Progress Over Perfection | How Leaders Pilot, Sandbox, and Pivot – Ep 06

Hosts: Courtney Acosta & Mario Acosta Bios: https://www.theedleadershippair.com/about-us Podcast: The EdLeadership Pair – Unfiltered Conversations for Today’s School Leaders 

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Episode Overview 

Build the plane while flying it, without losing trust. Schools and districts rarely get perfect conditions, and waiting for total clarity usually means waiting too long. In this episode, Courtney and Mario unpack why iteration is not a sign of weak planning but is actually a core leadership skill. They explore the pressure leaders feel to have the “final version” before acting, and why momentum often matters more than certainty. Using practical examples (like pilots, sandboxes, and PLC implementation), they share how leaders can create safe spaces to test ideas, learn fast, and improve over time. The conversation also tackles a hard truth: leaders must be willing to abandon ideas that aren’t working before ego, time, or “pot commitment” traps the organization in a bad move. Finally, they close with a leadership mindset that protects trust: give away the credit when things go right and own the responsibility when they don’t.

Big Ideas from the Conversation 

Iteration is a leadership skill, not a planning failure. Progress and momentum beat paralysis by perfection. Pilots reduce risk by testing with a small group, on a timeline, with clear success criteria. Sandboxes create psychological safety so teams can experiment, break things, and tell the truth about what doesn’t work. Culture is a litmus test: if the organization rejects a pilot, leaders must listen before scaling. Great leaders avoid being “pot committed”, they pivot when data and feedback show an idea isn’t right for this context. Trust grows when leaders share success with teams and absorb accountability when things go sideways.

Leadership Actions Recommended in This Episode 

1. Name the work as Version 1 (and say what Version 2 will improve) Communicate that improvement is a learning process. Set expectations that the work will be refined as data and feedback come in.

2. Design pilots with guardrails Pick a small group, set a short timeline, define what “working” means, and identify the measures you’ll use to decide whether to scale, revise, or stop.

3. Build a sandbox with psychological safety Create a low-stakes space to test tools and processes. Make it safe for early adopters to report failures without fear, and celebrate the learning.

4. Let culture speak before you scale Share early pilot results with adjacent teams and listen closely. Enthusiasm is a green light; resistance is information to address, not something to bulldoze.

5. Avoid “pot commitment” Set decision points where you will pause and evaluate. If the data says it’s not working, pivot quickly and don’t throw good time after bad time to protect ego.

6. Protect trust through ownership Give away the credit when the work succeeds, and take responsibility when it doesn’t. That combination strengthens followership and keeps people willing to try again.

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Join our growing community of school leaders navigating today’s challenges together.

Transcript

SPEAKER_00 0:00

A lot of leadership feels like you are building the plane while you're flying it. The question is, should that scare us, or is that just the reality of being a leader? I'm Courtney.

SPEAKER_01 0:17

And I'm Audio.

SPEAKER_00 0:18

And this is the Ed Leadership Pair Podcast. So schools and districts rarely get the luxury of perfect conditions. And waiting for that perfect clarity often means that we are waiting too long and we miss an opportunity. Iteration is not a failure of planning, it's actually a leadership skill. Why do you think leaders feel pressure to have everything figured out before they take action?

SPEAKER_01 0:47

The hard part I think about being a leader is you are held to the ultimate accountability for your organization. I think part of why iterating is so spooky is because if at any moment you're held to account and you say, well, this is not, this is not my final version, right? I think there's a lot of there's a lot of uh, I can understand that angst and that fear that as leaders we're held accountable. Just because we are making progress doesn't mean we're lowering our standards, right? So I think for leaders it's hard to say, like, this is just a step in the right direction. It doesn't mean that I've I'm settled for where we are, it's just where we are right now.

SPEAKER_00 1:23

I think leaders also want the very best for their kids and they want to put that work forward. And so it's really hard to go into something knowing I'm gonna make this better in the future as we learn and grow together, and knowing that it's not the best that it possibly could be or the best that it's going to be, that it's going to get better because you're not giving them up front the very best. But sometimes you got to go through that, yeah, those iterations to get it there.

