Mastering Complexity Through Systems Thinking and NLP Coaching | Bernie Maloney

Summary

Podcast Summary

Scrum Master Toolbox Podcast: Agile storytelling from the trenches

Episode: Mastering Complexity Through Systems Thinking and NLP Coaching | Bernie Maloney
Host: Vasco Duarte
Guest: Bernie Maloney
Date: September 10, 2025

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Overview

This episode explores how Scrum Masters can master complexity through systems thinking and neuro-linguistic programming (NLP) coaching techniques. Vasco and Bernie deep-dive into handling real-world, emergent challenges by examining a live problem: a last-minute change of plans for their own podcast recording. Using this lived example, they illustrate how empathy, rapport, multiple perspectives, and reflective practice are crucial for Scrum Masters working in dynamic, complex environments.

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Key Discussion Points & Insights

Agile Work Lives in Complexity (01:22 – 03:25)

• Vasco frames the Scrum Master’s daily reality as one of constant flux: “As Scrum Masters, our work happens in the middle of complexity… the way we approach these challenges defines how we grow as people and as professionals, but also how we help our teams.”
• Complexity isn't just a background reality; it’s a daily challenge to be embraced as part of the Scrum Master’s journey.

A Live Example of Navigating Complexity (02:35 – 06:11)

• Bernie recounts how he received a late-breaking change to the show’s agenda due to time zone differences—a story that mirrors the sudden scope changes developers often face.
  • “When stuff comes up after the beginning of a sprint, what are you willing to give up to get it?” (03:25 – 03:40)
• Bernie highlights the principle from NLP: “Everybody is doing the best they can with what they have.” (03:55)
• He uses gentle questioning and persistence to build understanding and empathy with Vasco, ultimately turning the situation into a coaching moment.

Applying Three Coaching Positions (04:39 – 07:45)

• Bernie describes the three coaching perspectives:
  • First position: In your own head (your experience)
  • Second position: In your client’s head (their experience)
  • Third position: Outside observer of the whole system
  • “Sometimes what you have to do is get people to see that whole system that they’re in, get them out of their own head to kind of see that bigger picture.” (05:02)

From Interpersonal Friction to Systemic Reflection (06:11 – 09:50)

• Vasco recognizes he acted as “the annoying stakeholder that brought a scope change right after the start of the sprint,” paralleling common team frustrations.
• Both agree that productive coaching involves “modeling what a coaching conversation can sound and feel like… helping our teams and stakeholders learn to practice that conversation as well.” (07:20)
• Bernie references the Lean principle of “see the whole,” and points out:
  • “Instead of a problem being between us, it’s a problem before us. So now we’re looking at the greater system.” (08:23)

The Power of Retrospectives & Making New Mistakes (09:50 – 13:11)

• Bernie advocates for retrospectives, asking, “What did we learn from that so that we don’t make the same mistakes again?” (09:26)
• Vasco reflects on stakeholder behavior, noting that when stakeholders have thought about an idea for years but the team only hears it at the last minute, it creates natural tension:
  • “They are taking all of those five years into the conversation. But you just heard it five seconds ago.” (10:38)
• Both discuss the virtues of being open to new mistakes rather than repeating old ones.

Psychological Safety, Mindset & Systemic Thinking (13:11 – 16:20)

• Vasco and Bernie credit experience in coaching and therapy with building resilience to discomfort and mistakes.
  • Vasco: “I wasn’t thinking that [the conversation] would represent failure. I thought that just represents trying to find a new thing to do.” (13:45)
• Bernie references Amy Edmondson’s book, Right Kind of Wrong, which distinguishes basic mistakes (things we should know), complex mistakes (unknowns in complex systems), and intelligent failures (intentional risk for learning).
• Bernie outlines societal biases towards “plan and predict” thinking from the industrial age, contrasting it with agile’s “sense and respond,” and emphasizes the coaching goal:
  • “Get really good at getting into third position… being able to go back and see the whole system and then work from that position versus your own emotional reactions.” (15:35)

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Notable Quotes & Memorable Moments

