What Do I Do As An Executive Director - Engaging in Hard Conversations

Nathan Ruby: 0:00

Focus on the process. In my experience, hard conversations are seldom resolved in just one meeting. It usually takes multiple meetings or even a whole series of meetings to achieve your desired outcome. By focusing on the process, you won't be emotionally invested in what happens in the short term.

Tim Barnes: 0:22

Welcome to episode 101 of the practice of non-profit leadership. I'm Tim Barnes.

Nathan Ruby: 0:27

And I'm Nathan Ruby.

Tim Barnes: 0:29

Well, nathan, I'm excited about our conversation this morning because I think we're pushing into something that I know I struggle with sometimes, and I know a lot of leaders do, and that's having hard conversations, being willing to step into that.

Nathan Ruby: 0:45

You know, and as executive directors, those hard conversations are coming and if you haven't had one yet, there's one right around the corner. And I think hard conversations are a indicator of how I don't know what the word I want, tim how hard an organization is pushing or how, if your organization and you as a leader, if you're not having hard conversations, you're probably in the status quo and there is no growth that takes place in the status quo.

Tim Barnes: 1:23

Well, I have to say that one of my favorite books over the last 15 years or so was the Four-Hour Workweek by Tim Ferris, and he made a comment in there. He said a person's success in life can usually be measured by the number of uncomfortable conversations they are willing to have, and I think that's so true. But, nathan, before we dive into this conversation, I just want to say I hope our conversation with our listeners have enjoyed our 100th episode last week. We sure enjoyed recording it with Christina Edwards. It was great. Christina did a wonderful job and it was great to look back and talk about why we even started this podcast and as well as thinking about some of the successes and some of the not so successes as well, but it was really fun.

Nathan Ruby: 2:15

Yeah, there's plenty of both plenty of successes and plenty of not successes as well. And just to let you know that, tim and I, when we come up with this stuff, with these things that we talk about, we actually are practicing what we preach. After we recorded the 100th episode, we had our own hard conversation, and that conversation was well, what's next? What's the next 100? And we did talk about a little change and we did talk about some new things that we'd like to do, so we're not quite ready to announce those yet, but there's some different things coming up that we'd like to do, so we're working on those behind the scenes.

Tim Barnes: 2:58

Well, as we went back, and we looked at our most downloaded shows just to kind of look up for some trends. We realized that our number one downloaded show is actually show number 75. How do I spend my day as an executive director, which dropped on February 15, 2023?

Nathan Ruby: 3:19

Yeah, and not only is it our most downloaded show, we still, six months later, get questions from listeners about that episode.

Tim Barnes: 3:29

So we've decided to dive in a little deeper to this topic and over the next few weeks we're going to keep coming back to this topic and get a little more specific about how do I spend my day. We're going to try to share out of our own experiences and just kind of wrestle with some of the questions that we get about that as well. So, nathan, hard conversations where are we going to go on that today?

Nathan Ruby: 3:54

So what we're going to? Well, first of all, we're going to define what a hard conversation is, and then we have four key points that you can use as a way to make those hard conversations maybe a little bit easier, a little bit better and have a little better outcome after those conversations. But first let's define what we mean by a hard conversation, and a hard conversation refers to discussions that are emotionally challenging or difficult to approach. These may involve conflicts, disagreements or sensitive topics that require careful communication to avoid further complications. So that's what we're using as a definition. So let's go into point one, and one of the things that you've got to do before you ever even get into these conversations is have a very clear definition of what your outcome is. So what are you looking to achieve through this conversation or these series of conversations? Are you trying to change a behavior? Are you trying to change a decision that one of your staff people made or a volunteer made? And as you're looking at that outcome and what it is that you're trying to achieve, make sure that you're addressing the root issue, or the root cause of the issue, and not the symptom.

Tim Barnes: 5:26

It's always interesting to me when do you decide to dive into this kind of a conversation and when can you just like, oh, it's no big deal, just let it go, I'm not going to have to worry about that, and the outcome probably helps us decide that If there's a behavior that's really dragging us down, or if there's someone just really did something, made a bad decision or all those kind of things. But trying to figure out when do I really need to have that conversation and sometimes can be challenging too.

