When Stepping Back Becomes Stepping Away—A Leadership Failure Story | Bernard Agrest

Summary

Episode Summary: "When Stepping Back Becomes Stepping Away—A Leadership Failure Story" | Bernard Agrest

Podcast: Scrum Master Toolbox Podcast
Host: Vasco Duarte
Guest: Bernard Agrest
Release Date: June 30, 2025

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Episode Overview

In this insightful episode of the Scrum Master Toolbox Podcast, host Vasco Duarte welcomes Bernard Agrest, a seasoned Agile Coach and Certified Scrum Master. Bernard shares his personal journey through various roles in nonprofit organizations and educational institutions, culminating in his current position overseeing a major ERP implementation at the University of Wisconsin Madison Medical School. The episode delves deep into Bernard’s experiences, particularly focusing on a significant leadership failure early in his career and the valuable lessons he gleaned from it.

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Guest Introduction: Bernard Agrest

Bernard Agrest brings a rich background in project management and Agile practices. His career trajectory includes:

• University of Wisconsin Madison Medical School: Leading a large-scale software implementation affecting over 10,000 employees.
• Tech for America: Building a Project Management Office (PMO) and steering data and learning initiatives.
• Veteran Service Nonprofit: Redesigning operations, co-leading national initiatives, and launching an alumni program.

Bernard’s unconventional path to becoming a Scrum Master highlights his adaptability and commitment to continuous learning.

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Failure Story: When Stepping Back Became Stepping Away

Bernard recounts a pivotal moment early in his career while working at a veteran service nonprofit in New York. Tasked with leading an internal initiative to track veteran salary and career retention, Bernard was eager to prove himself. The project was high-stakes, with implications for securing future funding and demonstrating the program’s effectiveness.

Key Points of the Story:

1. Project Initiation:

   • Assigned by the CEO to lead the project.
   • Goal: Demonstrate the positive impact of the mentorship program on veterans’ career retention and satisfaction.
   • Bernard established workflows, aligned team goals, provided training, and offered rough project timelines.

2. Assumption of Autonomy:

   • Bernard trusted his team and decided to step back to avoid micromanagement.
   • Initially, all team members appeared confident and committed.

3. Emerging Challenges:

   • Weeks before the deadline, Bernard noticed that one team member hadn’t started their tasks.
   • Upon reviewing project work, he discovered significant errors in the data handling process.
   • Realization that the lack of structured feedback loops and regular check-ins led to project derailment.

4. Crisis Management:

   • Faced with impending failure, Bernard took on the bulk of the work himself.
   • Worked extended hours, including weekends, to salvage the project.
   • Despite his efforts, the project outcomes were compromised, marking a significant leadership failure.

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Key Lessons and Insights

Bernard’s experience underscores several critical lessons for Agile leaders:

1. The Importance of Feedback Loops:

   • Host Quote [10:07]: “It's in the doing of the work that we discovered, the work that must be done.”
   • Regular check-ins and iterative reviews are essential to identify and address issues promptly.

2. Balancing Trust and Oversight:

   • Trusting the team is vital, but it should not equate to relinquishing all oversight.
   • Empowerment involves creating spaces for questions and ensuring accountability, not stepping away entirely.

3. Adaptive Leadership:

   • Leaders must remain engaged and adaptive, especially when projects are high-visibility and high-stakes.
   • Proactive problem-solving and maintaining open communication channels can prevent escalation of issues.

4. Structured Project Management:

   • Implementing basic structures such as weekly stand-ups can facilitate better project tracking and team alignment.
   • Even simple frameworks can significantly enhance project outcomes by ensuring consistent progress monitoring.

Bernard’s Reflection [12:15]:

“Empowering doesn't mean I disappear. It means I create space for people to say, hey, I have a question, and I can then make them accountable for that work.”

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Notable Quotes

• Bernard Agrest [08:54]:

  “I just worked like crazy for that go, by the way, because I imagine it must not have been easy at the time.”

• Host Vasco Duarte [10:07]:

  “It's in the doing of the work that we discovered, the work that must be done.”

• Bernard Agrest [12:15]:

  “Empowering doesn't mean I disappear. It means I create space for people to say, hey, I have a question, and I can then make them accountable for that work.”

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Conclusion

Bernard Agrest’s candid recounting of his early leadership failure provides valuable lessons for Scrum Masters and Agile Coaches alike. His story emphasizes the necessity of maintaining structured feedback mechanisms, balancing trust with active oversight, and the importance of adaptive leadership in navigating project challenges. By sharing his experiences, Bernard offers actionable insights that can help practitioners avoid similar pitfalls and enhance their leadership effectiveness within Agile frameworks.

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Stay Tuned: For more enriching conversations and actionable Agile insights, subscribe to the Scrum Master Toolbox Podcast and join the community shaping the future of Agile.

Transcript

[Vasko]

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[Host]

Scrum Master Toolbox Podcast. And this week, joining us from the US is Bernard Agrest. Hey Bernard, welcome to the show.

