Leadership: What we need to know (Part 2)

In this episode, we learn from two leaders who participated in a leadership program specifically for emerging leaders of color. We’ll hear what they learned, how this program was different, and their advice for future leaders of color.


Cynthia Rojas 0:02
Hi, everyone. Welcome to Coffee Time with Masterminds. We are continuing our conversation about leadership, my favorite topic, and I’m sure you’ve heard me say that before.

But if you’ve been following us a few weeks ago, we featured a guest who is working on building a cadre of leaders of color in her community. And we talked about, what is different about such a leadership program and what is she learning. Well, today, is part two of that show because we have two participants who actually went through the program and we get to hear from them. What makes this leadership program so special. Stay tuned.

CTMM jingle 0:55

Cynthia Rojas 1:20
Welcome everyone to Coffee Time with Masterminds, a 30-minute conversation with four leaders of mission-based organizations. As I mentioned before, we are continuing our conversation about leadership. We want to first welcome our listeners in the US, our listeners in Australia and people from all over the globe. If you are joining us today, please put your name in the comments box and say, hi. We love to hear where people are listening from. I am Cynthia Rojas one of the co-hosts, and I want to introduce my other co-host, Pieta Blakely. Pieta, how are you?

Pieta Blakely 2:06

Good. Good morning. How are you?

Cynthia Rojas 2:10

Good morning. I’m really good, you know why, right.

Pieta Blakely 2:13

It’s your favorite topic, again.

Cynthia Rojas 2:15

I could talk about leadership all day. It is something that I truly believe in and I love to watch people rise to their own leadership.

Pieta Blakely 2:30

I’m learning. There’s a lot to unpack.

Cynthia Rojas 2:32

There is. And today, I’m super excited because the leadership program that we talked about a couple of weeks ago with Jackie Downing is a program that I am a part of. So,

I got to spend nine months with our two guests and the transformation is just amazing. Let’s bring them on. I want to introduce Kimani Sioux Williams and Christian Aviles. Okay, there they go. Christian, did I pronounce your last name correctly?

Christian Aviles 3:08

You definitely did. Thank you for asking.

Cynthia Rojas 3:10

Great, that’s important. Well, how are you guys?

Kimani Sioux Williams 3:16

Doing well, thank you. How are you?

Cynthia Rojas 3:19


Pieta Blakely 3:20

Thank you for joining us today.

Christian Aviles 3:23

Yeah, thank you for having us.

Pieta Blakely 3:26

So, I’m going to start with Kimani. What inspired you to apply to this particular leadership program.

Kimani Sioux Williams 3:35
My boss, Reverend Todd Foster, politely sent me an email. Letting me know that I needed to apply so application was linked and he said this is something you need to do and I did it.

Cynthia Rojas 3:45
That’s fantastic. That’s awesome. One thing that I love about that is part of leadership is helping others rise to their leadership. And so, what it shows is the support you have. I just want to know Jackie Downing, who is the mastermind behind the program, along with her partners at Uconn and Fio Partners, just gave us a shout out. She says, “excited for today. Jackie Downing from New Haven love to Kimani and Christian. Thank you, Jackie.

Pieta Blakely 4:28
Christian, how did you come to apply to this program?

Christian Aviles 4:32
So very similar to Kimani. I got an email from my boss and I think no one has helped me rise to leadership more than my Executive Director, Julie Greenwood at Squash Haven. I saw an opportunity I didn’t really initially think I was going to apply for. I never thought like, oh, I’m going to be a leader or I’m going to rise to a position of leadership. But I think with her encouragement and support. I was able to go through the application process and I was really excited about this particular opportunity of being with other people of color. So, that naturally drew me to apply.

Pieta Blakely 5:06
Yeah, say a little bit more about that, like why this particular program.

