Transcript Episode 116 – Stop Settling for Crumbs in Nonprofit Fundraising with Kailee Scales on The Prosperous Nonprofit

[00:00:00] Stephanie Skryzowski: Hey there. If you’re looking for the 100 degrees of entrepreneurship podcast, you’re in the right place after a hundred amazing episodes, we’re changing things up to serve you the most inspiring content in a fresh new way. Thanks for being here and keep listening.

Welcome to the prosperous nonprofit, the podcast for leaders who are building financially sustainable and impactful nonprofits and changing the world. I’m Stephanie Kowski, a Chief financial Officer and founder and c e o of 100 Degrees Consulting. My personal mission is to empower leaders to better understand their numbers, to grow their impact and their income.

On this show, we talk to people who are leading the nonprofit sector in new, innovative, disruptive, and entrepreneurial ways, creating organizations that fuel their lives, their hearts, and their communities. Let’s dive in.[00:01:00] 

Hey everybody. Welcome back to the Prosperous nonprofit. I’m so glad you’re here because today we have an episode with Kailee Scales. Now Kailee and I work together at her organization. She’s the C e O of Pencils of Promise, casually referred to as pop. And you may have heard of Pencils of Promise before their award-winning a globally recognized nonprofit and.

Not only is she the c e O of pop, but she has spent her career in various fundraising and organizing type roles. And so we talked a lot today about fundraising, but more from a mindset perspective. And there are like several mic drop moments here. Kailee is just a brilliant mind and it was really cool to sit down with her and chat about her take on the way that we need to approach our work in the nonprofit sector a little bit differently.

And I especially loved when she talked about I. Instead of nonprofit, sort of picking up the crumbs that are left [00:02:00] behind and sort of fighting over those crumbs instead going for the whole cookie. So my mind was blown by this subtle shift in our mindset that shifts us from this scarcity thinking to more abundant thinking.

And I just had a huge light bulb moment. So listen for when she starts talking about cookies, because it’s a really, really powerful take. And observation so, Let me read you her bio so you can hear all about how fantastic Kailee is and then we are gonna get right into the episode. So Kailee Scales is a Chief Executive Officer of Pencils or Promise, which is called pop, the Award-Winning and Globally Recognized for Purpose education organization whose mission is to support access to high quality education for children around the world to help lift the barriers to education for the world’s most vulnerable children, pop build schools and helps create safe and engaging learning environments and emphasize.

Literacy, wellness, self-discovery and kindness so young people can achieve their dreams. Pop seeks [00:03:00] to improve and expand school-based and community-wide resources and education on hygiene, clean water, and works to end menstrual poverty. Since its founding in 2009, POP has built nearly 600 schools and impacted over 800,000 children, families and community members in Laos, Guatemala, and Ghana.

Kailee is also the founder of Think Free Global Strategies, a boutique full service firm that offers end-to-end consultation to corporations, organizations, and individuals for equity solutions, organizational and resource development, as the name implies. Think free global strategies, challenges, all those interested in developing forward thinking solutions to complex issues to define freedom and explore, adopt and implement core principles and tactics into their respective cultures.

And just a little side note from Stephanie here, I feel like a lot of our conversation really centers around exactly this, developing forward thinking solutions to complex issues to define [00:04:00] freedom. So really excited to dive into the episode. I got a little more to tell you about Kailee. Kailee has an extensive career leading social causes at the intersection of global development and social justice.

She is sought after for her perspective, spanning the spectrum of both her frontline grassroots experiences and the thought leadership she offers to both private and public sectors. She began her career as a fundraiser and organizer in New York and has worked in 17 countries across the world, throughout Africa, Asia, the Caribbean, Europe, and North and South America.

She’s contributed to social justice goals around the world, including racial injustice, education, empowering women and girls, environmental and health inequities, and has worked closely with the World Health Organization, the UN Global CEOs and heads of state, including her Majesty, queen Sylvia of Sweden.

Tony Blair and countless celebrities and influencers in developing solutions to the world’s most complex problems. So if you just listen to that bio and you’re like, oh my gosh, Kailee is a genius. Yes, she absolutely [00:05:00] is. And I am super excited to share this episode with you because I know that there are going to be some major mindset shifts as you listen.

