The Difference: Nonprofit Fundraising in a For-Profit World
In every community, nonprofits compete within a narrow band of funders. Many struggle to stand out and make their case the most compelling. What difference allows your nonprofit to reach fundraising goals and achieve financial sustainability? In each episode, an expert addresses what makes the difference for major investments, feasibility studies, campaigns, and effective organizations.
The Difference: Nonprofit Fundraising in a For-Profit World
Servant Leadership’s Blind Spot: When Caring Gets in the Way
Mission-focused leaders often prioritize compassion and team harmony—but sometimes at the expense of accountability. In this podcast, host Jay Werth and guest Chris Wong, who advises both nonprofit and for-profit organizations, discuss how leaders can hold people to standards without abandoning empathy, and how this balance improves culture, performance, and impact.
This is The Difference, a podcast for nonprofit fundraising in a for-profit world. Presented by Convergent Nonprofit Solutions, a leader in nonprofit fundraising. Convergence professionals can help your nonprofit secure sustainable funding now and for the future. Welcome to The Difference.
SPEAKER_02:I'm Jay Wirth, and I'm very pleased to have Chris Wong with us. He's a licensed therapist, executive coach, and co-host of the Art and Science of Difficult Conversations, his podcast for people who want to lead with more clarity, confidence, and courage by leaning into the hard conversation. He has over 15 years of experience in the nonprofit and healthcare sectors, and Chris specializes in helping purpose-driven leaders navigate messy transitions, fix dysfunctional teams, and lead culture change that actually sticks. He's worked as a therapist, built leadership programs from scratch, and coached hundreds of leaders who were brought in to turn things around under pressure. Chris, I remember a time when I was in another industry when I was brought in to turn things around. I didn't. I wish you were there.
SPEAKER_00:I run into a lot of people that say that. Oh, I wish I had you two years ago or three years ago. It always makes me wonder where are those people now?
SPEAKER_02:What's a difficult conversation that you avoided early in your career that taught you why we shouldn't avoid them?
SPEAKER_00:One of them is actually not a work-related one. It's when I was in high school, I had talked myself up. I was gonna ask this girl out. I was like, okay, this is it. I told all my friends, this is it, this day I'm gonna do it. That day came, I chickened out that day. But the next day I did call her. I was like, okay, no, I can't just I can't go back and not have said anything. Next day I called her and she said, Oh, sorry, somebody else asked me out yesterday. I think for me, that was like the clear time of my life that I was like, I cannot delay any of these kind of conversations ever. And it doesn't mean that I was always perfect, but then I know that when I was uh a chair of a board of a church, we had a member, we have one of the board members who was posting stuff online that was not necessarily wrong, but it was also certainly hurtful towards some of our members. We didn't talk about it at first, we kind of let it go and we kind of let it kind of fester a little bit, and it really hurt kind of our reputation, hurt kind of his own reputation. So when I finally had the conversation with him, he was not repentant or sorry at all. He was like, Nope, I said what I said, that's the truth. And uh he couldn't even see that it was hurtful, even if it was true. It doesn't mean that it wasn't hurtful to people the way he was describing it and communicating. And so uh eventually we had to part ways and we weren't able to resolve it. It was a conversation that really sticks out of my mind of like, oh, we really have to lean into these conversations harder. And I knew that lesson already, I just wasn't following my own advice.
SPEAKER_02:Our audience is primarily mission-focused organization leaders and members, development officers. What makes tough conversations particularly difficult with these types of organizations?
SPEAKER_00:More so than any other type of organization. I find that mission-focused organization leaders always fashion themselves as servant leaders. They always love the idea of servant leadership. I want to help people, I want my people to succeed and do the best. And they do it because they care about their people, they want their people to succeed, very good intentions, and they forget that part of it is also having those hard conversations of because they feel like it's either hurtful or they feel like it's gonna destroy the relationship, and they don't realize that that's part of it is holding that accountability and holding people to standards is part of caring for them and helping them succeed. And so they think of it as let me just work around it, let me ignore it because they're doing so well in other ways, or they're a good person, so let me just not talk about this stuff with them. And then it just kind of like somebody said, it festers, it grows, it gets worse, and then eventually you have a decision's made for you about it.
