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Serverless Craic Ep64 Environment for Success

• Serverless Craic from the Serverless Edge • Season 1 • Episode 64

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🎙️ Environment for Success & Psychological Safety
Welcome back to another episode of Serverless Craic! After a short hiatus (thanks, ServerlessDays Belfast!), Dave Anderson and Mark McCann return to dive deep into one of the most critical – and timely – topics in modern software delivery: creating the right Environment for Success.

In this episode, we unpack Chapter 9 from The Value Flywheel Effect and explore the fundamentals that enable high-performing teams, including:

🔹 Psychological safety and why it’s the foundation of great engineering cultures
🔹 The danger of hero anti-patterns and the myth of the “rock star” developer
🔹 Challenging assumptions safely – using artefacts, not egos
🔹 Simon Wardley’s doctrine and Dr. Ron Westrum’s organisational culture model
🔹 How aligned autonomy and clarity of purpose help teams focus on what matters
🔹 Why generative, learning organisations adapt best to AI-driven change

Whether you’re a tech leader, architect, or engineer, this conversation is a masterclass in building sustainable, modern digital organisations.

🧭 Referenced resources:

The Value Flywheel Effect by us!
The Fearless Organisation by Amy Edmondson
Accelerate by Nicole Forsgren
Simon Wardley’s Doctrine
Dr. Ron Westrum’s organisational models

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Dave Anderson:

Hi folks. Welcome to the next edition of Serverless Craic. We're back after our 'brief' hiatus. Keen to get going again. We've been dying to get back. Like any sort of modernisation projects, we've all been busy this past couple of months, especially with ServerlessDays Belfast, which was a brilliant event, and we will talk about that in another episode. We are starting to come up for air. Mark, what do you think?

Mark McCann:

It's been busy. There's lots going on with modernisation. A lot of the things we've captured in the book are becoming more and more relevant to organisations as they try to go faster. With the added accelerant of AI now sprinkled on everything, it's becoming more and more important to focus on the foundations and the fundamentals.

Dave Anderson:

I'd love to say we're living the dream, but let's maybe say we're living the book. Mike will be back next time, but he's currently in his happy place. He's on a plane. He's probably sitting going through his pre flight checks, waiting to be asked to land the plane. He's probably sitting raring to go. He's on a short trip at the moment, but he'll be back next time. The AI stuff has been absolutely mental this past couple of months. It's everywhere, and we've been doing a bunch of stuff ourselves. Maybe that's something we can talk about another time. There's lots to talk about there.

Mark McCann:

A series of talks on that would be very useful, even just to articulate what we've been thinking about and what we've been trying to drive in our own organisations. So it's definitely on trend, I guess,

Dave Anderson:

Super exciting. And I will say everybody, the answer is not replace all your people with AI. It is definitely not a recipe for success. So we want to continue the series about the book. Last time we coveed 'map the market' and 'A Cloud Guru'. So I think next is phase two of the flywheel, which is 'challenging landscape', and chapter nine, which is'environment for success'. This is a funny one. I mean, well, this couldn't be more important, actually, in the current climate, it really couldn't. And even looking back over the chapter, this is 'bang on the money' with creating the right environment for success.

Mark McCann:

It's more relevant now than it has ever been. And I think some of the key tenets we call out in this phase are: psychological safety, team first, environments always win, the system is the asset, socio technical systems, map the org for enablement and enable empowered engineers. Those are strong tenets now and into the future. And they still hold up from when we wrote them.

Dave Anderson:

And not wanting to leap ahead, but organisations that have not done enablement properly, and as AI takes over, they're just going 10 different directions.

Mark McCann:

If you don't have a good environment for success, you're just building a house on sand.

Dave Anderson:

One of the interesting things about this, is the idea of the team. We've spent lots of time, many years in software teams. There are lots of personas. Without calling anybody out, let's gently talk about some of the anti patterns. The one that always resonated with me was the

hero anti pattern:

'Jimmy's brilliant. He's amazing. He can do anything, he stays up and works all weekend or all night. He calls everything out'. But that's not good for anyone, it's not good for Jimmy, it's not good for the company and it's not good for the team. It's one of the original anti patterns of a good team. It's the 'hit by a bus' syndrome. People say it

more nicely now:

the 'win the lottery syndrome'. You are dependent on one person, and everyone looks to that person for all the answers. It doesn't help the development of the team.

