Mission-driven leaders often struggle under the weight of doing everything themselves because they fear project failure and lack structured frameworks for team development. In this session, executive coach and licensed therapist Chris Wong outlines how organizations can transition away from accidental leadership bottlenecks and embed continuous learning directly into everyday operations.

What You'll Learn

In this session, you’ll learn:

• How to establish regular operational check-in bookends that make constructive reflection and mutual accountability part of your weekly workflow.

• Practical methods to overcome the psychological barriers of delegation, including perfectionism, martyr habits, and fear of failure.

• Why explicit expectation-setting must accompany leadership modeling to successfully anchor a continuous growth culture on any budget.

Key Timestamps:

• 00:00 - Introduction

• 01:52 - Building Regular Reflection into Everyday Workflows

• 03:47 - Breaking the Executive Director Bottleneck Through Delegation

• 09:47 - Implementing Continuous Growth Practices on a Shoestring Budget

Embedding Continuous Reflection into Daily Operations

A resilient culture of continuous growth begins with creating regular, protected space to evaluate performance without assigning personal blame. Rather than treating organizational reviews or project retrospectives as rare annual events, high-performing mission-driven teams build recurring feedback loops into their existing meeting rhythms. Structuring simple Monday planning sessions and Friday operational check-ins enables staff to identify friction points, discuss needed support, and adjust tactics while work is actively unfolding. When leaders treat psychological safety as an active operational practice rather than a buzzword, teams develop the confidence to examine missteps and continuously refine their mission delivery.

Delegating with Intention and Overcoming the Fear of Failure

Sustainable leadership development requires executives to move beyond the martyr complex and recognize that doing everything personally creates an operational bottleneck. True delegation requires managers to accept that errors and learning curves are an inevitable, necessary part of developing capable, independent leaders. Overcoming this hurdle means documenting internal processes, defining explicit non-negotiables, and directly communicating standards rather than expecting staff to learn through observation alone. By coupling structured apprenticeships with consistent coaching, organizations build deep succession capacity that empowers teams to work autonomously and frees leaders to focus on core strategic goals.

Move From Insight to Action

Ready to move your projects and plans forward with more clarity and confidence? Let's Connect to explore the support your organization needs, or learn more about Our Approach to turning strategy into action.

Full Episode Transcript

Prefer to read or search the content? Below is the full transcript from this session. Note: Transcripts are lightly formatted for readability.

All right, hello everybody, and welcome to our impactful projects and planning series. I'm Jami Yazdani, and I'm excited to be here today with Chris Wong to talk about creating a culture of continuous growth. And so, Chris, tell us a little bit about your work and your business and who you are and and the impact that you are hoping to create for your clients.

Yeah, thanks for having me on. I am a licensed mental health therapist and I'm also an executive coach. And my main company, as I where I'm an executive coach, I I run a leadership development company where I work with human service nonprofits. So think domestic violence, food and housing insecurity, child welfare, mental health. I work with them to strengthen their leadership team. So I run a six-month leadership cohort called the Impact Leadership Academy, and we strength and everybody gets coaching and training, and everybody we level everybody up. So we solve that accidental leadership problem.

Wonderful, thanks. Yeah, and I I know you know I I try to have these topics relate to projects and planning, and this might not seem like an obvious connection, but I I feel like you have to plan for continuous growth. Continuous growth is parts of projects, and and I also feel like projects and planning are an element of sort of leadership development. So, so thanks for for joining us today. So, what we often hear about the value, right, of continuous growth, of continuous improvement, but what does a culture of continuous growth really look like? Are there programs or strategies that nonprofits should be implementing or thinking about?

Yeah, there's definitely structural things you could implement to to do that, but at its heart, it's really creating a culture where everybody feels ownership over it, and they're willing to do best practices and learn and grow and learn from mistakes. So you know that I think psychological safety is an overused term, but it is about that idea of do people feel comfortable making mistakes, sharing and getting feedback and coaching from other people, so that the goal is to fulfill the mission, and so if that's the goal, how do we do it better over and over and over again, and continue to get better at that mission? And even if your goal is to grow like physically, then grow physically also. But it starts with is everybody even willing to have the conversation and and talk through that and learn from each other.

