One-on-One Insights—Building Change Strategy Through Individual Conversations | Bernard Agrest

Summary

Scrum Master Toolbox Podcast: Agile Storytelling from the Trenches

Episode: One-on-One Insights—Building Change Strategy Through Individual Conversations | Bernard Agreste
Host: Vasco Duarte
Guest: Bernard Agreste
Release Date: July 2, 2025

Introduction

In this insightful episode of the Scrum Master Toolbox Podcast, host Vasco Duarte engages in a compelling conversation with Bernard Agreste, a seasoned Change Leader. The episode delves into Bernard's firsthand experience managing a significant digital transformation at Teach for America, highlighting the strategies and techniques that facilitated a successful overhaul of critical internal tools.

Context and Challenges

Bernard begins by setting the stage for the massive change initiative undertaken at Teach for America. The organization was grappling with an outdated internal tool that was pivotal for staff operations, impacting approximately 12,000 to 15,000 students annually across 23 school districts.

[01:46] Bernard Agreste: "It was a very old school tool with so much tech debt that we were just duct taping new features onto it. But it needed a rebuild."

The primary challenges included:

• Technical Debt: The existing tool was burdened with accumulated technical debt, making it inefficient and costly to maintain.
• Unclear Requirements: Developers were creating patches without a clear understanding of evolving organizational needs.
• Stakeholder Misalignment: There was confusion and disagreement on prioritizing which components of the system to address first to minimize disruption.

Identifying Solutions

To navigate these challenges, Bernard adopted a grassroots approach by conducting one-on-one conversations with team members to gain a comprehensive understanding of their workflows. This method revealed a critical insight:

[03:00] Bernard Agreste: "Teams weren't viewing their work as cyclical flows, but more as straight lines, like passing a baton in a race."

Realizing the need for a holistic perspective, Bernard mapped out the entire workflow continuum across teams for the year. This mapping highlighted the central role of the onboarding team, which was instrumental in supporting multiple other teams and processes.

[04:36] Bernard Agreste: "By mapping out the full continuum, we saw that the onboarding team was involved in every cycle and had their own core work to do as well."

Involving the Team

Understanding that successful change requires buy-in from all stakeholders, Bernard emphasized the importance of engaging the team in the transformation process. This was achieved by:

1. Active Listening: Asking team members to provide feedback on the existing tool and how it could be improved to better serve their needs.
2. Collaborative Design: Incorporating the team's input into the redesign to ensure the new tool addressed real pain points.

[09:09] Bernard Agreste: "We spent a ton of time working with everyone on staff who needed to use the tool to really vest them in where their value add was."

Example: Enhancing the Onboarding Process

One significant improvement involved automating the tracking of teacher qualifications required by California standards. Previously, this was managed manually using Excel spreadsheets, leading to inefficiencies and errors.

[05:04] Bernard Agreste: "We were tracking qualifications in an Excel spreadsheet, which became cumbersome with hundreds of entries and varying deadlines."

By redesigning this process, the new tool not only streamlined data management but also positively impacted related teams such as hiring, coaching, and program metrics.

Impact and Results

The strategic focus on the onboarding team as the catalyst for change yielded remarkable results:

• Budget Allocation: Enhanced visibility into budget usage allowed for more effective allocation of resources.
• Support for Teachers: Reprioritizing funds enabled one-on-one support and tutoring for teachers, increasing first-time success rates by 25%.
• Operational Efficiency: The redesigned tool facilitated smoother workflows across multiple departments, reducing friction and enhancing overall productivity.

[07:04] Bernard Agreste: "After redesigning, we saw a 25% increase in first-time success rates for teacher qualifications."

Key Insights and Lessons Learned

Bernard's experience underscores several critical principles for successful change management in agile environments:

1. Start with Understanding: Conducting individual conversations to comprehend the nuances of existing workflows is essential.
2. Map the Workflow: Visualizing the entire process helps identify central nodes that can drive impactful change.
3. Engage and Empower: Involving team members in the design process ensures the solutions are practical and gain widespread acceptance.
4. Focus on User Needs: Tailoring the tool to address specific pain points can transform resistance into enthusiasm.

