Expert Insights: Talking Tough Conversations with Lisa Hunt

Let’s be honest—most of us would rather do just about anything other than have a tough conversation. (Clean the fridge? Sure. Reply to 87 unread emails? Why not.) But avoiding the hard stuff doesn’t make it go away—it just makes it harder later. That’s why we’re so excited to bring the Navigating Challenging Dialogue® Essentials workshop to High 5 starting on November 4th!

To give you a closer look at what it’s all about, our Director of Team Development and workshop facilitator, Lisa Hunt, joined the Vertical Playpen podcast to explore why tough talks feel so tricky—and how this training helps turn discomfort into growth.

You can watch the episode below or read a transcript of the discussion beneath that.

Phil Brown (00:00)
Welcome to the podcast. I’m with Lisa. This is a me, Lisa and me, myself episode or Lisa, myself and me. And, um, but I’m with Lisa and we’re, we’re to be talking about a program called Navigating challenging Dialogue. So I will throw it straight over to you, Lisa, to explain the backstory of navigating challenging dialogue.

Lisa Hunt (00:07)
Absolutely, thank you, Phil. It’s great to be, I feel like I haven’t been in this mode with you for a bit. So Navigating Challenging Dialogue is a thing that we humans do all the time, right? Like we navigate dialogue that is challenging. It’s also a model that has been developed and researched and delivered by a great partner and friend of High 5 called Beth Wonson, Beth Wonson and Company.

And Beth is on our Board. And over the years, Beth has invited me and others at High 5 into her workshops. And through my work with her and my own real interest in this topic, I have become a certified trainer of Navigating Challenging Dialogue. And High 5 has the privilege of being the first organization to be authorized to offer this content to our participants in an Open Enrollment Workshop, which I’m sure we can link some of those details to that session in the show notes. But so Navigating Challenging Dialogue in short is a concept, things that humans do, and it’s also a process that has been developed and researched by our colleague that we are now authorized to deliver as a workshop.

Phil Brown (01:37)
So we’re to get into looking at some of the framework and then like a sneak peek into the workshop offerings. But let’s just talk about this in a broader sense. In your experience, what makes a conversation challenging and then why do so many of us avoid them?

Lisa Hunt (01:51)
Yeah, I mean, I can’t think of anybody who could be listening that doesn’t relate to this idea of, some conversations can just be tricky. And a lot of the times it’s in the anticipation of the conversation where we can get in our heads, we can tell ourselves, this is how it’s going to go. This is going to be the result. So there isn’t one answer to that, but I would say from what I’ve learned from Navigating Challenging Dialogue, which I’ll probably brief to NCD.

In my experience in this training model, a lot of folks, including myself, think things like, “I don’t want to rock the boat.” “I don’t want to upset this relationship.” “I don’t know if I have the emotional fortitude to be clear in my approach with somebody.” We also can tell ourselves things like, “Well, who am I to give this feedback?” or “Maybe somebody else will come along and do this.” So I think there’s a lot of wanting to, wanting to preserve relationships and not being sure how to get, have a direct conversation with somebody that needs to be had without there being some kind of emotional fallout or damage to this. This is what I love about this process is that it can acknowledge a lot of emotions, but also sort of take that and put it on the shelf so that it becomes a very clear and clean communication.

Phil Brown (03:10)
No doubt, as people are listening to this, can relate to either some of us who are really comfortable with these kinds of conversations and some of us are more avoiders. I’m certainly the latter of that. I’m not always the best at being able to have a challenging conversation. I think I’ve worked on it as I’ve grown older. But I know that we’ve had the opportunities at High 5 of having some of this training and some of this framework delivered to leadership at High 5.

But can you give us a sneak peek into what like the framework might look like for people who attend?

Lisa Hunt (03:42)
Sure, and I want to start with a caveat, which is that this process is meant to apply to conversations that are sort of about relationships. Maybe it’s between two peers, a supervisor and somebody that reports to them or vice versa. But what it’s not, we’re not suggesting that this process applies to every tricky situation that you might be in. So for example, this is not meant to include sensitive HR matters or personal safety. Those are different conversations that organizations should have a process for. So the premise of Navigating Challenging Dialogue is, for me, I would describe it as a lot of the work is in the preparation for the conversation. So there’s really four major steps to Navigating Challenging Dialogue. And the workshop that Beth has offered, that we’ll now be offering, really covers in depth those four steps in the workshop so that folks can then go back and do that independently. And those four steps are sort of looking at what is the story that I have in my head that I need to then have a conversation with somebody about? And we can think about an example of that after I finish sort of framing out the four steps.

