Hard School Conversations: Talking With Families, Admin, and Colleagues When You’re Scared To

Some of the most stressful moments in education aren't with students; they're with adults. In this episode, executive assistant and advisor, Ashly Smith, joins me to unpack hard conversations with team members around contentious topics like behavior, safety, or intervention and support. You'll get language, perspectives, and planning tips to help you speak up without burning bridges or burning out.

This week, I have Ashly Smith with me. She is the executive assistant to the CEO of a company that acquires and supports small businesses, and is the partnerships advisor to the board of TLC nonprofit. So, Ashly, I know in your current role, as well as a bunch of former roles, you have navigated all kinds of contentious conversations, with all kinds of different murkiness around that interaction in and of itself.

I've also had the opportunity to be part of conversations where you have navigated dissension really, really well. And I do believe that that is a skill set. And in education, in my opinion, a lot of what we do can kind of bubble up into these contentious conversations, or if not managed early, can then become contentious. And so I'm curious for you, as we start thinking about just navigating these contentious conversations and engaging in conflict in productive ways, what are some of the first thoughts that you've got coming up?

It's obviously something that no one is ever excited to have a contentious conversation, a difficult conversation, when you're in any workplace, whether it be education or otherwise. I obviously have experience outside of the education sector, but I have been a manager of people, I have been managed by people, and I think that having those kinds of difficult conversations is never fun. But I think with the right preparation, they can be a lot easier, and they can be super productive if you want them to be. And I think that it's just as important to be prepared to give them as it is to be prepared to receive them.

If somebody has to have a difficult conversation with you, don't get super defensive; take it for what it is and use it as a learning experience. And that's always how I've kind of come up and out of those. Maybe in the moment, I'm very frustrated to be having them, or I'm frustrated by the critical feedback or whatever the case may be, but I think that there's always something to be learned from those kinds of conversations.

Yeah, I mean, the phrase "Don't take it personally" sounds so great, but that is so hard. Especially when the feedback may feel very personal, maybe in how it's delivered, or maybe it is actually personal, corrective feedback. But how do you then... how do you do that? How do you receive something that could feel really hurtful and still be able to walk out with that perspective of, "So, where do I go from here?" As opposed to just being run over by all of the other thoughts that can be coming up at that moment.

Yeah. I think that one of the things that I really try to remember is that we're all human beings, and we all have so much going on in our lives, whether it be personal or professional. Maybe this is like you've had a really hard day. Maybe you're, you had a difficult time getting your kids out of the house, and you were late for work, and you hit traffic, and it feels like sometimes we just hit one thing after another, after another, and then somebody comes in and wants to have a conversation with you about your performance, and it's like, that's it.

It feels like the end of the world. It feels like the last thing you needed in that moment. But stepping back from it and understanding that this isn't a personal attack. It's a learning opportunity. It's an experience that you need to be having, and it's something that's going to ultimately make you better in the long run. But I also think from the other side is to understand that they are a human being and it isn't a personal attack, and that it is something that they wouldn't be telling you if they didn't care and they wanted you to improve.

I feel like I try to do that in all of my experiences, professional and otherwise, is to understand we are human beings and we come from places that are shaped by our own lived experiences. And so when some people are really direct with their feedback, and some people sort of tiptoe around it, "Well, maybe you could get better by doing, um, you know..." And so, it's like, "It's okay. Just be direct." And giving people permission to be candid with you if you can take it. But in the moment, I think it can be a little difficult depending on what your day was like, what your week was like, and how your interactions have been with this person previously. That all takes a factor.

Yeah. Thank you for calling that out, because I think it's, it's two-sided on this. It's on the receiving end; it's knowing, am I in a place that I can actually handle this type of feedback right now? And do I then have those words that I can put to it to communicate where I am personally at in this moment? Not to negate or delay engaging in receiving that feedback, but then also if I'm the one providing that feedback, doing that in such a way that I am allowing that person to provide that feedback and then honor it. So, I know when I've had hard conversations, especially within our team, because I know, the folks who have stuck around TLC, there's just, like, this internal drive that is what is getting them to show up and do hard things with people who are walking through hard things. There's just a certain kind of person that really seems to land well in TLC, but that does mean that then any type of feedback is almost immediately personal. Like, it feels that way. Although it is not at all intended to be that way whatsoever.