[Bernard Agrest]

Hey Vasco, thank you so much. I'm really excited to be here.

[Host]

So, Bernard currently leads a major software implementation at the University of Wisconsin Madison Medical school, serving over 10,000 employees. Previously, he built a PMO and LED data and learning at Tech for America. And his journey began redesigning operations for a veteran service organization where he co led national initiatives and launched a new alumni program. Bernard, that was a short intro. Tell us a little bit more about yourself and how did you end up becoming a Scrum Master?

[Bernard Agrest]

Yeah, thanks, Vasco. So I think I might have backed into the role that I have now in a pretty untraditional way. So I started my career at this point like 12, 13 years ago, which feels weird to say, as a youth sports coordinator, a nonprofit in Brooklyn where I grew up. And so I spent four years running those programs, learning how to solve problems, coaching people. I never heard of a project plan at that point. Really it was just about showing up, listening, having empathy for people and getting things done. And so doing that for four years, I realized I really like this kind of work. And I want to get more information about how things work at a system level. How does policy, funding, operations, how do they all intersect? And so I got my master's degree in public policy at the University of Edinburgh in Scotland. I learned a ton of that program. By the time I graduated, I realized, oh, I don't know anything. And I really needed to get back more Hands on experience. And so that led me to a role as an operations associate, sort of case manager at a veteran service nonprofit in New York. And in that role I facilitated veteran mentor relationships. And that was really the first time where I started leading cross functional projects into small teams. Also the first time I started kind of getting a sense of the mechanics of project delivery. So things like timelines, budget, stakeholder management, things like that. Right before that I didn't know what they were and I didn't know what I was doing. Honestly, I didn't really know what I was doing at that point either. So I was in that role for about three years, had a really great time there, learned a lot, made some friends, and I had always wanted to go back to the education world, which is where I got my start. I found and won this really cool education policy fellowship through an organization called Education Pioneers and moved to Oklahoma from New York to be the manager of data and learning at Teach for America. This really was actually my first exposure to agile practices. I still remember having this meeting with my manager at the time and she was like, hey, I learned this new concept that she was talking about an mvp. And I was like, oh, this is really cool, right? And so it was kind of funny. Like both of us, you know, she was much senior than I am, but both of us were just getting our first real understanding of agile in some way, just project management theory in general. And in that role, that's where I really started running sprints, clearing blockers, helping teams iterate things of that nature. And after the fellowship I actually stayed on at Teach for America. It was a one year fellowship. So kind of after the fellowship there was a question of whether or not I would stay or go and actually joined the Bay Area team this time. This was right as Covid happened. So my fellowship ended, I had this mad scramble to go, oh, I don't have a place to live in Oklahoma anymore, so I'm going to go move back to New York with my family for a bit. And ended up working remotely as a director of data and learning for Teach for America in the Bay Area this time. And in that role I was really actually setting up a one man PMO without quite realizing it. I led redesigns, I was coaching team leads, I was facilitating retros. So again, not the title, but definitely the job. And unfortunately got laid off at Teach for America a couple of years ago. Thankfully though, it didn't take me too long to get a job and here I am in my current role. I'm the senior PM for workday readiness, which is this massive ERP implementation that we're doing across the universities of Wisconsin. And I am specifically focused on readiness for the School of Medicine and Public Health.

[Host]

Yeah. And when you think about it, I mean, that career has a lot of stories that I'm sure you can pick on to share, because as you said, you are learning things on the job in many of those stories. And when we do learn things on the job, sometimes we learn it the hard way. And today's Fail Monday here on the podcast. So we want to explore one of those stories, Bernard. A story of when you tried your best, but the best just wasn't good enough. But on the other hand, you got some lessons learned. And we'll dive into the lessons at the end. But tell us that story first. Bernard.

[Bernard Agrest]

