Embracing MESSY Leadership: How the Experience of 20,000 School Leaders Can Transform You and Your School

[00:01] Announcer:

Welcome to Principal Center Radio, helping you build capacity for instructional leadership. Here's your host, Director of the Principal Center, Dr. Justin Bader. Welcome everyone to Principal Center Radio.

[00:13] SPEAKER_00:

I'm your host, Justin Bader, and I'm honored to welcome to the program Alyssa Gallagher. Alyssa co-leads BTS Spark America, helping American and Canadian school leaders to access leadership coaching. Alyssa has broad-ranging experience serving as a teacher, school principal, and assistant superintendent. Under her guidance, Los Altos School District became a nationally recognized leader in educational innovation, and her work was featured by Forbes, Wired, The Economist, CNN, and CBS' 60 Minutes. She also served as director of global leadership for the Wiseman Group. And Alyssa has co-authored two books on using design thinking to improve teaching and learning.

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And we're here today to talk about her new book, Embracing Messy Leadership. How the experience of 20,000 school leaders can transform you and your school.

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And now, our feature presentation.

[01:00] SPEAKER_00:

Alyssa, welcome to Principal Center Radio.

[01:02] SPEAKER_01:

Thanks so much. Excited to be here.

[01:04] SPEAKER_00:

I want to get right in to the kind of origin story of the book. Now, your organization has worked with many, many school leaders around the world in a coaching capacity. Talk to us a little bit about that work and how the book Embracing Messy Leadership came out of that work.

[01:19] SPEAKER_01:

yeah happy to start there so as you mentioned bts spark we do a combination of one-on-one coaching with school and district leaders we also do what we call pod coaching which is small groups of leaders i'm connected with a leadership coach and all of these coaching sessions bts spark has been coaching for almost a decade in the education space all of these coaching conversations are confidential so you can imagine you know i don't know if you've ever experienced coaching But coaching is a place where you can really show up authentically as a leader with, you know, really like what you're struggling with. You know, it's that there are confidential conversations. And so in these coaching conversations, we ask all of the leaders to set like a mindset shift. Like, what are they striving to achieve? And then our coaches do take anonymous notes on the back end. So they're never attached to a specific leader.

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But you can imagine having coached over 20,000 school and district leaders, we have a lot of insight into what leaders are really struggling with. And so we sort of had this aha, my global director, Rosie and I, of we're sitting on so much data from actual stories of school leaders to say, you know, these are the top struggles. And we started to play with the idea of like, can we use this data to turn around and help leaders? So essentially, that's how Messy Leadership came to be. We dug into the data. We were able to identify the top nine sort of common challenges globally that leaders experience and then offer sort of tools and solutions that our coaches offer in coaching sessions.

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But we know that not every leader can afford a coach or even wants to make the time for coach. So our goal in writing Messy Leadership was really to provide solutions some action-oriented sort of tools for leaders and a book where leaders hopefully feel really seen their experience leading schools.

[03:08] SPEAKER_00:

Yeah, well, I think it's so powerful for leaders to know that they're not alone, that the challenges that they are facing are in most cases not unique, but that these are things that lots of people deal with. But it is the very nature of the job that they are confidential. We don't get on social media and blab about them and commiserate publicly because they are those confidential issues. And it almost sounds like you're coming full circle with some of those insights from coaching conversations and saying, how can we be proactive about this? How can we not just deal with you know, the fallout of a challenge, but actually get ahead of a challenge through the book. So take us into some of those insights that informed the book.

[03:47]

And maybe we could start with the acronym. So messy leadership is an acronym. Is that right?

[03:50] SPEAKER_01:

Yeah, messy leadership is an acronym. You know, like in education world, it seems like everything is an acronym. We figured why not throw one more in there, right? Make it add to the messiness. Messy is an acronym. Each of the letters correlates with a chapter and with sort of an area of leadership that we really wanted to help leaders sort of solve problems, be a little more proactive, a little more nimble and future focused.