So I've gotten better over the years of saying like, "Hey, I have some feedback and maybe like some curiosities that might feel a little critical. Are you in a headspace that we can have that conversation now, or do you want to send me a calendar invite for when you're ready?"And putting something like that out there or being like, "Hey, this is time-sensitive. I'm so sorry. We need to have this conversation because we got to figure this out now. What is the best way for me to share my observations and ask you those questions so that it won't feel in any way that I'm not intending for it to feel? How can I navigate that conversation with you in this moment?" That I have found to be so protective, because then I am truly in that moment, giving all of the control to the person who's technically on the receiving end, but they can drive that.

Now, if they don't have the words for that, then I'll support like, "Are you feeling this way? Is this okay? Is this not okay? I'm noticing this. Do you want me to change that?" As we're having that conversation, but that's the behavior side of me coming out. But when you're walking through these conversations, what are you noticing? And I know you've been a manager of people. You've also been managed by people. What are some of those examples of times that you've seen it really work, either as you're providing that critical feedback or if you've been receiving the critical feedback, being like, "Oh, that was hard, but I really appreciated how they framed that," or like how that experience all played out even though it was hard.

Yeah. So I think one of the reasons you and I get along is because I think we take a similar approach in understanding who we're talking to, and you're really good about knowing your people and knowing their strengths and weaknesses, and understanding that if I say this in this way to this person, it's really not going to land and it's going to make a bad situation worse. Whereas if I said it to Ashly, for example, like, “Oh no, she can take it. She just wants it straight. She does not need me to tiptoe around her feelings. She has a tougher skin and therefore like…” You know? So I think really getting a good understanding of the people that you're trying to have these conversations with.

And I also think that the way that you even use your words, sometimes it can be really hard to articulate our thoughts, or you get nervous and then things jumble out the wrong way and you end up hurting somebody's feelings unintentionally. When you recognize that you've done that, make it right. Coming back to it and saying like, "Hey, I wish I had handled that a little bit differently. We're all human. We all make mistakes. And when I was providing you with feedback the other day, I think I was not clear on what I was intending, and I just really want to clear that up because it's important for me and you to have a good professional working relationship."

That, I mean, I literally just did that the other night. We were in a time crunch, and I came out a little more direct than I typically would with someone who's usually pretty thick-skinned, so I'm not as concerned about it. But in that moment, I noticed that shift. Because we're on a video call, I noticed that shift and I was like, "Oof, I misstepped here." So I called it in the moment being like, "I'm sorry. Let's reset and try this again." But then, after we'd hung up and what needed to get done was done, have you ever had that like that- like it's just kind of eating at you? That kind of moment.

And so I literally messaged them and was just like, "Hey, this still isn't sitting with me. When would be good for me to debrief this? Because I owe you an apology, and this is on me." But to just own that and then it's up to them. If they take me up on it, okay. If nothing else, then I at least communicated like, "Yeah, that was me. I get that. I own that." But I guess I didn't recognize how uncommon that was until some of our folks were giving me feedback, being like, "Nobody does this." And I was like, "But why?" If it's mine to own, I'll own it.

I feel so strongly about that. I'm such a processor, and I replay conversations that I've had for typically an hour or two after I've had them, especially if they're difficult or if they're just something where I'm like, I'm trying to get at the root of somebody's psychology of why they're acting the way they're acting or why they're making poor choices in their life. And then, if it's like a friend, for example, they're coming to me with the same issue constantly, and after we talk about it, I typically take several hours to process all the things they said, how I reacted to the things they said, and why they're making these choices.

And so it's always been really interesting for me to understand what makes people tick and how I can support them and say things that maybe they hear differently coming from me. I'm not in your situation. I'm not trying to run your life. And it's that age-old adage: are you looking to vent, or would you like feedback? Are you looking for a solution, or do you just need somebody to yell to? Because if that's the case, I just want to know what we're looking at upfront.

Yeah. And again, I think that goes back to being able to not only open that space for I can be part of this conversation in multiple ways. What is what you need right now? And I've definitely been in situations where I've offered that. Like, is this venting or is this solution-seeking? And I'm game for either one. And if someone's venting, then it's like, cool, that needs to happen. Get that off your chest, get that out of your head. That needs to happen. There's absolutely a time and space for that.

