May 13, 2026

A Playbook for Tough Conversations

A Playbook for Tough Conversations
A Playbook for Tough Conversations
Catching Up with Casey
A Playbook for Tough Conversations

Are you avoiding the high-stakes discussions that your school community needs most? Join Tiffany Burns and Erika Bare as they share about their practical playbook for navigating tough conversations, de-escalating tension, and ensuring every interaction leads to a successful resolution. Gain the tools you need to overcome communication barriers and lead your team with greater confidence.

Connect with Erika and Tiffany: http://www.connectingthroughconversation.com

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0:05 Welcome to Clear is the new Confident. I'm Casey Watts, speaker, author and the host of this show. If we haven't met yet, there was one important thing you need to do, and that is I am completely obsessed with clarity. I've seen too many brilliant women stay silent or feel stuck because they didn't have the tools and strategy to be courageous. If you are ready to stop second guessing yourself, say the things that need to be said, and stand firm in your integrity, you are in the right place. I am on a mission to spread the message that clarity precedes capacity, helping you lead those around you with great courage and confidence. Now, with all of that said, let's dive into today's episode and gain some.

0:53 Clarity. Well, hey everybody, welcome to another episode. It's going to be a really good one because we are talking about tough conversations today and I am joined with two authors who have written a book recently titled A School Leaders Playbook for Tough Conversations. So I think it's safe to say I've got some experts in the house tonight who are going to be sharing about all the things that are going to help you guys to have have these kinds of conversations that feel uncomfortable really confidently. OK, So welcome to the show, Tiffany Burns and Erica Bear. Guys, tell us a little bit about who you are and the work that you do.

1:47 Tiffany, let's start with you, if that's OK. Absolutely. Thanks so much for having us, Casey. We're excited to be here. So I'm Tiffany Burns. I've been in education for over 20 years. I've taught all the levels. I've taught elementary, middle, high school, now university. I was a school principal for 12 years. Erica and I met in our administrative licensure program and I made her be friends with me. So she's stuck with me now. And I, we wrote this is our second book. Our first book was, is titled Connecting through Conversation, a playbook for talking with students. And Eric and I get to travel all over the country working with folks in districts and in organizations and in schools to help them really transform student behavior with kids. And then we started this second book that we'll get to talk about.

2:36 And yeah, I now work in higher Ed, I coach principals and I get to do this work all over the country. So I'm having it's been a really fantastic time in life right now. I love it and I can see it, guy, if you're just listening to this on the podcast, you can't see it. Maybe you can hear it through her voice, but Tiffany is just has this beautiful bright smile on her face. So it's so inspiring and encouraging. OK, thank you for sharing that. Tiffany and Erica, what about you? Thanks so much. So I also been an educational long time. I was a special education teacher when I got started and got to work at all of the different grade levels, transitioned into administration and did all those kind of jobs at at, again, multiple levels.

3:21 And I'm now a school district Superintendent in Southern Oregon with my awesome family. And as Tiffany said, we just came out with this new book about tough conversations, and that's where we've been spending a lot of our time and energy lately. So we're really excited to be with you today. Yeah, OK. I can't wait to get into this conversation, but I've got to know something that makes you guys just, you know, the average Jane Doe. Like, just unique. But also, yeah, I, I resonate with that. Well, I'm a mom. I have the coolest kids on the planet and probably every mom says that.

4:03 So I have an eighth grader and I have an 11th grader and they are just the most fun people to be around. I love them so much. Boys. Girls. My son is junior and my daughter is the 8th grader. OK, awesome. All right. And Erica? Well, I'm in an interesting phase of life right now. I have two graduations happening with my two kiddos. My daughter's graduating from college and my son is graduating from high school and my husband and I are desperately seeking some good hobbies because we are about to have an empty nest except for the ridiculous number of cats and dogs we have in our life. But other than that, it's we're in a period of extreme transition.

4:53 So I know there are others out there that can relate to that, but it's an exciting time. Yeah, that is an exciting time. So a fellow mom and in this space as well almost said room, we're kind of in a room, right. But fellow mom here and yes, so I've got children from freshman to or freshman in college right now. So we are experiencing all of those things and you you talked about having dogs and cats in your house and I just heard one of my dogs starting to bark a little bit. So we might we might get to experience that here in this podcast episode, we're talking about tough conversations. You guys have written a book, a school leaders playbook for tough conversations.