So without further ado, let’s go talk to Kailee.

Hey everybody. Welcome back to the show. I’m super excited to be here with Kailee Scales. Kailee, welcome. 

[00:05:22] Kailee Scales: Thank you. Thank you so much for having me. So excited.  [00:05:25] Stephanie Skryzowski: Yes. So I would love to hear, so we work together at Pencils of Promise, where you are the C e O, but I would love to hear a little bit, About your journey to get you to pop?

Like where, where did you start? What has your career looked like and how did you get to where you are now? 

[00:05:41] Kailee Scales: Yeah, so I’ve had, um, I don’t know if there are any people, I started this whole social impact career in development, so I started out as a fundraiser and I have, ever since then, I just, I’ve never met anybody who woke up and said, I, when I grow up, I’m gonna be a fundraiser.

Like, you know, art stories. No. [00:06:00] Our stories are a winding road, right? And so my story, um, Is interesting. Uh, so I had the background. I grew up in Queens. I grew up in an area where, you know, everyone was extremely, I, I, I grew up in New York and in New York you can’t be in New York and not be politicized. So very early on I understood things like how to change your community.

I did a lot of volunteer work. Some of my earliest memories was conducting volunteerism, so I always had this very, I had a keen awareness for my community and what I was able to affect within my community. Um, I had parents who grew up in like, I. When they grew up, they were very like active and was a part of this whole vibe of change.

Like, just change the world. If you wanna change the world, just like change it. And so, um, that was always like latent within that, or not even latent. That was always a part of me. Mm-hmm. But I also was very talented, so. Um, [00:07:00] obviously clearly, um, I was, I’m an artist, so I, I was a singer. Wow. I started singing when I was like really young.

Like I was, I was in a choir at age three and I sang my whole life. And, um, I studied classically, um, And so my plan was to be a famous singer and sing in jazz clubs, which I got to do, um, but to sing in jazz clubs. And that was like my gonna be my life. I was going to give my soul to the arts. And so, um, I went to Hampshire University.

I studied, um, music performance. Like I was all in, you know, all the auditions. Mm-hmm. Like I said, I was a jazz singer. And then, but there was always like something missing. Like I always felt like, but there’s this other part of me, this other part of this nagging part of me that was like, You have to use your brain to do things to change the world.

And I’m like, well, I do through my talent, but. One day, um, in the middle of all of this, um, as I said, I’d always volunteered and I started volunteering for this man who was [00:08:00] running for Congress in Brooklyn. And that’s just the way it is in New York. If you wanna get involved, easy. And so he was running for Congress.

He was connected to a friend of mine and I was just kind of volunteering on his campaign and doing all kinds of things. And one day he said to me, he is like, Kailee, I think, you know, I want you to work for me full-time as my fundraiser for this campaign. And I was like, First of all, I’m a singer, so you’re rude.

Like, no.

Um, secondly, I don’t know what that is. And so, um, and he was very clear. He’s like, well, it’s, it’s who you are. You are a person who is able to connect with people and you’re able to take those relationships and, and help change things. Change and make things happen, and achieve things in the world. And I was like, well, does sound like me?

And I took a chance. I don’t know why, but I took a chance and I was like, all right, well I’ll do this. See how it goes. And he was right. And, you know, and that was, I was 20 years old. Um, so it was really early on in my [00:09:00] career. Mm-hmm. And then, um, we did an amazing campaign. We did lose by a very, very small margin, which was very unusual for this particular race because it was like a heart, a contested, highly contested race for an incumbent.

And so, you know, I had the bugs. I was like, oh. Um, mm-hmm. I can do things and we can move mountains. And it was just like that, that fire that it, it, it struck. So then, you know, I needed to find out to find my next journey. And, and the candidate, his name is Barry Ford, um, he said, you have to go in the world and do stuff now.

Like now you go off and you fly. And I was like, oh, so just say I’m unemployed. And so I was, I was like, you know, trying to find out. What I was going to do next. Mm-hmm. Like what was my, mm-hmm. Pathway was my journey because again, this was very new to me. I had, I thought I had it all planned out. All of a sudden I got bitten by this.