I will say I kind of time-block that a little bit because, especially when I'm working with teams, sometimes it can become like glorifying the problem, which then is really hard to come back from when you're then trying to find solutions. But regardless, there is a human need to like, "Let's get this out there. Let's get it out in the open." And then it's, "Okay, now are we at a place where you want some solution-seeking support? If yes, now or later?" Is it something that you're ready for now? Do you feel better in this moment and now we've got a clear mind and we can start trying to find some potential angles here? Or do you still need to brew on this a bit more, and then let's come back to the table and figure out where to go from there? But I think in both of those, it's still like- I'm here for it. But what do you need in this moment? And then can we continue to keep moving?

Yeah, let's keep it productive. Let's not get stuck on it. Let's not circle the drain and beat the dead horse, and yeah. I think a lot of people, specifically people who get stuck in that negative spiral or- I was just talking to somebody yesterday about how some people just feed off of drama. It's their standard. It's what they know. And so if it's not happening to them naturally, they'll create it, and they just tornado through life and tornado through people's problems to create difficulty where there just isn't any because it's what they thrive on and what they feed on. And that is, I mean, it's just such toxic behavior. And so I think it's really important to be like, “Okay, that's a tough situation, but let's get back to how we can solve it and not get stuck on the negativity of the issue.” I think that's a really good point you're making.

Man, you're making me think of a case we supported last year, and it was one of those situations where we had kind of identified some of those tendencies within some team members where it's like, if these problems become non-problems, then some of what seems to be driving certain members of this team, we're gonna need to find something to replace that. Because then what we started noticing is as progress was being made and everything was moving in the right direction, there was a lot of really solid collaboration, and then we started noticing some of those team members going a little rogue. We noticed one team member in particular almost seemingly sabotaging some pieces.

And so we ended up having to sidestep some of what was going on and really learned that there was some fear around, "Well, if there isn't a problem, then I don't have a job." And when, when you're tasked with supporting problems, when there are no problems, then is the support no longer necessary? And we had to walk that through with the team members to say, "Look, just because you're not solving current problems doesn't mean they're then not preventing future problems." It's just a matter of if it's active now or if you're kind of keeping it from becoming active.

But both of those are very valid roles. It's just a matter of whether you're on the reaction or are you the prevention? But both of them- there are problems that are either happening or would be happening, and your support is that game-changer. But it was that perspective of if there isn't a problem, then other fears start creeping in to the point that there just needs to be problems.

We've also worked with team members that are so used to having those hard kids and being able to have that almost be part of their professional self-image that, like, "I work with hard kids, and then I need to have the valor stories of how hard these kids are to show that I am that professional that cares for them." And I will say, as someone who has spent my entire career working with kids that all kinds of systems have defined as the hardest of the hard kids, I get it, and I've been surrounded by it, but that is a really hard one to break down where it's like, well, yeah, they are hard. That's why they're here. But, if it's working, then that's also a marker of your professional expertise that, like, it's working. And that's not necessarily a problem, but it's really tough then when "I solve problems" becomes who you are and now all of a sudden you're not solving problems. So then, professionally, who are you?

Yeah, I can understand that. I used to work with a guy who we would call the pot stirrer because it was like he was always just trying to justify his job. He was just this person who was constantly like, "Well, I come in at seven o'clock," and then he would just almost create a problem, and then he would ask four or five different people to solve it. And, and then it's like... So eventually, I had to have a hard conversation with him. "Hey, listen. I noticed that you brought this problem to three or four different people. I'm not sure that that's a really good use of all of our times. So maybe in the future, we could just schedule one meeting and, and talk about the problem together and then figure out which one of us is gonna solve it because we all have a lot of work to do here. And I know your job is important and I, I know that..." It was obvious he needed his ego to be boosted a little bit and that, like, "Hey, don't worry. We don't think you're not working here. We just also need to not spin up six people to solve the same problem and hope to get the same result. It's just not a good use of anyone's time."

I know I've worked with some teams that felt like some of the families that they were trying to support were doing something similar. They were back-emailing, or they were dropping people off of communications and only sharing certain pieces of information with certain people and then holding that against other people. I've also watched team members do some of that amongst themselves as well. So I don't think that's unique in terms of inside of school or outside of school. I think it's just human dynamics.