Christian Aviles 5:09
Yeah, I think, like I said, like I didn’t really see myself as someone who was like, oh, I’m not going to be an Executive director or Program Director, so why would I do a program like this. I think particularly what caught my attention about the program and what piqued my interest was that it was specifically for leaders of color, I think. I had done other professional development workshops on some of the topics we covered, but sort of on a smaller scale, and it was with people who did not look like me. And I think, I always found those experiences to be intimidating but also a little bit alienating. So, I think the opportunity to be in a leadership program with people who were going to look like me. Who were going to come from communities like the one I grew up in, I think, is what served as like the real motivator and the push for me to apply for this program.

Cynthia Rojas 5:57
Kimani, did you see, did you feel a difference in the program, it being targeted for leaders of color?

Kimani Sioux Williams 6:05
Absolutely. For me, it being for leaders of color made a big difference. Once I sort of got the information. I felt a little nervous, initially, but once I got there and started interacting with everyone there. I felt like there were layers of I don’t know, discomfort that just dissipated. Just because we had a lot of shared experiences and everybody was different, but there were just some things that we understood and could relate to. And so, that for me made the program very exciting, not so much in the application phase, but once I was there.

Cynthia Rojas 6:50
Yeah, I got to see how important it is to come together in the room with people who have shared experiences and be able to talk about it in a safe space. One of the unique things about this specific program is that at the end of every workshop we had some time to reflect. We would talk about what we were learning but from the lens of a person of color and that always brought on interesting conversation because we do see the world with a different lens.

You’re building a network of other leaders that look like us. And this is what’s so great about the program, is that the Community Foundation Uconn and Fio Partners are bringing together and building a huge network that you get to keep forever. I think, I said at graduation 12 years from now, you’ll be able to call one of your cohort mates and they’re always going to be there, so which is awesome.

Pieta Blakely 8:04
All right, I want to, you know, spend a little bit more time on the fact that both Kimani and Christian were pushed into the program. And Christian said, “oh, I never saw myself as somebody who was going to be an Executive Director.” I think that it’s really important that somebody has identified this pathway for you. Did that change? How you think about yourself and your career and your role?

Kimani Sioux Williams 8:37
That’s a good question.

Christian Aviles 8:38
Yeah, I would say definitely. I think like, I again, not ever seen myself in that role. And I think part of it of maybe why I haven’t seen myself in that role or didn’t see myself in that role before was because I also didn’t see people who looked like me in those roles. I think that like was really challenging, and so, I think I never sort of associated myself with that particular like leadership. But I think like, having someone like having my boss identify me, like really.

I think it did serve as like a as an important step of like, oh, maybe I am a leader and maybe people do see leadership qualities in me that I can tap into. And that was really motivating to hear from my boss, who again, was great at supporting me at every stage of this program. I was really grateful for the opportunity that she encouraged me to apply.

Cynthia Rojas 9:30
Yeah, I also think that leadership looks differently, right. So Christian, you’ve lifted leadership as a role, but leadership is also a process, and it’s also action. And so, I wonder, how you’ve changed as a result of the program. You and Kimani, so, either one of you can answer that. How have you changed.

Kimani Sioux Williams 9:59
I have changed so much since starting this program. I love my job and I was so excited to be serving my community, but I also was sort of just figuring out life, so to speak. I think this program really highlighted a passion that I have for non-profits, which I don’t know that I knew before. Before I knew it. I worked at one and I was doing my job and getting to serve people, but now, I really love the nonprofit space. I want to be present there. It has changed. I’ve gone back to school to pursue more education to advance that. So, it really has motivated me and given me a lot of confidence and just launched me into a lot more direction in my career, as well.

Cynthia Rojas 10:53
Wow, that’s awesome.

Pieta Blakely 10:54
Yeah, it changed your entire trajectory.

Cynthia Rojas 10:56
Yeah. How about you Christian?

Christian Aviles 11:00
I totally agree. I think like the trajectory, I feel, like my career is now totally different than it was a year and a half ago or a year when I started this program. I think on one level, for example, like, I started to become more interested in things like strategic planning, in development work, in marketing work and all that stuff. Because we covered a lot of those topics in our leadership program and I think being able to bring those back to my organization.