5:35 I'm going to say that this episode, even if you are not a school leader, is going to be applicable to you. So I, I think right off the bat, I want to know what led you to this book specifically because you were focused on students and then it shifted into this newest book about tough conversations for leaders. Yeah, Well, I think the biggest reason for us, we got into this work because we love kids. And I think that's true for most educators. That's what we're passionate about. That's why we choose to do it. And as we have continued in education, what we've realized is the pathway to success with kids is through the conversations and influence that we have with the adults that serve them.

6:21 So being able to really navigate those tricky conversations and gain momentum and the direction that that a building is needing to go or a classroom is needing to go is really how we're able to impact change for kids. So that really drove the book. Our first book was all about how to talk with kids to transform behavior. And inevitably we'd be in a room and a leader would come up and say, this is so great, I need this for my building. But what I really am looking for, what I really need help with, is how can I have the conversations with the grown-ups so that we can really make a positive difference. Tiffany, anything to add to that? Yeah, absolutely.

7:04 Well, just, you know, those, those tough conversations with adults, I didn't learn how to do that in school. You know, nobody. I didn't have a class that was like, here's what to say. And when somebody is livid and screaming at you, this is what to do to calm them down, right. So I just got it wrong a lot of the time and sometimes got really lucky and got it right or was able to use. What did he say? Eric and I were just recently talking to a friend and he called us Jedi communicators, which I was like, we can we copyright that, but you know, using some of that Jedi communication and then just really thinking about why did that work and why did this not work? And so, you know, Eric and I were able to, we were lucky enough to be hired in the same district as administrators. And so we, we would have these monthly dinners and we would have weekly phone calls and sometimes daily phone calls of just what do I do?

8:02 This situation went poorly or I have this coming up and what do you, I'm going to try this out. You have a sentence stem or a frame that I can use. And is there a different way that I can maybe explain this? And what we realized is that excellent communication does not happen by accident. It takes practice and it takes preparation, and it takes time and intentionality. And we would love for people to be able to learn from some of our mistakes and be able to have this playbook that you can just open up and go, I have to have this really tough conversation. What exactly should I say? You know, I want the playbook. So we wrote that. It's a playbook with framework, sentence stems, you know, templates, just all these different back pocket strategies that you can use in the moment. The other piece is that when you have to have a tough conversation, you know, often times those are the things that keep us up at night or wake us up at 2:00 AM. And those are not good problem solving times for me. So I'd like to help people sleep hygiene by having them have some preparation so they don't, they don't have that stressed and angst and they can be more effective and they can think, OK, I'm, I'm actually really prepared for this conversation. Yeah.

9:17 So you guys, it sounds like you were writing this book and you didn't even know it. You were have, right? Like you were having all of these conversations with each other. And in the midst of all of that, you're building this content that you didn't know you needed and you didn't know other people needed it until you started to realize, wow, I've never had this before. And that means that there are so many other people out there who have never have this, I say it all the time that we have this, this assumption, we make this assumption that because we are adults or we're working with other other adults, these adults inherently have the skills to be able to collaborate well.

10:01 And we do not at all. And it was the same for me growing up. Like the at no point was I taught specifically in grade school, I wasn't really taught how to collaborate well and have productive conversations or to have tough of conversations. And then when I moved into my college career, that didn't happen either. It was just, you're going to get into group work and who wants to hear the term group work? No one, right? No one wants to hear that term. But we're thrown into it and we're kind of forced to muddle through this work without having developed the necessary skills that make us successful, much less feel great about it. And then, you know, the trajectory continues where you go into your career and now you've had all this time where you've built up skills that are not the appropriate skills to be able to collaborate well with other people or have tough conversations.

11:00 So I think it's phenomenal that you have created this resource for school leaders specifically, though. So I let's dive into that a little bit. What is it that makes these kinds of conversations so different for school leaders versus other people? What do you think they experience that's different? Well. When you're a school leader, you are balancing so many priorities and so many different you know, different needs, different audiences. You're working with all of the students in the school. You're working with all of their caregivers and families.