SPEAKER_02:What actually changes things? I would imagine that conversations go through phases, and when you're having a particularly difficult conversation, what changes things? Uh, give me a dynamic that typically happens.
SPEAKER_00:If there's somebody whose boss or their own manager is demeaning or disrespectful or maybe even gaslighting, just speaking up is makes a big difference and just sharing it. And again, if you have somebody who thinks of themselves as a servant leader, they probably didn't realize they were doing it. They probably just thought they were living their life and leading the best way possible, and they didn't realize, oh, the things I'm doing are not landing the way I wanted it to. Through conversation, is how they change the dynamic of, oh, I need to figure out a new way of interacting with my uh team member who I'm leading.
SPEAKER_02:These difficult conversations that don't go well, is it be I know there are a variety of reasons, but is it oftentimes a lack of self-awareness? Just you don't understand who you are and how you're impacting others?
SPEAKER_00:I think, especially if you're not doing it a certain way, you know, if you're or if you're behaving in a way that you don't realize how it's coming off, most of us aren't trained to think about like how everybody else is perceiving us all the time. I have good intentions, I'm doing this for the best of reasons. I'm a reasonable person, so hopefully everybody else is experiencing me that way. And we forget that nobody else can read our minds and we can't read their minds, so they don't know that we're doing it because we care or because we want the best to happen. We're just missing the mark because everybody's style is different too. Uh, a simple one is internal versus external processing. I like to process out loud. I'm an external processor, so I'll talk through an issue. It may sound like I'm disagreeing, but I'm not. I'm just talking out through the all different options. Whereas somebody, if they're if you have a silent processor or an internal processor, they're just sitting there thinking quietly, and you could easily misinterpret that as they don't care or they're not thinking about it, or they're just trying to avoid the conversation altogether.
SPEAKER_02:I think self-awareness is is a real key. And if you can put yourself in the other person's situation, their mind then the conversation's going to go a lot better. So you talk about leaning into these hard conversations. Well, what does that look like if you're hey, I want to get out of here? And that's your internal reaction.
SPEAKER_00:Yeah, leaning in is just uh getting the courage to say it. You just have to say what it is, and you have to use. I'm a big proponent of using plain language. You just got to say exactly what it is so it's not misinterpreted. In the meeting, you spoke over me, or in the past few meetings with our vendor, you keep speaking over me, or you keep every time I make a suggestion, you say it won't work. That's not landing great for me. It's just that concreteness. The more you can be specific and concrete and just go into it. And as you go into it, also thinking through what do you want to be different? What's the goal of you sharing this? Do you want to just vent or do you want a behavior change? Do you want something to be different? The more you can understand that and lean into that idea of I want this change, I want this to be different in some way, the more you can gain that confidence. But you have to start start with just knowing what the goal is and just saying the words, even no matter how scary they are, they you just have to say them.
SPEAKER_02:I think you said something key in your response, and that is my takeaway is stay away from the you, which is often accusatory, and rather talk about how I feel. Is it am I on track here?
SPEAKER_00:That's a stereotype we all have from difficult conversations, right? Like use I language, not you language. And it's it's true. It's trying not to put the other person on a defensive, and it's not certainly not trying to say that the other person is a problem. It's the more you can align yourself, it's you and me against this problem. Let's figure it out together. So I say the next evolution of I language is just saying we. How can we figure this out together?
SPEAKER_02:In my introduction about you're working with dysfunctional teams, and when a nonprofit leader inherits a dysfunctional team, they come in, maybe have limited resources to uh make immediate changes by replacing people. What's the kind of conversation you want to have in that environment?