• On Adaptability:
  “When stuff comes up after the beginning of a sprint, what are you willing to give up to get it?”
  – Bernie Maloney (03:25)
• On Empathy:
  “Everybody is doing the best they can with what they have.”
  – Bernie Maloney (03:55)
• On Perspective:
  “There’s in your own head, your client’s head, and then third position, looking at the whole situation.”
  – Bernie Maloney (05:00)
• On Framing Problems:
  “Instead of a problem being between us, it’s a problem before us. So now we’re looking at the greater system.”
  – Bernie Maloney (08:23)
• On Dealing with Stakeholders:
  “They are taking all of those five years into the conversation. But you just heard it five seconds ago. You have no insight into that.”
  – Vasco Duarte (10:38)
• On Mindsets:
  “A lot of the way that management, leadership and even teams have been coached is plan and predict. Get it right, get it right. So when a challenge like this comes up our first reaction is very emotional: I got it wrong, I got it wrong.”
  – Bernie Maloney (14:25)
• On Reflection & Growth:
  “Make new mistakes… If we recognize this is actually something that’s complex… [it] starts to soften things up.”
  – Bernie Maloney (14:25)
• On Coaching Goal:
  “Get really good at getting into third position… and then work from that position versus your own emotional reactions.”
  – Bernie Maloney (15:35)

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Timestamps for Important Segments

• Agile Work as Navigating Complexity: 01:22 – 03:25
• Live Example of Complexity (late scope change): 02:35 – 06:11
• Three Coaching Positions Explained: 04:39 – 07:45
• Making the Problem "Before Us" Not "Between Us": 07:45 – 09:50
• Retrospectives and Making New Mistakes: 09:50 – 13:11
• Mindsets, Psychological Safety, and Systemic Thinking: 13:11 – 16:20

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Recommendations & Resources

• Book Mentioned:
  • Instant Rapport by Michael Brooks (08:25) — Introductory book on building rapport through NLP
  • Right Kind of Wrong by Amy Edmondson (14:20) — On the nature of mistakes, learning, and psychological safety

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Conclusion

This episode provides a real-time masterclass in using systems thinking and NLP coaching strategies to tackle complexity, unexpected changes, and interpersonal misunderstandings. By modeling vulnerability, empathy, and reflecting on their own dynamic interaction, Vasco and Bernie exemplify how Scrum Masters can turn friction and ambiguity into shared learning and stronger team culture. The tools and mindsets discussed are practical and broadly applicable for any Agile practitioner.

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Transcript

[A]

Hey there, agile adventurer, just a quick question.

[B]

What if, for the price of a.

[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.

[B]

Hello, everybody. Welcome to our Wednesday the biggest challenge question. Which Bernie. Hello, Bernie. Welcome back.

[C]

Hi, Vasco.

[B]

So, Bernie, our guest this week will have the privilege of being the first to experience this question. And I will have the uncomfortable position of being the person who created the reason for our conversation. But here's the question first, so that everybody knows what we're trying to tackle now. As Scrum Masters, our work happens in the middle of complexity. Teams, stakeholders and organizations. Projects, goals that are constantly changing. And that means that we're always facing evolving challenges. In fact, we could say that as Scrum Masters, we're moving forward from challenge to challenge. And the way we approach these challenges and experiments that we try. We've talked about experiments a lot. This week already defines how we grow as people and as professionals, but also how we help our teams. The people we work with also grow as teams and professionals. Yesterday we talked about a coaching skill called triangulation. Maybe this is what we are going to use today. Because the question is, Bernie, in your current role or assignment, what is your single biggest challenge right now?

[C]

So these, you know, at this point in time where we're recording at Vasco, I don't have any coaching clients, y'. All. If you want to hire me, okay, great, I'm available, but that's not the point. So I'm going to take something that in theater is you, it's called utilization. When something comes up, you do it. So for everybody, Vasco is in Finland, I'm in California, and Vasco sent me an email that. Oh, hey, we're going to change the question at 12 minutes past midnight, my time. And I didn't get to see it until five minutes before we got on to start recording this week. And so when we got on, Vasco said, hey, you know, we changed this question. And so in a situation like this, this is a challenge right here that we're facing in front of us. It's complexity.

[B]

Oh.

[C]

You know, and I thought through as. As I read, it's like, oh, how would I coach in this situation? You know, one of the things that I tell teams routinely is when stuff comes up after the beginning of a sprint, what are you willing to give up to get it? So it's like, okay, so we'll talk through this with Vasco. And, you know, it could be we defer making this recording. Could be we record on the old topic. It could be, you know, we do the best, you know, okay, there's a bunch of different things that are here. And the way the conversation evolved. Um, what you want to do when challenges come up, recognize that everybody is doing the best they can with what they have. Okay. That's a principle out of neuro linguistic programming. Everybody has challenges all the time, and they're doing the best they can with what they have. And so Vasco hadn't recognized that I was in California with a time difference, and so just to kind of get him to see a bigger picture. So, Vasco, I think the question I asked you was, hey, Vasco, what time do you go to bed? And. And. And your reaction was quite puzzled.

[B]

Yeah, I was like, what. What does that have to do with the question that I have on the script? I'm. I'm confused.