[10:53] Bernard Agreste: "They were excited for the change because it would actually make their lives better. And we achieved that by simply asking them."

Conclusion

Bernard Agreste's narrative provides a compelling case study on the importance of strategic planning, team engagement, and user-centric design in driving successful digital transformations. His approach at Teach for America exemplifies how agile principles can be effectively applied to navigate complex change initiatives, ensuring minimal disruption and maximum impact.

For Scrum Masters and Agile Coaches seeking actionable strategies to manage change, this episode offers valuable insights and practical techniques that can be adapted to various organizational contexts.

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Notable Quotes:

• Bernard Agreste [01:46]: "It was a very old school tool with so much tech debt that we were just duct taping new features onto it. But it needed a rebuild."
• Bernard Agreste [04:36]: "By mapping out the full continuum, we saw that the onboarding team was involved in every cycle and had their own core work to do as well."
• Bernard Agreste [05:04]: "We were tracking qualifications in an Excel spreadsheet, which became cumbersome with hundreds of entries and varying deadlines."
• Bernard Agreste [07:04]: "After redesigning, we saw a 25% increase in first-time success rates for teacher qualifications."
• Bernard Agreste [09:09]: "We spent a ton of time working with everyone on staff who needed to use the tool to really vest them in where their value add was."
• Bernard Agreste [10:53]: "They were excited for the change because it would actually make their lives better. And we achieved that by simply asking them."

Transcript

[Vasco]

Hey there, agile adventurer, just a quick question. What if, for the price of a fancy coffee or half a pizza, you could unlock over 700 hours of the best agile content on the planet? That's audio, video, E courses, books, presentations, all that you can think of. But you can also join live calls with world class practitioners and hang out in a flame war free and AI slop clean slack with the sharpest minds in the game. Oh, and yes, you get direct access to me, Vasko, your Scrum Master Toolbox podcast. No, this is not a drill. It's this Scrum Master Toolbox membership. And it's your unfair advantage in the agile world. So if you want to know more, go check out scrummastertoolbox.org membership, that's scrummastertoolbox.org Membership. And check out all the goodies we have for you. Do it now. But if you're not doing it now, let's listen to the podcast.

[Bernard]

Hello everybody. Welcome to our Wednesday the Change Leadership episode, this week with Bernard Agreste. Hey Bernard, welcome back.

[Bernard Agreste]

Hey Vasco, how are you?

[Bernard]

So, Bernard, Wednesday is the Change Leadership episode. So we want to explore one of those stories of change. So tell us the story, a bit of the context, what kind of change process was it, and then walk us through the steps from beginning to end how that process went. And as you go, highlight for us the tools, the tips, the tricks and the techniques you learned back then that you still apply today.

[Bernard Agreste]