SPEAKER_00:If you're coming in, you're new, you're just trying to get to know the team, it's not working out great. You have to do an assessment of some sort. It doesn't have to be a long, drawn-out assessment with like lots of different things and you're paying all this money for it. It could be as simple as going to each of your team members and saying, what are what's working well and what's one thing that could be better? Asking that, doing like a essentially a mini 360 of your team. From there, you have, you know, whether it's a person issue or process issue or a leadership issue, you have your ideas of, okay, this theme keeps coming up. Let's fix one thing at a time and let's see what helps.
SPEAKER_02:You brought up a topic, and it's a little off topic to our conversation today, but what's your thoughts about using a 360 instrument or process as a whole?
SPEAKER_00:I think it's the best tool you have is doing a 360. And so my background is doing learning and development also. And when you're doing learning and development, one of the things you do is a needs analysis. You have to go and see what's going on in the teams or the organization or the department, whatever it is you're creating a solution for. Same thing. When I was doing leadership and organizational development, I went to every single team, every single department, every single leader, and I asked, what do you what is working well? What do you need? What are the gaps? What are the issues and this whole issue? That was the foundation for everything else we did. We were able to implement lots of really great leadership development programs, mentorship programs. I was able to fix some gaps in communication between departments that were pretty easy to fix, but nobody had just asked these questions of where, you know, I'm missing this, I just need this, and it was a very simple fix. Going in and doing a 360, I find a lot of times just as, if not more important than any of those assessments you pay money for, is that 360 is helpful to get what's really going on in the in real time. You're just trying to do a real life gap of figuring out what's working well, what needs to be fixed.
SPEAKER_02:Mission-driven organizations, people are passionate. They're in it for the cause to address an issue, solve a problem, uh, strong value orientation. How does that make conversations either um easier or harder?
SPEAKER_00:Everybody takes everything personally. It's everybody, when you have this conversation about their performance or the way they're not doing it, they won't say the words out loud. Maybe they will, but they usually won't say the words out loud. But internally, they'll also they'll kind of feel like you're attacking their dedication. I give 100% to this every day. I work hard, I'm giving it my all. Either I'm working after hours, I'm answering emails all the time, or I'm picking up extra shifts if it's a shift work kind of thing. It's easy to take that any kind of critique as personal. Like you're saying that I'm a bad person altogether because it's connected to I want to do good in the world. And so that's what makes it hard is that that connection. And so it takes a little bit more effort to pull it apart and say it's not about your effort, your intention, your purpose in life. It's about how you're actually performing at this specific task.
SPEAKER_02:What do you think about the phrase? It's not personal, it's just business.
SPEAKER_00:I have a a weird relationship with that phrase because I'm a Penn State fan and we just fired our head coach for our football team. And it wasn't personal. He was a great guy, he's fantastic, he's led us really great over the past 12 years. He just didn't have the skill set to get us to that next level. Uh and so like that's the epitome of you're a great guy, you led us through some hard times, you're good for what we needed at this time. It's just hard is just you don't have the necessarily the skill sets. I do think it's a true phrase. I think it's sometimes misused, like any phrase. I think if it's misused a lot or misused not genuinely over time, then it just it loses its meaning or ends up having a negative connotation over time.
SPEAKER_02:It seems to me that it could sound like an excuse. Hey, I just said something harsh to you, but you know, it's don't take it personally. It's just business.
SPEAKER_00:If you were in a coffee shop and you were carrying a cup of coffee and you walked into someone and you spilled it by accident, you total accident, would they be okay if you said, Hey, listen, my friend gets coffee spilled in them all the time and they're okay with it?
SPEAKER_02:That is so perfect. No, you're not okay with that. Let's talk some other real-world scenarios. You just gave me one there. What's your framework for having uh this isn't working conversation then? Particularly with a longtime employee who, again, mission-focused, dedicated, but isn't performing.
SPEAKER_00:Let me ask you this to clarify the scenario. Is this after you've had other conversations and you've tried the kind of other interventions, or is this like the first time you had the conversation?
SPEAKER_02:Let's let's start with the first time.