SPEAKER_01 1:49

Right. Well, and I think a lot of it is too as leaders, we maybe have to keep in our mind that really action and momentum are at a priority. Um, so it's it's a hard, it's a hard thing because you don't want to just act without thinking. I think for a lot of leaders, you see when something you're like, I gotta make sure I have thought this through, but that can be paralyzing too, right? I mean, because you could think yourself in circles. So it's like the, you know, and and you know, learning the skill of I've collected enough information and I have enough clarity of outcome. That's another thing I think why it's hard for leaders to get started or hard for leaders to accept an iteration. Because do you have a clarity of what you believe the outcome will be in the long run? So I always found I was comfortable saying this is version one because I know where we're going. If if I didn't know where or where we were going in the long run, it was harder to know is this version one or not.

SPEAKER_00 2:44

Yeah.

SPEAKER_01 2:45

So I think as a leader, you got to be able to have that vision to say, okay, I think I can get us all the way over there, but today we're just gonna be right here. Yeah. Right. So that we can get to action and not just uh ideation because that that ideation can be paralyzing too, right? Just sitting there ideating and ideating and ideating that can be paralyzed.

SPEAKER_00 3:03

Yes. I I I am have always been a strong proponent of you know progress over perfection. Like let's let's get started, let's just get going. And I can't tell you how many times we talked about at my at my high school where I was, yes, we are building the plane while it's flying. And that is what we are intending to do. And we've made the best plan possible to this point, and we're gonna keep making it better as we go. But I have been on teams where their whole goal was to ideate and to just be a think tank. And it drove me insane, insane. This this idea of going in and just thinking and thinking and considering and considering, like at some point we got to take some action.

SPEAKER_01 3:42

Yeah, well, and I will back it up too. That you know, in this show we try to give some studies too. The National Implementation Research Network, this is uh from 2022. They they emphasize in in management of change, especially change management, that um there is an emphasis on when leaders treat improvement as a learning process and not a single-time rollout. When change is less necessary, leaders are more effective when they know that it's going to be an iterative process and they plan the process. We're just gonna start and they communicate it that way. We'll figure this part out and then we'll figure that out. And when leaders tried to hit it all in one shot, those those implementations were far less effective than when leaders implement change, knowing it's going to be multiversion. Yeah, you're right. And what comes with that is communicating, right? And and activating the right people early in the change process and all of that.

SPEAKER_00 4:35

So yeah, and something, you know, when we were principals at the same time, we heard the guy at Google talk and he talked a lot about iterations, and that caught both of us really hard. We were like, yes, iterations, yes, just one after another. And that it's scary to do in schools because it's scary to say, I know this isn't gonna be the best, but we're gonna get it there. But being in ed tech now, the things that I hear when we wanna create a new project or something's gonna be rolled out or whatever, the words pilot and the words sandbox. Yes. And I am in love with this because it takes all of this stress away of the idea that it has to be perfect the first time it comes out in the rollout. Like you intentionally say, we are going to pilot this with a small group of teachers or a small group of students or just one campus or whatever that is. We're gonna pilot it. And we know the intention of the pilot is to find the gaps, to identify where the weaknesses are, to see what needs to be changed about it. Like you go into it knowing with intention that we want to see how this could work with our organization. And I love that it's so freeing. Yeah, like it just takes all the weight off your shoulders. Now, not that you should not have a well-planned pilot and you shouldn't have goals for this pilot and outcomes that you're looking toward, and what exactly are you assessing and a timeline, like you can't just pilot it forever. All those things need to be said, it needs to be very thoughtful. But the idea of a pilot is I think so helpful. And we do it all the time in ed tech. It we're so free to do that, and it's great.

SPEAKER_01 6:18

Yeah. Well, and you're you're giving a shout-out to Jamie Cassip, and we want to make sure that's a good idea. Thank you. Yes, Jamie Cassip. Jamie Cassip, who was uh an educational evangelist at Google. And again, Courtney and I went through a lot of Google training because we are Austin area-based educators, so lucky to have a Google campus near us. And that was something I took away too is at Google, why are why are they who they are at Google? Well, one of their core values is iteration, um, just iteration and and the fact that Google is like, we're never done being better Google, but today is the best version of what we've got. And then we're gonna continue to work to keep building out better versions as as they go. Um, and as a matter of fact, Jamie told us a story that, you know, and Google how they change their banner head uh style all the time. Like, you know, it's always a different uh if it's the World Cup, it's got the soccer on it or whatever. They say that's their little nod to iteration that their little banner never stays static because they're always getting better. It's just their little internal nod. It's always changing that like we're we're always working on this, absolutely.