Nathan Ruby: 5:59

Yeah, and the phrase is always used you don't have to die on every mountain and you don't have to address everything right off the bat, and I think sometimes it's also some of the bigger issues that you may have to deal with. Maybe you practice on some of the smaller issues so that you could grow as a leader, you grow as an individual, you get a little bit better at this and then you tackle progressively more difficult issues. However, tim and I'm sure you've had these as well there are times where, even if you're not prepared and you don't feel ready, there's something that has happened that you have to address, and in those cases, you've got to tackle it and do the best you can do. So I think, an example of figuring out outcomes. So here's kind of a common issue that pops up for executive directors You've got a board member who dominates the conversation. They talk over people and they actually influence the outcome of votes on really important issues, because other board members are really reluctant to speak up. So what do you do? Well, all right. So first of all, you obviously have to define the outcome. What is it that you want from your boisterous board member? What do you want that board member to do? Do you want that board member to stop talking so much? Do you want them to continue to express their position but tone it back a little bit and just kind of chill out and not be so aggressive in it? Do you want them to? Do you want to ask that board member to wait five minutes into the discussion before they launch off into whatever their position is? And there's probably other ideas as well. The point is is that before you would have that conversation with that board member, you want to be very clear in what it is that you see as the best outcome. And then the last thing I would add to that, tim, is changing a behavior is much, much more difficult than changing an action or saying, hey, you know, this is the action you took this time, and next time I'd like for you to think about taking this action. That is a much easier thing than trying to change somebody's behavior.

Tim Barnes: 8:30

People may not even realize they're doing it. You know, sometimes it's not necessarily going in confronting all at once. Sometimes it's just asking a couple of questions to help them begin to see the impact they might be having with their actions, until they realize that it's kind of hard to change things right.

Nathan Ruby: 8:49

Yeah, absolutely. And you know, as a leader, in that situation where you've got that board member and you know that other people on the board would like to make input or would like to speak, and they're just because of their personality they're struggling to do that, one of the things that I've done in the past is, I would say, let's say, the boisterous board member is Mary and the board member who's not responding is Sally. And so as the executive director, I would say well, you know, we're pretty clear on what Mary's position is, and I would say it with a little bit of humor and get a little bit of a laugh or a little bit of a response that way. And then I've said you know, sally, I'd love to hear what you think, and that gives Sally the microphone, so to speak, and it gives her the permission and it gives her the encouragement to give her position. And typically what I found is what I say, mary, then it's also a social queue for her to ok, mary, it's time for you to Zip it, and I don't say zipped, but it's not. Most people will get that, that queue. So that's another way that you can handle that. But you, that is something that I would, if you're gonna do something like that, you know kind of mentally, practice that ahead of time and have your what you're gonna say, maybe even Practice what you're gonna say, that so that when you're saying it it kind of rolls off your tongue, as opposed to stumbling all over it.

Tim Barnes: 10:22

I do appreciate. What you're saying to Nathan is that it is important to consider the outcome. Sometimes it's easier, it's easier just to go with. I wish I would just be quiet, but it's really good to be able to say, hey, wait a minute, what is? What is a good outcome for the conversation I might have to To have with them, so that's a really good point number two.