Transformation, social change, social impact bug, like hardcore, even though it was latent inside me. And so [00:10:00] now I’m just like, what do I do? My gosh. And, um, I got a role, um, this weird blind interview. I didn’t, I don’t know if they still do those, but at the time they wouldn’t tell you like the org. You just had to go for the interview and.

It was weird. Um, what? 

[00:10:15] Stephanie Skryzowski: I’ve never heard of such a thing.  [00:10:17] Kailee Scales: Oh my gosh. I had never heard about it. Never heard it since. It might have just been this Oracle, but they were pious at the time, uh, ngo, and they just won, I don’t know, whatever the point is put on this and didn’t know what to expect. I thought I was like, for temp job, and I got this role to work as an entry level fundraiser at the Muscular Dystrophy Association and back then, That was like a big deal organization and you know, it raised lots of money and it had like a telethon every weekend on Labor Day, and it was like this big deal.

So I was just like, okay, yeah. All right, well maybe he was right. Maybe I’m gonna keep going. And at that organization I experienced, uh, a whole different life, a whole different world of [00:11:00] fundraising. It, it had all those things that. Working for a candidate had like passion and um, urgency and um, so when I worked at the organization, I focused on raising money for research for Lou Gehrig’s disease, which is a maternal illness for those who are familiar with it.

And the people that I worked with and the volunteers and the committee members and things like that, they were people directly affected or had family members that were directly affected by the disease, which is quite awful, um, to experience. And that brought this heightened level of urgency and change and, um, fixing problems.

Um, and the people that I worked with had that. Level of urgency. So that just kind of further that doubled down on what I knew this career path could be. Mm-hmm. And I was incredibly successful. We raised more money. I, I remember as an individual fundraiser, I ended up raising more money than any fundraiser had in the organization.

Wow. At that [00:12:00] time, 50 year history. And so that was like, oh yeah, okay, let’s go.

And it kinda, you know, snowballed from there. 

[00:12:11] Stephanie Skryzowski: That’s amazing. Do you feel like you approach fundraising like differently than others do? I mean, you like broke all the records at muscular dystrophy, so what did you do that was maybe different than what others had done?  [00:12:26] Kailee Scales: Um, because I think the reason why I told about my, you know, journey is because I think that that linear pathway of connecting resources to change was extremely clear to me.

It was a, so any, when I first started, the organizations that I worked for, I was very closely connected to the outcome of what those resources did, of what the, that the enthusiasm of the volunteers or the community or whomever, the corporations, like whomever I was working with, I was very [00:13:00] connected to their ability to affect the, to pull that lever.

And so to me, that was inextricably linked. That’s all I know about what this. Role with this entire world. Does, it pulls a very direct lever, and so when I under and, and those organizations that were in the early days and then continued, they had urgency around their impact. Um, it was an immediate deliverable.

It was like highly necessary. I went on to work. For things like, um, the climate group where I focus on climate change. I worked for, uh, this organization called the Mentor Foundation, where we focus on drug abuse prevention. You know, there were so many, I worked with children and educational organizations.

I worked in women’s health and family planning, like things that had a real impact, like immediately that day. Um, and people, or, or at least the people believed that it did. And so I understood though that connection and. By understanding that connection, I was able to embody that impact. So when I met [00:14:00] people, when I was introduced to people who just kind of were under trying to understand how they could affect change in the world, I knew that I saw it.

Like clear as day. And when we would have conversations, when I would talk to donors at any level, at all levels, any type, I knew that what they were seeking truly and what they could do truly, and that’s the way I spoke and that’s the message I bring in literally every environment that I’ve ever been in.

[00:14:29] Stephanie Skryzowski: Mm-hmm. I feel like for a lot of people, that’s a struggle to like effectively communicate the impact between the money and what your money can do. And it sounds like that’s just something that just like is naturally in your brain. Like you don’t, you don’t have to try hard to like make that, make that connection when you’re talking about the work that you  [00:14:50] Kailee Scales: do.

