Episode 4: A Conversation with Dr. Charles Dedrick and Jacinda Hall Conboy Esq. of the New York State Council of School Superintendents

[00:00:05.210] – Steve Barkley 

I’m pleased to welcome Dr. Charles Diedrick and Jacinda Conboy from the New York State Council of School Superintendents to leaders to Leaders Learning from Leaders. Chuck Diedrick serves as the executive director and Jazz Conboy as the general counsel. Welcome, Jazz and Chuck. 

[00:00:22.670] – Jacinda Hall Conboy 

Thanks, Steve. 

[00:00:23.470] – Dr. Charles Dedrick 

Thank you, Steve. 

[00:00:25.770] – Steve Barkley 

For starters, when I went to the council’s website, I found this post: “We exist for one reason only to help our members succeed on behalf of the children and the communities they serve. One way we pursue that goal is through advocacy for, with, and by our members.” I’m wondering if you might take a few moments to introduce your roles at the council and maybe connect your role to that statement of advocacy. 

[00:00:54.690] – Dr. Charles Dedrick 

Sure. So my role is to oversee the whole organization, and very often everything ties back to advocacy. But one of the important things about advocacy and NYSCOSS is that I feel we are probably one of the most respected organizations in New York State when it comes to advocacy because of that word, “children” in our description. Groups who we talk to about what’s needed to happen in education in New York know that we are there on behalf of the children. Yes, we serve our members, but our members’ main purpose is to serve the children of New York State. So our words carry a lot of weight with the people in power and often we’re asked opinions on things behind the scenes, not publicly on “what do you think about?” because they know that we’re going to give an honest answer that directly relates to the success of children in school. And that’s one of the things that I’m probably most proud of about NYSCOSS, the New York State Council of School Superintendents, that while we support our members, we support our members by doing what’s right for kids. 

[00:02:24.030] – Jacinda Hall Conboy 

Yea so Steve, my role is a little more indirect in terms of advocacy. I’d say my role is more directly related to getting the best qualified people into leadership roles in education and especially into the superintendency. So I do a variety of things. I negotiate superintendents’ contracts, and then I do quite a bit of professional development and speaking to our members on leadership issues. And one of my favorite leadership issues to talk about is women in leadership. And so over the years, we at NYSCOSS have developed what we call our Women’s Initiative, and it’s aimed at getting number one more qualified people, more really great leaders into the superintendency and also more women into the superintendency. And we’re really looking at gender equity and running those programs. 

[00:03:20.770] – Steve Barkley 

As I’m listening to the two of you, I’m wondering to what extent your organization, as well as your work, includes the education of the public in order to advocate for the superintendent’s focus on children. 

[00:03:40.550] – Dr. Charles Dedrick 

We actually don’t try to do a lot of education of the public. What we try to do is we try to help our superintendents so that they can educate their public. Our state is so big and so diverse that a small district in the southern Tier is very different from a district on Long Island and very different from a district in the Adirondacks or the Capital Region or Buffalo. So we don’t try to sway the public on issues because, again, the diversity of New York State, but we try to educate our superintendents and help them to inform their public, because how they inform or what they inform them to may be different from place to place. Just like all people, all superintendents aren’t going to agree on things, and trying to weave that quilt of agreement together isn’t the easiest thing sometimes. We do have a legislative committee of superintendents from all over the state. They do meet regularly, and they do come up with a unified proposal every year that superintendents then carry out into their districts and then use that with their public. 

[00:05:05.170] – Steve Barkley 

Makes a ton of sense because my connection with superintendents – I’m frequently asked to provide coaching as to how the Superintendent is looking at communicating a message out to their public and equal, out to their board. So I can see the “what” is dramatically different, but the support that the superintendent needs to carry that out would be very valuable. 

[00:05:43.480] – Dr. Charles Dedrick 

Jazz knows this better than anybody, but the biggest thing we hear from board members is they want more communication from their superintendents. And I will say this – this is said with a grain of salt: it doesn’t matter how much communication is taking place. It never seems to be enough. And that’s one of those things where sometimes it’s not the amount of communication, sometimes it’s the type or the quality of communication. And Jazz works with superintendents on that a lot too. 

[00:06:22.330] – Steve Barkley 

I know that another part of it is just the change in style. So one superintendent leaves and a new superintendent comes in, and that kind of communication might switch because of the style of the person. So it’s a thing to set up front. 

[00:06:41.800] – Dr. Charles Dedrick 

One example is that our current president, Jason Andrews, Dr. Andrews, he’s made a recommendation to our newer superintendents where a lot of superintendents do a memo home on Friday afternoons to their boards of education, telling them what happened during the week. Well, then what happens is over the weekend, board members are calling or texting the superintendent and saying, “what’s going on?” And the superintendent may not be available, the communication may not be attached the way it should be, or sometimes board members won’t read something over the weekend. So Dr. Andrews has suggested instead of a Friday memo, doing a Monday morning memo or a Tuesday memo, and that seems to be something that has really worked out well communication wise with superintendents. 

[00:07:32.130] – Steve Barkley 

I’m wondering what you’d identify as some of the most critical issues that are facing folks in the superintendency today. 