Nathan Ruby: 10:44

Number two is mindset. And you know, if you go into any conversation, any difficult conversation, with the mindset of oh my gosh, you know, this is terrible, I don't like confrontation, I don't like to, I don't want to do this, you know you get up at, you know, whatever time you get up in the morning, you got the meetings at nine o'clock. We're gonna have this conversation and you just, you know, you kick the dog and don't actually kick the dog, but you know, you yell at your spouse and you yell at the kids and you're just, you're in a, you're in a cruddy mood because you just don't want to have this conversation. Well, guess what you're gonna? You're gonna take that mindset into that conversation and you're not, probably not gonna have a good outcome. But on the other hand, if you look at these hard conversations as opportunity and it's, it's an opportunity to make things better, to have better understanding, to have a better connection with whoever you are interacting with, whoever the conversation is with. So, if you look at it as an opportunity, you will feel better going into that conversation. And you know another thing mindset is focus on the process and in my experience, hard conversations are seldom resolved in just one meeting. It usually takes multiple meeting, meetings or even a whole series of meetings to achieve your desired outcome. And by focusing on the process, you won't be emotionally invested in what happens in the short term. And because some of these, some of these situations that you're gonna be dealing with there, it may take days or weeks, or even months maybe, to to get that outcome that you're looking for. So you're taking little baby steps and if your mindset is okay, I'm gonna suck it up and put on my big boy or big girl pants and I'm gonna go into this meeting and I'm gonna have it and then, when I walk out of there 45 minutes later, everything's gonna be solved and everything's gonna be perfect. Well, that's not how this stuff works. And if you're believe, if you believe, that I just gotta do suck it up for 45 minutes and I'm done, well then that you know as, as it takes longer and longer and longer to actually solve it, you're gonna get more and more negative and depressed about it. So, right mindset and focus on the process.

Tim Barnes: 13:14

I remember hearing a friend talk about. He was. He was sharing about how he was having a really Hard conversation with his spouse and really kind of going back and forth. They were trying to work through some things. And he said, hey, do you think I like having these hard conversations? And she said she looked at him and said what are you talking about? That's what relationships are. If you really care about someone, you have these hard conversations. It's all about relationship. And it really challenged him because it's like I don't want to do this, I don't want to have to argue about this, I don't want to ever. Relationships require challenging conversations and that's a mindset. It's not like, hey, I want to get the best of this person or I want to do whatever, but we're going to be better if we actually have these challenging conversations.

Nathan Ruby: 14:11

Conversations like these is a signal of growth, and you can't grow without these types of conversations. And because change, we'll call it change, because if you're having a hard conversation, that means something is happening that needs to be adjusted or changed. So we're talking about change here and you can't grow from point A to point B without growth, and that brings these opportunities. So the faster, quicker, larger that you're growing, that the organization is moving towards its mission, moving towards its vision, the more of these you're going to have. Thinking of it as a okay, there's an issue, you can't stick your head in the sand and say, nope, I'm not going to address it and we're just going to pretend like it's not happening. And you can't do that. But on one hand, you could say, oh, wow, we must be having some progress because these issues are coming up. So look at it as a positive sign of growth, not of a negative sign of oh my God, I hate my job today. Okay, number three empathy. And empathy is a good one For me. It is a little. I'm not going to say, well, I don't know, tim, maybe I'd say it's hard. Let's just say I have to focus on that. I have to focus on what the other person is thinking, what the other person is feeling, because empathy is what is the other person's perspective and every hard conversation that you go into, and because sometimes the conversation is one-on-one, it's you and one other person, it could be you and a group of people, it could be two, three, four, so it's not always one-on-one. But the other group that you're talking to you have to understand that they have a preferred outcome. They have what they feel is the right thing to happen after this conversation. And so and I think, as you look towards that empathy, and what is the other party? What is their preferred outcome? We're not doing this as a way, like in politics, they do opposition research so that they can develop ammunition to go negative campaigns with, and in this situation, you're not doing opposition research so that you can come in and impose your will on them by having an answer to all of the things that they're going to argue. That's not what we're looking at. What we're looking for is to consider their preferred outcome, so that you can look for common ground, and common ground is so important because it gives you a starting point, it gives you a place where you can hey, I know that we agree on one, two, three, four, on these things, and you can talk about those and then slowly move into whatever the issue is that you have to address. If you've listened to some of our shows, tim and I are big Cardinals fans, st Louis Cardinals fans, and it's not the best year for the St Louis Cardinals this year, but we're toughening it out, we're sticking with them and there's always next year. And if you're not familiar with the US baseball, one of the Cardinals arch rivals is the Chicago Cubs, and very strong rival, and if you talk to a Cubs fan, they don't care if they win or not, as long as they beat the Cardinals. It's that type of thing. And so you can go into a conversation with Cardinals fans and Cubs fans and have a lot of good nature animosity towards each other, but a common ground that Tim and I have with all Cubs fans is Wrigley Field, which is the baseball field. That's the name of the field that the Chicago Cubs play at. And hey, tim and I love baseball and if we get a chance to go to a Major League game, even if it's not the Cardinals, we're going, and Wrigley Field is an iconic baseball park that is a fabulous venue to watch baseball at. So if we were in a hard, difficult conversation with Cubs fans, we could start with that as common ground. We could talk about Wrigley Field and the experiences that we both had going to games there and some of the interesting architecture and some of the interesting things that's unique to Wrigley, and so that's where we would start our conversation. Then we would go to that. They have a terrible team and they have no idea what they're doing those type things. But that would come after we talked about Wrigley Field.

