who struggle with these issues.

Rebecca Ching: Sure.

Daniel Stillman: You need a place to work through experiencing the full range of their emotions and their identity and then asking themselves pretty much the same question a woman would ask, like, “How can I be in this situation to get what I want in a way that feels holistically myself and doesn't cost me too much, right? Knowing that I need to be a little different than I am to make things happen, how do I show up on purpose in a way that gets me what I want that is in harmony with who I feel I really am and can I extend my range? I mean, I think with a lot of men anger is either the default or forbidden, right?

Rebecca Ching: Right. 

Daniel Stillman: Actually having boundaries. Saying, “Look, guys, that’s not gonna work. That’s not gonna fly. I’m gonna be firm on that boundary. I’m just not gonna flop over on that.” So I think  men having their own space to do that work outside of a work context is really, really important so that they can come into the work context and actually just -- 

Rebecca Ching: I want to touch on that in a moment, but I think my takeaway is that quality of power is probably one of the most -- for facilitators to be really, really in tune to the power in the room, to address the pitfalls of mansplaining, manspreading, and those types of things. To address it, to name it, and to facilitate around it. We’re continuing to be in a reckoning.


So I’d love for you to share -- you talked about co-leading a mens’ group outside of work.

Daniel Stillman: Yeah.  

Rebecca Ching: I just would love for you to speak, personally, how this group has been transformative for you and how you show up in conversations with those whose gender identity is not male.

Daniel Stillman: That’s a great question. I think it’s like going to the gym, right? I would say about 80 to 90% of the time that’s mens’ group, and sitting with difficult emotions (either my own or someone else’s in the group) is a really powerful skill, right? I think it’s increased my ability to be in quote, unquote, “difficult conversations,” right? To be able to manage and to hold space for more complex, multi-threaded, emotionally-charged dialogues. 

Rebecca Ching: It’s increased your range. It’s increased your range.

Daniel Stillman: Certainly, it’s increased my range. Yeah, well, ‘cause, I mean, we’ve all been in that situation where if a parent loses their shit, it’s really scary when you're a kid, right?

Rebecca Ching: It sure is.

Daniel Stillman: And so, there’s this feeling that, like, oh, negative emotions are bad. It means that I’m gonna get in trouble. It means I might be outcast from the group, and so, for me, I mean, certainly, in my personal relationships, certainly, in my relationship with my wife, the ability to say, “Hey, that was a really difficult conversation. Can we circle back around to it, and can we actually play the tape step by step and look at what happened?” We have a process. There’s a process in mens’ group, right? 


If you've got an emotional charge with somebody, you say, “I’ve got a charge,” and we say, “All right, let’s circle up. What are your facts? What happened? Just the facts,” and then talk about your feelings. What are your needs? It’s non-violent communication at the core.

Rebecca Ching: It’s the space where you do your reps so that when you're out -- 

Daniel Stillman: Yeah, it’s the space where I do reps.

Rebecca Ching: Yeah.

Daniel Stillman: So the ability to say -- in those moments, when we feel like our boundaries have been crossed, as we said earlier, we can either shut down and clam up and feel like we can't say or do anything or we can say, “That didn't feel good. I’m wondering if we can circle back around to that.” I would call it my emotional metabolism - the ability to digest and process difficult emotions more rapidly.

Rebecca Ching: Yes!

Daniel Stillman: You know, instead of having to chew on them for weeks and months, it’s like I can process them literally, and I can process them by myself. I also have a place to process them, right? I have mens’ group. I have therapy. 

Rebecca Ching: Mm-hmm.

Daniel Stillman: I think having a space to process difficult emotions means that I can go out into the world and just meet it where it is instead of --  

Rebecca Ching: Reactive.

Daniel Stillman: -- bringing too much of my own baggage on a regular basis.

Rebecca Ching: I appreciate that, I really do. Thank you.

Daniel Stillman: I wish all men had one. I think we all -- I mean, everybody needs one.

Rebecca Ching: Yeah.

