Strategic challenges are important in Tech. We talk about Challenge in our book: The Value Flywheel Effect.
In a previous episode we covered the Value Flywheel in general. And the four phases: Clarity of Purpose, Challenge, Next Best Action, and Long Term Value. We are deep diving into each one of the phases.
Today, we’re going to deep dive into Challenge, which is phase two. Strategic Challenges need an open environment. When you decide on a strategy, do you have the right environment to challenge it? We’ve found this to be hugely important. Do you want to share anything on what the Challenge phase is about?
Creating a safe environment for Strategic Challenges
Mike O’Reilly
In the last episode, we talked about Clarity of Purpose and setting direction. Part of bringing people along with you, is creating an environment where they can question purpose and challenge direction. But also, it’s doing it in a safe and constructive fashion.
What techniques can we leverage in order to challenge. And what sort of environment allows challenge to occur? How can teams participate?
It’s worth thinking about the socio technical aspect of the organisation. To allow for different types of teams and needs. Who process information in different ways. It’s about how we talk to each other. And how the organisation collaborates and communicates? It’s a meaty topic to unpack when you sit and think about it.
Mark McCann
Don’t have your architecture leaders setting the direction and imposing it. You need to do it together. And you need to do things in a collaborative and facilitated to invite challenge. Techniques we use, like Wardley Mapping, Event Storming and Threat Modelling are done as a team and collaboratively.
People have an opportunity to challenge the process and artefacts. They’re not challenging the individuals. That’s very important. Use techniques, processes and practices that are open and invite challenge. It’s not a case of presenting a PowerPoint deck and files. And this is what we’re going do. So make it so!
Challenge helps to set up an effective feedback loop
I want to invite challenge. Because you need to have a good feedback loop. To understand if it can be better. Or if this could be improved. In high performance organisations in the cloud, things move very fast. You can’t know at all.
Mike O’Reilly
My challenge to the audience is to ask have you ever fully understood anything by listening to a PowerPoint? If you want to understand something, you have to dig into it. You have to ask questions And make sure you understand.
Dave Anderson
That’s why challenge is so important. My computer science teacher told me:
‘Show me the person who knows it all, and I’ll show you the fool’.
I think the concept of challenge is misunderstood. Challenge is a good thing in the right environment. You need to take that feedback on board. But in a bad environment challenge is dangerous and damaging.

Strategic Challenge is about engineers
This area is about engineers. Our greatest engineers know the nuts and bolts and the nooks and crannies of the system. If you silence their voice, you’re going to lose a huge amount of value. If you create a good environment, your engineers can point out where things won’t work. Or bring new ideas to the table. You get richer system. So design your organisation and your tech around the ability to challenge. It’s absolutely critical.
Mark McCann
Set up the team as the fundamental unit of delivery. And make sure the org is flipped on its head. To enable teams to deliver value to customers that is aligned to the clarity of purpose.
The architects and senior leadership teams are there to enable and empower teams to deliver the best outcomes they can. It’s about flipping the hierarchy. The team is at the top of the pyramid. And from a hierarchical point of view, we’re there to enable and support. That’s the type of environment you need to set up for success.
The team does the most. You need to give the people who have the context, every ability to make decisions. And have rapid feedback loops to validate their decisions to see if they are good or bad. So getting the right environment is critical for success.
Dave Anderson
We talk about why is Challenge important. If hire smart engineers, your best technical strategy is to get out of their way. Make sure they know what the goal is, and get out of their way. You have got to put in the right support systems to make sure people can work effectively.
Traditional Leadership struggle with Strategic Challenges
In traditional leadership, there can be a struggle. The team is carving out their own way and traditional leaders don’t like that. But if you hire smart people, you need to let them do the work.
Mark McCann
You need enabling constraints as well. To guide engineers along the path. You need to enable teams to grow really fast, but you want to do it in a secure andwell architected way. So that you’re not going fast and creating lots of technical debt. Part of an environment for success is making sure guardrails are in place to enable engineers go fast responsibly.