Tim Barnes: 18:59

I have to say, growing up in Central Illinois we are split down the middle. Here we have Cardinals on one hand, cubs on the other hand. But my family and I we moved and worked in the Chicago area for about 10 years and it gave me a whole different perspective on this. When you actually, when most of the people around you are Cubs fans and you start to appreciate, you start to appreciate their passion and their loyalty and some of those kind of things which before it was easy just to throw stones a little bit probably. But when you actually Get in the mix of it and I and I appreciate that and I agree you know really feel is a great place to watch a baseball game.

Nathan Ruby: 19:47

See, you just saw some empathy coming from Tim and an example of that, and it's a good thing that they got out of there and back down further south so you were saved just in the nick of time. So you know, a common, a common conversation, where empathy comes into play in the nonprofit world is is maybe dealing with a vendor and a lot of time. And I've seen a couple of different mindsets on on this topic and one is okay, let's say A vendor be. Let's say snow removal. You know we live in the northern hemisphere, snow is the is part of our life in the winter and snow removal can get pretty expensive, especially if it's snowing every other day. So let's use as an example. And so you have a vendor who plows the snow and one one concept says well, we're not profit and you know, none of us are making a ton of money and we're doing something that's great for the community. So that vendor, that snow plow company, they should donate their services to us. We shouldn't have to pay for that because we're a nonprofit. The other mindset is, or the other concept of that is hey, we're business just like every other business and we need to build in expenses into our, into our, into our budget, and snow removal is a common budget. It's just part of what we do, and so there's a and I think I come down on the this side of listen we're a business and we have expenses, and this is why we raise money, this is why we generate revenue to offset those expenses. And but that doesn't mean that you couldn't go to a vendor and have a conversation of hey, you know, is there a way that we can get a discount or something, that those conversations are okay. And I think what happens, though, if you are, if you are Going after free Vendors, free services from vendors all the time, that is often built on the relationship between an aggressive executive director and these vendors, and so when the new executive director comes in, maybe not as aggressive or not as good when it comes to those conversations, when you have the expectation that snow, that snow removal is free, and now, all of a sudden, you're getting a bill for it, that creates friction. So, anyway, so having empathy for the snowplow company they're trying to make money, they're trying to stay in business and and going into those conversations with that understanding takes you a long way.

Tim Barnes: 22:38

I think that's one of my pet peeves a little bit, nathan is I've seen nonprofit leaders, organizations who feel like they deserve to get special treatment and Without realizing the challenges your vendors or whoever have as well.