I think like at my weekly meeting with my Executive Director, I told her like, oh, we just learned about this, we should be doing this at squash events. I think one of the great things about this program is that we now get to work on a project our second year, that we get the design. And that’s just been really exciting, to see myself connected with our organization in a different way because of the lessons that we learned as part of this program.

Cynthia Rojas 11:48
Yeah. This is another part of the program that is amazing. And also unique in its way is that the Community Foundation for Greater New Haven also provided funding to the organization to support Christian and Kimani and the others to come in and spend time.

Two times a month two days a month on workshops and learning, and then the program extends to year two where the cohort members take on a project with their organization and they get to lead it so they get to practice a lot of those skills. So, I think it just makes the program amazing. Kimani how’s that project going, or is it going to launch soon. How’s year two going?

Kimani Sioux Williams 12:43
Year two for me is starting with a little bit of a delay and so I got the evaluation, the C-cap that they helped us set up for my organization. And so now, we’re launching into reviewing that, and then, we’ll figure out exactly what kind of change.

I’m going to get to bring it, but my mind has been spinning because I’m so excited, there’s so many things that I’ve said. Some of it is what the program drew out of like, oh, we should be doing this or I want to do this. So, it’s just nailing it down and seeing what everybody thinks makes sense.

Cynthia Rojas 13:19
Yeah, and so, one thing about leadership is also being able to hyphens who wrote a really famous book about adaptive leadership. Talks about being on the balcony or looking at things from thirty thousand feet, right. Leaders are constantly having to do that balance from being on the balcony to going down to the dance floor, which is the exact metaphor that hyphens use. I wonder, have you been able to bring yourself up to 30 000 feet and look at your organization from that perspective and how is that different for you?

Christian Aviles 14:05
Yeah, I think that’s exactly what we were doing in this program. I feel like as part of the program we spent the entire nine months at 30 000 feet. And I think every time we brought in a guest who spoke about a different topic, even about budgeting or against strategic planning or diversity equity and inclusion. I think we were asked to put ourselves in that balcony and see our organization from that balcony. And I think, I found that really empowering in terms of the amount of information we were getting. Because the guest speakers that we had, I think, encouraged us to ask questions of ourselves and of our non-profits.

That, I found just really incredible because again, we got to see it sort of more from like a strategic planning perspective that I just then was able to bring back to my organization. I think it was really interesting. I think we’re on that balcony because we’re like the people who were in the program. I think we were in direct service. We’re like doing the work every day, like in the day to day of our work. But then, this was an opportunity for us to sort of just step back and actually see how we can shape and impact the day-to-day work that we’re doing.

Cynthia Rojas 15:05
Yeah, Kimani, how was it for you. Were you already at 30 000 feet or did this program help you see it from that lens.

Kimani Sioux Williams 15:17
I’m in operations at my organization, so I was supposed to be at 30 000 feet and I realized maybe I was more at 25 or 20 in certain areas. It elevated me to be able to say wait a minute, this is the next step. It was also something that Christian hit on a little bit, really, because there was so much self-reflection required in learning these different things.

And seeing how you’re serving the community or how your organization is doing in evaluating or whatever it might be, it made me self-reflect a lot. And so, in terms of leadership, sometimes it’s not just, do you know how to plan or do you know how to have the marketing strategy, but are you, integrity wise, character-wise. The way you’re navigating a leader, and that’s one place where it really helped develop me, as well. I’m seeing the benefit of that in the relationships with the folks I work with, and I know that that is going to then bring forth the changes and the improvements.

Pieta Blakely 16:13
This reminds me of the conversation we had with Forrest a couple weeks ago about thinking two levels up right or two levels more senior than where you are in the organization. The point that he was making was that a lot of times we are so focused on the day-to-day of our jobs that we’re not really clear on how our job and our function is fitting into the strategy of the bigger organization. And how we need to build opportunities for people to see from a balcony even as they’re doing their day-to-day jobs.