Yeah, and I think you’re right. People, I, I encounter this. Constantly. Even now, even when I talk to board members and I talk to, you know, others, other champions and [00:15:00] advocates, they really struggle and they look for things that are less important than they think. They, they automatically look at things like, O I and data, and I’m not saying that’s not important at all.

Um, and they look at things like, like numbers. And I’m not saying that that’s not important at all because of course it is. But I think that there’s a disproportionate emphasis that we place on those as either fundraisers or as people hearing those numbers and the that impact so that it exacerbates the importance, it makes it bigger, it feeds the beast, and it’s truly not the truth.

The truth is, is that people want to feel that they are helping, they’re helping the plant, they’re helping animals, they’re helping children, they’re helping, um, with our individual health. They’re helping. They’re helping ellipses. People wanna feel like they are helping, and that comes from. [00:16:00] Understanding what, what needs to happen like in the world to affect change.

And that also happens in being able to tell the stories of the people that they impact. Numbers are great, data is great, but people want to know that they are making a difference in this world. And the only way to really re and that’s an emotional need, peop, that’s an emotional, it’s not a tactical need.

It’s not a transactional need, It’s not a need that’s based in Dan. It’s a need that’s based in. Love, really. And we’re afraid of that language. We’re afraid we’re like, no, no, no. They wanna see the numbers. Mm-hmm. Oh, I wanna see the numbers. Mm-hmm. And you don’t, you don’t, you wanna feel the impact you wanna feel.

Um, the change. You wanna feel the connection. That’s what you want. Because if you want numbers, you can invest in the stock market. You know, there are other things that give you numbers. You’re not calling me for that, and you’re not calling any fundraiser for that. And fundraisers don’t need to pretend.

[00:17:00] And it’s this thing, it’s like this. This like self-fulfilling thing that we do. It’s like this feedback loop that we all create. We participate in this thing that, and we make it bigger and bigger than it really is. And that’s just not true. And I want people to understand the truth of why we are doing this and why we all show up and why we support each other, because we shouldn’t be afraid of that.

That is the truth. And we have to make that bigger and that other things. 

[00:17:26] Stephanie Skryzowski: Mm-hmm. Yeah. That power of, and the sort of the magic of storytelling, it sounds like you’ve, that’s just, just naturally a part of the way you work. And you’re right. I mean story and that that passion and that love for the mission is so much more compelling than a bunch of spreadsheets, and I’m a numbers person still like that coming from me.

Like, yes, the story is much more powerful. Than the numbers for sure. Um, one thing that I find. Is just like rampant in the nonprofit sector is [00:18:00] this scarcity mindset where we just believe that there’s a limited amount of resources. We’re constantly trying to do more with less, and we’re just, I, I feel like we just tend to think so small because we fear that resources are going to run out now.

Okay. That’s kind of a real thing, right? Like funding is getting harder to, to come by. And to a degree that’s a real thing. But I also feel like that scarcity mindset versus more of an abundance mindset like really holds us back. And I just wonder your, like, your thoughts on that as a fundraiser, as a leader of, you know, a prominent organization, how is scarcity mindset?

Or maybe not, maybe you don’t have any scarcity mindset whatsoever. You probably don’t, but, um, Yeah, I was gonna say like, wait a second. Who, who am I talking to? Yes. How have you seen that, like really impact organizations and what do you do to like, not let that, you know, take over? 

[00:18:56] Kailee Scales: Yeah. I’m not that person.

Um, [00:19:00] because, but, but I understand it and I can answer your question and I think, well, first of all, I, back to what I said earlier, we, as you know, Fundraising prof, like the world of social impact consists of those who contribute and those who are the bridge, right? And that’s the fundraisers. The fundraisers are like the bridge.

Then there are people and places and things that we, that are beneficiaries. And then there’s those who want to contribute. And so it’s all an ecosystem. So we all contribute to that ecosystem and that environment. And so it’s not an us against them, like, you know, it’s not everybody’s in a bubble like.