Yeah, absolutely. So one of the biggest challenges I faced, and this was a massive change initiative, a digital transformation effort, an internal tool that supported at Teach for America, our staff, but then also about 2 to 300 teachers every year, 23 school districts, and kind of indirectly touched something like 12 to 15,000 students every year. Also touched all of our internal ways of working. So onboarding, hiring, partner coordination, program, metrics, you name it, the tool touched it. And it was a very old school. So it had so much tech debt that we were just duct taping new features onto it. But it needed a rebuild. Right? We were being billed by developers a lot more, but really we were being built because they were making up for unclear requirements and a tool that wasn't built for what we needed it to do anymore. Our organization just evolved and so there was alignment that it needed to be rebuilt, but nobody could agree on where to start. And to be clear, this was not a turf war. This wasn't like, oh, my thing needs to go first. It was genuine disagreement and confusion over how can we do this so that the disruption to, to kids, school staff would be as minimized as possible within the workflow that we had. And so the thing that I did to start was had a one on one with everyone to understand how they thought of the workflow itself. And then in my own role, being the PMO supporter for everyone else, I realized that teams weren't actually viewing their work as cyclical flows, but more as straight lines of like almost like a race where I pass a baton off to the next person and then that's it. But like they don't realize that it's not like this, it's like this. And so what I did was I actually mapped out the continuum of our year across teams. And what I highlighted was not just where teams responsibilities were kind of front and center of the work, but also all the other teams that were supporting them so that work could get finished. And they were, and where those teams were most proximate. So in mapping out this full continuum for the year and seeing where roles overlapped, there was a very clear pattern. And it was that the onboarding team wasn't just a starting point. It wasn't just like, oh, we take the baton. The onboarding team was the, was the team that gave the baton to everyone all the time. They were involved in every cycle, every phase, and then they had their own core work to do as well. And so they were propping up so much other, so many other teams that starting the rebuild from them actually allowed us to redesign with impact in mind. And so we weren't just redesigning for features. We were now redesigning so that the tech worked for us in a way that onboarding had figured out would make everybody's lives easier.

[Bernard]

So what you realize is that, okay, we were confused about what part of the system to start developing, but then when we started mapping out the process, we understood that actually this onboarding team is kind of the center, kind of the catalyst for a lot of the other teams. So if we start there, then it will be easier to enable the other teams to take on the work because the onboarding team will basically trigger all of the other teams themselves. Right?

[Bernard Agreste]

Yep. And I can give you an example if you're interested too. Yeah. So one of the things that the onboarding team did was make sure that teachers were legally allowed to be teachers. In California. And through our program, Teach for America, there was two kind of larger exams that they needed to qualify through. One was called CBest, one was called CSet, but it wasn't like one exam. It was CBest was for basic Skills, math, reading, writing. CSET was for your subject specific skills. Tons of different ways to qualify for those first skills. We didn't have a single way of tracking that. There was no automation. We were literally tracking in an Excel spreadsheet. And so when and when you're doing that for hundreds and hundreds of people at different deadlines across the year, right, that becomes really cumbersome. And so in working with the onboarding team, right, like kind of starting with them, that process impacted our partner teams for hiring. Because you couldn't interview someone to become a teacher until they had a minimum number of qualifications. It impacted program team handoffs. So once you became a actual teacher, it impacted the fluidity of, hey, I am now your teacher coach and I'm here to support you. Because the teacher coach didn't know what they needed to support their student. Their teacher was. It impacted data metrics because now we didn't know whether or not we were hitting our grant funding. And like it just keeps going and going, right? Grant metrics rather of how many was the percentage of our staff that is, you know, actually eligible to teach at a given point in time of the year. It just kept going and going and going. And even redesigning that one process impacted every single team and also made our onboarding teams lives way easier.

[Bernard]

Yeah, absolutely.

[Vasco]

So how did it go then?

[Bernard]

So you understood that we needed to start from that onboarding team. What were the next steps?

[Bernard Agreste]

The next steps were full project plans and timelines and all that fun stuff. It went really well. Right. I mean, I'm not going to say that this was like a project that had no hiccups, but like, we had a vision for what the goal was and we understood how, like, what the impact would be not just for our staff, but like downstream into the communities that we work with. And so that was really powerful because people were actually vested in the change. Right. There was no, like, there was obviously people who had differences, but we didn't have any, like, you know, ad card detractors. It was like people were genuinely on board with it and we just needed to then like realign on what onboard exactly meant technically. And at the end of the process, so we redesigned, we created these new six hubs for our, you know, our tool and you know, almost immediately we started seeing results. So we were better able to allocate our budgets. We were able to do like a deep background retrospective on some data and realize that the onboarding team budget for like how they could support teachers was actually not being used as effectively as they Could. And so we reprioritized spending money into getting one on one support for teachers for tutoring for these exams. And so that gave us a 25% increase over a year of first time success rates. So like more teachers were becoming more potential teachers are becoming teachers faster as a result of us being able to see the data clearer. Yeah.