SPEAKER_00 7:20

Yeah, I love that. The other one that I hear all the time and that we use is the idea of a sandbox environment. So a pilot is when you're taking a small group and you're you're putting this into place with like a small part of the organization, and a sandbox is setting up a space where educators can go in and intentionally mess around with the tool or with the whatever it is that you're bringing in, but and actually try to break it and see if they can mess it up to the point to go. Yeah, exactly. You can test your ideas safely, it encourages innovation because it feels comfortable. It's like, oh, I'm not gonna mess anything up in a sandbox environment.

SPEAKER_01 8:03

Sure. Well, let's take that to like a practical level. So I, you know, again, working with principals and teachers across the country, superintendents and district office folks, um, the concept of a PLC and PLC meetings and and all the structure that's behind PLCs and answering four questions. And while you and I have been classically trained that way and um, you know, we we are fans of the PLC process, what would it look like to tell a team of teachers at a school that's struggling with PLC implementation, hey, we've gonna create this sandbox for you in your meeting space, right? Here's a here's a sandbox opportunity for you guys to play with it, break it, you know, poke holes in it, and make the make this structure actually um be as effective and efficient for your team as possible, with the mind of then once you guys figure out kind of how to make this work well, then we're gonna lean on you as a model to then bring in other teams behind you.

SPEAKER_00 8:58

And we're gonna ask you for feedback on it, and we're gonna get your input on how it gets implemented or doesn't get implemented, and get all like all of those pieces too, and they then they have ownership over it.

SPEAKER_01 9:10

Yes. So many principles that I come in and I'm hey, help us with our PLC teams. Well, this is a great way to do it. Pick a team that you trust and say, look, we're gonna build you a PLC sandbox. How would this look for it to work well for you? What could you guys do with this time and space given these parameters and and create that that opportunity? So again, maybe not every team on this campus is ready for full PLC rollout, right? But we said progress over perfection. So pick a team, build a sandbox, and now you got a PLC sandbox team to play, like you said, and collaborate and poke holes and and and figure out okay, at this campus, this is how PLCs might work best. And now we can make those iterations behind them.

SPEAKER_00 9:51

Yeah. And how do you, as a leader, make sure that you are creating a space for psychological safety where they can tell you, here's how it didn't work. Yes. Whatever tool that you are putting into that sandbox space for them to play with, how can they safely come back to you and say, actually, this didn't work? And it maybe it didn't work because we didn't have these resources or this data was not a part of the tool that we were trying to use, or whatever. But how do you create that safety for them to tell you as a leader, here's what we're gonna need to make it work? Or even honestly, I I don't see this functioning within our organization. Yeah. And here's why.

SPEAKER_01 10:32

Absolutely. There's a book right here over my left shoulder that I wrote. Uh, it's got change management in it, all of chapter three, and and in uh this protocol in there is some detailed leadership steps on how leaders can create that safety for your early adopters, your sandbox players, yeah, to get in their safe and not just to figure out what works, but what doesn't work. And so leaders, it's a book called The Schools Our Students Deserve. It's available anywhere you can buy your books, Amazon, other places. So there's a tool for you there if you're interested in that idea of sandboxing with safety.

SPEAKER_00 11:02

But I do think calling something a pilot or putting a new tool that you're wanting to implement into a sandbox so teachers can use it, I do think it changes the way that people show up for that.

SPEAKER_01 11:17

Well, you know why? Because there's this learning through action idea, right? The best way you get good at something is to put your hands on it and play with it. But unfortunately in schools, everything is so high stakes, right? Um, because you're dealing with human children. So it's hard to say, hey, go ahead and make some mistakes. Um, so as a leader, right, is creating those safe opportunities to say, where can we allow our teachers, or if you're a superintendent or principal supervisor, where can we let our principals, where are the safe places to play? Because I think what holds and what paralyzes a lot of us in the education sector is, you know, if we make a few mistakes, it's not like we're just gonna like uh throw those those circuit boards out and start with new circuit boards. Like we are dealing with, you know, our children and the lives of and their education. So it's like getting really specific and and and safe with how we allow that sandboxing in education.