But so, how do you walk that in a way that is acknowledging the problematic form of communication that is occurring, but also trying to then rally people back into, like, "So let's figure this out together 'cause clearly there's a lot of moving pieces here and we all have different strengths to play, so can we then get all the facts on the table and then figure out where all of our expertise will land to be able to actually support whatever it is that's going on?" How do you move from all these back-channel pieces and playing people off of each other to now it's all out in the open? How do you walk teams through that?

I think one of the, my most famous lines via email is, "Just to be clear," or, "As a point of clarity," because I'm such a believer in transparency and I just don't want there to be that kind of... Sometimes it's necessary to backchat if you're discussing something that's confidential in nature. But let's get all on the same page here. Let's just be clear on what we're asking for and what we're talking about and what we need from each other, because I don't find that that's like... It's like that drama that you're creating and it's unnecessary, and let's just all be clear, let's just all be transparent, let's just all get on the same page. I know there's a way we can work together. Let's find it. Let's work together to solve this problem. Let's have it be us versus the problem and not us versus each other, and all trying to justify our jobs in order to get the solution first or whatever the case may be.

Yeah, and I think you and I align on that really strongly. But I think as a result, we both really struggle to work with- I don't know if I would consider it people-pleasing, but just almost so conflict-averse that they just become completely passive, but they're not in agreement. And even walking out of those conversations, even if they sign themselves up for things that they don't agree with, they may not even follow through with that, which then causes the whole conversation to come crumbling down anyway. How do you walk that with folks to draw out their actual thinking when they're so conflict-averse that they won't even engage it? Is there anything you do before that group conversation or any follow-up after? How do you support those who are so anti-contentious conversation that they just really don't bring their voice to it?

Again, it goes back to knowing your people and knowing what they're going to sign themselves up for. And you always talk about it really well in the keep/toss list. What are we going to keep? What are we going to toss? What are you working on that maybe you're not super passionate about? And so you allow people to have that kind of productive control or that sort of control over what's in their domain, and so it doesn't make it to where you feel like, "Oh gosh, I don't want to let Heather down by telling her I don't want to do this anymore, even though I agreed to it." And so I think when you create-that's something I learned from you- is that you create this environment where people can be honest.

And even the person that ran partnerships before me, you saw that she was burning out and that she just didn't have the time for it anymore, and you gave her that ability to say, "Hey, it's okay to step away. I know this matters to you. I know this organization is so important to you. I know that this role is important to you, but also, you have a life, and you're a human being, and you can step out of it if you need to. We'll be just fine. We'll pick it back up, and we'll figure it out."

And so I think a lot of that comes down to creating that environment where people can be open and honest with you and know that they have your support and that they're not letting you down or letting the team down or making somebody feel bad. But I think the other thing is when you do have somebody who's really conflict-avoidant, one-on-one communication is always going to be the number one solution to that. If they are conflict-avoidant and they are not going to speak up in a group- like, there's no way. You have to talk to them one-on-one and make sure you're making them feel like it is a safe space and that they can come to you with that kind of information. Like, "Hey, I know I signed up for this, but I'm not on board for it anymore."

Or, so much of the time, like when I first started with TLC, I was just like, "I don't know what you're talking about," or, "That happened without me." And I never felt stupid asking you questions because you never made me feel stupid. You never made me feel like, "Well, gosh, Ashly, you've been here for two months already. How come you don't know that?" You never ever made me feel that way. And so it made it so much easier for me to raise my hand, "Hey, sorry, I actually don't know what you're talking about. Can you give me some more detail on that?" Or, "Can you give me more clarity on that?" That's my favorite way.

Yeah, and I think in those group moments, I think I'm just being very aware of, I know this person has thoughts and they're typically sort of forthcoming, and in this moment they're not. So it's like, okay, then for whatever reason, and I may never even know what that reason is, but for whatever reason, they're not perceiving this as a situation where they can speak freely. And so for me, that tends to then be the, "Hey, I feel like you've got thoughts you didn't just share. When would be a good time for you to just unload on me?" I would love to still hear what you're thinking, even if it's not with the group or even if a decision has been made and things are moving; I'm still curious.