As we tell the story, then the next step is we look for like the anchor points. Right. What are the things that are really important in this conversation? And again, I’ll give an example of this. We then sift the story that we’ve written down, writing it down is important in the learning process and we look for like, what are the actual relevant facts? And they remove the things that aren’t actually facts. Emotions are important, but we don’t need to include them all in these tricky conversations that we have.

And then we look for, we do what’s called a relevancy check. And that can include things like, “Am I the right person to do this?” “Does this need to be said by me now?” Some of those things. then, and then we need to set the stage and prepare to have the conversation. And that can be some principles that we could all benefit from like, “Hey Phil, I’d like to have a conversation with you. Can you set aside a few minutes? What would be a good time for you?” Which if you’re like a normal person, which I know you are, you’re going to be like, “Uh oh, what did I do?” Right? It can bring up some of that. So there’s also some tips around how do you try to reduce some of the stress and drama when it comes to approaching somebody to have a difficult conversation?

So that’s the sort of the gist of the process. And in the workshop, there’s, I think, one of the things I love so many things about this workshop, but in particular, I’m very proud of the written materials, the worksheets and the coaching that get us to go through this. 

Yeah, maybe later in the conversation, can give an example of like how, what the process looks like in real time.

Phil Brown (06:24)
Sure. What’s your experience in terms of running this? Where have you seen kind of like maybe like an aha moment or someone who’s had this realization that like, oh, actually, yeah, this has value. This is really valuable to me.

Lisa Hunt (06:39)
I have, yeah, I like that question. I have a few thoughts about that. And I, I harken back to when Beth was here last at High 5, when we offered this as an Open Enrollment Workshop where I was Beth’s co-facilitator, there was a, the school administrator in the workshop and she volunteered to have her scenario. Like she, participants bring a written scenario with them so that they could receive coaching and support. And she volunteered to do this in front of the whole group. And she was going through with Beth was helping her sift for the facts and the relevancy. And this educator, this administrator said, “I guess I just assumed that this conversation was going to damage the relationship. And what I realize now is that this is actually going to be helpful to the other person.” So I think that that aha moment, and it was shared with so many people in the workshop that after this “challenging dialogue”, the relationship is gonna be worse. And I think my hope is that the opposite is true, that the relationship can actually be improved because the recipient of the “challenging dialogue” has an opportunity to ask questions and get support. So it really can be like the beginning of a new iteration of a friendship and relationship. So that was a cool aha moment. And then for me personally having taken this workshop many times before I got on the instructor track. A lot of the scenarios that I’ve written out, Phil, are like, I’m just annoyed and I want to, and I write it all down and then we sift through the facts and I realize I’m just building a case about why it’s okay to be annoyed. I don’t actually have a difficult conversation to have with somebody. I just want my annoyance to be justified. So I think there’s something very liberating about this sifting feature where you go through and I’m looking for facts and I’m like, yeah, I have a right to be annoyed, but there’s nothing I want this other person to do differently. So I think that’s a feature for me as an aha moment. And I think another aha moment that I’ve had that I continually have, because it doesn’t stick right away. It has to become a practice. And I’m still constantly learning here is I always thought that if I was going to have a conversation that I would label difficult, like give you some feedback, for example, I would have to bring like years of evidence, like a lawyer, like here’s all of my “and then this time,  and then in 2017, you did this” and da da da. And what I’ve really learned and like completely internally get and appreciate is that I don’t, I can really just have my focus on one interaction, one topic.

And that’s better for you as the receiver and that’s better for me as a giver. Right? Because have you ever had somebody say, “Well, and you always do this” and then every time and all of a sudden you’re like, you shut down. So this process also helps focus on one situation. And yeah, I might need to have a conversation with you multiple times, but it’s isolating that which can then inherently reduce stress, reduce a negative emotional reaction.

