What It Really Means to Be a Strategic Leader

Strategic leadership may be one of the hardest — and most vital — skills for school leaders to master. Liz City, senior lecturer at the Harvard Graduate School of Education and a long-time coach to school and system leaders across the country, points out that strategic leadership is not innate but a skill that can be learned and strengthened over time.

“We're in a context which, over the last five years, has been full of uncertainty and ambiguity,” City says. “I think that makes it harder for people to be strategic. It puts people in a kind of reactive survival mode, which is not our best place to be.”

Learning how to be strategic can mean the difference between finding success over being less effective, doing too much, and burning out, she says. 

Drawing from decades of experience and recent research, City emphasizes that being strategic is not just about setting goals — it’s about taking intentional action, maintaining focus over time, and deeply understanding people and systems. In her new book, Leading Strategically: Achieving Ambitious Goals in Education, she and co-author Rachel Curtis outline five key elements of strategic leadership: discerning, cultivating relationships, understanding context and history, harnessing power, and think big, act small, learn fast.

She explains how leaders often get stuck, especially around power and discernment, and offers practical advice for moving from reactive leadership to purposeful progress. 

“You can lead from lots of different vantage points. I think we assume that if you have formal authority, you have power, and you'll be able to get things done,” City says. “It turns out, though, that most things are accomplished through a large measure of informal authority.” 

In this episode, City shares what it really means to lead with purpose, especially in today’s climate of uncertainty and change.

Transcript

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JILL ANDERSON: I'm Jill Anderson. This is the Harvard EdCast. 

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Liz City knows how to help people become more strategic in their work. And it's essential for school leaders to embrace this way of thinking. Strategic leadership doesn't always come naturally, but it can be learned. She's a senior lecturer at Harvard and long-time coach to school leaders. Her latest research shows that being strategic isn't just about setting goals, it's about taking intentional action, maintaining focus over time, and deeply understanding the systems and people around you.

She outlines five key elements of strategic leadership and explores how leaders can develop each one, despite some of the biggest challenges facing them. I asked Liz whether people really understand what it means to be strategic.

LIZ CITY: I think people have lots of different definitions of what it means to be strategic. So, I think most people are walking around with some idea, but people have pretty different ideas. When I ask people that I work with in the field, what do you mean by strategy, or what do you mean by strategic, a couple things are pretty consistent, but with different words. 

And one is, trying to accomplish some kind of goals, outcomes, vision, people use different language, but we're trying to go somewhere. And then the other piece is intentionality. We're trying to go somewhere with intention. Maybe we have some really concrete steps or ideas, but we are trying to act with intention. And so, I think those are the common things. But I think people walk around with different ideas about it.

JILL ANDERSON: What does it mean to be strategic in leadership?

LIZ CITY: It does include going towards some hopefully ambitious goal on behalf of the people you serve and alongside and with the people you serve with intention. It includes those things. But it includes more than that. Being strategic is about sifting through all the distractions and the noise to figure out, what am I going to focus on?

What am I going to prioritize? And why? And who do I need to do that with? And how do I need to engage with them? And what are the trade-offs I have to make with intention? And while you do that, how do I hold myself steady and not react to all the things that are happening around me?

JILL ANDERSON: Is this something that you noticed in your work with leaders that you were seeing them really struggle with?

LIZ CITY: Absolutely. I think one of the most common things leaders struggle with is, they are trying to do too many things. So, they have too many meetings in their schedule. They have too many things. And it comes from a good place. It's like, I'm trying to help people. I'm trying to serve kids. I'm trying to serve my community. I'm trying to help teachers. 

And I think especially those of us who are involved in social justice work and work we're trying to do to help people, there's always more you can do. And so, you always feel like you’re kind of not doing enough, which then leads to being not strategic because you're like, well, maybe I should try this thing and maybe I should try that thing.