It’s one thing, it’s an industry if you will. Um, and so I like to call it an ecosystem cause the industry sounds, man. And so when, when, when we think about the ecosystem of philanthropy, we all contribute to that experience of scarcity cause it. It doesn’t exist. Okay? So I refuse to believe, love that in a love [00:20:00] old where there are more billionaires than ever in a world where I’ve watched, I told you I started when I was 20, so I’ve watched numbers and gifts, like, you know, back in the day, um, $10,000 was a lot of money.

Now as fun fundraisers we’re like, That’s, yeah, that’s great. Um, we’re, you know, that’s been a major gift in many organizations, right? Mm-hmm. So we know that scarcity isn’t real. There’s plenty of money to do lots of things. To consume. We’re talking, we talk about over consumption. We, like I said, there’s, there’s unprecedented numbers of billionaires.

So we know that resources are not stairs. Resources are not allocated to the places that are where important, so, I think that when you think about that abundance mindset, what an abundance mindset does, is it the people within an abundance mindset are activists. [00:21:00] They advocate for, for resources. They’re not like, well, they’re so few, so we’re gonna be happy for what we get, and we’re going to all struggle and compete against the for the crumbs.

We ask mm-hmm. In a, in an abundance mindset, we ask for the cookie. We know there’s a cookie. We’re not, we’re not talking crumbs. Right. And so mm-hmm. We see the cookie. And so our job is not to scrounge for the crumbs. It is to advocate for our peace of the cookie. So we are not solicitors. We’re not, uh, people who are, we’re not beggars.

We’re not, you know, we’re, we’re, that’s not what we do. We are advocates. So we have to advocate for the allocation of those abundant dollars to come to where it is important. And, and, and when you, when you make that shift, when you’re like, I’m an advocate, I know without a shadow or doubt that all of those abundant resources [00:22:00] belongs here.

I know that. Mm-hmm. And so my job is to advocate for those resources to come here. When you make that subtle shift, your conversations are different, your outreach is different. Your connectivity with those who can provide those resources are different because you are not coming from a place of lack.

You’re not coming from a place of, uh, handout. May I have. You’re coming from a place of We deserve, This works. Mm-hmm. Fix this. And so when I, I learned very early in my career that I hold that I am the bridge between those who want to affect change and change and, and that makes me. Very special. Right?

Because I, and, and that is what I offer. I offer, if you could buy, and I’ve said this to donors, you could what? Go on vacation again. You could, you know, put another re renovate your bathroom. Like there’s a lot of things you could do. [00:23:00] There’s a lot of things you could do or you could transform the world.

I’m giving you that opportunity. You go ahead and choose. I’m not gonna judge. I’m gonna judge, but you choose. You go ahead and choose what you wanna do. And my job is to tell you how you’re gonna transform the world by allocating your vast resources to this thing. And it doesn’t have to be vast. That could be $3.

That could be $20, That could be a million dollars. I’m going to tell you how that investment of $3 is gonna help transform the world. Tell me you’re not gonna do that. And instead you’re gonna buy eggs. Cause that’s how much they cost. You know, anywhere between a hundred and $200. That you are not gonna transform the world.

And that makes me an advocate, that makes me an activist, that makes me someone who is out asking for my piece, our piece of the cookie, because that’s what we describe. Mm-hmm. So anyway, that’s how I think of that scarcity versus abundance mindset. [00:24:00] 

[00:24:01] Stephanie Skryzowski: I love how you’re just so casual. I’m like, that is a mic drop.

Like that is huge. I think that’s so huge because you’re right. I feel like a lot of times nonprofit leaders, we see like, okay, there’s this, there’s this limited pool of resources and we’re all like fighting to get what’s in this pool. And you’re like, yeah, no, I’m not doing that. I’m just gonna make the pool bigger.

Like, how can we just make this pool bigger? That’s a huge shift I feel like. Yeah. Okay. We’re done. That, that was all I needed. No, I’m just kidding. I’m just kidding. That was, that was a huge shift. 

[00:24:30] Kailee Scales: It’s a, it’s a huge shift because I, and I need us all to, I need us all, everybody on, everybody listening to get on the same page because as I said, this ecosystem we all contribute towards.