Daniel Stillman: But I think especially in this moment, I think men need to be not relying on the women in their lives to be their everythings - their nanny, their accountant, their lover, and their therapist. That’s a lot. That’s a lot to ask. 

Rebecca Ching: We are disrupting so much right now, but the bottom line is, though, we have to be doing the work and having that inner conversation (the hardest one to have) so that we’re not causing pain, we’re not offloading pain when we get hit with discomfort, and so, yeah, this is really, really helpful.


Just briefly, I’m curious what you consider a successful conversation and when did that idea of a successful conversation shift to what you teach today?

Daniel Stillman: Well, David Boehm’s (who’s a physicist who has written extensively on dialogue) perspective was that a real dialogue is like a real chemical reaction where everyone leaves it changed, everyone gets transformed. I think I do believe that’s true. It’s a challenge 'cause sometimes I’m running structures or processes for other people, and there’s a line between me and them, but if it’s really transformative, I get pulled in too and I feel it as well, and so, I think, really, for both facilitator, convener, conversation-designer, the people in the conversion, nobody gets out unscathed in a good way. We all get changed, and I think that’s really what is truly transformative.

Rebecca Ching: Ah, that’s a great word.

Daniel Stillman: You don't leave the same person. 

Rebecca Ching: That’s a great word and a great call-in, a great challenge for all of us to be a part of those conversations.

So I want to wrap up with some quick-fire questions for you, okay? What are you reading right now? 

Daniel Stillman: Oh, man. I’m reading a really, really weird book. Well, I’m reading two books. One is The Reflective Practitioner by David Schön. It’s a classic which I’ve never read. It’s slow-going. Faster-going is a book a friend recommended called Blitzed. It’s about the extensive use of methamphetamines in the Third Reich. 

Rebecca Ching: What! 


Daniel Stillman: It is a surprisingly fun and interesting book about, like, basically how much methamphetamine made the Nazis’ rise to power possible. I was like this is fascinating. It's fascinating.

Rebecca Ching: All right. On the list. I’m married to a historian, so he’s probably gonna be into this too. What song(s) are you playing on repeat these days?

Daniel Stillman: Oh, man. I just went to Portugal with my wife for this conference and for some time around. I already loved Fado music, and when we were cooking dinner the other night, I don't know if you've ever listened to any Amalia Rodrigues, she is the queen, the originator of Fado music, and if you're unfamiliar with Fado music, it’s this incredibly passionate vocal music with backing of classical guitar. It’s really beautiful and very melancholic music.

Rebecca Ching: All right. Best TV show or movie you've seen recently? 

Daniel Stillman: Oh, man. That’s a tough one. I just started Obi-Wan Kenobi --

Rebecca Ching: So good!

Daniel Stillman: I’m pulled in. I’m pulled in.

Rebecca Ching: Favorite ‘80s movie, TV show, or bit of pop culture?

Daniel Stillman: Oh, man, I grew up on Three’s Company.

Rebecca Ching: Oh, my gosh! [Laughs]

Daniel Stillman: I mean, that was, like, yeah.

Rebecca Ching: Oh, my gosh. 

Daniel Stillman: That was the age I was at.

Rebecca Ching: It’s so problematic. I haven't thought about Three’s Company, though. Mr. Roper. Oh, gosh. It’s hard to watch some of the stuff now, but that was what we had on after school! We’d watch this.

Daniel Stillman: Correct.

Rebecca Ching: Okay, what is your mantra right now?

Daniel Stillman: Oh, man, I’ve got, like, a wall of mantras on the other side of this camera, but there’s three. They're from my coach. The first one is, “How have I been generous?” The second one is, “Will I be of service?” The third one which is the kicker is, “Will this create the life that I love?”


Rebecca Ching: Love it. Thank you. What’s an unpopular opinion that you hold?

Daniel Stillman: I mean, I think I’ve shared a lot of them today. [Laughs] 

Rebecca Ching: True, true.

Daniel Stillman: I don't know if I want to put a red pen and underline any of them, but, yeah, I don’t know if men needing to do their own work is unpopular, but it’s not common.