And then we're in a context which, over the last five years, has been full of uncertainty and ambiguity. And I think that makes it harder for people to be strategic. It puts people in a kind of reactive survival mode, which is not our best place to be.

JILL ANDERSON: Right. So, what made you go into this direction? Because I know you've been studying leaders, researching leaders for quite some time. And my understanding is you were seeing that they were getting kind of stuck, some of the things that you just mentioned, and really putting this work into action, is that right?

LIZ CITY: Yeah, I work with lots and lots of leaders across lots of contexts and just seeing really common patterns of good people working really hard and not making as much progress as they want towards their goals, and also getting burned out and not feeling sustained in the profession. And seeing those two things and saying, we got to do something different, and saying, I've learned quite a bit about this, actually, over the last 20, 30 years, especially about the little things that add up. And so, a lot of my work has been about practices of improvement. How do we use data? How do we use rounds? How do we make a strategy? 

And that all helps. But leaders make dozens, sometimes hundreds of decisions in a day, just like teachers do in classrooms. And what does it look like every day to act in a way that's going to help you get closer to your hopefully ambitious goals as well as be sustained? 

And so just have learned a lot from working alongside leaders who do that really well, as well as leaders who are struggling and saying, I think we some things. Let's see if I can help people by naming specifically some of the things that effective leaders are doing, and then also saying we can all develop these things. We can all get better at this over time. 

And so, hopefully, by naming and then giving people tools and questions and things like that, you can say, you can do this too. if you can just pause a minute.

JILL ANDERSON: What have you identified as those elements of strategic leadership, if you want to just walk us through them?

LIZ CITY: There are so many. But in my current work, the way I think about this, based on a lot of research and practice and being in relationship with lots of leaders, is the first thing is discerning. And what I mean by discerning is just pausing, sifting through all the noise and the things trying to get your attention, and deciding, what am I going to focus on? And how is it connected to purpose? How is it connected to root causes?

Then, what am I going to do about that? That's the first thing. And often, it requires taking a breath. I'm going to not react. I'm going to take a breath. And I'm going to discern what's most important here. The second thing, which lots of leaders I know do part of very well and naturally is cultivating relationships.

And we tend to think about that among people, because education is essentially a people-based profession and endeavor. And lots of leaders I know are good at building relationships with people. The other part of building relationships that we tend to be less good at in teams and organizations is building relationships across bodies of work.

So, most organizations are pretty siloed. And so how do we help connect work so that people aren't being redundant in their efforts or disconnected? The third thing is understanding context and history. So how do we acknowledge that any place or at any moment we're in, there's stuff that's happened before here? So, if we're trying to implement a new math curriculum, what happened the last time we did a curriculum? What can we learn from that? 

Or what's really important in the context we're in right now to understand as we try to do something? That can save you a lot of times as a leader is being really mindful of that. And also, just accelerate your learning. The fourth thing, which is honestly the thing I have been worst at, but I've grown a lot in my own practice, is harnessing power. I used to avoid this. When I was a principal, I would just say, I'm not really focused on the kids. I don't do power and politics. But I've come to realize, if you're trying to do something different than what's already happening, you need some kind of power mobilized to do that. And it can look lots of different ways. It doesn't need to be coercive. It can be through allyship. It can be by ceding power. But fundamentally, power is about relationships. And so, if you can match, what do people care about, what resources do we have, then you can start moving things in the right direction. And then the last one, which comes out of my work over the last 20 years, I would say, really trying to help people with improvement, is think big, act small, learn fast.

And the basic idea there is, what's the big thing you're trying to accomplish? What's that why that gets you out of bed in the morning? But let's not try to act really big because that doesn't work. Let's try to find something quite small. We can try, connect it to that big. And then the key is how do we learn very quickly from that and improve?

Those are the things I see effective very strategic leaders do. Nobody is good at all of them in equal measure, but they are the things that I think if we can say in this moment, this thing I'm trying to figure out, what are my strengths that I bring to it, and also, what am I not paying as much attention to that might serve me well here? It can help.