SPEAKER_00 12:08

Now, I do want to talk about the idea of you put it, you you set up a pilot, you put the tool in a sandbox, whatever it is, or you start moving forward with an idea that even maybe you have already piloted and you thought it was ready to go, and you're all in on it, and the data starts showing you it's not working, it's not going well, it's not your intuition is telling you, uh this doesn't feel right when we go whole school or whole district or whatever it is. And it makes me think of when I was um staying at home after I had our first daughter, our oldest child, and at you know, one o'clock in the morning, what's on just the world series of poker is what's on in the middle of the night.

SPEAKER_01 12:54

And y'all need to know Courtney's a dangerous poker player, too. You don't gotta be careful to sit down playing with her. Don't let her poker face fool you.

SPEAKER_00 13:02

Not at all. I have no poker face. What's glass face? See right through it. Um, but I remember watching that, and there's this idea of being pot committed. And if you don't know what that is, it's like you have played too many rounds and you put too much into the center of the pot. You've got too much money invested, too much time invested, and you feel like you can't fold. And a little bit of it is ego, and a little bit of it is fear, and a little bit like maybe you're just a risk taker and you're ready to go on with that risk and you're, uh, they're bluffing. Nope, I'm pot committed, I'm gonna take the chance. Yeah. But I just think sometimes when you've got something new happening and and you feel like it's not working well because you're getting that feedback or you're getting that data or whatever it is, you can't, as a leader, ever feel like you are fully pot committed. You have to be ready to say, got it, this was my idea, or this was somebody else's really good idea, but this is not right for us.

SPEAKER_01 14:04

Yeah, that's tough, right? Because, you know, it makes me think like really great leaders, they fall in love with like the process that leads to the outcome. So really great leaders are like outcome driven, and it's not always your idea that's gonna get you to the outcome that is best for your organization, right? So, like great leaders are about outcomes and and not so much about my idea or your idea. So it is hard. You're like, God, I really know this could work. Or one of the big leadership traps, and and you know, I was a principal in more than one school, so it's easy to say, well, at my last place this worked. Yes, it doesn't always work here, yes, right? Like it, it's it's not that simple that you can just oh that the same idea is always gonna transfer. So as a leader, right, being in love with the process and the outcomes and not with the necessarily the individual mechanism or the individual idea that that gets you down the road.

SPEAKER_00 15:01

Yeah, I I have seen leaders try to take one idea that was beautifully and perfectly implemented at one school and try to go to the next school and implement the same exact thing, and it was a flop. Yeah. Either because it wasn't supported by the community, it wasn't supported by the district, it wasn't needed in the same way that it was needed in that other school or district. And it's so upsetting. And I have seen people just hold on with claws and teeth and they won't let it go. And it's like it's going down in flames, man. You gotta let it go. Like let this be gone because it's it's time to move on past this. Not that you can't find other solutions for what you feel like you need and what your data is showing that that you need, and it's not a failure to get data back that says it's not working, that's just information. And so you have to make decisions based on that data, not on your ego.

SPEAKER_01 16:01

Yeah, yeah.

SPEAKER_00 16:02

Which is hard. That's really hard.

