I have, for many years, been involved with business projects. Some small, some huge, some amazingly smooth, ands others, well, less so!
One of the things I’ve found interesting is how poorly thought through their views of risks are, and for many of those those that had a bumpy ride, the yawning void between the risks identified in the plan and what transpired. Very few considered risks that could double the cost and timescale, or indeed cause the work to be abandoned.
What do I suggest – Adopt a black mood, and push it. Walk to the edge of the abyss and stare down, contemplating how deep and jagged it is, and how bad the consequences of falling in would be. Immerse yourself in how the project might go horribly wrong. Imagine how you would feel as people point out what you missed or didn’t want to see. This sounds pretty negative, and I have at points been accused of looking for ways that things can fail … correctly, as it happens. But that absolutely, completely misses the point.
The intent is not negative. It is only by really understanding the consequences and likelihood of various failures that you can determine where to put your defences, and how solid you need to make them. But, psychology is typically against us here. Many risk reduction efforts are stymed by innate biases in how we think that tends to make us anchor our views on what we think will happen. We tend to think of small variations, and risks only occurring one at a time. We tend to be optomistic. We tend to miss the huge stuff. So, by wargaming how bad it could get, by starting by assuming real disaster then working out how it could occur, by looking into the abyss, it is possible to get past the bias. That is what allows you to aim high and have a decent chance of hitting it. Or you could just hope to get lucky, or get away with explaining why the failure wasn’t your fault.
Greg Pyes blog 
I couldn’t agree more Greg. Sometimes we seem so conditioned to be positive and upbeat that we collectively fail to adequately think through the real risks to projects and situations. It isn’t negative to brainstorm what can go wrong and what we could sensibly and cost effectively do to prevent the worst or near worst happening.
The problem is most of us only look backwards – to things that have happened or nearly happened previously. Whilst this is useful the reality is that the next issue/problem/glitch that throws us off track will not be a replica of the last. We need to think wider and, metaphorically, look forward not backwards.
The future is not a replica of the past and if we are looking for the next banana skin, as opposed to looking backward at the last skin we either slipped on or narrowly avoided, we will be a lot better off at preventing unpleasant surprises. That is difficult to do. It is easier to deal with the known and the familiar.
I also do not underestimate the natural human tendency towards what I call “herd certainty”. We need to be prepared to challenge the established view when considering risk because as someone I can’t remember said “men go mad in herds but only recover slowly and one by one”.