Yes. So, are there? You know, I think a lot of culture cultures talk about psychological safety and and continuous growth. But I think that, as you said, learning from mistakes is something that I often see organizations struggle with, particularly some of the organizations that I work with because you know there's people don't want to make mistakes and they don't want their organization to make mistakes. But how is that something people can kind of bring into their culture without fear of of what that might look, particularly when you're talking about donors and funders. You know, you don't want to be known as the nonprofit who makes makes mistakes necessarily.

That's right. I think it's from all these interviews I've done with with these nonprofits for my book. I think it's there's a few different things, but it all comes down to: Are you going to prioritize time to actually have these conversations. That's the first step you have to do. You have to actually make space for these conversations. And so, some organizations will input it as like the first 15 minutes of every staff meeting that they have like every week if they're small enough. Some will have a meeting. I was just talking to one this morning where they will have a staff meeting on Monday to plan for the week and everything going going on, and then Friday they'll have another staff meeting where they will review everything that happened and what went well, what needs to improve, and where do we need to shore up, or where do people need more support with each other? And like those bookends to the week help them talk in real time about how do we continue getting better, over and over and over again, and it's not about who's at fault because you can't change the past. It's really about what do we need to make sure we put into place so that we continue to grow. And there's those countless examples of the best organizations that are doing it. They're able. They're just prioritizing time to focus on it. In addition to the mission, the the programs, the services, all that's important too, and the finances. But if culture is important to you and you want to create that and you want to support your people, you have to prioritize time for that too.

Yeah, that's and I I love that. It sounds like it's really built in. Into kind of their day-to-day operations, it's not sort of a oh we're doing this once a year, you know we're doing it when something big happens, and you know in in project management doing retrospectives like that are are kind of a piece of best practice, and I think people often think about only doing them at the end, and that's great. You you absolutely should do them at the end. But if you can do them in the middle, then you can make changes while it still while it still matters. And you know, a lot of organizations do like you say that they're kind of on a regular basis, even if it whether it's as an organization as a whole, but in a project, in particular, will kind of meet regularly and say, "What are we going to start doing? What do we want to stop doing? What do we want to continue doing?" There's bunch. There's so many ways you can kind of structure those kind of of conversations.

Right. Right.

So you know, a piece of this too is really about kind of growing leaders, right? Leaders who feel comfortable facilitating those conversations, who you know can help folks move sort of beyond blame and into to growth. And and a piece of this is really about succession planning as well in in your organization. And so, how does that support a growth culture? And what should organizations do to to do that well?

I mean, at the end of the day, your executive. If you're an executive director, you have an executive director. The goal is not for you to do everything by yourself, right? If you're a small organization, yes, you're probably carrying, holding more hats than you should be. But as you start growing, the goal is to not do that. Right. The goal is you want your people to be able to do things and and manage things, and be able to do things without you having to look over their shoulder all the time. And so the only way to do that is by developing them so that they can they can properly take on tasks, work independently, and and do whatever they got to do. I would one interview one organization is a is a global nonprofit. They produce change makers. They facilitate groups all over the world. They only have three staff, and they have like 5060 different facilitators of different groups throughout everywhere. There's no possible way that the executive director or those three staff could facilitate all those groups all the time. The only way to do that is to strengthen all of those leaders through their process. They create. They have like an apprenticeship program where they purposely build people up in their skill sets in real time, so they're learning the skills, and then they're able to grow go independently. But then they use the processes I was just talking about, like about having like regular check in meetings. They learn from each other. They see what's going well. How can others learn from other people? And that's the real thing. Is that way the executive director he can focus on other things. He can focus on you know fundraising. He can focus on working with donors and and other outward facing things, or the admin stuff that the facilitators don't need to look at, right? They can they're able to be more effective. Everybody's more effective when the executive director is not the only person doing everything or being the bottleneck, essentially.