Mark McCann:

You never want to call people out for going the extra mile and putting in extra effort, but it's a symptom of the team notfunctioning, if everything goes through one person. You need to think about distributing knowledge and upskilling everybody by sharing the load and trying to make sure that you have a healthy team, not just one rock star. Some of this is indicative of the environment

Dave Anderson:

'Rock star' is the phrase that we had always heard over the years. And I actually think this is quite an innocent mistake, because sometimes leaders will say they're operating in as well. Make sure your incentives are'Mark's a rock star'. But it's one thing praising someone, but it's another thing, helping them to share the load and helping them develop. Sometimes you can get stuck. If you're a rock star you can't even move to new things. aligned with people being team players. So you're not penalising people for doing teamwork and things that are beneficial to the team, and not just to them individually. Another thing I thought was really interesting with this chapter was the idea of challenge. I remember a few my colleagues have said in the past that I used to always use the phrase challenge! Or being in an environment where you can challenge ideas and challenge the thinking, which I think is healthy. It's the same with a Wardley Map. If you're working something out, you challenge the map, not the person. A lot of my colleagues in the past have said'I'm not very comfortable with you talking about challenge'. And used to say, I'm not challenging you, I'm challenging this direction, which should be healthy because at the end of the conversation, it will be a good outcome regardless. It's not about me versus you.

Mark McCann:

We've seen this with Wardley Maps, and with creating artefacts that you can coalesce around or challenge is a much healthier process than challenging somebody who's standing up giving a narrative or telling a story. Sometimes it's good to have a lot of the thinking articulated, whether it's an ADR, new tech designs, confidence docs or, lucid or mirodiagrams. It's good to create an artefact that you can challenge and it takes a lot of the personal challenge away. It takes the heat out of It. So it's easier to challenge artefacts than it is to challenge people telling a story or creating a narrative.

Dave Anderson:

There's a big thing about the leadership culture in the environment. Some say it's poor management when

teams become tribes or packs:

this is my team and that's your team and we're going to win. We're going to build this thing and it's not going to be you. There's a lot of bad behaviour that happens around that. If I go back to the whole clarity of purpose stuff, if there is poor clarity of purpose, then that type of behaviour will happen, because people arelooking for things to do or looking for land grabs, etc. There is a cultural shift when you think about the value we're working towards, as opposed to how can I make my manager look good.

Mark McCann:

It's that aligned autonomy, that clarity of purpose, knowing who your users are, what their needs are, and making sure that what you're doing is actually beneficial to them. It sounds simple but harder to do in reality, but it's incredibly important that you work on things that are impactful and matter. You're not just doing busy work.

Dave Anderson:

There's a huge amount of content written about this type of leadership. Organisations like the military do this really well. And it's like new companies do it well and old companies don't do it well. It really is a mix. Some brand new companies are absolutely brilliant because they're super clear. Some very old companies are brilliant at this because it'sbeen locked in. But you can lose it quite easily with different leaders. It is a fascinating area.

Mark McCann:

We've covered this in earlier chapters, but if you find that it's a bit ambiguous and you're not quite sure what your clarity purpose is, doing a quick North Star exercise is usually a good way to discover what your purpose should be and remove some of that ambiguity.

Dave Anderson:

That probably brings us to some of the behaviours. There's a wee bit in the book called behaviour supporting challenge. And we printed Simon Wardley's doctrine. Simon actually spoke at ServerlessDays Belfast a few weeks ago. We were super pleased to get him over. As usual, he blew the entire crowd away. So the doctrine is brilliant, and is a universally useful set of patterns that a user can apply regardless of context. It's a well thought out list. Simon hasbroken it into like four phases with different headings on communication, development, operation, learning, leading and structure. And it's natural to want to go down to the end to do the more advanced one. But the first one is know your users and stop self harm. So it starts off at a basic level as there are serious fundamentals before you get into the more advanced stuff.

Mark McCann:

Simon says he's talking to organisations who want to do more advanced capabilities and phases. He

asks:

have you done the 'stop self harm'? Do you know who your users are? Do you know what they need? Do you know your landscape? Do you have reasonable situational awareness? Just start at the basics first, and then work up the phases.

Dave Anderson:

One of the first ones is challenge assumptions. And that's a different way to think about challenge. It's

because often somebody will say:

it's just language, we should do this. And maybe they could have said, maybe we could do this, and that'll open up a conversation. But as a senior person, if you say we should do this, often people take that as gospel. That's the direction, and it's often very hard for a

leader, they actually say:

'I don't really know what we should

Mark McCann:

It can depend on the age of the organisation as do. I'm trying to figure it out.' well. But a lot of these assumptions are baked into the code base or legacy documentation. So there is tribal knowledge, and people who've been there the longest as'heads'. So it's always good to challenge those assumptions and start to uncover if an assumption still holds true. The world has changed significantly in the past few years. Is this still a true assumption? We'll cover this in other episodes, but some AI capabilities and tooling can help uncover and discover if those assumptions still hold true, quickly.