Rebecca Ching: Who or what inspires you to be a better leader and human?

Daniel Stillman: Oh, my wife down the hall. Everything I do is to have a more peaceful, joyous relationship with her. We started at a pretty good level, but there’s always new heights, depths, [Laughs] heights of depths to go to. Yeah, that’s what it’s all about for me.

Rebecca Ching: That’s beautiful, Daniel.

Daniel Stillman: She’s my teacher.

Rebecca Ching: Ah, I feel that way about my partner too. This has been a treat, and I’m gonna be thinking about this for a while. I’m gonna go back into your book, and I hope everyone listening to this does get this book ‘cause I think it translates to wherever we show up, and there are so many good rumbles in it. So, Daniel, thank you so much for joining me today.

Daniel Stillman: Thank you very much, Rebecca. 

Rebecca Ching: This will benefit many. Yeah, it’s been a pleasure.

Daniel Stillman: Thank you. Folks can get a free set of chapters at theconversationfactory.com/goodtalk. 

Rebecca Ching: Wonderful, we’ll make sure to put that in our show notes, and you also lead a lot of workshops there, too, yes?

Daniel Stillman: I do. I do. I run a facilitation masterclass twice a year. There’s another cowork coming up in the fall and, like you, I do one-on-one coaching.

Rebecca Ching: Thanks for being here. I appreciate it, Daniel.

Daniel Stillman: Sweet.

Rebecca Ching: I appreciate you. Take care.

Daniel Stillman: Thank you. Bye.

Rebecca Ching: The way we talk to ourselves is deeply connected to how we talk with each other, and the external pressures and expectations to quickly fix any signs of doubts or fears, and do so quickly, feel really intense.


We’re moving so fast these days, and we’re just pushing though again and again while overextended and exhausted, and then our tired default leads to piling on ourselves when struggle surfaces. So we seek comfort through the quick-fix promises from many offerings in the personal development space with the hopes to get relief from the toxic conversations we’re having with ourselves, and when they don't work, the shame spiral only deepens. 

Now, Daniel gave us a framework on how we can lead transformational conversations with others, and he reminded us that the most important (but often the most difficult) conversations are the ones we’re having with ourselves. What steps do you need to take to help cultivate transformational conversations around you? How are you navigating hard conversations with yourself and others? Where can you offer yourself some more patience and compassion as you seek relief and change from the toxic conversations between your ears?

When we get curious and befriend the parts of ourselves that are judgmental and fearful instead of exiling them, we help create space for the transformational conversations within and around us, and this is the work of an unburdened leader.

[Inspirational Music]

Leading is hard, and leading is also, often, controversial as you navigate staying aligned to your values, your mission, your boundaries. Navigating the inevitable controversy can challenge your confidence and clarity and calm. Now, I know you don’t mind making the hard decisions, but sometimes the stakes seem higher and can bring up echoes of old doubts and insecurities during times when you need to feel rock solid on your plan and action. 

Finding a coach who gets the nuances of your business and leading in our complex and polarized world can help you identify the blocks that keep you playing at safe and small. Leading today is not a fancy title or fluffy bragging rights, it is brave and bold work to stay the course when the future is so unknown and the doubts and pains from the past keep showing up to shake things up. Internal emotional practices and systemic strategies are needed to keep the protector of cynicism at bay and foster a hope that is actionable and aligned and helps us have the hard conversations with ourselves and with others.

When the stakes are high and you don't want to lose focus, when you want to navigate inevitable conflict between your ears and with those you lead, when time is of the essence and you want to make hard decisions with confidence and clarity, then Unburdened Leader Coaching is for you and where you deepen the capacity to tolerate the vulnerability of change, innovation, and doing things differently than the status quo.

To start your Unburdened Leader Coaching process with me go to www.rebeccaching.com and book a free connection call. I can’t wait to hear from you! Thank you so much for joining me on this episode of The Unburdened Leader. You can find this episode, sign up for the free Unburdened weekly email, find the show notes and other Unburdened Leader resources, along with ways to work with me, at www.rebeccaching.com.


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