JILL ANDERSON: Have you noticed leaders get stuck more on one of these elements over another?

LIZ CITY: I think harnessing power is the place people will say they get the most stuck. When I work with leaders and I talk with them really explicitly about things, power is the one people have a physical reaction to. They kind of tense up their shoulders and they kind of shrink. Very few people kind of lean in like, game on, let's do this thing. So, I think power is the one people often feel the most uncomfortable with. And it often needs some reframing for people like, what are your own sources of power? What does it mean to mobilize other people and their power? Many, many of us, including myself, struggle with power. I think the discerning is actually —

JILL ANDERSON: Oh, interesting.

LIZ CITY: — often the hardest one for people. Because the incentives are around acting quickly and trying to solve problems as fast as you can. But if you don't pause and figure out what's the root cause here, what are some different data sources. What can I interrogate about my own assumptions, other peoples, that leap to action often addresses something superficial or addresses the wrong thing or doesn't have people alongside you. 

I think discern might be the one that, actually, if you look at what's getting us stuck, I would honestly focus there first.

JILL ANDERSON: It's interesting because people, as you were just saying, feel a little bit nervous about this idea of being in a position of power, which you usually are when you're in a leadership role, but in reality, they're getting stuck in what's the problem, and how do I move past it, which is interesting because the problems often seem so obvious in a lot of ways, but really aren't.

LIZ CITY: Yeah. I mean, many of the symptoms of the problems are quite obvious. Like right now, we see a lot of kids not coming to school as much as we would like. Where are they? Why aren't they coming to school? And we want to solve that quickly. But do we really try to understand why aren't kids coming to school? Are we trying to talk with the kids and families about that? Are we talking with teachers? Because you can very quickly come up with some idea to try about that. But it might be totally not addressing the reason why they're not coming to school. And different kids may have different reasons. So, we may come up with one solution, but it only addresses it for some of them. So, I think we, out of good intention, try to act quickly, but we often don't choose the things that are most likely to work. So, I think the power part is also because if you have formal authority — I think of leaders in a broad sense. Lots of people can lead from lots of different positions. So, it might be you have formal authority from a positional role, like a principal or central office superintendent, school committee kind of thing.

You can be a teacher leader, for sure. You can lead from lots of different vantage points. I think we assume that if you have formal authority, you have power, and you'll be able to get things done. It turns out, though, that most things are accomplished through a large measure of informal authority.

So, people think like, ‘Oh, if I were just the x, fill in the blank, I could get this thing done.’ But then they get in that role and they're like, ‘Oh, my power is limited by this and that and that constraint. And so I think strategic leaders learn, ‘Oh, a lot of getting things done is actually about being in relationship with people, helping understand what people care about and what the real problems we need to solve are, and having the people who need to solve the problem be interested to solve that problem and excited to solve it with you.’ 

And sometimes you can do that through formal authority, but a lot of times it's through something else. Power is important. But I think we can get distracted by it too. That'll solve the issue.

JILL ANDERSON: As you've already said, a lot of the problems and challenges facing schools in particular, and probably even outside of schools, there's not an overnight solution or a quick solution, even though we're often looking for that. How do you balance this long-term vision with the day-to-day demands of leadership?

LIZ CITY: Well, this is where I think the think big, act small is really helpful. So, if you have a big idea about what you're trying to do, and you can think about what are the smaller ways, what's something we can do over the next month that might make progress towards this thing, it makes it more concrete and manageable for yourself, but also whoever else is implicated. It also makes it less risky. So, if it's something smaller, then I don't necessarily need to do it today. But if it's some time we're doing it in the next month, that lets me have a little wiggle to respond to things that come up, but also say, we're going to try on this thing in the next month and we're going to learn from it. And then we're going to try something else again right after. So, I think one of the things to do is to hold that big idea and commit to some small things.