Right, right. I wonder because I see that you know, I when I do some leadership development work, I see that tendency for executive directors or even sort of department heads, you know, and larger organizations to try to take on kind of everything, and there's a fear Of sometimes it, I think they don't want to put a lot on their staff that already have you know a lot going on. But what do you think's behind that hesitance or that desire to sort of or that need to feel like you have to do everything? I don't know if that yeah yeah. There's

a I mean there's a few different reasons, right? There's number one. There's like they don't want to overburden. There's they're like a real quote unquote servant leader. They don't want to overburden everybody. Everybody's already stressed out. They don't want to burn people out. The second reason they've done it before. They've tried to delegate and people just aren't very good, or they just didn't have the right support, so they didn't do well. And so, the executive director in their head is thinking, "I can't afford a mistake or a failure on this, so I'm just going to do it because I know how to do it right." Third reason is that martyr complex. Like I'm the only one that knows how to do this. I am the best person at this. I I will save the day and do everything. And another reason I come across a lot also is they don't even know where to begin on delegating because they're so used to carrying everything. Everything seems like it's in my head. It seems so bespoke. Everything I do, how there's no process. How can I hand this off? It's like if you were holding the. Analogy I was given was if you're holding like 100 different grocery bags walking into your house, and somebody says, "Hey, can I help you get a bag?" You don't even know what bag to give them. You're like, "I don't even know what bag I want to give you because I don't want to drop this, and I don't even know how to like start untangling myself from this and that." And so I think there's also a good portion of leaders who would love to delegate, they don't even know where to start because all this time they've done everything just by the seat of their pants, and they haven't created a process. And so it becomes, yeah, you are the only person that can do it because you're the only person that's been doing it, and you do it your own way. And of course, no one can follow you because there's no way anybody can do it. Also,

right, and and but that comes to sort of a question of expectations, right? I mean, I think you know something I had to learn as a new leader is that when I let go of things, I also had to let go of some of my expectations that it was going to be done exactly the way I wanted it, or I would. I would do it, but you have to let other, and that's part of the continuous growth, right? You have to to let other people grow into their own way. And I also think it is hard to make time, you know, to document processes and to talk to someone about how you do something. But the value, of course, is great for for you, you and your staff. And I think being able to delegate is a leadership skill, and it's often not not one that we're taught very specifically. You know, you kind of are taught these big picture ideas, how to be a servant leader. But what does that look like on Tuesday afternoon? That's the

yeah. Well, not only that. Not only we not taught how to delegate really well. Even like every delegation training I've ever been to or seen, not many talk about the idea that you have to get comfortable with failure. Also, that you have to, in order to delegate well, that means you have to be okay with somebody's going to make a mistake, even if you explain it 100 times. Somebody's going to make a mistake, or do it the wrong way, or do it a different way than you expected. Not many trainings will talk about that, like mental aspect of learning to live with those mistakes and being okay that it's not going to turn out well, or maybe the maybe the program won't work out well, you know, at first, or maybe there'll be a step, a disruption. Excuse me, a disruption in service. You know, for for a little bit, and that's okay. Depending on kind of what your what your need to have and your non-negotiables are, but you have to be okay with failure to a degree.

Yes, yeah, you definitely do, and I think that's hard. I think sometimes people who rise up, or particularly in nonprofit organizations where, you know, that passion for the the cause is so great, you know, you don't want things to to fail or go wrong, but they're going to. And I think we often forget all the times we've haven't done it right as a leader either. You know, or all the years that it took to to get us to the point where we can just do it with without thinking about it, but yeah, that that mental sort of challenge of of letting what happens happens. But I sometimes tell leaders who you know haven't been delegating for all of the reasons that we talk about that sometimes you're going to be in a position like an emergency or some urgency, or you've got to take leave where you have to delegate. And if you haven't done it before, how can you ever expect people? You know, if if they're never comfortable sort of doing something that's maybe a stretch for them on the regular. How how can you expect them to do it sort of in a in a crunch time? Yeah, yeah. So it's really about preparing people. But yeah, the the not wanting to fail is a is a challenging thing for leaders, and the people doing it don't want to fail either. But we all have to

right

learn. So. yeah, it's

it's a balance for sure.