SPEAKER_00:First time, I think that's the easier one, really, because that's really more like, hey, I'm noticing on this paperwork you keep missing the mark because of this reason and this reason, and this is why. And or this is the outcome because you're missing the mark. We're not getting billing, we're not getting reimbursed, uh, people are pulling back money. So I need you to do this. And so, how do we fix this? And so that's just the coaching conversation, some feed straight feedback and just have it, yeah.
SPEAKER_02:Okay, so now you've had several conversations with this individual that's not working out, it's not performing. What are the phases that those conversations can take?
SPEAKER_00:They should know that if this doesn't work, or you still have this issue, we're gonna have this conversation again, or you've had this conversation like two, three times. You're like, hey, listen, if you still can't do this, the next step is we got to escalate it to either a performance improvement plan or a verbal warning, a written warning, whatever it might be, the processes. You have to be really clear. This is the process. If this doesn't work, this is gonna happen next. And they have to know the process. You know, they have to be aware, and it's not punitive. You're just saying we just want to be on the same page because we can't let this happen forever and ever. And so you're letting the actual, the normal process be explicit, be on top of mind, and just being clear about what those next steps are.
SPEAKER_02:And then you have to act on what you said are the consequences because employees talk to one another. If you don't act what the consequences are, that sends the wrong message to the organization. Oh, well, you can get away with things here.
SPEAKER_00:I've worked with many leaders who, especially in this field, because they're again they're they're servant leaders, they want to care for their team, they think of performance improvement plans or warnings. Well, that's kind of harsh, right? They're just missing some paperwork, they're not that serious. Is it like, do I have to go that intense of a route? That's just part of playing any game, any anything you do in life. There are boundaries and there are rules, and it's not there to always punish you. It's the how they define how well the game can be played or how well that you're you can do things. And you need those boundaries, otherwise, you run into situations where your superstar employee is allowed to come in late or destroy the culture or be toxic, or even your poor performing employees are allowed to do that. And then what message do you send by that by having all these poor behaviors happen because you don't want to address it, because you don't want to be seen as mean?
SPEAKER_02:Our conversation is focused about uh having difficult conversations and preventing poor outcomes for and and replace them with better outcomes. And you might, as a listener, say, well, what does this have to do with fundraising? Well, it has everything to do with fundraising because we want to have a culture that's open and accepting and where people can have these kind of difficult conversations so that you're not demoralizing, let's say, your fundraising team, the development directors and associates, so that they go out into the the bigger world when they ask for money or cultivating relationships that they're feeling good about themselves and uh emotionally balanced. Another group, the board of directors, is often faced with difficult conversations that they have to have or the leader has to have with them. So that's a different dynamic. How do you say, take a board that you have a member or two that they are focused on or they have a pet project in mind? And how do you walk them through that when you know that's a little off mission or off plan?
SPEAKER_00:That one-on-one conversation. If you're the leader there, you gotta have that conversation with them one-on-one. And I want to understand that going in with that curiosity, that's the first step is maybe their pet project does relate to the mission in some way that you can't see for whatever reason. Go in with that and talk about that and have and the quality with which you ask questions will show that you are investing, you care about them. At the end of the day, I want to be seen, be heard, be understood. And so when they, especially these board members, when they're talking about their pet projects, a lot of it is they want to just because they care, they're joint, they're voluntary for some reason, they care about the mission in some way, they want to do their best to help. And they think this is their way of helping, even if it's not logistically or resource capable, possibly. Understanding why they're doing it and then having that conversation of okay, I understand you want to do that. Here's the mission that we're working on, and here's the constraints that we're working with. I want to make sure that I respect your desires because you want to help the organization grow. How do you see us doing this? Being clear about like, hey, these are the constraints, we can't do everything.
SPEAKER_02:Let's say you're in a board meeting, though, and your encounter is with this difficult person who brings up their pet project. How do you handle that situation in front of their peers?