JILL ANDERSON: Can you share an example of strategic leadership where it is successful versus maybe a case where it wasn't successful?

LIZ CITY: I'll give a couple of examples. I also think we're very afraid of failure in education. I often call it, the F word in education is fail. We're very allergic to it. And it means we do things to mitigate failure often that make us unstrategic. So, one way we mitigate failure is by, well, we're going to try lots of different things and hope that one of them works out as opposed, we've thought really carefully about this, and we're going to do this one thing and see how it goes.

We don't like to place our bets like that. We don't like to focus like that. That's one thing I'll just say up front, is failure is not necessarily a bad thing if we can learn from it quickly. That's an example of success. So, I know a superintendent in a small rural district in California who, over the last 10 years, has been working with his teachers and principals to really transform the way learning happens in his school district.

And I've been in this school, and I can say what was happening 10 years ago or in the school system is very different, what the kids are doing is very different, and what they're talking about, and how they're engaged is very different now than it was 10 years ago. One of the keys to their success is the superintendent has understood that relationships matter a lot. 

It was not a place where the teachers union and the teachers and the administration all got along happily together initially. But the superintendent really valued relationships and thought the key to powerful learning is relationships between the teachers and the students, which means that there need to be strong relationships between administrators and teachers. So really focused on that and has left a lot of choices and learning up to the teachers while really supporting them.

And so, the strategic part has been saying, we're going to try to be really ambitious about what we think kids can do. We're going to have high expectations for kids. And that means we're going to need to work differently because what we're doing right now isn't working great for kids. But we're going to figure it out together.

And they've also moved at a pace that has been a little bit outside the comfort zone of the adults, but not so far that they don't know how to handle that disequilibrium. And over time, the teachers are really the ones leading that work now. So that's a successful example. 

Less successful example, I'll be more obtuse about context. But I can think of a district that has also been trying to really focus on positive relationships between kids and adults as a way to help improve things. But they have lost sight of the learning, what I would call the instructional core, as the key to that.

So, they've focused on all sorts of programs around the classroom to strengthen relationships. So, we're going to have advisory, we're going to have mentorship programs, we're going to have affinity groups for teachers and for kids, all of which can be very important. But they haven't fundamentally changed what's happening in classrooms.

Whereas the successful example that I was highlighting, they have a practice of visiting each other's classrooms and really looking at, what are we asking students to do? And is that going to produce the kind of learning we want? And how are we implicated in our own practice in changing that? Whereas the less strategic example is, well, let's try a bunch of stuff with intention, but it doesn't get all the way to what's happening in classrooms.

JILL ANDERSON: It seems like that is a common problem that you see in education, where there's a tendency to add a bunch of things in to try to make that difference, when in reality, it almost seems like it's a lot simpler to do something smaller, which I guess is reiterating what you just said a few minutes ago.

LIZ CITY: Well, I think it's also just keeping in mind the question of, how do we expect whatever it is, as an individual, what am I doing as a team or as an organization, how do we expect this to make a difference for the people we're serving in whatever our core work is? So, if you're in a school or school system, the core work is about learning. 

And so how do we expect this to make a difference? And just keeping that as a central question and having people explain what the connections are. So, I think part of being strategic is making explicit, here's what I see, the connection between this thing and that thing. So, if I think building relationships is really important, I agree with that. I just said that's important.

And how do we expect that to make a difference in learning? So always trying to make explicit what the assumptions and connections are between things, I think, is also part of being strategic.

JILL ANDERSON: It's interesting, as you pointed out, that we tend to think of, or at least I think of leaders as these people who've been appointed into these roles that are very high up in an organization versus the informal leaders. And I'm not sure people think a lot about those informal leaders in the system as much or as often, and how much power and influence they may have over things getting done.