[C]

Right. But. But I. I was persistent. You know, I. I wanted Vasco to see my point of view. If, you know about the three positions in coaching. So there's first position, which is you're. You're in your own head observing what's going on. Okay. So you're in your own experience. Second position is you're in your client's head thinking through what might be going on for them. And third position is you're imagining yourself outside the conversation, like, observing the whole system that you're working with. Sometimes what you have to do is get people to see that whole system that they're in, get them out of their own head to kind of see that bigger picture. So I was persistent, wasn't I, Vasco?

[B]

I can vouch for that.

[C]

And. And. And I got you to admit what time you went to bed. Okay. And then I said, so what time do you get up and it was 6:00am yeah. And then my question was, and do you read email in between?

[B]

In between while I'm in bed? Which took me a second to recognize that was the question.

[C]

Yeah. And your answer was no. Okay, so what I was able to do with that is then say very gently to Tabasco. Well, you know, your, your message came in at 12 past midnight, you know, after you would be going to bed. And I got it, I picked it up at five minutes before we started recording here at five minutes of 6am but just like you, I hadn't read it yet. So it's kind of hitting me cold. And that built a lot of empathy, didn't it, Vasco?

[B]

No, I. At that moment I understood there's no way you could have seen the email and prepared for it even if you had seen the email. So at that point, and so I was the annoying stakeholder that brought a scope change right after the start of the sprint in this particular case. And the position that I took is, okay, well, there's a fallback plan, right? We keep the old question. But then I took a. Another perspective, which is, but wait, this is actually an important question. Like, what is your single biggest challenge right now? Because we are all facing our single biggest challenge right now at every point in time. And I thought, hey, we can explore. Maybe Bernie has an example from the past that we could explore. Because as he said, he didn't have a coaching client at this precise moment. And Bernie made a suggestion. And I was surprised by the suggestion, but I thought it was a great suggestion, which is, well, what if you are the problem? Because I just had a big change in scope after the beginning of the sprint. And that put me in a position of, oh, wait, this is perfect. This is exactly what I want. Which is to model for our audience what a coaching conversation can sound and feel like. Because that's what we need to be doing. That's what we need to be doing with our teams, with our stakeholders, and. And also helping our teams and our stakeholders learn to practice that conversation as well.

[C]

So the. Getting people to see a different point of view. Well, first, recognizing they're doing the best that they can with what they have, getting them to recognize another point of view than what they have is a key thing when you're facing challenges like this. Because now people can see, you know, this is. This is the lean principle, if you want to see the whole. So you want to do global optimization, not local optimization. Now, I've referenced that. I study neuro linguistic programming and yesterday in Team Tuesday, we talked about books. One book that I didn't mention there, but it's another good book to put on your list, y'. All.

[B]

There you go. Give it to us.

[C]

Is Instant Rapport by Michael Brooks. So it's a very easy to read primer on neuro. Linguistic programming. And rapport building is honestly a key skill that Scrum Masters need to have. Understanding how to build rapport themselves to get people to see that bigger picture, and how to help other people, other groups, build rapport so that collectively, just like I talked about with triangulation yesterday, it's instead of a problem being between us, it's a problem before us. So now we're looking at the greater system. And that. That's really a key thing that is kind of universal when challenges come up is you want to do that. Now, the other thing that when those challenges come up and, you know, we've done great utilization here, I think, Vasco, of taking this situation that we've faced here and, you know, in the past 30 minutes as we started this and used it as an example, the other thing to do is do a retrospective. So once people go, oh, okay, great, then it'd be okay if this comes up again. Going back to. I think I said it on Monday, make new mistakes. What did we learn from that? So that we don't make the same mistakes again. So just do a simple retro. So I've already had time to think about this, Vasco. Have you had time, any time to think about, like, in a retro, what could we have done better? Like, I know now the most obvious.

[B]

Thing is I could have sent you the question earlier, but I didn't know. I wanted to send you the question earlier and to put my stakeholder perspective. I had been thinking about this question for five years, and I didn't put it into the script. And at some point, and then I'm.

[C]

Honored that you threw it at me for the first one.

[B]

And we're handling it right now, like, you know, as they would say, live, although this is recorded, but we're not editing too much of this. But then I realized that, wait a minute. The question is so important, and it embodies such an important aspect of what we do in our role as SCRUM Masters that we can't wait anymore. And I'm pretty sure that people listening to us actually have been in the receiving end of that kind of stakeholder. We can't wait anymore. Like a stakeholder that comes in with a feature. They've been thinking about it for five Years. And when you react to it with defensiveness and resistance, they are taking all of those five years into the conversation. But you just heard it five seconds ago. You have no insight into that. So I didn't tell you that I was thinking about this question for five years. So you didn't know. But for me, for my retrospective, coming back to your question is that I realized that I would rather run the risk of this bombing than not ask the question anymore. And of course, I gave you the option to go back to the old question because I, I realized that, okay, I can't force this on Bernie. That would be unfair and probably counterproductive anyway.

