Reflections on Pioneers, Settlers & Town Planners

Did you, like me, play simulation computer games (think SimCity, Command & Conquer or Farmville) as a kid – or adult? If so, please think of them while reading this longform article, which explores three different groups of people, business evolution, and some reflections based on my career experiences so far. In fact, one of the reasons behind the appeal of the concept is the imagery it conjures in our minds! 

Years ago, a colleague of mine with an IT background told me about a model he’d heard of which described the different skills needed for successful IT projects: pioneers, settlers, and town planners (PST). People have preferences for which of the characters they’re most comfortable acting as, and there can be clashes between the types too. Simon Wardley, who coined the PST concept, noticed that “some people were more adept at one end of the spectrum than the other”. He also highlights that the idea is a “derivative” from IT journalist Robert Cringley’s 1993 book “Accidental Empires” which discussed commandos, infantry and police.

​I suspect there is a correlation with the personality dimensions of openness and conscientiousness, but I’m getting ahead of myself here. A healthy (but not necessarily equal) balance of the three groups is necessary in organisations, depending on their purpose and stage of evolution. Read more to unpack the three groups, reflect on which you (and your colleagues) are most like, consider how ideas, products and organisations evolve, and see my thoughts on the concept in different contexts (including industries and professions).

Before I unpack the details of each of the three groups, a word of caution please: all three groups are brilliant in their own ways, and a mixture is needed for long-term success of an organisation. You will naturally feel an affinity to one or more of the groups, perhaps – like many – wishing you were a pioneer because it sounds cool. Who wouldn’t want to label themselves as an innovator? However, each group innovates, but in very different ways:

• Pioneers invent, conceiving of a new idea, activity or process
• Settlers commercialise, arranging things economically to use the invention in practice 
• Town Planners scale and industrialise, spurring further adoption of the utility/service

The three groups feed off each other, each using the previous group’s efforts as inputs for their brilliance (including pioneers recombining industrialised elements to hack together their prototypes).

‘Pioneers’ / ‘Commandos’
These people love the thrill of parachuting into a new-to-them situation. The fun is in exploration of never before discovered concepts. They thrive on chaos, uncertainty and the adventure of taking risks – to them that’s exciting! High on openness to new experiences and flexibility/adaptability, they view situations as learning opportunities, experimenting rapidly to discover new possibilities or novel combinations. Their agile & DIY approach is built on whatever components they can get their hands on, even if their creation only just works. They’re disorganised (because they hate bureaucracy, and structure slows them down) and unpredictable. Their inventions can be amazing, but they also fail a lot. Much of the time what they’ve built doesn’t work properly, with bugs and major failings unimportant to them, or requires major redesign. Speed is what they live for: arrive, explore, setup something, get bored, move on to something different. Their discoveries and inventions are fuel for the settlers / infantry. 

In start-up terminology, they disrupt by crafting prototypes and figuring out product-market fit (or getting bored first and moving onto something else to avoid the drudgery!). Happy with failure, gut feel, assembling the plane mid-air, experimenting and exploring, they want feedback loops to be a fast as possible in order to maximise their learning and try something else. They love undefined and constantly shifting environments, where new opportunities can arise at any second. But, their flakiness and disdain for structure and stability can rub others up the wrong way. 

‘Settlers’ / ‘Infantry’
The second group excel at spotting new opportunities (such as those invented by pioneers), nurturing them, and getting them to scale. Their brilliance comes from recognising the brilliance of the pioneers’ prototypes and making them functional i.e. they draw the map in order to take advantage of the emerging opportunities. To extend the historical analogy, the settlers were the homesteaders, cattle barons and gold miners who turned the natural resources discovered by the pioneers into money, and later opened saloons and stores to support the early pioneers. These days, settlers are the ones who create the tools, processes, design patterns and training material. In a software project, they test the code thoroughly, improve it where needed, write documentation and define business rules – all essential activities despised by pioneers. 

Settlers turn the prototype into a manufacturable and marketable product, useful for a larger audience of mainstream users, building trust and understanding. With lean methods in their toolbox, they also refine the concept (listening to customers), making the potential future actually happen. In other words they commercialise the concept. 

They enjoy spotting trends, making improvements, analysing and growing markets, listening and gathering mainstream feedback, and increasing education. Their work helps the product to achieve profitability, and mature. Their successfully structured solutions are then taken by the third group who industrialise and commoditise them. 

‘Town Planners’ / ‘Police’ 
This group’s superpower is industrialising the products crafted by settlers. They bring rigour, (infra)structure and governance that supports the ecosystem, enabling predictability, scale and efficiency. They can turn a fast-growing organisation into an efficient and well-oiled machine that’s optimised to do what it does extremely well. 

They have a strong focus on operations, and minimising risk. Stability is key to them, and planned, waterfall and/or six sigma approaches are their preference. They’re also happy to outsource in order to reduce costs. It’s best to apply these skills at optimising long-term performance once the settlers have shown a large and ongoing market, else the town planners might just build a ghost town! In other words, it must be big before economies of scale can be taken advantage of. 

They find ways to make things faster, better, more efficient and more economical, in a way that can be fully trusted. They are driven to maintain order, not disrupt it (and the flighty pioneers have likely been long forgotten). Monitoring and metrics are essential to ensure things operate as they should. Data warehousing infrastructure, established data models and watertight internal processes are examples overseen by this group. 

While pioneers would see this work as dreadfully dull, it is crucial in order for the product/service to achieve economies of scale and become universally accepted. Town planners deal with high volume, making it standardised and reliable. They’re conscientious, love operational efficiency, modelling & analytics, and they build what is required for stability. Shifting business requirements, and how new technologies would interoperate efficiently with the existing infrastructure/estate worry them. 