So if we’re out here putting out this, please give me whatever you got left over kind of business. That’s what we’re going to get. I don’t, no, no, no. We are. Mm-hmm. Changing the world. Most invaluable thing on this planet. There’s nothing more important than changing the world [00:25:00] because it’s broken and it’s a mess.

Right. We can all agree to that. Mm-hmm. Mm-hmm.

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[00:26:05] Kailee Scales: I think a lot of that. Scarcity mindset comes from that whole ecosystem and the, and the, and the feedback that we get from others. And, and it’s, it’s frustrating. It’s just like there’s the nose. I, I always think, I don’t care how many nos I get, all I need is a yeah. One. Yes. Mm-hmm. And so, and we’re frustrated by what we see in the world and the feeling like things are never gonna change.

And I go through this all the time. But I remember that this is, this is very key. I remember that this is a marathon. This is not a sprint. We are, we are a part of a linear thread of humanity that has gone on before us, and that will go on after us. There has been progress, not maybe as much as we want, maybe not as much that that will change and affect the material conditions of our everyday lives, but we cannot deny that progress happens.

Sometimes it happens slowly. Sometimes it happens in verse sometimes, whatever, but. Evolution happens. It’s inevitable. And so if we [00:27:00] understand that we are a part of that, that long line that that run that marathon of change, of evolution, of care for one another, for our environment, for animals, for everything that makes humanity human, and we are a part of that, then there is no cap.

There are no limits. It is nothing but blue sky and abundance because it goes on forever. And so all we have to do is show up as our authentic selves advocate, revolutionary selves and say, listen, we have a job to do. I need you to help us. We’re, we’re all doing this job together. Let’s keep moving. Let’s keep doing it.

There’s no limits, zero limits. 

[00:27:44] Stephanie Skryzowski: I love that. That’s so good. That’s so inspiring that I, I just love how you mentioned like, doesn’t matter how many nos you get, like the one Yes, it’s all that matters. You’re gonna get a hundred nos, you’re gonna get a thousand nos. But that one, yes. It’s really all that matters.

And I, I love that. And I think that will [00:28:00] encourage someone listening who’s like in the throes of getting all the nos that it doesn’t matter, like we are on this journey and that it is a marathon. It’s not a sprint. In terms of being a leader in the nonprofit sector, I have found, um, and I’ve heard that it can be kind of lonely along the way where, you know, you’ve got your board that you report to and you’ve got your team that reports to you and you’re kind of like in this middle place.

And it can feel kind of lonely. I wonder if you, um, if you have experienced that and how you have sort of found yourself a community so that maybe it doesn’t feel quite so lonely. 

[00:28:41] Kailee Scales: I think leadership lonely is because of the extraordinary responsibility that leadership brings. I’m an oldest of three. Um, I’ll, and I remind my sisters of that every day.

Um, and so, and if you’re the oldest [00:29:00] girl child, um, you generally, I mean, study, show that you generally have a lot of responsibility at an early age, right? Mm-hmm. Like you are the caretaker. You do a lot of the things. So I’m the oldest by like four years, right? And so, I’ve had a whole life of feeling responsible and in a leadership position.

Mm-hmm. Where I’ve had to understand the responsibility that comes with leadership. And so, you know, as that has manifested professionally, I understand the loneliness because it is a responsibility like no other, especially if you sit at the highest level in an organization or a department or your a group, right?

Mm-hmm. Mm-hmm. You are. It, it. The responsibility that you hold is, and especially if you take it very seriously, it can be isolating because you know, at the end of the day, you have to make decisions. If you are wise and a wise leader, you’re gonna make decisions on behalf of the collective, which could alienate [00:30:00] individuals.

And you have to observe what the collective needs, which doesn’t really give you the opportunity, uh, always to engage on an individual level so that. Contributes to loneliness because you’re constantly observing the, the needs of the collective and making decisions based on what the collective needs.

And so I, I feel like. The responsibility of leadership is lonely because you have to be able to kind mm-hmm. Sit at a different level and observe things differently, but I think the, the activity, the daily engagement is not lonely, especially if you are the type of leader who. Values, humanity and people, um, it’s not lonely because you, you are still able to develop relationships and ask for, you know, advice to contribute to your decision making.