[C]

Yeah, so it's a, it's a great example of make new mistakes. So, you know, I, I honestly love this. One of the things that I thought. So when I prepped, I waited to do my, my prep for our recordings until yesterday because I had a whole bunch of stuff that I've been working on. It's like, okay, you know, that's why we, we deferred until today to, to record. And so I went and I pulled your Dropbox file with the questions and I went through and I took notes and it's like, okay, great. I got stories that I can talk to. And so when I got your messages, like, does he have it in that Dropbox file? And I already had one up, and it's like, no, it wasn't on the one that I pulled, but I pulled the Dropbox links that you had in the calendar invite. It's like, okay, he stuck it in here. So one of the things I thought.

[B]

Today, by the way, as we are recording this, this is exactly when I stuck it in there. This is the last minute change from stakeholders turned all the way up to 11.

[C]

Yeah. So, you know, some of the things that I thought of is I could have sent you a message yesterday and said, okay, so I'm about to prep any changes now that may have. Because of the time difference between us. You may have missed that as well. So it, you know, I could have sent it on Friday. Recognize the time change. We could have been really much more explicit about the time change because there's. Everybody makes assumptions about things. So go back to recognize everybody's doing the best they can with what they have and take it out from being a problem between us to being a problem before us. The problem's over there, not between us. So let's kind of work on, work on that now. That's a, that's a lot to unpack. Just from that particular question. And that's really what scrim masters are doing, is helping people see that. That bigger picture. I know there's a thought running around in my head, but it has escaped Vasco.

[B]

But there's one thing that I would like to add that over our conversation. I mean, of course we have an advantage here over the average person out there because we are both coaches. We've been doing this for many years, and I myself have been very vocal about this. I've also been in therapy for many years, which has helped me recognize that there's no problem when things don't work as you expect. You adapt. Right. So I was ready for having a conversation that I knew might have felt uncomfortable. I bet it did for you. Or puzzling and confusing like it did for me. I was ready for that. I wasn't afraid of that. I wasn't thinking that that would represent failure. I thought that just represents trying to find a new thing to do. And that could be, you know, go back to the old question or like we did, to utilize this opportunity to explore it from a coaching perspective. Right. We built the rapport. We tried to frame the problem as not you or me, but rather what we are trying to do. I explained the goal and the meaning behind the question. And you graciously accepted, yeah, let's try it out and even offer a solution that I think was much better than I even could think about, which is, hey, let's use this problem right here and talk through it live.

[C]

So I want to go back to something I referenced yesterday on team Tuesday, the book of make new. Sorry, it's not make new mistakes. It's right kind of wrong by Amy Edmondson, and she referenced three kinds of mistakes. One of the things that gets people in their emotions when these challenges come up is they think the mistake is basic. They think the challenge is basic, that this is something simple I should have anticipated. And we get very judgmental. But if we recognize this is actually something that's complex. Oh, okay. Neither of us knew this. And if you get. Or this is intelligent, let's go utilize this. It starts to soften things up. And that's really what you want to do, is you want to take people out of. See the way that we're wired as human beings, the way that we've been wired for almost 200 years in the western educational system is for plan and predict. The short version, Prussian system came up in the 1830s for teaching soldiers, perfect for the industrial age, for factory workers where people were just a pair of hands. Gave rise to the whole plan and predict mentality. But we're moving much faster now, so we actually need a sense and respond mentality. But a lot of the way that management, leadership and even teams have been coached is plan and predict. Get it right, get it right. So when a challenge like this comes up, it's like our first reaction is very emotional. I got it wrong. I got it wrong. I got it wrong. And, you know, we get into topics of growth versus fixed mindset. So I was like, oh, isn't that interesting? So for Scrum Masters, again, if you know the three coaching positions, there's in your own head, there's in your client client's head, and there's third position. Looking at the whole situation. Get really good at getting into third position, like being able to go back and see the whole system and then work from that position versus your own emotional reactions to the situation. All right, I just went into Advice Wednesday.

[B]

There you go. There you go. That was perfect. Advice Wednesday successfully completed. Thank you very much for sharing all of that and for being so generous and accepting of this experiment, Bernie.

[C]

Oh, you're welcome. Thanks. Thanks for the curveball.

[A]

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[B]

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