Cynthia Rojas 16:56
Yeah, so when we had forest who leads a lot of leadership development programming for the state of Connecticut and throughout the colleges. He mentioned this two-level and I haven’t, I’ve never thought about that, right. His thing is that just thinking about moving one level up might be a little short-sighted and really constantly thinking two levels ahead.

He’s probably at 60, 000 feet, but it was a really interesting takeaway and one that really resonated with me. This question, oh, my god, I just lost my train of thought. I want to ask like, what do you see yourself or where do you see yourself in terms of leadership moving forward? Kamani’s smiling, she has something, she’s thinking.

Kimani Sioux Williams 17:51
That’s such a big one for live on a Friday morning. But I think what I’ve gained from the program and just from the experiences that it connected to throughout the year. Plus, so far it is just that I definitely do want to rise in my organization and beyond. What does it look like to kind of create. We have some challenges in Milford that are connected to organizations not being connected enough. Seeing even beyond just my one organization into like the ecosystem of our area.

 And how do we connect organizations and provide service to people on a level that is seamless. You’re not going to one place and then you have to. So, that’s kind of where my brain is headed and hoping to get into that space, as well.

Cynthia Rojas 18:53
I love that. A relationship builder.

Pieta Blakely 18:58
Ultimately, like one of the features of these types of programs, right. Connections and seeing relationships across organizations.

Cynthia Rojas 19:05
Yeah, how about you, Christian?

Christian Aviles 19:05
Yeah, I think one of the things that I really appreciated about this program that I think helped me see a little bit more was I think like I’m in the area sort of like of college access and equity and inclusion and education. And I think one of the things that I often find sort of frustrating in this type of work is that like, you know, we are doing sort of direct service work. I’m doing direct service work and it often feels like more of like a band-aid approach or a band-aid solution to like this bigger problem of equity. I think what leadership can afford us and what this program sort of helped me see is like, well, let’s take what you know at the ground level right if you’re on the dance floor.

Let’s take what you know about the ground level and put you on the balcony so that you can start designing structures that address the larger issues in the community. As opposed to just like the one doing one-on-one work with a student because the student next year might have the same issues with lack of access or lack of equity in education. How do you start building systems that address the root of those problems. I think I saw this program as sort of launching me into leadership in that field. I’m really excited about continuing to explore not just that Squash Haven but also in the New Haven community. And sort of like to Kimani’s point like, how can we learn to collaborate so that we start addressing these things as like, systemic structural things, and not just like the day-to-day work of our own non-profit.

Cynthia Rojas 20:27
Yeah, I love that. Jackie must be doing a dance right now.

Pieta Blakely 20:30
This is system thinking here, right, not just the individual thinking at a more system level in their organization. But organizations thinking at a system level in their region or country.

Cynthia Rojas 20:45
Yes, because Jackie’s mission is really to strengthen the non-profit sector. This is one way that she’s doing, is she does it in many different ways through the community foundation for Greater New Haven. She just put in a smiley emoji, but she does it in many different ways. Jackie is all about strengthening and strengthening and you guys are proving that, so kudos to Jackie.

Pieta Blakely 21:18
So, Kimani and Christian that you guys are sort of picked for this program, so it might be a little bit of an unfair question. But, you know, if you were talking to somebody like you two years ago about leadership programs in general or next steps in their career. What advice would you give them, like what makes a good fit between a participant and a leadership program or opportunity.

Kimani Sioux Williams 21:51
I would definitely encourage them to take the risks, take the step into maybe an environment they’re not used to or they’re uncomfortable with, in theory. Because what I found when I did so was that there were people ready to understand, accept, embrace, and encourage me. And so, I would say you cannot get the things you need if you stay isolated and if you do not get out there. So go, go, go, do it, and then come back and tell me how wonderful it was because it will be.