LIZ CITY: Yeah. I mean, one of my colleagues from long ago, Harry Spence, used to say, one of the most important jobs of a leader is to make everyone around them more strategic. And I think if you think that way, you think more broadly about who can be strategic and how and what it means to be a leader.

I also think, again, just pause for a moment and say, who knows a lot about this? Or who could sink this thing that I think we should do? Or you start to think about some of the informal people. Or who is the wise person who has been here for 20 years and can help me get some perspective on this? You start to attach it less to the role people are in and more the strengths they bring.

Really strategic leaders think very carefully about who are the people in this place who know a lot of things I don't know. Maybe it's because they know people I don't know, maybe it's because they bring different experiences I don't have. Maybe it's because they know something about this particular context I don't know. But who knows things I don't know? And not be distracted by the formal role they have, but just who knows things I don't know.

JILL ANDERSON: We always have folks on this show who come in to talk about leadership. And a lot of the emphasis is not only how difficult it is, especially in this day and age, but that they come into these positions with not a lot of training. They work their way up in the system, they follow this pattern, and then they get into these roles and realize that they don't know what to do or how to do them, really. Do you have advice for folks stepping into these strategic roles and how to really do this work?

LIZ CITY: Yes. I think we very much have lots of people in roles they have not been trained for, and also, once they're in the roles, don't get very much support for. The assumption is, you've been very successful in some role, so now take on this one, which has a completely different band of influence and lots of different constituents. And so, I definitely think we do that.

One piece of advice is to take really good care of yourself, which I feel like we talk about a lot. But if you are sleeping and if you are exercising in whatever form works for you, if you are finding your joy, when I was director of the Ed.L.D. program, I would always greet a new cohort and I would tell them in their first week at Harvard, cultivate your joy, whether that's playing an instrument, or cooking, or connecting with family, whatever that, that will nourish you and keep up your energy sources and remind you that everything is not all about the work.

So that's actually really important for sustaining yourself, because then you can follow my next piece of advice, which is to give yourself permission to pause and not react immediately, which will then give you the opportunity to just sleep on that email you wanted to send, or not respond to other people's urgency, except in a legitimate crisis. A lot of things seem like a crisis that aren't. And some things are.

But a very small percentage of things that leaders face are actually crises. But all of the things are treated that way. So, pause and give yourself permission to figure out how to respond, including consulting with other people.

So, my third piece of advice would be, have people you trust who you can talk with, preferably some people you trust unequivocally who aren't in your workplace at all, and some people in your work context who you can talk through things with and not think it's going to hit the newspaper. Because we all need people to help us get perspective on things. 

And I feel like new leaders often isolate themselves so that they don't give off the perception that they don't know what they're doing. Whereas actually, admitting you're not sure can be a very powerful act of vulnerability. But I'm not going to advise that because that's heavily dependent on context. [LAUGHS] So those would be my pieces of advice.

JILL ANDERSON: So even that just sounds like you need to be strategic about everything that you do. But again, I think it reiterates this idea that, in schools, we're always in a rush to find the solution. And maybe we need to work against doing that and rushing to the answer.

LIZ CITY: Yeah, I'm one of those people who's like, let's go, let's do it, and we'll figure it out as we go. So that's my natural wiring. And I have learned over time in my own leadership, as well as working with lots of leaders, that that kind of energy is motivating and inspiring, and you can get a lot of people along with you, but you want to do that when you have a pretty good sense of what the best thing to do is. And for that, it is very helpful to pause and be in dialogue and relationship with people, looking at lots of different data sources and that kind of thing. So, we don't give enough credence to the value of the pause.

JILL ANDERSON: Great. Thank you so much.

LIZ CITY: It's been my great pleasure. Thanks for the conversation.

JILL ANDERSON: Liz City is a senior lecturer at the Harvard Graduate School of Education. She's the co-author of "Leading Strategically: Achieving Ambitious Goals in Education." I'm Jill Anderson. This is the Harvard EdCast, produced by the Harvard Graduate School of Education.