[00:07:44.020] – Jacinda Hall Conboy 

There’s so many issues, it’s difficult to identify just a few of them share. [laughter] 

[00:07:51.320] – Steve Barkley 

Some, and it doesn’t have to be number one. [laughter] 

[00:07:54.680] – Jacinda Hall Conboy 

From my perspective, I think one of the most critical issues that impacts our members is the challenges of the job and how political the job has become. It’s always been political, but as our society becomes more political and the political issues become more divided, it’s a huge challenge for our members because our members just want to do what’s right for kids. They just want to protect kids, they want kids to be safe., they want kids to learn, they want kids to feel like school is their place where they are accepted. But that becomes very challenging in the society that we have today. So I think I would say probably those political issues. And then when the rest of the leaders in education are seeing how difficult that is for our superintendents, then trying to recruit and get really great people to enter the superintendency becomes even more challenging and even more difficult. So we struggle with our candidate pool of trying to get really great leaders into these positions that want to do this job because of the challenges that they face. 

[00:09:12.020] – Dr. Charles Dedrick 

I would say one of the biggest issues right now is, besides the political issue, clearly that is an overriding fact everywhere, but right now, just a lack of candidates for positions. From the Superintendency and Jazz talking about getting more qualified candidates to the superintendency, but I take it down to the positions like school psychologists and mental health professionals, school social workers, there just aren’t enough who are graduating from college and going to work in the schools. And as a result, what used to be difficult, where you would have one guidance counselor for 200 students, it’s now one guidance counselor for 300 students, the people just aren’t graduating from those programs. And there’s no question that the mental health issues that have been identified post COVID are real and have to be dealt with. And we don’t have the professionals in the pipeline right now who are able to step into the positions and deal with it. 

[00:10:22.840] – Steve Barkley 

Well, that kind of takes me in the direction of another question, and that’s two related questions. So what role do you think the current superintendents should be playing in the recruitment of people into the district level and superintendents kind of positions that we need? And I think that crosses over then to, Jazz, the comments you made about supporting women in those leadership roles. 

[00:10:53.070] – Jacinda Hall Conboy 

Right. So I do think our members do a great job at recruitment, mentoring, and sponsoring aspiring leaders into the superintendency. It oftentimes comes with resistance from people because of the challenges that I mentioned, but they are natural teachers and leaders, and for the vast majority of our members, their goal is to improve education and get great leaders into their position. So we oftentimes will see our superintendents thinking about their succession plans early on in their career. Who do I see in my district that’s a great leader? Who can I sponsor and mentor into administration? Who can I support? Who can I encourage to go back to get their administrative degree? I think that goes on on a daily basis with our leaders. And then, like you said, one of the things we’re doing at NYSCOSS is we’ve been running our Women’s Initiative for about seven years now, and we run leadership conferences around the state looking at the gender dynamics in the superintendency and in those leadership positions. So if you just purely look at the statistics nationally, you have about 77% of your professional staff in school districts are women. But in New York State, we have only about 28% of our superintendents are women. 

[00:12:32.790] – Jacinda Hall Conboy 

so we have a pretty significant divide in terms of gender equity in the superintendency. So we’ve been running regional conferences. We oftentimes speak at the national level on this issue. We’ve partnered with the national organization AASA on this issue, and we’re here in Buffalo this week, starting tomorrow, to run a program. We have over 100 people registered for our Women’s Initiative, which is a two day conference aimed at inspiring and hopefully ultimately promoting women into leadership positions. 

[00:13:13.760] – Dr. Charles Dedrick 

So one of the things that I have found, I was a superintendent for 20 years. I was tapped on the shoulder – metaphor, by my first superintendent, who told me, you will make a great administrator. Please go back and get your administrative degree. And I did. And I have found that some of the best administrators are the people who are identified by other administrators as being the ones that should go on. That is a responsibility that I think all superintendents have and take seriously to identify the next generation of leaders. The problem comes in with succession planning to some degree, because the problem with succession planning is that people tend to pick people who look and act like themselves. So what we’re trying to do is we’re trying to broaden the scope of what people think about as necessary in the next generation of leaders, and whether it be through our women’s program or our diversity program, all of that’s important. We spoke to a large group of superintendents one time. I think it was like there are about 40 superintendents, 38 of them were men, and there were two women in the room and we were talking about the women’s program, and one of the men said, “why are you talking to 38 men about this program?” 

[00:14:53.360] – Dr. Charles Dedrick 

And Jazz answered as calmly as she could, “because you’re the ones that hold the door open for people. You’re the ones that are identifying who the next leaders are going to be.” And if you’re only identifying gray haired white guys, then you’re doing a disservice to the kids in your district and to the New York State. If you’re not identifying people of color, women and the many other groups of people who live in New York State. 

[00:15:27.820] – Jacinda Hall Conboy 

And Steve, one of the things that we’re trying to do is change people’s thought around the fact that men are oftentimes hired for their potential, but women are hired for their experience. 

[00:15:42.770] – Steve Barkley 

Wow. 