11:43 You're working with all the educators that you support. You're also working with all of your colleagues, your your fellow principals and directors and administrators. You have, you know, with, I always said as a school principal, I had one boss as a Superintendent, but I really had everybody else where my boss is, you know, and you're under this microscope. You're also not able to share so much of so much of your job as a school leader is confidential. And so, so I can't just go out as a regular person, You know, not that we're not regular people, but but, you know, as a as a teacher or as an educator, I could complain about folks or I could say, you know, well, here's what really happened in the situation as a school administrator, there's a sliver of what I can share. And I was a elementary principal for nine years. That is a really lonely job.

12:41 I was the only supervisor in the building. I was the only evaluator. So a lot of times it felt really lonely. And I had to make these really hard decisions. And I had, you know, myself to consult with. So it there's so many parts of it that make it challenging. I think the skills absolutely translate to other fields, but it's extra tricky as a school administrator and Erica's a Superintendent, so she gets extra, extra tricky. Well, it it is tricky and I don't think it's that unique from so many folks. Anytime you have to engage in conflict or anytime you have to provide difficult feedback or critical feedback or try and solve a big issue, it's complicated and challenging, right? And I think for school leaders, that just happens a lot. There's just lots of opportunities for that. The other piece that's a little bit different is, you know, and I said this in the beginning, we, we're, we're all about how can we support the kids in our building? How can we make sure that they're having the best possible experience and learning at the highest levels? And, and that's a, that's a mission critical and we're really passionate about it.

13:59 And so the conversations that we have are for that purpose. And so it gives it a little extra meaning, a little extra importance. And so it's all mission driven. And all of the conversations are so passionate because we're talking about kids. And so if we're talking to to a caregiver or family member of a student that is their baby, no one, there's no circumstances under which there's going to be more passionate involved than that. And so it just adds a layer. But all of the techniques are they would work in any difficult conversation. Great, good to know. I'm excited about that.

14:39 Can't wait to get my hands on the book. I am curious what it is you feel like makes it challenging for people to engage in tough conversations. I mean, besides our, I mean, I know our previous or prior experience has a lot to do with it, but what are some other things that you feel like makes it uncomfortable for people where they kind of shy away from it? I don't think anyone wakes up and thinks, gosh, I would like to be in conflict today or I would like to, you know, bring this really difficult thing to someone else's attention. It's hard. I mean, I think that's the that's the real truth of it. It's hard, it's difficult. I think there's a lot of fear around damaging relationships or making someone feel uncomfortable or sad, and nobody wants to do that. And so we talk a lot about the reason that we have to engage in these conversations that are difficult. And that is because because we care. We care about the students, we care about the person that the people that we serve.

15:48 We care about the culture in our building. And so we have to engage in those conversations because we care. And that doesn't mean that it's easy. I've been doing this for a lot of years. I've had lots of tough conversations and it's easier, but it will never get easy. I think, you know, the tools that we try and provide, the frameworks that we try and provide are about building confidence, building skill sets so that you're more likely to engage, you're more likely to feel confident and comfortable enough to move forward and have it be successful. And, and that's one of the biggest messages in the book is that it is absolutely necessary to have the conversation.

16:35 Even an imperfect conversation is so much better then no conversation at all. And it really comes down to, you know, what you talk about, which is just clarity. We have to be clear. We have to make sure that folks understand the impact that they're having and negotiate through those trouble spots so that we can move forward together. Clip that. So when I say clip that there's this new like in stream yard, it'll, I can say clip that and it will clip that segment so that we can make sure that that is something that we that we share on social media. So it'll have a little, we'll have a short snippet of that. It's so funny because I just wrote down on this sticky note. Does it ever get easier?

17:21 Was the question I was about to ask you, and then you answered it. And yeah, but I wanna know you said it. It gets easier. Hash that out. What do we mean by it gets easier? Will you go into it? No, I well and it it doesn't get easy, but it does get easier. You go in becoming more comfortable in the discomfort. You know, you become a little bit tempered, you know, like you're just more used to it. You know what to say, you know how to say it. You just become more more comfortable with that situation. The other piece that I really think about is part of the reason why it's harder for us to step into those conversations is it's so much easier to just think maybe this will just solve itself.

