Who is at the top of any organisation? Assuming that you have moved beyond the one-man-band or founder-run organisation, then the answer is the people who have proved themselves most successful in the past. The historical paradigm is that you join a company, build a track record and move on up. The thing is this tends to assume that what has gone before is the best, and possibly only, indication of what is to come.
Let me illustrate, think back to the first World War, the men in charge of the conflict in 1914, such as general Haig, were born in the Victorian age, round 1860, they were weaned on tales of glory and cavalry charges, such as the charge of the Light Brigade in 1854. As boys these were the games they would have played. They had no conception that war could be so radically changed by things like the airplane, gas and the machine gun. They were referred to afterwards as donkeys leading lions.
"Rules are mostly made to be broken and are too often for the lazy to hide behind" Douglas MacArthur
I would suggest this is a far easier trap to fall into than you might think. Last month I was writing an article quoting from David Maister, here is the quote again "As evolutionary biologists have taught us, the more adapted (ie. Comfortable) you are in your current environment, the less likely it is that you'll be adaptive to environmental changes." In other words, it is yesterdays winners who control the rules by which we will play tomorrow's game. If you consider the global scale of the present economic challenges, such as:-
Do we really feel that tomorrow's game will be the same as yesterdays or has someone just invented the next 'machine gun'?
Rules are for the obedience of fools and the guidance of wise men." Douglas Bader
You need people in your organisation, or if not within it, then working with you, who can challenge your thinking and ask those dumb questions. Can you honestly think that any normal person would think it was ok to give mortgages of 120% and 5 times salary? Where might Lehman Bros, Halifax or Northern Rock be today if someone had just spoken up and said "That seems like a daft idea to me!"
You need to ask questions like "What is the best way to do it?" rather than "How can we do it?" Perhaps rather than asking how to win this game, you should be considering how to change the game so that you can win it….
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If you have always done it that way, it is probably wrong. - Charles Kettering