SPEAKER_00:I think it's just acknowledging, hey, I understand this is important to you. I want to be respectful of everybody's time on the agenda. Can we find another time to follow up? And I want to learn more about it one-on-one.
SPEAKER_02:You promote culture change that actually sticks. What do you mean by that?
SPEAKER_00:A lot of times it's thinking through not just what do we want, like what does that future look like, or what does the values we want to believe in? It's going that next step of what does it actually look like day to day? What are the behaviors that demonstrate these values or what this culture needs to look like going forward? How am I as a leader going to role model that? What are the things I'm gonna do to keep championing that every day? What am I gonna start acknowledging and recognizing? And also being clear from the beginning, what are we not gonna tolerate? What am I as a leader not gonna tolerate anymore? When I say not tolerate it, what does that mean? Does that mean I'm gonna address it and start going through that discipline process? Does that mean we're going to just ignore it? You need to start thinking through what happens if people aren't following these new rules. Then you have to have a way of addressing it in real time.
SPEAKER_02:I'm sure that we have a nonprofit leader or two that's listening now and knows they're avoiding a difficult conversation. What's the one thing they should do tomorrow?
SPEAKER_00:Have the hard conversation, think through what's the goal, what do you need to say, script it out, practice it. You gotta go have it. Whether it's tomorrow, whether it's the next day, because you need a day to prep and you need to set a meeting and set the conversation time, whatever it might be, logistics. But you just gotta have it. You know, I think most leaders know in the back of their head they're avoiding a conversation in some way. You just gotta go have it, and you gotta go start sitting through it and recognizing that you might not get a fun solution right away. Go leaning into it doesn't mean that everybody's gonna be happy and you know you're gonna get the behavior change you want. Sometimes you might just leave the conversation as we're gonna continue talking about this because we're both getting too riled up, and that's okay. What you're doing is you're opening the communication lines. You you can make lots of progress if you're communicating, even if you're arguing. That's communication. What it won't help is if you don't talk about it at all, if you just ignore it and never say anything. Nothing will change.
SPEAKER_02:Before those difficult conversations, I would think that most people do a little bit of self-talk to get them in the frame of mind to present that conversation or have that conversation. What's what are some good practices for that? I guess the getting ready from an emotional standpoint.
SPEAKER_00:Number one, knowing what your own triggers are. It comes down to the fight, flight, or freeze response. Number one, figuring out what is your triggers. Is it somebody yelling? Is it somebody not saying anything at all? Is it somebody talking about the past? You're trying to give them some kind of feedback, and they're like, well, 10 years ago it wasn't like this, and blah, blah, blah. And they go in circles and they talk about other people. What is your trigger so that you can have a plan? What's your plan going to be when you go in there? When they bring this up, you're going to take deep breaths, or you're going to slow down and take notes, or you're just going to ask more questions, or you're going to ask for a break, but you have to think of a way, manage your own emotions in the moment. You just have to practice it to get better at it. You can't expect to suddenly be placed in a high stress situation and suddenly be able to manage your emotions. You got to be able to practice it. So mindfulness, uh, deep breathing, grounding skills, all those kind of things, the more you can practice it, and even if you want to practice with somebody else, have somebody else pretend to be the other person, have those difficult behaviors, and then you just practice slowing the conversation down or managing yourself, that's to be the best way to do it.
SPEAKER_02:Chris, this has been a very enlightening conversation, and folks may want to reach out to you and further the conversation. How do we best get in touch with you?
SPEAKER_00:Follow my podcast, The Art and Science of Difficult Conversations. So we're on all the major platforms. We're on YouTube. I'm most active on LinkedIn. So if you find me Chris Swang, LMHC, that's where I'm most active. And then you can always just reach out to me, Chris at myleadershippotential.com. I'm always happy to answer questions and continue the conversation again.
SPEAKER_02:For a library of fundraising resources from white papers to podcasts, open your web browser to convergent nonprofit.com. That's convergent nonprofit.com. I'm Jay Wirth for the difference. Thanks for listening and for making a difference in your corner of the world.