18:14 Maybe this problem will just go away if I just ignore it long enough. Maybe it will just go away and you know the truth, maybe that sometimes happens, but the overwhelming majority of the time is not only does that make it worse, then we sometimes have to do conversation cleanup because we didn't have the conversation or we have to do something to clean it up because we let it go on. The piece that is just so tricky is that sometimes we enter into conversations and we have this picture in our head of how it's going to end and what the outcome is going to be and how the other person is going to be. And we'd like to control that. And the truth of it is when we are in a conversation, the only person that we can control is ourselves.

18:58 And so we just want to really go in knowing that, OK, I'm going to do my best to say what I mean, to stay calm, to make sure that I say the things that need to be said, that I do that clearly, compassionately, confidently. And then regardless of how they take it, I'm going to leave knowing that I showed up as my best self in this conversation. And I feel proud of the way that I showed up. When we go in that way, often times we do get a great outcome, but we're can't, we can't bank on that and we can't walk into it wanting to control the other person. OK. Are there, you mentioned this a little bit, but are there conversations do you guys ever think about before going into a conversation?

19:45 Is this conversation one that needs to be had or is this a conversation that does not need to be had? Like are there ever situations that could go in the direction of not having it? Yeah, Although, yes, there are times and the way that we kind of determine that is really getting clear on purpose. What would the reason be for me having this conversation? What is the, what am I wanting for me? What am I wanting for the other person? What am I wanting for the relationship? And if those things are about care, if those things are about improvement, if those things are about strengthening relationship and culture, then we need to have that conversation. There are times that even the most reasonable person might be tempted to enter into a conversation because they're really angry or they're feeling like they need to win something or they need to kind of put someone in their place. And so we do caution people that if that's the feeling, if that's kind of where where the purpose is coming from, then at least pause.

20:59 That doesn't mean that you're not going to have the conversation. It it might mean that you need to have the conversation a little bit later when you're a little bit calmer and can get clearer on the direction that you need to go. But we want, we want to be clear on our motivation and in entering into the conversation. With that said, it's not very often that I think, gosh, I feel like this is a conversation I need to have. And the answer that I ultimately come to is actually, no, I don't. There have been lots of times where I've been like, oh, do I have to have this conversation? And if I don't, almost inevitably, I'm going to regret that decision because having the conversation is, you know, 3/4 of the battle and bad things don't get better with time.

21:50 It is really just something where sometimes you just have to get in there and have it. And I don't think there's a such thing as too much communication. So even if you get in there and you have the conversation and it, you know, maybe wasn't entirely necessary, I don't think anything is lost when your aim is to build connection and communicate with folks. Yes. And I think the part that I've noticed, I totally agree with Erica. Yes, having that conversation, but really choosing the method of conversation so important. When I very first started as a principal my first year, I had this teacher wrote me an e-mail one night that was super long, like the longest e-mail not ever, but it was long. And there were so many pieces in it that I was like, OK, I'm going to respond to this and I'm going to respond to this. And this part isn't true.

22:48 And I literally responded to every single part of this very long, you know, I, I wrote myself a little novella and I had the wise sense to send it to my mentor 1st. And so I emailed it to her and I said, will you take a look at this, please, before I send it off to the teacher in the morning? So the next day she calls me and she's like, Tiffany, how you feeling? And I said, well, you know, I'm feeling better. Did you get my e-mail? And she goes, I did, how was that? Did you feel? Was that cathartic? And I was like, yeah, I've actually, I got a lot of stuff off my chest. I feel so much better. And she goes, excellent, go ahead and hit delete. We do not send novels to other people. Like what I want you to type is 1 sentence or two. You know, thank you so much for your e-mail. It sounds like we have a lot to talk about. Let's set up a time to meet.

23:37 And that that was the most brilliant advice that has just carried me through because I do that with text messages, you know, like we get communication in all different ways. And there are times that you need to sit down and have a conversation because you cannot spend tone in an e-mail. Right. Yes, so great. OK, this leads perfectly, Tiffany, into what I'm hoping you guys can share with our audience. And that is like a snippet of an example from your book. Like what? What is something that you feel like people are most drawn to or that you guys were most passionate about writing in your book?