[Bernard]

So one of the things that is interesting for me is that typically it, let's say deliveries are complex, not only because it's hard to get to the requirements. And you illustrated that in your story by not knowing what team to start with and what did they need and.

[Vasco]

So on, but it's also because why would they change?

[Bernard]

I mean things are quote unquote working now. Why would we now start using, using the new tool? How did that part go? Because taking a new tool into use, it's usually one of the hardest parts in a IT tool deployment.

[Bernard Agreste]

Yeah. And I mean this is where we spent a ton of time working with everyone on staff who needed to use the tool to really vest them in where their value add was. And I think the first thing that we did was not just say, hey, we're doing this thing. We kind of like said, hey, we are going to change this tool to make it better. And we want to hear specifically from you on how are you using this tool right now in a way that doesn't work for you, but if you tweaked it in some specific way would work for you. And like an example I could give around that was our coaching team, right? These, these coaches of teachers, they could see their portfolio of teachers and like, you know, give them grades and give them notes and give them feedback. But what they couldn't do was they couldn't cut the data in any way. So they couldn't differentiate between first year teachers or second year teachers. They couldn't differentiate between English or math or schools or districts or even things like gender. Right. There was no way to slice that data. And so they were downloading all this data in really manual, clunky ways to try to get like filters in place to analyze how they could support their teachers not just individually, but as a cohort. And so, you know, the coaching team just said, hey, like if you can give us this, it will make our lives a lot better. Right. And then once we got them, once we said, yeah, this is absolutely doable. Right. Then they got excited for the change. They weren't just like, oh yeah, another change, sure, whatever, I'll deal with it. They were, I can't wait for this to come out because it will actually make my life better. And the way we figured out how to make people's lives better was by, I mean, just ask them.

[Bernard]

That's an important point because part of the, in an IT delivery process, part of getting people on board is to actually do that, to listen to them and to make them part of the story of what we are doing. Because at the end of the day, they will need to decide to use the tool.

[Bernard Agreste]

Right.

[Bernard]

Because if they don't use the tool, what we did is not going to help and the benefits are not going to materialize.

[Bernard Agreste]

Nope. And I mean, that was what was happening already. We had a tool that, you know, had all this information, but it wasn't presenting information in a way that made sense to people. And so they just, they use the tool as like an export instead of like an actual tool.

[Bernard]

Yeah, that's a story I've heard before. That was a beautiful story. Thank you for sharing that, Bernard.

[Bernard Agreste]

Yeah, thank you so much, Oscar.

[Vasco]

Alright, I hope you like this episode, but before you hit next episode, here's the deal. This podcast is powered by people like you. The members who wanted more than just inspiration. They wanted real tools and real connection to people who are practicing agile. Every day we're talking access to over 700 hours of agile gold, CTO level strategy talks, summit keynotes, live workshops, E courses, Deep dive interviews, books, and if you're into no estimates, we got the pioneers of no estimates in those deep dive interviews as well. Agile, business intelligence, creating product visions, coaching your product owner courses, you name it. You'll get invites to monthly live Q&As with agile pioneers and practitioners. Plus a private Slack community which is free of all of that AI slop you see everywhere. And of course, without the flame wars. It's a community of practitioners that want to learn and thrive together. It's the best place to connect with community and learn together. So if this podcast has helped you before, imagine what you will get from this podcast membership. So head on over to scrum mastertoolbox.org membership and join the community that's shaping the future of Agile. We have so much for you, so check out all the [e-mail] membership because listening is great, it's important. But doing it together, that's next level.

[Bernard]

I'll see you in the community.

[Bernard Agreste]

Slack.

[Vasco]

We really hope you liked our show.

[Bernard]

And if you did, why not rate this podcast on Stitcher or itunes, Share this podcast and let other Scrum masters know about this valuable resource. For their work. Remember that sharing is caring.