SPEAKER_01 16:03

I think you're saying like leadership is to have the strength uh and the ability to abandon a bad idea, right? Absolutely. What you were talking about, the poker example, like throwing good money after bad money, like that's just ego now. Yeah, right. And that's not helpful for your organization, it's not helpful for the students that you're serving or the community that you're serving. So yeah, I I I wrote a note when we were preparing for this as the organization doesn't need you to be right, it needs you to be effective. And so yeah, right. Again, leadership is hard. So it is hard to say, God, but I know this worked before, I've seen it work somewhere else. Or um, you know, a colleague next door made it work. And and so you start to feel like a personal leadership failure when really, like you said before, it's just a matter of it may not be the right time or place for that, and so not letting your ego be in the way. But that's where to connect to the start of our podcast, like that's where those sandbox and and pilot opportunities are so helpful because it prevents you from getting too pot committed. You know, you say, Hey, we're gonna run a pilot. The third grade team is gonna test this out. They work it, they work it, they work it, they come back and they say, Yeah, this really sucks, right? It makes it easier for the leader to be like, all right, we tried it. That's not the best way to do that, right? Let's just move another direction. So I think as a leader, too, what helped me not get to pot committed point was if you're running these, if you're if you're smart about the way you run your pilots and that you go kind of go slow to go fast. One of our great uh professors who in our doctoral program, Dr. Olivadis, used to say that all the time: go slow to go fast. And I think this is that application of that. Like you want to be moving, you want action. So not sit there and do nothing. Like take action, but take action slowly so that you can measure it, so that you can make sure that it's pointed in in the direction of effectiveness, and and it keeps you from getting too, as you said, pot committed or too wrapped up in in uh all of our personal egos. And listen, we all have them when you're a leader. You have to have them to be a good leader. So you're always kind of balancing your own internal personality of not letting your your ego be in the way of of effectiveness.

SPEAKER_00 18:07

How do you how do you set up a pilot or something? How do you know, yes, move forward? No, we're not gonna move forward. How do you make that decision?

SPEAKER_01 18:16

Yeah. Well, I think part of it is is does the culture support it? I think that the culture is always an important part. So we run a pilot and you know, and we start to show it to other people inside the organization, inside the school. Third grade team does it. All right, let's go show the second grade team. If the second grade team looks at it and goes like, oh my God, that's the thing we've been missing. Yes, we love it. Okay, that's a good marker that that this is something we probably want to start to lean into. Or we show the second grade team and they're like, that's awful. We would never do that. The third grade team are a bunch of morons. Like, none of the rest of us are ever gonna do that, right? That's your culture speaking up, right? And that's the nice thing about school culture is school culture is quiet when everything's okay. The moment things are not right, the culture speaks up. And so I think one of the litmus tests as you're running these pilots is you gotta let your culture have a peak once you've gone far far enough down the road. You know, you've run some pilots, you've done some sandboxing, you think you got something on your hands. Now you got to let the culture start to take a look at it. And yet don't be pot committed because your culture might say, hate that.

SPEAKER_00 19:19

Yeah, right. Yeah.

SPEAKER_01 19:20

Um, maybe you could talk briefly about you did something like this, and then I ended up copying you, but you put in a really important intervention period into your large high school, and that was one of those things that just was a big, big move that needed that uh progress over perfection.

SPEAKER_00 19:35

Yeah, um, that was a little bit of a scary one, and that was a jump out and take a risk thing. And it we called it flex time, and we actually stole it from a neighboring district. Like I didn't create this thing. We wanted to create an intervention time during the school day that kids had time to stop and take a breath and could go get extra help during the day. And we had to bring a group of teachers together. We started with my my leadership team. I've talked about them before. They were super open, such a great group of teachers that always wanted to do great things for kids. It was a whole process of we had meetings with kids, we had meetings with parents, there was a lot of salesmanship going on and trying to like advocate for this, but also acknowledging if it's not right, it's not right.

SPEAKER_01 20:23

Yeah, but I, you know, and I think the the story here ties to the fact that, you know, year one, when you implemented, there were a lot of things that didn't go well. And then it wasn't, hey, abandoned. It was it's all right. This is the first year we knew there were going to be kinks, things that we had to work through. And so we worked on it and improved the process year over year as we as we went by. But every year, I know every year we had it at my school, it it just got a little better. And we knew that we we knew that it was never a finished product again. Progress over perfection.

SPEAKER_00 20:53

Yep, absolutely.

SPEAKER_01 20:55

Well, let me throw this at you then. Have you ever come across this the struggle or or the situation where you can be with with a leadership team, um, or you can be around other people where the ideation um never moves into progress? What happens if you're working with somebody who just is looking for for for perfection before progress? Um, you know, what are the risks of that? What are the risks of trying to find the perfect solution before you begin implementation?

SPEAKER_00 21:26

Uh you just get stagnant. Like you just sit there and you spiral and and I know we've seen teams and been a part of teams where that's happened, and for both of us, it's really frustrating to consider every possible angle that could ever maybe happen and what percent chance every piece of that could go into play, but you just you never move. You're it's never gonna be perfect when it's something when it's a big change you're trying to make. And so that's super frustrating to me.