So I think that’s a big aha for me is that I don’t, I’m not like a lawyer going in presenting a case. I hope my case is strong. my case is weak, you know, calling witnesses. It’s really just, it’s a little bit, it can be a little bit simpler than that.

I really think that all humans want to have the skills to have conversations that are difficult. We just, what I love about NCD, it’s like, okay, here’s a process. You can follow it. And it’s not terribly complicated.

Phil Brown (09:59)

Yeah, and I think that that is the crux of it. It’s like there’s a skill set that you’re going to learn and a process that you can follow that will avoid some of that distress of like building the case, feeling you need to build the case and then ultimately realizing once you have the conversation, it’s normally okay. But this gives you the opportunity to practice those.

You referenced the bringing in real life conversation. So I want to come back to that. Maybe we can use that as an opportunity to show an example, but you ask participants to bring to real life conversations to the training. Why do you believe that is so impactful bringing in those real life experiences? Because that might be nervous for people as they come into this like, “Oh, I have to really bring in some real ones?” And that might be a level of vulnerability. But where’s that where’s the benefit there?

Lisa Hunt (11:08)
Yeah, I’m happy to talk about the benefits. And I will also say that in the preparation for writing out these scenarios, the level at which people share is completely at their choice, right? So the preparation is really for the learner and not necessarily… at no point does anybody’s story have to be publicly shared with the group. They are looked at by the instructors. For a High 5’s offering, would be me and giving feedback, but it does not need to be brought out to the class if somebody doesn’t want to.

I’ll share the value that I got in the first time I took this workshop. I wrote out three pages and really the writing process is like, it can be cathartic. Like I was so upset with the administrator at my mother’s memory care facility, which is a very emotional thing. Like we moved her in here this day and I had this interaction with the Director.

I had three pages of writing about how this person was terrible and evil and how dare she, and I brought this scenario to class. And the sifting of it was, I realized I didn’t really have an anchor point. There wasn’t something that I wanted this person to do differently. I wanted her to see how tacky and, I mean, I don’t know if I want to get into the details of it, but what I realized is that it was okay for me to feel that way, but there wasn’t anything that I needed her to do differently. And so sometimes it happens. It seems like it maybe happens a handful of times where you look at your story that you’ve written out and you realize, I don’t actually have a dialogue to have. I don’t have feedback. I’m just upset. And it’s, and it’s like, that’s not to minimize being upset, but, but anyway, getting back to your question, which was why do we have people prepare? One is so we can, it’s an efficiency thing partly so that in class we can actually work on sifting through looking for anchor points, doing those relevancy check, a fact check, and doing those in front of an expert instructor can also be really helpful because we’re sneaky humans. Like we want to tell ourselves, no, like for me, when I first got coaching from Beth, it was like, yeah, but it may not be relevant, but it’s a really important fact. And she’s like, yeah, but it’s not relevant to this conversation. So having somebody who is outside of our head can also help us see things a little bit more clearly. And I do find that in the class, we’ll definitely get to at least one person’s scenario live in person. Everybody benefits from seeing that analysis, even if they can’t relate to the situation, being like, why isn’t that a fact? Or, why isn’t that relevant? Or why does this not need to be said by me? So that conversation can be really valuable to the collective.

Phil Brown (13:49)
I think that, you know, I can analyze that like, I could see myself needing this because maybe I struggle with challenging conversations. But I, I also wonder if like those people who are considering and hearing this and thinking, “Oh, I’m really good at this stuff.” That there’s probably a great benefit to them. Also, it’s not so much the, being able to enter, engage in a conversation, but like the outcomes of that might not be great. They engage into conversations, but everyone kind of leaves upset.

So who would you say this is for? Like who is this we’re listening to? Like who is this aimed at when we’re considering this workshop? Is this for everyone? Is this a skill that we all should work on?

Lisa Hunt (14:26)
Yeah, I I think I have two answers to that. One is just as a human being in the world, I would love everybody that I interact with to have Navigating Challenging Dialogue in their back pocket. Cause I just think it would make everything easier. In terms of who this workshop though is aimed at – I think that the, sort of most appropriate target audience would be people who are in a situation of giving feedback, supervising others, but it’s not limited to that.