24:21 That's such a good question. What do you think, Erica? What's a piece that you're like? This for sure. I think for me, the part that I really think is a through line throughout the book is, and Tiffany alluded to it earlier, we can only control ourselves in these conversations. And so the parts of that that kind of bleed through, we talk a lot about the fact that emotions are contagious. And so when folks come in and they're really heated and they're really upset, they're really angry, likely pretty anxious, those emotions are super easy to catch. And if we let ourselves kind of take that emotion on, what happens is as we get angry and frustrated, we're also escalating the other person. And so it becomes this like escalation ladder. And so we talk a lot about the different strategies to help other people catch our calm, how to de escalate, make sure that as they're going higher and faster that we're going lower and slower, that we're really intentionally on matching from whatever emotion they're bringing forward and putting out emotions that we want the other person to catch 'cause they catch our emotions too.

25:41 If we if we're intentional about it. And so taking those deep breaths, taking a drink of water and really watching our speech and then leading with a lot of curiosity. So really thinking about how can we listen Well, this is the most foundational part of any communication is how well we're listening to the other person. And so asking good questions, making sure that we've truly heard them and that they feel truly heard will go a long way towards de escalation and also problem solving and finding that common ground and figuring out how to move forward. So for me, the, the, the part of the book that I'm probably the most passionate about or think about the most is how do we show up as our best selves in these conversations?

26:30 What are the strategies we can use? Because we're all going to have the opportunity. There's going to be a caregiver who comes in really, really upset. There's going to be a teacher who comes in super angry about something, and we have to kind of be able to check ourselves and make sure that we stay centered and that we're not letting ourselves kind of go go down an emotional roller coaster with somebody else. And instead are really setting the tone for how we're going to both act and what sorts of emotions we're putting into the space. Yeah, it sounds like there is a lot of mindset work that has to take place in order to have tough conversations. Oh yeah, we actually had.

27:22 We were at a conference I think last year, and this was, we were talking about this topic and this woman came in and at the end, she's a, she's a principal and administrator and she came out to us at the end and she goes, Oh my gosh, I'm so glad I came in. You know, I was avoiding a conversation that I was supposed to have. I was supposed to call somebody in my building and I just came to your session. Instead. I was putting it off and she goes and now I have all these tools and strategies to use. So it kind of cracked me up. I was like, yeah, I get that. I think the snippet, Casey is have you heard, and we've all heard, right, this this idea of a feedback sandwich where it's, it's you give the really good, you know, the really kind compliment.

28:06 And then I kind of slide this thing that I need to say that is going to be hard for you to hear in the middle. And then I finish up with another compliment. And what we know is that people remember most the first and last things that we say. So often times people leave that conversation thinking everything's great. They have no idea there's an issue because they missed that piece. And we are such. I mean, your podcast title is perfect and we're such huge fans of Renee Brown and her clear as kind. And really just thinking about how do you speak clearly and share a message clearly so you don't soften it so much that you lose the actual message that they don't hear what it is that you're actually trying to say. If you went through all the angst of getting ready and getting prepared to have the conversation, let's make sure they leave understanding what you're, what you're meaning, the purpose of the conversation is.

28:57 Yeah, we don't want a thin stuffed Oreo. We want double stuffed Oreos. There you go. That's the only thing that came to mind when you were thinking about the Sandy. No, I love that I. Always thought about the Oreo. Yeah, yeah, yeah. Oh man, that's so good. And I think to just to kind of pull on that thread of clear as kind. We, I think so many people when they hear the phrase clear as kind, they equate it to, oh, it's a difficult conversation. It's a tough conversation, whatever. But when you read on in Brene Brown's book Dare to lead, she says paint done. We're, we're developing this just crystal clear understanding and not only for ourselves, but for other people. And I think a lot of that has to do with the question, the curiosity that you're bringing to the conversation. Like what are the questions that I'm asking to ensure that we both have at least a similar perspective on this or can go about our solving this problem in a way that's going to benefit both of us and, you know, the the people outside of our little circle.

30:07 So yeah, that's fantastic. And and also two really considering how do my follow up actions align with the words that just came out of my mouth in this conversation? Yeah, yeah, absolutely. Yeah. Well, we, we, I love, I love the concept of painting done right, being very explicit about what success looks like, what is the end product that I'm looking for, what changes need to occur, and then providing the supports to get there. It's not fair to look at someone and say do better, like get better, do a better job if you're not really clear about what's necessary. And then here's the supports and tools to help you get get there. Here's the kind of coaching that we're going to provide. Here's some training we're going to provide, whatever the pieces are, Tiffany and I believe strongly that our primary job is to coach up and help people get better. And that doesn't happen just because we tell them to. It takes a lot more, a lot more finesse than that. So.

