Came across this post at Idea Sandbox on developing bullet proof plans:
Measuring twice means making sure you’ve thought of all the things that could go wrong before you launch. It means making sure you’ve thought of all of your different audiences… not just the customer, but the salespeople as well. Do you have a “Plan B” in case the project or program does not go as planned? What if the project or program is much less or much more successful than anticipated… do you have a plan to deal with either situation?

I like to use a similar approach in project planning drawing on de Bono’s six thinking hats using the red, yellow and red hats to develop our initial plans – it feels right, we’ve cranked the numbers an it works and we’re all feeling generally positive. At this point, getting negative and critical as possible can be really difficult – but ‘enabling’ negative thinking through the black hat seems to work (along with help from people outside the planning team – and is also really valuable. By knocking the thinking to date and kick starting a process of rebuilding the concept and plans to address identified weaknesses generates better planning, greater team commitment and senior management buy-in in my experience. I’ve also found it an excellent process to support team learning.

Where the size and complexity of the project or programme of work justifies it, testing initial concepts and plans against a set of future scenarios to test risks and assumptions as well as support team and stakeholder understanding of the broader context of the project/ programme. I’ve only done a few scenario exercises with stakeholders but the impact on stakeholder engagement later in the project has been immense.

As the theory suggests, the process of testing and exploring possible (risky) aspects of projects and programmes enables far better responsiveness by the team and stakeholders once implementation is underway.