Knowing yourself & your team
You can probably think of people you know who roughly fit into each of the groups, and you may have observed firsthand some of the tensions that arise between pioneers and town planners. While each group has a different mindset (and priorities), all three are needed for a business (or project) to be successful in the long run. But, not all together working on the same thing. Instead, each at their time. For example, when attempting to industrialise, a commando can actively harm the project in an attempt to make it more exciting for themselves. Similarly, without settlers to take over from pioneers, your project will stall. 

After all, leadership is about achieving effective change through allocating the right people at the right times. And, teams can be multi-disciplinary, with various technical skills working together. There is a popular structure in scaling organisations of self-sufficient teams, made up of people with different functional aptitudes, who own the end-to-end delivery of a project.

Simon Wardley highlights the preferences of different IT professionals like this: “Take a pioneer software engineer used to a world of experimentation and agile development and send them on a three week ITIL* course. See how happy they come back. Try the same with a town planner and send them on a three week course of hack days & experimentation with completely uncertain areas and lots of failure.” Certainly not good for their mental health! 
*ITIL refers to Information Technology Infrastructure Library, a set of detailed practices for IT activities such as IT service management (ITSM) and IT asset management (ITAM) that focuses on aligning IT services with the needs of business. 

Evolution
Simon used the PST framework to explain how inventions evolve from genesis to custom-built to product to commodity (+utility), with different teams forming and ‘stealing’ the work of earlier teams over the cycle. Settlers steal from the pioneers in the organisation and outside ecosystems and productise the work, which forces the pioneers to move on to something else. Equally, he says, the town planners steal from the settlers and industrialise it, forcing the settlers to move on. 

Older/established organisations can be too set in their ways or boxed in by policy, and at risk of irrelevance, when the environment starts to change. They need some pioneers to take advantage of new opportunities. And, once the pioneers have discovered something interesting, settlers can turn it into a new revenue stream, keeping the system flexible. 

Neil Perkin, a digital consultant, highlights the nurturing role settlers can play: “Too often early stage concepts emerge from a lab situation into a business-as-usual environment and are immediately shackled with expectation, targets, forecasts, departmental silos, strangling the idea before it’s had a chance to find its place.” 

Different industries & professions
In the final part of this article, I reflect on the PST model based on my experiences, touching on a few industries in my thoughts. Please do add your own reflections in the comments – I’d love to hear them! 

Firstly, I’ve experienced both waterfall and agile methodologies during my career, with agile becoming more popular over time. Waterfall works best in large, established organisations, full of town planners seeking to minimise risk and disturbance. But, it is too restrictive (and takes too long) in smaller organisations who need to quickly follow an iterative strategy to see what works. As Simon Wardley says, “engineering in the uncharted space is agile but in the industrialised space it is more six sigma”.

I’ve also gained extensive product experience over my career so far, from different perspectives and in different markets internationally. In fact, I started out my product journey in the B2B space, where, after building things properly that didn’t catch the attention of customers, we shifted to a customisation strategy instead i.e. building things for specific use cases to understand demand better. And, if those worked, we put in place more structure to support and industrialise them. For example, applying some of our development across into the B2C/retail market where efficient operations and systems were crucial.

Another lesson from the B2B world is the importance of finding settlers at your client who see the opportunities in the concepts you are proposing. Town planners will not buy a mere proposal – they want it to be tried and thoroughly tested, with minimal (ideally zero) risk, before they’ll consider disturbing their estate to incorporate it. 

Interestingly, the PST approach can also be helpful in thinking about how a startup scales. Blitzscaling (by Hoffman & Yeo) describes 5 size-related stages: family, tribe, village, city and nation. The original pioneers may have a hard time as the organisation grows and the excitement wanes, preferring instead to start something else i.e. be serial entrepreneurs. Also, town planners would go crazy at family stage, although are immensely valuable as the organisation scales – their structure and process actually enable the scale. One example of this is the expansion of operations roles over recent years – aimed at helping different functions scale e.g. DevOps, BizOps, ProductOps, PeopleOps...

Given the origin of PST (as well as Robert Cringley’s background), it’s natural that many of the examples and explanations are from the information technology world. However, the model applies to other industries too, including financial services, data science, and more… 

Some industries are protected to an extent from the parachuting in of slapdash pioneers making grand promises. Regulation (aimed at protecting customers by ensuring things are done rigorously) can provide a significant moat, making it more challenging for commandos to attack – a major factor behind why tech entrepreneurs began making headway in Fintech and Insurtech later than other industries like transport and accommodation. 

One last thread of thoughts, focused on professions. Ideally, professions should have a mix of people across the three groups, although in practice they’re likely to be heavy on one of the types. For example, risk management and compliance professionals are probably town planners. Similarly, many actuaries are likely to be town planners, although consulting actuaries and product actuaries may be settlers (very generally speaking). And, perhaps those in the widest of the “wider fields” are pioneers, searching for new and interesting opportunities? Related to this: newer careers may attract more pioneers at the start (because they’re higher risk), but then settlers and later town planners as they become more established. Think of data science as an example here. 

Perhaps pioneers need to be generalists in order to adapt and adjust quickly, and the degree of specialisation increases for settlers and is highest for town planners? What do you think?

Footnote:
Given the PST model is useful in considering business or project evolution, it shares some similarities with Geoffrey Moore’s ‘Crossing the Chasm’ concepts (and Everett Rogers’ theory on the ‘Diffusion of Innovations’ those insights are built on). You’ll have heard of Everett Rogers’ categories: innovators, early adopters, the early majority, the late majority, and laggards. However, Simon Wardley argues that diffusion and evolution are different.