Yeah, yes, and I do think it's a balance, and I think when organizations are so busy, it feels like you can't let any you you can't let any one of the bags drop, right? You know, and because you just don't have time, but at the same time, a little bit of time delegating and working with people and and letting them have the space to grow, I think saves time later. And like you said, allows you to focus on the the strategic things that that you should be focusing on. Exactly.

Yeah.

Right. So, what do you? What advice do you have for organizations who want to support a continuous growth culture but are operating on those sort of shoestring budgets? You know, small staff. What? What would you recommend specifically?

I mean, that's. I would say anything we talked about. Here, like every every example I gave are organizations that are under. Let me just confirm. They're like under $500,000 in revenue. They have three staff. They have 10 staff, 18 staff at most, and they're doing it. All they're doing is creating a time to actually talk about it out loud and to address it in an open and unbiased and really just curious way. That's all. Even if you started with just your, if you have a weekly staff meeting or monthly staff meeting at the very least, if you just devoted 15 minutes at the beginning, say, "Hey, what's going well for everybody? What's not going well? What do we need to work on? You would make a lot of, and then just make sure you keep following up on that. Obviously, like you can't just like say, oh well, yeah, it'd be great if everybody was if we treat everybody with respect. Oh well, too bad. No, but you got to follow up on that stuff. On as you choose one, you can just like start develop getting better at that. So doesn't take any money. It just takes like 15 minutes of time a month or a week, and just start developing that. And then, once you start seeing some results, maybe you're like, "All right, maybe let's devote a separate meeting just to this, so we can really fast forward this progress." But the teams that are focusing on this, they are going to outperform the teams that are not focusing on culture at all, to a very any degree. It won't matter what. It won't matter how many all day retreats you send people to. Won't matter how many team building activities or you know icebreaker questions you ask in your team meetings. If you don't focus on it intentionally with a process to move forward, it's not going to matter,

right? Yeah, I mean, I think that you know, continue because I often see, which I think we're all a little bit guilty of. Sometimes you go to a session or a conference, or you read a book, and you get excited about an idea, and you have that sort of first meeting, and maybe it doesn't work exactly the way you you thought it was going to, and then we just sort of let it let it drop, and and you know I think that commitment to you know kind of doing something for even if it's just six months, you know, and then and following up, and I think having those conversations, as you said, is is probably the most important thing, and you're modeling, you know. And I also think leaders can model continuous growth. So if you've made a mistake,

yeah,

right, yeah, you you need to be able to sort of say, "Wow, I made a mistake, and this is what I've learned. I was wrong about this." I think modeling is really, really critical.

Yes, yes, and as I say, modeling is a good reinforcement tool, but it's not a good teaching tool. So you can't do it and then expect everybody to just start doing that as well. You have to actually tell people what the expectation is, and then as you do it, you're reinforcing like, hey, this is how things are going. But by itself, it's not a it's not a good teaching tool. You have to actually explicitly tell people what to do,

right? Because folks aren't paying as much attention, you know, and aren't seeing it maybe in the same way that that you are, you know. And also, if it's new to them or it's it's new for a change for the culture, it is going to need some more intentional, clearer communication. That's absolutely right. Yeah, wonderful. So, what's the best way for folks to reach out to you if they they want to learn more or work with you?

Yeah, you can follow me on LinkedIn. I think I'm I'm most active on LinkedIn. That's the only place I'm really active, LinkedIn, Chris Wong, LMHC, and then if you want to follow along with my work or follow along with my book and see the progress and get on the waiting list, you can just go to tinyurl.com forward slash future nonprofit. That's a biweekly newsletter. I'll give you updates on the the on the book as well as kind of strategies to implement all the stuff that I'm learning from the book into into your work.

Wonderful, yeah, and we can add that into the the chat on the the LinkedIn Live so that people can get to it. So thanks so much, Chris. It's been been great talking to you, and I think I appreciate sharing some really concrete things that that even small nonprofits can do to to start changing their culture. So thanks again, thanks everybody for participating in our impactful projects and planning series. We'll see you next time.