Dave Anderson:

It is very interesting asking some of models the same question, because it'll just spit it out. There are universal behaviours you can look at, they are on page 111. That leads on to psychological safety. When I think about phase two of the flywheel, and the environment

Mark McCann:

It's hard to continuously improve if people for success, I simplify it down to psychological safety, because won't speak up for fear of getting shouted out or punished that's the best way to summarise it. We referenced Amy Edmondson and her 'Fearless Organisation' book, which is brilliant. It's a for raising issues, right? So it's critical that you have a really good read on psychological safety. It's a very interesting idea. I remember mentioning this to people in the past, and some people laughed at it, thinking psychologically safe environment where challenge is accepted. And it was funny. But it's not funny at all. It's very deep, and it's how you feel you can show up and work, you can say what you ideas are accepted. They're not going to shoot the messenger, think, and you're in an environment where you don't feel threatened. You can speak your mind and be honest. It's safe to right? And it's hard to do. You have to continuously iterate on have an idea. Sometimes there's meetings, like maybe a customer meeting or sales meeting or play going on. That's fair enough. But if you're within your team, you should be in a space where this, keep an eye and make sure that you are creating as safe as you can kick around ideas and ask any questions. an environment as possible. It's hard to set up properly, and it's easy to lose. You have got to be very mindful, especially as leaders, on how you approach this.

Dave Anderson:

Let's talk through a fairly safe example. We haven't talked about this, but when you're working with a bunch of developers, you'll decide to standardise on language, not for any old reason. For your dev, pipelines, deployments, testing and a lot of utilities, you base run language. And it's better to standardise one. At the moment a lot of us are standardising JavaScript, for example, because that works for a lot of the technology. But a developer may say they like to use.net and you say: 'Why?' And their response is ofter because they prefer it. And you have to politely say, it's probably better for some things, but we need to standardise on one to make everything more effective and we can't have 15 different languages. But then there's a point when a langauge like Rust comes along and someone says, Rust might be really good for this use case. You think, yeah, that's a good point. Maybe we should look at that. So you need to have the psychological safety to allow you to look at a different language, versus the fear of asking for .net andbeing shot down, and not being allowed to do anything else. A good example of psychological safety is when engineers can talk about other languages and you can explain why the organisation has made the decisions they have made.

Mark McCann:

Bringing an artefact into this like a well crafted ADR, architectural decision record on the language choice gives you something to challenge. You're not challenging Dave, you're challenging an ADR that says JavaScripts are the go forward language, but Rust has a new capability that might fit this use case? Can I challenge the ADR? That's an easier, safer conversation, then I'm going to

Dave Anderson:

And then the answer is always yes. Go for it. challenge Dave! Add some stuff to the ADR. If you've spotted something then it probably is better. But let's explain that so it doesn't turn into a free for all. That's clearly a very simplistic example and there's lots of more sinister examples that we won't get into. Let's move on to the Westrum stuff. This was first in the 'Accelerate' book by Nicole Forsgren. Dr. Ron Westrum is a psychologist. (I actually met him a couple years ago at a conference.) He's a lovely guy. He did the study on Westrum's organisational culture in the public and military sectors. So he's not a computer guy. He talked about how information flows around an organisation. An d based on how the information flows, he came up with three ways of organisation. Pathological, which is power orientated, there's low cooperation, information doesn't flow very well, in other words this is what we know and we're not telling. Bureaucratic, which is role orientated, we can tell you, but you have to go through that process, and everything in that process is very slow. And then Generative, which is performance orientated, sharing information tobuild context and capability. When he published this, the word generative was not familar. Now Generative AI is everywhere! I always find it interesting sitting with the leader, going through this table seeing where they think they are in an organisation. And I like the tenet 'create in the open'. If you're writing a doc, just open it up. The only stuff I keep locked down is something quite personal. By default, keep everything open.

Mark McCann:

It's a learning or generative organisation. So if you are in a learning organisation, you can adapt more easily to the changing landscapes. If you are psychologically safe and in a learning performance orientated organisational culture, you are better able to adapt to the wave of AI, for example. Because everyone's willing to try, share and cooperate and challenge each other with new emerging capabilities. So it's much harder for a pathological or bureaucratic organisation to adapt to this new wave of

Dave Anderson:

AI is a brilliant example. In the pathological org modernisation. they would figure out a way to generate API specs in their team, but they're not telling anyone because they want to go faster. Bureaucratic - there's only one team that are allowed to useAI togenerate API specs, because they're the API team. No one else can do it. Everyone else doing it themselves. Everyone should be peed off. And for performance orientated, we're all going to learn about this. We're going to put something on Slack. We're going to put out a video. Everyone will do a little bit, and you give back. We're seeing a lot of generative behaviour. There's a massive learning opportunity to figure out this new space. So let's all just share what we know. It's worth looking up Dr. Ron Westrum. The last piece of the chapter is a map and psychological safety, which we'll not go through in detail, but it's a nice illustration.

Mark McCann:

Trust, clarity of purpose, environment, execute, and opinions are heard. The map still stands up.

Dave Anderson:

It's funny because we did that map five years ago and it still makes sense. Some of these things don't really age that much. It's not like there was a lot of tech from the time baked in. The'pioneer, settler, town planner' language has changed, but the principles are the same. The main point to focus on is psychological safety in that chapter. So it's definitely a good read and extremely relevant today with all the AI stuff going on.

Mark McCann:

Challenge is healthy! Invite challenge!

Dave Anderson:

Capture your thinking in a document, graph or map, put it out there and ask people to comment on it. Feedback is a gift, as they say.