[00:15:43.550] – Jacinda Hall Conboy 

Yeah. So when we talk to people just simply saying that statement, a lot of people have never heard that before. But if you think about it, we survey our membership. When we look at our numbers and our statistics around superintendents, women often enter the superintendency later in their career, and there’s a whole variety of factors that impact that. But trying to educate people around the reasons why we’re not getting more women leaders and we’re also not getting younger women leaders, just thinking about some of those statistics and some of those reasons is really helpful. And I always quote the Hewlett Packard study that says, “men will apply for a job when they meet 60% of the qualifications. Women will only apply when they meet 100% of the qualifications.” So how are you advertising leadership jobs that are available? How are you advertising the administrative jobs that are available? If you have a list of 20 items that are the qualifications for the job and I meet 19 of them, but not all 20, I’m probably not going to apply. So it’s little things, but things that make a big impact in the recruitment of great leaders into the positions. 

[00:17:05.640] – Dr. Charles Dedrick 

And I used to look at those things and the first line would say, Certified in New York State. I didn’t even look at the next 19 things. I’d say, I’m applying for that. Just put it out there. 5% was my number. [laughter] 

[00:17:22.960] – Steve Barkley 

[laughter] Your comments are so reflective of my past. I’m doing the work I’m doing in education today because as an early teacher, I got tapped by the superintendent of the district. And certainly you’ve labeled it well before I was prepared to deliver, but I got tapped and encouraged. So you’ve really established in my mind, why it’s so critical for those people in school districts in the leadership positions today to seriously be looking at the need to have a much broader lens when selecting folks to encourage. And I know the statement that you made about the tendency to look for yourself, I know that I made that mistake very early in my career. I knew that I was a successful trainer of other educators and when I looked out to expand and find people, my initial tendency was to look for people who did it the way I did. And my eyes got really opened when I had the opportunity to watch some people with styles dramatically different from my own be more successful than I was being. That’s a very important picture for us to have. 

[00:18:59.540] – Dr. Charles Dedrick 

In my first superintendency, it was a very small school district, but I was very fortunate to work with some very strong women. They weren’t in administrative roles, but they were in lead teacher roles and union roles. As a result of that, they became part of my inner circle of leadership in that district and it really taught me something that I took on to other districts and I think led to a lot of my success and opened my eyes to the possibilities. 

[00:19:36.140] – Steve Barkley 

Well, as we wrap up, I’m wondering what closing words of advice or encouragement you’d like to share with our listeners. 

[00:19:47.260] – Jacinda Hall Conboy 

Well, I would say look for the potential in people that may be different, that may think different, that may have different perspectives than you and I think support those leaders that are looking to learn and grow and have the most potential to be great leaders in education. 

[00:20:13.140] – Steve Barkley 

I think there’s a connecting part there. Bringing those people who are different than you onto your own leadership team has the potential of two payoffs. One is developing those folks, but also expanding the quality of your own leadership team by bringing that diversity onto the team. 

[00:20:36.590] – Jacinda Hall Conboy 

Yeah, absolutely. We know every day that diverse teams outperform homogeneous teams. Every day. So that diversity is going to bring growth and more success for everyone. 

[00:20:48.880] – Dr. Charles Dedrick 

And my suggestion is not to isolate yourself. So often we find the superintendents who are having issues around the state – fill in the blank with what the issue can be. But they have isolated themselves and feel that they need to be spending more time dealing with the issues and less time communicating with their regional colleagues or state colleagues. When there’s a problem, it’s usually too late to deal with the problem. The time to prepare for that is prior to there being problems. And the best way to do that is not through isolation. It’s by coming to a women’s initiative program and learning new things and getting a chance to sit down and talk to colleagues from across the state and really having some cross pollination of ideas. We have found that to be extremely valuable. 

[00:21:49.620] – Steve Barkley 

It’s interesting because one of my songs I’m constantly singing is that teaching is a team sport. And I’m hearing you run the same example out there for the superintendency, which is probably a spot that people least see. I think they tend to see it as an individual. 

[00:22:15.370] – Dr. Charles Dedrick 

Yes, the old “it’s lonely at the top,” and sometimes it can be. But that’s why you have colleagues. That’s why we have close to a thousand members in New York State who are colleagues. They are our colleagues, and it’s important for superintendents to have that relationship with each other. 

[00:22:41.620] – Steve Barkley 

Would you take a minute to share the website for the council so that people with questions for you can follow up there? 

[00:22:52.040] – Jacinda Hall Conboy 

Sure. Our website is www.nyscoss.org.  

[00:23:01.740] – Steve Barkley 

Well, thank you so much. I appreciate you giving the time and sharing your experience. And man, I really applaud the work that you’re doing and the voice of the importance of that role to meet the needs of kids just can’t be downplayed. So thank you for that work. 

[00:23:28.550] – Jacinda Hall Conboy 

Yeah, thanks so much, Steve, we really appreciate your time and appreciate you giving us some time here today as well. 

[00:23:34.490] – Dr. Charles Dedrick 

Thank you, Steve. 

[00:23:35.740] – Steve Barkley 

You bet. Have a great time in Buffalo. 

[00:23:39.000] – Jacinda Hall Conboy 

Thank you always.