Nathan Ruby: 22:54

so we need to change our mindset a little bit on that, I think yeah, and you know you want you, you want a free service, you want that snowplow company come in at and you want them there for a m so that you know when you drive in at six thirty the snow is clear. And you know you want, you want this, you want this, you want this. But then you're not willing to pay for the service and you're expecting the vendor to take the hit on that. Yeah, those are, those are those. With those, that would be a hard conversation. Tim number four expectations. A difficult conversation implies that there is some standard that's not being met or a misunderstanding, or at the very least some negative action has taken place and there are at least two parties and, like we mentioned before, sometimes more. There could be more than just two parties. And whenever you have multiple people involved, you have an automatic chance for mismatched expectations. When I was growing up, my dad owned a car dealership and he would always talk to his, to the guys out in the shop, to the mechanics, when they would have a car that would come in and would have. A process was back in the seventies and eighty, so before electronic ignition. So you know, two nubs were always a big deal and and so the car would be. The car is doing acts, whatever acts is, and what my dad wanted the mechanics to do was to start with the easiest, most simplest solution for whatever the problem was, and and it's it. This comes back to expectations, and I think sometimes we assume that we have a hard conversation to make and we put in a all of the bad, all we assume the worst. I guess that's what I'm trying to say, as opposed to maybe we could just start with the simplest solution. Maybe it's just the other person doesn't understand, or they don't have the right expectation or the same expectation that I have. So where does that come out at all, right? So A common mismatch of expectations in a nonprofit setting is when a staff person says that's not my job, and that's pretty common and smaller organizations, because you have a small group of people trying to do too much work with not enough pay and it is a, it is a perfect storm for the concept of that's not my job. And and that often happens when a staff person assumes that because it wasn't expressly written in the job description or covered by the HR department, and understanding that you, the executive director, you probably are the HR department which means you didn't bring it up in the interview that that means that somebody else should be doing that. And then, from your perspective as the executive director, you're thinking listen, what we're all in this together. Everyone is doing other duties as assigned, and so that's part of who we are is is you just gotta jump in? And if it needs to be done, you gotta jump in and do it. Well, if you have somebody who is not on that same wavelength and they're saying that's not my job, I'm not, I'm not emptying that trash can, or I'm not picking up that rapper in the yard when I walk in, and then you as the executive director is saying everyone should be picking up that rapper, I'm picking up that rapper. Well, you've got a mismatch of expectations and right off the bat, you have a situation where hard conversation is gonna have to be taking place.

Tim Barnes: 26:52

I think part of that, nathan is, is at least starting with, with giving people the benefit of the doubt and saying, okay, you know, I don't want to start by saying, boy, that person is really lazy or that person is a bad person or whatever. There are so many other things that could be part of this conversation, so let's, let's start with. I mean, expectations is great. They may not have had any idea, it wasn't communicated or whatever. So, starting with the benefit of the doubt and then working down towards, okay, what is the real issue here? Let's have that kind of a conversation.

Nathan Ruby: 27:28

Yeah, and that goes back to mindset. Your mindset should not be right off the bat Well, man, did I hire a horrible staff person? Well, no, let's assume, like you said, that we've hired the right person or a good person and we've just mixed our expectations here. Well, and then empathy could come in, because, as the executive director, you should be thinking okay, what is that their job? Should they be doing that? Maybe we've got a process breakdown here, because if there's opportunity cost, that comes in. If this new staff person is picking up a wrapper in the front yard, that takes two seconds, that's more about culture of the organization. But if this new staff person is being asked to do something that takes up 30 minutes of their day and that wasn't communicated to them at the beginning, we probably have a process problem. And so that has to come into the conversation. And, as the executive director, your job coming into these conversations, tim, is to not bring your baseball bat or a 2x4 with you and beat people into submission to do what you tell them to do. That is not a long-term solution, but to say, okay, maybe there really is something wrong here and so let's talk through it. You're going to get way better outcomes way faster by coming in with that attitude than coming in with I'm the boss. I told you to do it, do it.

Tim Barnes: 29:06

So I think what we're trying to say here is hard conversations are part of the job. Don't avoid it. You have to step into it. But there are ways or processes to have those conversations that hopefully lead to good outcomes.

Nathan Ruby: 29:24

Yeah, and as an executive director, you're going to evolve. Tim and I have evolved. We've gotten better with these things and not everybody you bring into your position. You're bringing in strengths, you're bringing in weaknesses, and if you're like Tim and I, you bring in two or three strengths and then you have like a thousand weaknesses and you spend your whole career trying to make up for the weaknesses. No, I don't mean that, but it is. And so handling these types of conversations you're not going to be an expert at it the first time that you try it, but you will be able to get better, you will evolve and your ability to navigate through successful outcomes, through hard conversations, will improve over time. And will there be some bumps along the way? Oh yeah, there are no doubt about it. There will be some bumps, but you will get better and, before you know it, you will have these conversations well, you will do them well and they won't be as scary as they once were.

Tim Barnes: 30:30

Well, thanks for listening today and we hope you're benefiting from what you're hearing on this podcast. We'd love to encourage you to leave a review so other people can hear about what's going on. We'd like to get in touch with us. Our contact information is in the show notes. That's all for today, until next time.