Cynthia Rojas 22:27
I love that. Christian, do you have a response?

Christian Aviles 22:30
Yeah, totally, I think, like if I were to tell someone, two years ago or someone in a similar position that I was in two years ago about doing something like this. I sort of like similar to Kimani. I would encourage them to see themselves in new ways and see themselves in new life. For me particularly, I never saw myself as a leader despite I think, playing a leadership role in my organization and having led in different ways in my community before.

I think like again, sort of like reimagining what our leadership could look like and reimagining what our roles could look like. I think, encouraging people to sort of like put themselves out there in these positions of leadership and in these programs. Because like Kimani mentioned, I found that like there’s a whole community out there that’s like, really excited about like uplifting us and working with us and supporting us. And I think that’s a really exciting part about leadership is that you don’t have to do it alone. You’re doing it in collaboration with other people and that’s something that I appreciated about this program.

And that I think I would encourage people to lean into is that like as you’re leaning into leadership, you’re not doing it alone. You’re going to have all this support and you’re going to find at the end of this process. That you’re going to see yourselves in ways that maybe you hadn’t seen yourself before. That’s a really exciting and transformative thing professionally, but also personally.

Pieta Blakely 23:45
Yeah, you know, that’s so important. We started this show, two years ago, talking about leading through covid. One of the things that we saw was leaders were really isolated and that’s one of the reasons that we started this show was like a lot of people were trying to lead their organizations through something nobody had ever seen before.

And because they were in charge a lot, of internalizing a lot, a lot of stress and trauma and discomfort. Part of the appeal of this show, we thought was just to just to make it clear that everybody was in the same boat. You’re not doing it, wrong, nobody knows. What they’re doing right now, but you know, leadership can be really isolating and so the idea of creating community across and among leaders is very powerful.

Cynthia Rojas 24:45
Yeah, one interesting thing that I want to point out to Christian is you’ve mentioned not seeing yourself back then as a leader. But what’s really interesting is that in the nine months that we spent together, your viewpoint on things was always amazing like, the way you see things. You always gave thoughtful and wonderful feedback and thank God, he went through this program and thank God, you see yourself as a leader. Because the way you view the world and the organization and the people you serve was just such a great asset to the organization. Thank you for that.

Cynthia Rojas 25:33
Thank you, Cynthia, for those wonderful words. I appreciate that.

Cynthia Rojas 25:38
So, have you guys kept in touch with any of the other cohort mates, like have you spent some time over the summer or talked or emailed since the end of the program.

Kimani Sioux Williams 25:50
I’ve joined, we’re connected on social media with some folks. So, I’ve interacted that way.

Cynthia Rojas 25:55
Nice, that’s important. How about you, Christian.

Christian Aviles 25:58
Yeah, I think sort of in the same way. I think, connecting with people on Linkedin, as is always the first step right in the professional world, but also just like starting to connect with folks like on social media. And like sort of seeing our folks in this program as like allies in this network, but also just like as friends and confidants that we also have in our corner.

Cynthia Rojas 26:22
Yeah, and my last point about leadership is well for this show because, well, about leadership forever. An important aspect is also helping others rise to their leadership. And so, I wonder if you’ve given that some thought and how you might help others in their pathway toward leadership.

Pieta Blakely 26:51
Or what now, go ahead and address that then I’ve got the following question.

Christian Aviles 26:56
Yeah, I mean, I am so fortunate that I get to work with young people and high school students and college students. So, the opportunities to tap into leadership potential in my role are endless, right. I think they’re infinite. I think like we have a lot of really creative, powerful, confident young people in the city of New Haven.

And, you know, get to sort of see them as middle schoolers. I get to see them as high schoolers. I get to see them as college students, as graduate students. I really get to see students over a long period of time and I’m always encouraging them to pursue positions of leadership on their campus at their high schools, right. Even if it’s not a formal position of leadership, because I think like that’s how we maybe traditionally think of leadership. Of thinking, how can you lead in other ways, like if you’re not going to be the captain of your team. In what other ways can you be a leader and I think that’s something that I try to infuse actively in my work.