It doesn’t, you don’t need a c e O to give your c e o advice, you know what I mean? Like, you know, you. You can speak to various people and develop deep relationships in order to contribute to the decisions that you [00:31:00] make. But we should, I wanna make sure, like, and I had to learn this like, you know, even as c e O of pop and just feeling the loneliness and realizing, oh, that’s not loneliness.

That’s, I feel the responsibility and I have to be a leader in that responsibility and I have to make decisions. And if I’m. Vocal about that. And if I am, you know, if my team understands the way I approach and my vision and the way I intend to lead, it won’t be isolating. I don’t have to isolate in order to be responsible, I have to be responsible.

Mm-hmm. And for me, as a person who I told you was the oldest of three, I’m okay with that. Um, for others it can be a burden, it can be challenging, it can be something they’re gifted in but don’t necessarily feel comfortable with. Um, I think for me, I just have that extra. Extra boost of, you know. Mm-hmm.

Having put at a young age, but anyway. Yeah. 

[00:31:51] Stephanie Skryzowski: Yeah. Well, I think that’s an interesting distinction too, where it’s like, yes, you’re feeling responsible, but that doesn’t necessarily mean you’re [00:32:00] feeling isolated. And I think you’re, you know, I’ve gotten to experience your leadership style at Pop. I feel like it’s very inclusive and it’s very like, let’s co-create something together.

Let’s work on this together. And so I can see. Like, I understand that distinction where you’re like, yeah, it’s not necessarily isolated because I’m work, you know, you’re, you’re very collaborative with, um, with the team. Has that always been your, your style, your leadership style? Or has that something that you’ve sort of learned and evolved over time?

[00:32:31] Kailee Scales: Interesting question. Um, has that been So, I think I sometimes struggle with it, like it’s something that I am very much aware of. Wanting to be and, and really being intentional about being collaborative because as like the oldest child with all the responsibility, I can think that I’m always right. I can think, I can think that my answers are like, I don’t.

You? No, just put it down. Let me do [00:33:00] it. You know, like I can, I can do right. I can have that tendency, but I also know that that, and I have been that like, you know, in, at times in my career, I have been that person who, and I choose roles that kind of make sure that I have, that I’m, I’ve, I’m always been a, the leader of the team, of the room, of the whatever.

Um, and so I, I will put myself in those positions where I have that opportunity to be like, sh, put it down. Um, But I also know that that’s not a sustainable way to be. That’s not, you can’t do that all the time. You will just be doing all the work and then you’ll alienate other people and then there you are, and you’re just, and then you get, and then this happened to me, you know, early in my career.

So I, I was that like, I’ll just do it. And then I resented and I’m like, why the hell am I doing everything? Why am I, why am I doing all the work? And I’m like, oh wait. 

[00:33:49] Stephanie Skryzowski: Right. This is what I wanted, I guess.  [00:33:51] Kailee Scales: Yeah. Isolated myself and I went on and then you were not right. Like it’s just not a way to be. So I’ve learned over the years that I’m very [00:34:00] intentional about understanding and seeing people and understanding that contributions are.

Valid that they sometimes take coaxing, they sometimes take, um, it takes a very intentional leadership style to be able to be collaborative because you, and especially if you’re a strong leader that thinks you kn know everything, um, you have to be able to understand and to tell yourself and to elevate the contribution.

Purposefully elevate the contributions of others because they are very valuable. Everybody’s background is different. Everybody brings them to a different place. Everybody’s experiences lended themselves to creating strategy change. All of those things. And so that much I learned, I learned not to one overburden myself with having to do too much.

And number two, acknowledging that I don’t know everything, couldn’t possibly, um, I know about being a queen, you know, coming from Queens and being the oldest child and if you want me to sing something, absolutely. Um, [00:35:00] and I have a little experience, but there are things I don’t know. And it’s very val and that will only make me.

Better. Right? Like it’ll teach me things as well. And so I think it’s really important to be intentionally collaborative and to frame conversations and situations in a way that, um, elevates the contributions of others. 