And that has helped people then see, “oh, maybe the situation that I viewed in a certain way actually wasn't,” and then they start to engage differently in the future. Other times, I have learned that there were some people that seemed fine, being able to hold their own and speak their mind, and it was a bit of smoke and mirrors. That they were not as confident as they were coming across. And by having that conversation behind the scenes, I was like, "Oh, you're a pre-meet person." And so then it's like, okay, so we're going to have this interaction or this thing is coming up, and I can tell that that's going to kind of raise a certain awareness or heighten this within that person.

"Hey, before we do that, when is good for you?" And then we'll have that conversation, and then when they get to whatever that moment is where it actually needs to happen, we've already walked it. There is no surprise there. Maybe other conversations or reactions in the room or at the table, kind of whoever is part of whatever it is that's going on, but they've already had that opportunity to process it out, to get some initial reactions, and then to even discuss how do we think this will land and what do we think are going to be some of the reactions that might happen?

And then, what are your thoughts there? And then sometimes I can just mitigate on behalf of. But then those times I have found it to be so helpful because people who may have shown up a little bit more meek, or withheld what they were thinking, they'll at least sort of do that initial- they'll baby-step their way into it, which has been really cool then because especially other team members start to see them differently.

And then it's like, "Oh, wait, what? Like, you were thinking... Oh, that's cool." And then you start seeing this other side start to show up when you're able to walk that out in such a way. But yeah, I think some of it is just assuming that maybe people have more to share when they're not sharing, and that there may be other pieces going on. And for me, I'm always just like, then fill in the gaps. And I don't really care if that's at this table, in this group or not, but, I want to know what you're thinking or kind of how you're perceiving the situation, because those conversations for me as a leader have been gold. Things that would never be said in a group I may have never even been aware of, but it's so informative well beyond just that one decision or that one conversation.

Sure, yeah. And I think it's always nice when you have the time to prepare for difficult conversations, because you're going to have them. And sometimes you don't have that luxury, and it comes up in the moment, and then you're like, "Oh, I have to, I have to deal with this right now. I don't have time to gather my thoughts. I don't have time to write up a draft of all the points of what I want to say or how I want to cover this." So, that can be difficult as well.

Yeah. I mean, I did that at a board meeting a couple of years ago now, where I thought we were all on the same page, we were good to go, we were moving a certain direction, sweet. I'm just filling in the details and rock and roll. And it was a full stop. And I just remember internally, I had, like, all the thoughts, all the emotions. Everything was like, "What the what?" But I literally just put it into words. It's like, "I was not anticipating this level of resistance. I'm sorry. I'm not handling this well right now. I promise I will pull myself together, hear your feedback, and then come back with some other ideas." But I just put into words, "I wasn't ready for this. This is not what I had anticipated."

And in that moment, kudos to our board; they walked it back. Not their stance, but the way that they were approaching it when they were like, "Oh, okay. So then..." And then it became solution-seeking still. The decision is not changing, but the entire interaction in that moment, simply because I just put words to, "Whoa, was not ready for this," then it became, "Okay, let's figure this out then," because they didn't realize we all thought we were all on the same page, and we were very much so not.

And so just putting that in the room allowed that entire interaction to completely shift and become so productive in that moment, and then actually be on the same page walking forward into whatever the next decisions were that needed to be made. Yeah, I was not ready. I felt very, very blindsided when typically we're very cohesive. But I also think I was lucky in that moment that I could tell them, "Hey, I'm feeling blindsided right now." That I saw them in that kind of a way that I knew that I could say something like that, and it wasn't going to have catastrophic outcomes or something to come from that type of a feedback live in the moment.

Nobody wants to be blindsided by anything. And so in my previous life before the job I'm in now, I was in renewable energy. And so I worked as a director of community engagement. So first of all, it's almost always contentious going into these local areas. There's so many people who are so supportive of renewable energy, but it's like a, we call it NIMBY, not in my backyard. So it's like, "Oh, great, you can build your solar farm, but we don't want to have to look at it." And so I had to do so much preparation leading up to these local meetings because I knew the stuff I was going to hear.

You hear it in one area, you hear it in all the areas. And so understanding where these people are coming from and letting them know that their concerns are valid went so far in letting people be heard and understood. And I think the same goes for those types of situations as you had with the board. Like, "I hear you. I'm, I don't want to be blindsided by this. Let me assuage your feelings by explaining where I'm coming from and how maybe we can find a mutual win here."