SPEAKER_01 21:58

Yeah, me too. I don't I I think leadership in schools is not about being a think tank, right? I mean, so what I don't mean to say is that leaders shouldn't think. Obviously, our job is to think and collect information and listen and make good decisions, but that has to happen with progress, right? It can't just be a think tank and sit around and um I'll never forget a team that that uh I've been on in my past where we were having some problems with students in in drug use on the campus. And so we knew we had a big problem on our hands and we had to come up with a plan. We have to react. You can't just ignore something like that. And I remember just meeting over meeting over meeting where we were pouring over all the incidents of what had happened and this frustration about this keeps happening and it keeps happening. And every time we walked out of there, just continuing to admire the problem and re-identifying everything we knew, and we were never making any now what? Okay, so what? You've got all this information, and then now what? Yeah, like let's try something. I know we don't know exactly what to do or who's bringing it, but let's just start. Let's start somewhere.

SPEAKER_00 23:01

Yeah, there's only so many ways you can look at the data before you go, okay, let's impact it. Let's do something to change the data. That's right. Something. Try something.

SPEAKER_01 23:11

And not just sitting here ideating. I used to say, man, you can't plan forever, right? Leadership requires some kind of tangibility. Um, that that you know, or else we just sit there spinning wheels in mud.

SPEAKER_00 23:23

Yeah, and when you don't take action, especially on something like what you're talking about, then you are opening the door for a loss of trust from teams who see inaction from teachers, from parents, from kids. There, there, you begin to erode the trust because there's no action on this now. And it's like, okay, how long have we been sitting here complaining about this? And we've taken every survey and we've you've looked at every possible data point, and you're like you're saying, now what? Now what?

SPEAKER_01 23:58

The people you are meaning to lead will see your in action and lose faith in your ability to act. Um, leaders are only as good as the people who follow them. Yeah. Right? Leading without people following you is just walking, you're just out there roaming around. And so I think this is one of those moments where you're a leader and you're like sitting around waiting for the perfect solution and you turn around and there's nobody behind you because you've been sitting there for so long that they got up and went and found some sort of solution on their own, waiting for the leader to make some sort of progress. So again, progress over perfection or the big risk is you lose, you risk losing trust and faith and and um the followership of the people that were meant to steward. I think the closure on all of this then is that really, really great leaders, while you're in this progress, progress, progress, when there is success, you got to give away all of the success to your teams, right? So everything that goes well, it's because of the great team that I worked with. Look at what these guys are doing. Share that spotlight. You share it, you pass out the success, you you you highlight and you lift up everybody that's involved in the work. And on the flip side, when things don't go well, then the leader has to take those, the, take those that energy, they have to take that, right? So the way I always used to like to say it is when things go wrong, it's my fault. When things go right, it's because of what they did. Yeah, and so as a leader, we keep saying it's a thankless job, right? And those of those of you listening, then nodding your heads going, yeah, that's what leadership feels like. So you have to find where you fill your bucket as a leader, but it is not this way, right? This is not where you stand up and say, I told you guys this was gonna work, right? Instead, it's look what you guys built.

SPEAKER_00 25:39

Look what you built. That's right.

SPEAKER_01 25:40

So you you give away all of the celebrations and you keep everything that that needs to be owned as far as didn't go as well.

SPEAKER_00 25:50

Absolutely. And that will reinforce the risk taking, it reinforces the innovation, it reinforces the psychological safety that your teams are looking for, and people will be more willing to try something new again the next time around when you celebrate them.

SPEAKER_01 26:06

Yeah, and flat out you just are a more respected and more well-liked leader, which which matters a bunch too. Yeah, well, thanks again for another great date. These dates are becoming really, really good, you know?

SPEAKER_00 26:18

It is a joy and a pleasure.

SPEAKER_01 26:21

Well, we will sign off again. You know where to find us on all of our socials, and uh please consider subscribing to our newsletter at www.theedleadershippair.com. Another good episode in the books. I'm Mario.

SPEAKER_00 26:33

I'm Courtney. We'll see you next time.