In youth development is also leadership development with young people. Particularly, with young people in New Haven. And so, I’m always really inspired and love to see the awesome and incredible things that young people in our city are doing. I’m lucky that I get to do that work every day, like tap into other people’s leadership. It’s incredible and it’s rewarding.

Cynthia Rojas 28:07

Pieta Blakely 28:08
So, what do you want to say to organizations that want to cultivate a next generation of leaders.

Christian Aviles 28:16
I like that, I think that the passion is there. I think, sometimes students just like want an opportunity and want to know a door or want just someone to tell them like go for it. I think oftentimes what I have found in helping young people tap into leadership is that like, one, maybe they didn’t know about an opportunity.

And then, you tell them about it and they’re like, oh, that’s amazing. I didn’t know about that, like I’m going to look into that. Or even just telling them like, I think you should go for that position or I think like you should go for that thing and then sort of them thinking like, oh, really. Sort of like in a similar situation to me. Like, really, me. That’s how you want it to be, but I think then then they take it and then they go and like thrive in those positions. I think that that’s something that all organizations can do. It’s just like a simple encouragement can go a really long way, particularly, for people of color.

Cynthia Rojas 28:09
Nice. How about you, Kimani. How will you help facilitate others leadership pathway?

Kimani Sioux Williams 29:09
I see this opportunity as one that I was tremendously blessed to have, and I know that while the community foundation and Jackie are doing this great work. It’s not yet happening everywhere, and so when I see people who are in a similar position to me.

Maybe they look like me, or maybe, they’re also a young woman at their organization. I always try to speak life into them, encourage them, but also, there’s some lessons that it took me a long time to learn. I definitely want to allow my ceiling to be their floor so that they’re skipping past the long haul of figuring out stuff the hard way. I think that that’s something that this program gave me in certain ways. And so, I’m just looking for those opportunities and paying attention to giving back to other people younger than me and around me.

Cynthia Rojas 30:05
That’s beautiful. Your ceiling is their floor. We are out of time but I just have to ask because cohort 2 is starting next week. Do you have any words for them? Some of them are watching. Do you have advice or words to impart for cohort 2.

Christian Aviles 30:31
Yeah, I would say, I think, with the lessons that you’re learning from the speakers, bring them back to your organization. But also think about the ways that you want to bring that to your work in the future. One of the things I love, Jackie always saying is that something like this program is not necessarily meant to keep you at your organization, but to sort of help you grow even at other organizations. Think about how these lessons I think can apply to your current work, but also think about the exciting possibilities that can exist in other places too. Where you might be able to bring that work. I found that really exciting and I hope that this next cohort does that, as well

Cynthia Rojas 31:05
Awesome. Kimani.

Kimani Sioux Williams 31:07
As non-profit leaders or emerging leaders, we do a lot of work for others. We put a lot of care into others. This program is so that you can be strong this is your time to get strengthened and recharged so that you can go out and do that service for others, but with your own arsenal of really strong weapons. So, take the time you need for you to apply it, to internalize it ask the questions. Whatever it is, make those connections because you need this for you. This is your one thing for you, do it, full force

Cynthia Rojas 31:42
That’s great. Well, we want to say thank you to our guests. Thank you to our listeners and we’ll see you next Friday. Take care. Thank you so much.

Pieta Blakely 31:49
Thank you so much. Have a great weekend, everybody.

Pieta Blakely

About Pieta Blakely

I help mission-based organizations measure their impact so that they can do what they do well. I started my nonprofit career as a teacher in workforce development and adult basic education. It was important work and I was worried that we didn’t really know if we were doing it well. In the process of trying to answer that question, I got a Masters in Education and a PhD in Social Policy, and became an evaluator.

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