[04:14]

And so I'm happy to run through the acronym if that makes sense. So the M in messy is really for meaning making. It's all about creating that shared vision and collaborating with your entire team. One of the things that we know is how hard school leaders work, and yet they seem to never get to the end of the to-do list. So we're trying to propose a different way of leading. We know the answer can't be Like, let's work harder, just work harder, just work more hours.

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And so we've got to shift some of that thinking. So the M is around that collaboration piece. The E is around emotional connection and this need for leaders to really be able to emotionally connect with teachers and their teams, not necessarily hide behind the superhero syndrome of being a leader or this professional veneer all the time. So E is really about that, you know, connecting with others and also having really honest conversations and feedback and how that actually strengthens emotional connections. Then we have two S's. So the first S is about sensing the future.

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And this is all about, you know, being really forward thinking in your leadership and being very nimble, right? being able to kind of have that five-year look out of where you're headed, but then also be able to adjust as things come up. You know, a year ago, nobody realized how AI would be at such a forefront of on leaders' minds. So being able to be really nimble and adjust. The second S is for seizing momentum. And so seizing momentum is all around being action-oriented and really being intentional with use of time.

[05:47]

One of the things that we know is leaders are time poor, and yet we also believe that leaders have much more freedom with their time than they realize. It's playing with the notion of time. And then the last, the why, is probably the most important part of the book because it's your presence. And it's really about you as an individual leader, your authenticity, how you show up, how you want to show up, and what might be getting in the way from you having the biggest impact you want to have as a leader. So one of the things, you know, we went into the research and analyzing all of this data. I mean, we just had so much data at our fingertips.

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And we went in with a lot of questions. You know, we had questions about, are the issues in American public schools different than the issues in Australian? Or... UK schools because those are our three real hubs.

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We had questions about, you know, independent schools. We had questions about are there huge differences between the stressors of a superintendent and a principal because we coach at all levels of leadership. So we went in with more questions than answers. And what we found is that there wasn't a huge statistical difference between any of those, between levels of leaders, between different countries. And I think the reason for that is because the work that we do with coaching really focuses on what I would call the human side of leadership. So we're really focusing on those softer skills, those character skills that you need as a running a school or improving student achievement, really that human side.

[07:19]

So kind of interesting, some of the, if I just, you know, we identified nine common themes, but some of like the top three, the number one theme that came up that leaders want to talk to their coach about is having courage to have difficult conversations. And it's just really interesting that like time and time again, you know, that leaders really want, they want scaffolds. They want to role play them. They want to make sure that they're not damaging their relationships because we're in the relationship business and, you know, wanting support around that. So I think that's really interesting. You know, that is a universal need that leaders are struggling with.

[07:56]

The second one I definitely related to both as a principal and as an assistant superintendent was, And the second theme is like not trying to run around and fix everyone's problems for them, right? Like really learning. How do you support teachers? How do you support your staff or your principals without actually solving their problems or doing their work? So that's kind of the second theme is all around empowering and coaching others to sort of step up and take ownership, right?

[08:22] SPEAKER_00:

Yeah, let's talk about that one because I feel like that gets at one of the dilemmas that's always present in this very human work of how much do I jump in and tackle this issue right now versus how much do I either, you know, let someone retain their ownership of it if it's their issue or how much do I pull back and look for more perspective, wait and see what's going on because, you know, people are not like printers, right? If a printer is broken, you can fix it. Maybe I'd have to get a new one. But people, as you said, they do own their own problems. And sometimes when we as leaders try to fix things for people, it doesn't work in the way we expect, or we end up getting in over our heads, trying to bring about change on too many fronts at once. What are some of the pressures there for leaders or some of the tensions in making those decisions?

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Because it sounds like your organization has talked with lots of leaders who have encountered that dilemma of, do I tackle this with this person right now? Do I wait? Take us into that one a little bit.

[09:23] SPEAKER_01:

Yeah. You know, it's interesting. I'm going to quote you. People are not printers. That's a great one. I'll remember that.

[09:29]

There is just so much tension for a leader here, right? And I think some of the tension comes from most education leaders. We're servant oriented, right? We're doing the work because we love it. We love students. We love people.

