Question 1: What is the most important distinction between a systems-oriented approach to analysis vs an event-oriented approach?
From what I understand, the two most important distinctions between a systems-oriented approach to analysis and an event-oriented approach is their differences in focus and linearity. However, these two concepts are very inter-related.
By focus what I mean is to what level outside factors are brought into understanding a problem. In other words, it is the difference between looking at a problem from a small vs a big-picture point of view - or even strategic vs tactical. The event-oriented approach tends to look at, as it's name suggests, isolated events and trends. In this approach we look at event "A" and ask ourselves, "how can we keep event 'A' from happening?" Well, from what we understand, if we implement policy "x" it should cause event "B" which should keep event "A" from happening. Clean, simple, easy. This approach is very short-term and very tactical in the sense that it is very narrow sighted; we see a problem and work to fix it without taking the time to understand how our decision might impact other factors related to the initial problem. The systems-oriented approach takes a step back from the problem and, instead of looking at a the individual events, it looks at the problem as it exists among a network of inter-related systems. This approach takes a big-picture, long-term, strategic look at the problem. Instead of looking at event "A" and asking what was its cause and how can we keep it from happening, the systems-oriented approach to analysis looks at the environment in which event "A" exists in the form of cycles or "systems." From here you can ask, "is event 'A' really something we want to stop?", "if we implement policy 'x', how will that impact the rest of the system/other related systems?", "how can we stop event 'A' while minimizing negative consequences that are produced by the other systems?"
The second distinction that I felt was most important was the difference in linearity especially in relation to polarity. The event-oriented approach to analysis looks at any one event as a product of a series of events whereas the systems-oriented approach to analysis looks at an event as a product of a system(s) of causal factors. Instead of looking at an event as a product of a series of events, the systems-oriented approach links together existing non-polar causal factors that help to form the causal forces (loops/systems) present in the situation in which the problem exists. From there, an analyst can assign a polarity to the causal factors to play out how the problem came to be. The ability to look at the situation without polarity is important because it allows an analyst to see in what other directions the system can go and how that could impact the other systems.
Question 2: What do you think will be the greatest challenge to practicing systems thinking as an intelligence analyst?
I see a couple different challenges in practicing systems thinking as an intelligence analyst. The first and I feel, the most obvious, is the challenge of time. Systems-thinking requires a fuller, deeper, and overall better understanding of not just the problem but the environment in which the problem exists. This level of understanding is going to take time, at least more time that getting a more brief understanding of the problem. While this level of understanding may produce a more useful product, if that product is not able to be produced within the time-frame in which it is usable then it is useless.
The second challenge is simplicity. Being able to tell someone that policy "x" will produce event "B" thereby stopping event "A" is much simpler than trying to describe a system of causal forces. If your product is over-complicated and therefore incomprehensible to the consumer, it is once again, useless.
The third challenge deals with coverage. When looking at a situation how do you decide what systems/causal forces you include and which one are more or less irrelevant. A great characteristic of the systems-thinking approach to analysis is that it is expandable and can be refocused to get a more or less broad view of the situation. However, the question then becomes how can you judge when you've zoomed in too much or zoomed out too far.