I think the other answers give you a good idea of some of the problems with this approach but I wanted to provide a different perspective.

We already do this.

**Game Theory**  
There is a branch of mathematics called <a href="http://en.wikipedia.org/wiki/Game_theory">Game Theory</a>.  In Game Theory, the goal is to figure out the best strategy/tactics to apply in a given circumstance.

> Game theory is the study of strategic decision making. Specifically,
> it is "the study of mathematical models of conflict and cooperation
> between intelligent rational decision-makers."[1] An alternative term
> suggested "as a more descriptive name for the discipline" is
> interactive decision theory.

A classic question in game theory is called the prisoner's dilema:

> Two members of a criminal gang are arrested and imprisoned. Each
> prisoner is in solitary confinement with no means of speaking to or
> exchanging messages with the other. The prosecutors do not have enough
> evidence to convict the pair on the principal charge. They hope to get
> both sentenced to a year in prison on a lesser charge. Simultaneously,
> the prosecutors offer each prisoner a bargain. Each prisoner is given
> the opportunity either to: betray the other by testifying that the
> other committed the crime, or to cooperate with the other by remaining
> silent. Here is the offer:
> 
>  - If A and B each betray the other, each of them serves 2 years in    prison
>  - If A betrays B but B remains silent, A will be set free and B will    serve 3 years in prison (and vice versa)
>  - If A and B both remain silent, both of them will only serve 1 year in    prison (on the lesser charge)

The problem is the best strategy depends heavily upon how you weight the different results.  Different strategies would be "best" depending upon that weighting.

It also depends upon independent rational decision makers making the best choice for their side (e.g. religious fanatics can't be depended upon to make the rational best choice for their side) and or some people weight goals and objectives differently than others.

**Military & Political Decisions**  
The <a href="http://www.rand.org/pubs/research_briefs/RB108/index1.html">US military and State Department use Game Theory</a> to identify probably scenarios and determine best strategies to deal with those scenarios.

When Russia invades the Ukraine, the State Department has already considered this possibility and worked through a series of responses figuring out most likely out-comes for each different approach.  When different situations happen they show the US President the different scenarios and results of each and this helps guide the President along a path of foreign policy (military and political) most likely to achieve his desired results.

Once again, we have not developed this ability to an analytic problem solving technique.  Rather they provide guidelines about different approaches and their probable conclusions.

It depends heavily upon the "other guy" weighting the different results the same as how you predicted those results.  He doesn't need to value them the same as you but if you guess wrong about his weighting, you results won't be valid.