[09:41]

We want to make things better. And so most leaders already have sort of that servant orientation to leadership. I also think that at all levels, leaders are very conscious that the people on their team, whether it be their team of teachers or their team of assistant principals and principals, are overwhelmed and overworked. And the jobs have become so big that there is a notion of almost every superintendent that I talk to wants to remove things off the plate of principals, wants to. So I think there's this real desire to want to help, to make life easier. we know we want the outcome to be one way and it's hard to sometimes sit back.

[10:22]

One of the things that happens in education is we've done, the higher up you go in leadership, you've done all of the jobs below you. So there's sort of this sense of, well, I know how to do it. I've done it. Let me just jump in and I can do it again. The interesting thing that I find though, and the dilemma there is that we actually don't grow people then. And as educators, we know from being in the classroom that learning equates with struggle.

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And if you're truly learning something, like there has to be some struggle and some opportunities to make mistakes and grow. And so I think, you know, that's where we want leaders to sort of step back and say, you're not letting people fail, but let people make some mistakes, let them grapple with things, ask if they need support, but don't own it, right? Like hand the pen back to them, let them own things. solving their problem. Let them just like you would with a student, you might show them how to get started, but ultimately you hand the pen back.

[11:15] SPEAKER_00:

Well, Alyssa, I wonder if we could talk a little bit about the matter of time and how we use our time and our sense of urgency, because I know this is something you talk about in chapter five about seizing momentum. And I think a lot of leaders feel like, you know, I have to solve this problem today or I'm not going to get to it. Right. There's an urgency for student learning. There's an urgency for student well-being. We want to solve problems.

[11:38]

And yet in the very messy world of school leadership, we're We're working with people who don't necessarily just change at the drop of a hat, right? We're not working with printers, we're working with people. And we can often be a little bit unsure how to approach that question of time and that question of urgency. Take us into some of your thinking about that question.

[11:58] SPEAKER_01:

Yeah, you know, it's a challenge. I mean, I remember being a school principal and feeling like there were days that I just fought fires all day, right? I went in with best intentions. I was going to be in classrooms and I was going to be working on, you know, some big projects of the year. And there were days that I just never happened, whether it be because there weren't subs or there's, you know, student issues or parent issues. And so I know there's a reality there.

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And so one of the things that we acknowledge is just the sheer reality, the busyness of being a school leader and all of the balls that leaders are juggling at all times. And so part of it is really identifying like which of those balls are rubber. And you know, if you drop one, they'll bounce, you know, you can get to it again on which ones are glass, and you absolutely can't drop them. And so working through sort of a priority list of just being really conscious and aware of how you spend your time knowing that you have to keep juggling but you can let some things bounce, right? And sometimes, and this doesn't always make district administrators happy, but sometimes there are things that the district office is asking that you may have to let lapse, right? If it's not going to get you to have your greatest impact.

[13:08]

And so we work through some tools to help leaders really think about prioritizing what can they delegate, what can they just dump and what is urgent and what can be done at a later time kind of thing. So- Yeah, not any easy answer, but also, you know, allowing time. One of the things that we find with leaders is that they are so conscious that it's a, you know, human relationship business that their door is always open, right? We're almost always told like, yes, my door is always open, come any time. And that actually can backfire and keep leaders from having that thought work, that time and that space to do really important thought work that will improve teaching and learning.

[13:46] SPEAKER_00:

Yeah, I wanted to ask about an aspect of that related to the role that leaders play for various people in their communities. Because if you have an open door policy, if you try to be available to support people with whatever they need, sometimes people are going to bring you issues that you can't help them with, right? Like if you've ever been in a conversation where you realized... this person really needs a friend or this person really needs a therapist.

[14:11]

And I'm going to do my best in this conversation, but I really can't commit to being this person's friend and therapist, whether they're a parent in the school, whether they're a staff member in the school, like we have a certain role that we're, puts us kind of on the front lines of triaging issues for people, of being a go-to person. But how do leaders recognize when they're being called upon to play too big a role or a role that they're really not cut out for? Personally, I'm not trained to be a therapist. It would be amateur hour if I would try. So help us think about that issue for leaders.