So in the last Open Enrollment Workshop that we had, we had some school administrators. We had a head cook at a restaurant who was struggling with communicating with all of her chefs at all of her affiliate restaurants. So certainly folks who supervise others is a natural target audience, but it doesn’t have to be limited to that.

At High 5, the leadership team has gone through this process and we have found it very helpful in our communication with each other, but also in the communication of the people that report to the leadership team as well.

Phil Brown (15:26)
The thing that I think that aligns nicely between NCD and also Adventure Education is we consider like things that are, I think a phrase that we often use on a ropes course is that it’s called a challenge course, not a success course that gets brought up. This has challenge in the name. Would you say that this can be a challenging experience to embark in this workshop? Is there, do people have to know going in that some of this might be challenging?

Lisa Hunt (15:38)

I love that question, Phil, and I’ve never really thought about that.

I mean, I guess I was really very much eased into this work versus just signing up for a workshop. I did the webinar, I read a book and, you know, over the years I’ve learned more. So I have that caveat. I would not describe the actual workshop as particularly spicy or emotional or difficult. There’s no intention to really push people or to create discomfort so that we can then get more comfortable. So there isn’t a lot of role playing or scenarios in that way. I would describe the workshop as pretty academic, if you will. So we present a model, we practice it, we move on to the next step, we practice it.

Phil Brown (16:40)
Awesome.

So as we conclude this conversation, I’m going to put into the description as noted links to more information and times and all those kind of things. Is there anything that you want to leave off this conversation with as regards to the NCD workshop or NCD as a whole that you think is important for listeners to know?

Lisa Hunt (17:00)
I would just say that I’ve taken Navigating Challenging Dialogue workshops and I encourage people to do the same so that I can make conversations at work easier. What I did not anticipate is that the skills, and again, it’s not like I’ve arrived in some, like “Everything’s easy for me now,” but as I continue to make these skills more integral into my life, they have helped me in every area of communication, which is everywhere, right?

So one of the things about NCD are these lists of mantras, if you will, or catchphrases. And one of them is, “At the end of the day, everybody wants to be seen and heard.” And that saying has gotten me out of so much emotional stress of whether I’m dealing with customer service or I’m debating with my husband something about the care of our two children. Some of those expressions and then just having the confidence be like, all right, if this does get tricky, we have the ability to talk about this. Like that is such an incredibly freeing concept instead of where I used to live, which was, if this gets tough, I’m out. I’m going to go and complain to my colleagues and then just hope somebody else comes and fixes it. And again, like that probably still happens to a degree, but the confidence of just knowing I have a process now that I can rely on that can make this approachable is huge for me. And I’ll be applying some of these concepts later today in a tricky conversation that I need to have that usually if applied right ends up really not being that tricky.

Very straightforward. So I think that that’s the piece I would say about the challenge aspect of it. Yeah.

Phil Brown (18:47)
And I think that like the, I think another key word in this is “navigating.” This isn’t like how to make challenging dialogues easy. You know, like that’s not the aim of this, but it’s how do we actually make it so that you can better navigate the situation and have a process to follow. And those benefits are so, so powerful having those in place to be able to make that process a little easier.

Lisa Hunt (19:13)
100%. I mean, I think anybody, I’m sure you, your listeners could think about, you have a conversation with somebody, whether it’s feedback or something that was difficult, and you walk away going like, I should have said this, I shouldn’t have said this – second guessing ourselves, thinking like, I’m the one who made that so much worse. This process allows us to enter a conversation and regardless of the outcome, know like the only person I can control is myself. I was clean and clear. I was direct. I was kind. It can help me separate the response from what’s my responsibility. And that’s been very freeing for me. I know that I didn’t do anything to cause more harm.

Phil Brown (19:57)
Well, awesome. Thank you for sharing about this, Lisa. And I look forward to seeing people come into the workshop and then also the progression of my own development in navigating challenging dialogues. Thank you, Lisa.

Lisa Hunt (20:10)
Thank you, Phil.

And a huge thank you to Beth Wonson who has been the pioneer of this and a huge champion of High 5. And I’m so grateful for our partnership.

Phil Brown (20:19)
Awesome.

Ready to Transform the Way You Communicate?

Join us Monday, November 4th for Navigating Challenging Dialogue® Essentials and learn how to turn those tough talks into opportunities for growth and connection.