31:11 Yeah, yeah. I want to know before we start to close the episode, are there tools or strategies that you want to leave people with or strategies or tools that you're thinking they're not going to gain clarity around this in this single episode, But if they could gain clarity around something, here's what they need to gain clarity around in order to have tough conversations that leave them and their dialogical partner both feeling confident. What, what would that be? What do you, what do you feel like after you listen to this episode? You've got to go really think about this. Well, we have actually, on our website, we have a planning guide for tough conversations.

31:58 And you can actually go print that off, Eric. And I've been doing this for years and we still print it off ourselves, right? But it's helping think through that conversation before we have it, you know, having that preparation, thinking about what am I going to say? How am I going to say this thinking about what exactly needs to be said? You're anticipating obstacles. You're thinking about how you want to wrap it up. You're what you said, Casey, about asking those questions to show curiosity. You're writing down. This is the question I want to ask when we're in the moment. You know, even like we wrote a book on this, I still my heart sometimes will race in these conversations. My hands will get sweaty. I'll be thinking, you know, about how I want it to go and there there's still stress that I feel. So I'm not going to do my best on my feet, feet thinking of the question that I need to make sure to ask or remember. I have to say this.

32:53 So I write it down. We fill that out and then Erica's going to laugh at me. But I like to have my notes with me. And if I'm sitting next to the person, I don't want them to read my notes, so I write in a very light pencil and so I can see it and they can't. Which is. Which is is helpful to be able to have it with me and it's way easier if I'm on the phone. But. That planning guide is is just. It's a really useful tool. And it's free download, so we encourage everyone to grab that from our website because it really is helpful. Yeah, and that will be LinkedIn, the show notes. So guys, be sure to check that out. I'm absolutely going to check that out. And I'm so, so, so excited to get my hands on your book because I don't have it in my hands yet. So tell us about where we can find the book. The best place to grab our book is if you just go to our website, we have links to Amazon and Kindle and all of those places, and you can get to it directly that way. That's the easiest.

33:57 You can also find all of our free resources and tools on that same website and our social media, which we would love for folks to to hop on because we share lots of free content and free resources all the time. So our website connectingthroughconversation.com and of course it's just on Amazon too. So if you're on Amazon, look it up and it'll pop right up. Yeah, great. OK, this has been so good. And I could talk to you. I could talk your ear off about having tough conversations. It is one of my favorite things to talk about because we were never taught not to have the tough conversations. OK, final, final thoughts. What do you want to leave our listeners thinking about after they listen to this episode?

34:45 I think what I'd like to leave folks thinking about is just if you're thinking about a conversation that you're like, I really feel like I should have this conversation, please do it. It's so important to just take that courageous step, step into the conversation, and you will be better off on the other side. And we hope that you'll pick up some of these tools and tricks that will help you do that with a little bit more confidence and skill. I think I would say just remember when we're in these conversations, if you can control yourself, if you're able to control your own emotions, the way you show up, your tone of voice, you've done a great job. So really just thinking about how do you how do you control you?

35:30 Yeah, yeah. That's awesome, ladies, Thank you, thank you, thank you for coming on this podcast. Everything that you guys have heard listeners is going to be in the show notes so you can check out the book, the resources, all of that in the show notes. And definitely you're going to want to connect with Tiffany and Erica and get your hands on their book. Thank you ladies for joining me. Thanks, Casey. Great to be with you. Yes, that's a good talk, Casey. Thanks for having us. We loved this. Absolutely. Okay guys, we will catch you in next weeks episode. Bye everybody. Hey listener, I am so honored that you listen to today's episode and I hope you gained something valuable from it.

36:11 I'd also be honored if you did ME3 solid favors. First, subscribe to this show. I've got a lot of great content coming up, and I don't want you to miss any of it. Second, be sure you're following me on social media platforms. You can find me at. Catch up with Casey on LinkedIn or Instagram. And finally, if you were looking to book a dynamic and relatable speaker for your next event, conference, or retreat, I would love to bring a message about how the crash of clarity makes a significant impact on both leadership and life.