[14:44] SPEAKER_01:

Yeah, I hear you. And it's interesting that you bring this up because that actually comes up in the top nine themes. One for leaders is where do I set my boundaries and how do I know how to set those boundaries, right? And I think it's really clarity of purpose and kind of reconnecting to your why. And as you said, also knowing your limits, knowing that this isn't the right role for me to play. And I think it's kind of reframing this idea of availability and being authentic, but that doesn't mean that people have access to you 24 hours a day.

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for any problem at any time right and so i think it's also as i said i think the principal job especially has gotten so big it's sort of a need to recalibrate it make it more doable for people

[15:24] SPEAKER_00:

And talk to us a little bit about how we can set those boundaries without coming across as cold or harsh. We resist setting those boundaries because we want to be there for people, right? There are good reasons that we try not to do that. So help us think about how to set those boundaries and yet still be a person who is looked to as responsive and present in the school community.

[15:48] SPEAKER_01:

Yeah, yeah, that's a good one. So two ideas come to mind. One is enlisting the help of your team, your broader team, right? That they can help set boundaries, communication, styles, tools, whatever works for you, but really to enlist the support of your team, especially whatever office situation that looks like. I think that's a good way to start with some boundary setting. And then I think the second suggestion I have is really to remain just very authentic and And, you know, you said it jokingly, like, I'm not a therapist.

[16:19]

Like, if I try to be amateur hour, you know, sometimes I think as leaders, we're put in a place where we are trying to be all things to all people. And I think it's okay for us to say, that's not really my role here. Let me connect you with somebody who can help you. Or here's a resource for you. But I'm not the best person, right? I don't think that we should be expected to solve everybody's problems all the time.

[16:40] SPEAKER_00:

It often seems to me like being a school leader is like one of those plate spinning acts like you used to see on television, right? I've got six or eight plates that I'm trying to balance on the dowels and I've got to keep them from falling. As you said, you know, we've got to figure out which can bounce and which will break if we let them fall. Any insights from the many school leaders that you've worked with about how to anticipate which of those plates or which of those balls, if they fall, are going to break and cause us some trouble? What are some of the warning signs that, okay, this is actually something that does need my attention right now versus maybe this could wait or maybe this could be more of a let someone learn, let someone experience things for themselves kind of situation?

[17:24] SPEAKER_01:

Yeah, I think there's some, you know, there's obviously some very basic ones like safety and health and well-being of, you know, staff, students, sort of your community. And I think there's probably some warning signs. I think having honest conversations with people about them, you know, if you're worried, is somebody struggling? Do they need support? I think rather than jumping in and keeping that plate spinning, it's to have a conversation around it. In terms of like thinking about broader plates that might be spinning, you know, I think about right now leaders are grappling with.

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We're back to like cell phones in schools and what do we do there and AI. And there's some big plates that are spinning for leaders. I do think that is where sensing the future and kind of having your eye on, you know, the trends and what's happening and what other schools are doing, what other districts are doing can help you in making decisions about which plates need to spin or spin faster, or maybe can slow down a little bit as well.

[18:16] SPEAKER_00:

Yeah. So just being in conversation with people, authentic conversations, listening, having your ear to the ground. Yeah, absolutely. Alyssa, talk to us a little bit about how the book is organized and how you see people using it because it doesn't necessarily have to be a linear start to finish read, right?

[18:32] SPEAKER_01:

One of the things that we get asked a lot about messy leadership is just about our intent in writing it, which I talked about is really to share tools, and also any suggestions. And my suggestion to anybody who's interested in reading Embracing Messy Leadership, it's not actually written in a way, it's not intended to be read from front to back cover. It's really intended to be read more as, I don't know about you, but when I was, I think about third grade, I was obsessed with choose your own adventure books. That's how I want leaders to think about this book, right? It's meant to be a resource. What I hope when leaders pick it up, we have actual quotes and comments from school leaders.