[00:35:23] Stephanie Skryzowski: Hmm. Yeah. Yeah, I absolutely love that. Um, well, my final question is one that I ask all of our guests, but what does a prosperous nonprofit look like to you? [00:35:37] Kailee Scales: I think, um, a prosperous nonprofit is a, an organization that has. A very clear message, a very clear intervention, and has found its tribe. So a lot of what I was saying earlier was about having this abundance mindset and ensuring that. You know, we’re not [00:36:00] limiting ourselves and our abilities to engage those who want to support the work.

Uh, I talked about getting nos a lot and things like that, and, um, I think one of the things, and, and I talked about, you know, I. That it only takes one. Yes. And, and what I mean by that is it doesn’t just take one. Yes, it does take a few yeses, but what I mean by that, um, which will create a prosperous organization, is there are people who experience the same passion for whatever it is that we are trying to accomplish in this world.

Whatever it is we’re trying to get done as organizations, there are people, the world is huge. There are people who want the same thing. And we have to find those people. We have to. Rally those people, when I think of that, activist and advocate words, those words, those terms, and so, and we have to mobilize those people and make those people feel a part of the [00:37:00] solution.

And a prosperous organization is able to effectively do that. They’re able to be very clear in what it is that they’re doing to change the world, to transform, to intervene, and they’re able to. Speak to find their tribe, to speak to that tribe consistently and in a way that connects them very deeply to the change and through the journey, then takes them through the journey.

To that change, and those people will be there for you. They will contribute to your cause. They’ll introduce you to other people. They will step up in leadership, They will be you because they will feel what you feel. They will. They’ll experience what you experience, They will know what you know. I think all of us, if we.

Are fully invested, which I think you have to be in the work that we do. We know things about the way this world works, We know things about the impact that change can make, We experience that many times firsthand. We meet the beneficiaries, we [00:38:00] understand the power of human connection, and we know the the truth, which is we are all here.

We’re here to take care of each other. That’s why we were all put on this planet. And so not to consume, but to. Give and to thrive together and we, we get to experience that and we can’t talk about it and expect people to be in that tribe with us. We can’t send you an email about it and expect people to be in that tribe with us.

We have to bring you in on that journey We have to. Give you that same experience. And so a prosperous organization knows how to do that very, very, very well. And they do that in all parts. Their leadership does it. Their team, their, the words that they choose do it. They’re, they’re, everyone’s isn’t able to be in, in.

Presence with our beneficiaries and, and hear stories firsthand. So we’re able to communicate from their perspective, those that’s what a prosperous organization is able to do. They’re able to [00:39:00] communicate from the perspective of the beneficiaries. In essence, they’re able to connect people. Things transformation change and they’re able to do that effectively and then they develop a tribe and that tribe rides with them and brings, as I said, new people.

That tribe leaves you money after they’re gone. They continue to support you even after they’re gone. Their children, they become legacy. Their children contribute. They bring other people into the fold. They will speak, you know, if they’re high, if they have, if they have platforms, they use their platform.

To also advocate. And so that’s what a prosperous organ, and you do that forever because as I said, it’s a marathon and you get better and better and better, and you adapt and change to the environment and to the current culture of the world, and you communicate differently. You always revisit that, and that’s what a prosperous organization is able to accomplish.

I 

[00:39:54] Stephanie Skryzowski: love that it really all stems from that message, from that story that we [00:40:00] are telling, um, and that connection to, to the change that is possible. So I love that. Thank you so much. Thank you so much for chatting with me today, Kailee. I really appreciate you. And for anybody listening, if you wanna check out what Kailee is doing over at Pencils of Promise, your website’s, pencils of promise.org, right?

Yep, I think so. Yeah. Um, feel free to check that out and support what they’re doing over there. And again, Kailee, thank you so much. Thank you 

[00:40:25] Kailee Scales: so much. Pleasure. Hi.  [00:40:30] Stephanie Skryzowski: Before you go, I just wanna thank you for being here. To access our show notes and bonus content, visit 100 degrees podcast.com. That’s 100 degrees podcast.com, and I’ll see you next [00:40:42] Kailee Scales: time.