Mike O’Reilly
The organisation and team needs to understand what type of they are. And how teams communicate and operate within the organisation was.
Mapping enables Challenge
A big part of this is understanding where we are on the journey. In the Value Flywheel Effect book, we talk about mapping within certain contexts. You maybe an organisation that’s trying to get up and running. You’re trying to define your team topologies. And setting up your system and environment for challenge. But, in order to get there, we need to move from A to B to C. This is where you need to get into mapping.
Challenge is also a good way to gather feedback. And it’s a good place for empathy to exist. Your leadership may be saying we’re going here. And the teams may be saying we need to do this.
With Challenge, leadership can acknowledged and explain why we’re doing these sorts of things. We’ve done that with Wardley Maps in the past. You map your stack, your platform, your area and your business. Challenge can help you work out your position. And the big things that we need to move in order to set up the org to operating in the right way.
Identify your capability gap
Mark McCann
By mapping your org capability and environment you can see if you have the capabilities to set you up for success. And if you have expertise for secure development, Wardley Mapping or Serverless, for example. If you don’t then what are you going to do to get them in place for your teams?
Because you don’t want to say that you are going serverless. And then not give teams any support or enablement to actually get there. You need to map out your org capability to see where you should be investing. And where you need components to enable the teams to go fast.
Mike O’Reilly
If your leadership wants DORA scores at elite. But you’re on a monolithic stack and running your own infrastructure, you can put a Wardley map together to show that a lot of the system is custom build.
That raises the operational concern of what are we doing to fix that! It’s a good Challenge point. We need to invest in our move to serverless. Or reduce our operational burden so that we can do more delivery. And do better at our DORA scores. It’s also a useful communication and collaboration tool to have conversations and challenge in a constructive fashion.
Pathway to production
Mark McCann
The last thing is pathway to production. By making sure you have a rapid feedback loop into the hands of real users you’re part of an environment for success. And the pathway from idea to production is as optimal as possible. Because you are removing impediments to the flow of value to end users. You have a well oiled pathway to production. So you’re not waiting months and sometimes years for feedback on the things that your teams are working on.
Dave Anderson
We have talked about what Challenge is and why you need it.
What happens if you skip over or ignore Challenge?
What happens if you don’t have a good environment for challenge. And what happens if you just skip over this and ignore it?
Mark McCann
You’ll start to see people disengage. They’ll feel that they are not listened to. And they will leave eventually. Especially if they’re talented engineers. If they don’t have an avenue to challenge, contribute or give their opinion, then that lack of engagement will drive them away. Also you’re not getting the best out of your teams.
You’re not going to be able to meet your Clarity of Purpose. Or your goals because the teams are following a plan that was decided in advance. So there is no push back on that.
Mike O’Reilly
You will see frustration and people will not feel part of the process.
Architects at the intersection of People and Technology
Mark McCann
Team interaction modes will be suboptimal. Lots of teams will do the same things. There will be repeat work because there’s no way to challenge. Or ask: ‘Hey, I should be doing this or you should be doing that!’. And so if your socio technical topologies are not set up properly, you’ll see teams competing with each other. Instead of enabling and empowering each other.
Dave Anderson
Sociotechnical is a good point. It’s a mouthful! But the intersection of people and technology is critical.
There are two systems. The system of all the employees in the company. And then the system or the technology we’re working on. You have to bring those two together and look at them through the same lens. And that’s something that I think architects have to do. Because it’s hard for any other leaders to do it. They will see one half not the other. You need to see both to make them work together. That’s going to be a massive area going forward.
One original writing talks about DP1 and DP2 systems. Purpose based and function based. And function based is everyone doing their own job function. They rarely work well together. The chapter on Challenge in The Value Flywheel Book is probably the deepest chapter.
But that’s the craic! If you want to see more and have a look at the blog: TheServerlessEdge.com. Follow us on Twitter @ServerlessEdge. And check out the Serverless Craic YouTube channel. Thanks very much.
Transcribed by https://otter.ai
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