[19:10]

Any tool that we suggest leaders try, we sort of have a use case or another example of how a leader actually implemented it to help them solve their problem. So it's really meant to be sort of like a messy, nonlinear book that you can kind of thumb through and go to the letter that inspires you or go to the problem you're having and hopefully find a solution.

[19:31] SPEAKER_00:

Well, Alyssa, as we've been talking about having authentic conversations and listening and just kind of meeting people where they are, one of the things that has really struck me over the past year is just the reality that we're working with the people that we have. And I remember I was doing some training for school leaders on feedback on teaching, and I found that leaders are generally pretty good at identifying problems and opportunities for improvement in teaching. But one of the things we have difficulty accepting and being patient with is the fact that we have the best available staff, right? In most cases, we're working with the best people we could get doing their best most of the time. And a lot of our improvement opportunities are not going to come from just trying to get water from a stone, right? Trying to get more out of people.

[20:21]

How can we think about developing people and building capacity in people that beyond just, hey, why don't you be better? I think sometimes we want people to be different from how they are, and we want to live in a different world than we live in. But it seems to me that a big part of success as a leader is accepting where you are currently. Not accepting it in the sense of complacency, but in the sense of accepting it as your current reality. So for leaders who have an ambitious vision for things to be much better and are maybe struggling with their own impatience and frustration with other people kind of not being as good as we know they perhaps could be, how can we use some of the ideas in Embracing Messy Leadership to gain some traction there?

[21:06] SPEAKER_01:

Yeah, you know, that's a really, I think a really great question, observation. And I think you capture very well sort of the reality in schools of, you know, a lot of leaders have this big ambitious vision, but then struggle to actually know maybe the right steps. of how to get people there. And so we do offer some suggestions and thoughts. One of the chapters is really on how do you coach other people using the strategies in Messy. So we offer some strategies there.

[21:32]

One strategy that I think works really well is to remember that we have to meet people where they are. And they may be a very far distance from the lofty vision that we've set as a leader. And so what I'd like to think about is, you know, when you think about your teachers, everybody's an individual. You know, our team is sort of like a skyline, right? Capability levels are very different. And so you have to kind of hone in on an individual, and let's just use in this case a teacher, and really think about what is the capability gap that you want to create, right?

[22:06]

If we can be very clear and we can create a capability gap, then people will usually step in to fill it. but it's narrowing the size of the gap as well. I think about it a lot like when we stretch other people, we need to stretch them. I don't know if you have kids. I have two boys. They're 13 and 15 now, but when they were little and I would buy them shoes, you never buy them shoes that fit on the day, right?

[22:27]

You always sort of buy them like shoes that are like a half size too big. And that's how I think about growing capabilities in other people, right? We don't want to make that... If it's too big, they're like flopping around and it's not comfortable.

[22:39]

And so it's really getting that right size challenge for individuals so that we can grow their capabilities. And by and large, people do want to grow. People want to accept the challenge. It's just sometimes it's not sized appropriately for them.

[22:51] SPEAKER_00:

That's a great way to think about it. Love that. So half a size up so there's room to grow, but not too big a gap. And you said you want to actually create a capability gap there.

[23:01] SPEAKER_01:

Yeah, you want to actually highlight. There's different ways of doing it. It might be giving somebody a stretch assignment, but you're essentially showing what's the next step, and then they all have to step into that capability gap. They'll have to learn and grow in order to accomplish whatever it is that you've asked them to do.

[23:18] SPEAKER_00:

So the book is Embracing Messy Leadership, How the Experience of 20,000 School Leaders Can Transform You and Your School. Alyssa, if people want to learn more about your organization's work in supporting leaders, where's the best place for them to go online?

[23:32] SPEAKER_01:

Yeah, best place is btsspark.org or another easy place to find us is on LinkedIn, btsspark. And we post a lot of content there, free resources, free webinars that folks can join.

[23:44] SPEAKER_00:

Alyssa Gallagher, thank you so much for joining me on Principal Center Radio. It's been a pleasure.

[23:47] SPEAKER_01:

Thank you.

[23:48] Announcer:

Thanks for listening to Principal Center Radio. For more great episodes, subscribe on our website at principalcenter.com slash radio.