Well, I know both you and I tend to be people who are like, we actively look for the silver linings. I mean, I've spent the bulk of my career working with students who, in a lot of different ways, express all of the challenges that they are personally experiencing. And even in those moments, I've always looked at it saying, like, "What can I learn from this?" So while a kid is cussing me out or destroying a room or all of these things, being like, "What am I missing?" And choosing to look, like really look, not just see the damage, but to see, like, "What am I missing here? What is this actually opening up for me that I didn't catch in all of these other ways?"

And I think I've carried that perspective from working with my students into working with adults, saying when I get the staff member that shuts down, when I get the administrator who just blows up on all of the things. Whoever that may be, however they're showing up, like, "What am I missing, and what is the opportunity here to learn how they're actually seeing something so that we can then figure out what is the angle, what is the direction, what is that opportunity to continue to make forward progress together on whatever it is that we're, that we're working on?" But I know you and I are just sort of built that way.

I know. Sometimes it's easier said than done with people who are like, "Yeah, that's fine for you, but I couldn't do that." I ruminate on it, and I overthink it, and then I beat myself up about it for three straight days, and I can't learn from it. I'm too distraught over the situation. Yeah. And you can't teach that. It's just something that's a natural tendency that people have, but I think coaching people like, "Hey, this is how I might handle that," opens their minds to a different way, which I think is always helpful.

Well, I mean, this time of year, we are talking about all the scary things in education. The honeymoon is over, and all of everything is showing up right now. So, hard conversations are part and parcel of everybody's experience this time of year in education. I'm curious for you if there's anything lingering, if you're picturing kind of yourself talking to these team members who are potentially staring down the barrel of early burnout, and, "I'm just done 'cause everything is hard, everything is contentious, and I'm not seeing that win, and I am taking things personally." This is that time of year when it starts to build.

So I'm curious, as someone who has figured out your own ways of how do you continue to persevere when things are really hard, or to see situations for what they are and then let them go, to put them in their place? I'm curious just what are some of your final thoughts that you can use to kind of encourage folks to continue to walk into the second half of this semester?

I guess I would say that whenever I have kind of a hard time, or if things are not going my way and it feels like it's compounding, we talked about at the top of this, that it is important to take a break from it. And I think when you see people who look like they are really struggling, to give them that kind of extra care and attention and like, "Hey, I noticed this." People just sometimes need to be heard and need to be seen and feel seen in a way that I think so many people are so self-involved, and they just don't notice other people around them.

And so it's really important to have people on your team who are that way, who see people and who see things in a way that maybe you don't because you're busy with 17 other things. If you can incorporate a team member, I think a lot of corporations these days are calling them chief people officers or it's some version of that within the HR structure whose job it is just to care for the people and to see people and let them feel seen and heard and that they're not alone. There's so much relatability in the world, like how people, they go online and they talk about these deeply personal things that have happened to them, and it's like, "I'm not sharing this because I want the attention. I'm sharing this so people who are in my boat don't feel alone."

I've had this chronic health condition for 20 years, and I had to lose a lot and gain a lot from going through that. And I know that telling my story might help somebody in that boat understand that you're not alone in having that experience. You're not alone in not being believed by doctors or being misdiagnosed or whatever the case may be, like insert said problem. But I think that when you have somebody who's just watching out for folks in that regard, it's really beneficial.

I could not echo that more. Yeah. Gosh, that could be a whole other conversation that is coming to mind right now. So thank you so much. I know it is kind of an unglamorous position to have to navigate contentious conversations, and especially for folks who are just built for it. I recognize how much of a thankless type of role that can be. So truly, thank you. Thank you for navigating contentious conversations in amazing ways so that it's not just a problem, it's not just these end-of-the-road moments, but it is actually productive, and it's good for everybody who's engaging in that moment as well as for any of those future outcomes that may come through it as well. So thank you. Thank you for showing up in those ways and putting some words around it here with me today too.

Yeah. Well, I could say the same to you because you have taught me a lot about difficult conversations and about how to navigate that and feel seen and feel supported, and I think you're really, really good at that. So thank you.