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).

Much of the writing on leadership (mine included!) concentrates on the positive stories and helpful hints, partly because it’s human nature to prefer the optimism. However, it’s also valuable to be aware of our blindspots and the traits we have that could potentially derail us in our leadership journeys. Career derailment typically occurs when an executive’s career is going well and should be progressing but it unintentionally fails. I’ve heard that roughly half of executives derail at least once in our careers (!) but given its nature, derailing isn’t widely publicised (unless high profile). 

It’s helpful for leaders to be sensitive to potential derailment of those around us too, especially in our own teams, so that we can offer support. There is some connection to burnout, although that is often caused by external factors wearing us down rather than inherent personality-based behavioural traits we have. The first step in dealing with our derailers is to recognise that we are fallible. And that imperfect human beings can still be amazing leaders. Acknowledging this frees us to learn to manage our derailers. 

Understanding derailers helps us better understand why talented leaders make poor decisions, overlook opportunities, alienate key people, and miss obvious trends, even when we genuinely want to do the right thing. Read more to see how our strengths and derailers are related, explore potential causes of stress, and unpack 11 behavioural traits that can cause leaders to fail. As you read, please reflect on yours, and their triggers, and do reach out to us if you’d like support in managing them on your own leadership journey.