Yeah. Oh, boy. I'm still failing, I feel like. But I'll actually talk about an experience I had very early on in my career at that nonprofit in New York job that I was talking about. And so I had been asked to kind of as a sign of, hey, you're doing really well, we want to give you a stretch assignment. I had been asked to lead an internal initiative to track veteran salary and career retention. After the program offering, which is a mentorship program for the nonprofit I worked at, the idea was to see if we could show a meaningful difference between veterans who went through our program and those who didn't, to say, hey, you stayed in your job longer, you were more satisfied in your job, you had a higher salary. Right. And just the statistics, unfortunately, around veterans in their first job out of, like, their service are actually quite sad. Like, something I think, like, you can check me on this. I don't. I'm not in that world anymore. But I think it's like 60% leave within the first year, which is a really just high. You know, I don't know if recidivism is right to work, but it's a really high lack of retention. And so this was a meaningful project. It had high visibility internally because the person who gave it to me was the CEO, the executive director. But it also had real world implications. Right. We were going to be using this project to talk with funders and make a pitch and all these kinds of things for why our program was so powerful. And so I was responsible for the outcomes and the team doing the work. And I did what I thought a good leader would do. I build out the workflow. I got everyone aligned on the goals. I made sure people were trained. And then I even gave Rough estimations to the leadership team. I'm like, hey, we'll have this in about three months. And then I kicked everything off and I said, hey, y' all, I'm here to support you. Let me know what you need. And then I stepped back because I didn't want to micromanage the team because I trusted them, right? And then about two, three weeks before we were due to deliver the project, I started checking in with team members. And these people were people who had other responsibilities in the organization. And at that point they started surfacing questions. One of them hadn't even started the work. And then I looked kind of briefly at one of the Excel spreadsheets that I got and I looked at what they were doing. I was like, oh, this is all wrong. This is not actually the way you're supposed to do it. And so there was a lot of questions, a lot of process problems there. And so in the moment that happened, I really kind of was like, you know what, I'm scrambling. I'm taking all this on for myself. And these are thousands of rows of data. And each person, because we were looking backwards too, each person could have three or four jobs at that point, and we had to manually find that data through LinkedIn. So this was.

[Host]

So you started to focus on the, how do you call it, the person who takes on all the responsibility. Like, you started to feel that, okay, I need to do this on my own.

[Bernard Agrest]

Yes, yes. I really went and said, well, this is my fault for not, you know, for not following up, for not training correctly, for not creating the conditions for people to feel comfortable, maybe, I don't know if that was the case for reaching out. And so I said, this still has to get delivered though, right? This is still a very important project. And so I just, I just worked like crazy for that go, by the.

[Host]

Way, because I imagine it must not have been easy at the time I.

[Bernard Agrest]

Was, I was really tired, man. It was, it was hard, right, because I still had my full time job. And so I was, you know, staying back. You know, I was coming early, I was staying back easily a couple hours every single day. I think at one point I might have actually shown up on a Saturday and I just spent four hours in the office. I had plans around that area. And so I was like, oh, I'm like, I can get some work in as well. And so I think I just did that as well. It was not fun, right? And of course I was really stressed because I was like, oh, crap, there's this big project that I've been assigned, it's my real first opportunity to kind of get positive notoriety in the office. And I'm completely bungling this.

[Host]

So one of the things that comes up from this story in my mind is this idea that somehow we believe that as long as we've got a plan, everything is fine. And then when you start, you have the plan, everything is all there. And maybe we've even talked about it and whatever. But it really is in the doing of the work that we find out the work that must be done. That's a quote from Wood is Drill says this all the time. Right. It's in the doing of the work that we discovered, the work that must be done. And what I understood from your story is that you expected that having an agreement and an understanding on the plan would be enough to get it done. Was that how you felt at the time?

[Bernard Agrest]

Yeah, absolutely. You know, I had said kind of like, hey all, does everyone, you know, we had like this big kickoff meeting. Everyone seemed good. I had a couple of sessions with people to kind of make sure that they understood the mechanics of the work. Right. Because I mean, like, this wasn't necessarily a very complicated project. It was just a lot of people that we were going through and everyone seemed like, yep, thumbs up, we're good to go. And I was like, great, I'm going to step back now. I trust you to do it. I don't want to micromanage. I've had micromanagers before. But yeah, I mean, I mean, for me, the real failure in reflecting is that there was no follow through. Right. I didn't build in feedback loop, feedback loops, structured check ins. No, there's no backlogs. Right. I don't necessarily know if we needed a backlog for that project, but there was just no structure or sense of what should we be doing here. And then like, you know, I think now, 10 years later in my career, I think I probably had the right idea of like, I trusted my team. But trust and empowerment, I would say, are different things. Right. Empowering doesn't mean I disappear. It means I create space for people to say, hey, I have a question, and I can then make them accountable for that work. And so I feel like even if I had built in a really basic foundation back then, maybe even something as simple as just a weekly standup, not even the daily one, we'd have caught those issues much faster and the project wouldn't have imploded on me quite the way it did.

[Host]

Yeah. And this comes back to that. Everybody knows it, of course, but that pattern that we have in Scrum, which is that you have a short time box, typically one week or two weeks, and then at the end of every one of those time boxes, you demonstrate the work that you have done. You show what you have delivered, because that surfaces questions, that surfaces feedback. And that feedback is incredibly important to set up the next step of the delivery. And that's one of those feedback loops you were referring to, this opportunity to see what's there, learn from it, and then set up the next step.

[Bernard Agrest]

Yep, exactly. Oh, hey, I had this veteran that I was going through their LinkedIn profile and they didn't have any information. How do we treat that right? Something as simple as that. In my mind, I knew the answer, but I had never thought that someone else might not have that question. And so I just never created those conditions in the first place.

[Host]

Yeah, absolutely. That's a great lesson. Thank you for sharing that, Bernard.

[Bernard Agrest]

Yeah.

[Vasko]

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