When's the Best Time to Fail?

Early. Cut your losses. Learn from your experiences. The sooner you get rid of bad strategies, the better your chances of finding good ones -- if only by the process of elimination. Getting used to the idea of failure can itself be a strategic advantage. The idea is not to pursue failure as a goal, but simply to realize that, statistically speaking, most strategies are bad -- or at least no better than average -- which is the same thing as failing when it comes to strategy. The point, after all, is to achieve strategic advantage -- so just being like everyone else is by definition really a failure.

In high tech "popular strategy" is an oxymoron.

This is one of the big lessons you learn reading a 2003 "classic" McKinsey article, "Hidden Flaws in Strategy," (registration required) by one of the firm's London directors, Charles Roxburgh. Mr. Roxburgh identifies seven flaws in the way people think about strategy -- and several, like "group think," "sunk cost effect," and "over confidence" all convey this general theme. And I think it's particularly relevant to high tech strategists since they are basically in the business of tryng out new things.

(Also see my May 2006 blog post about a related McKinsey article.)

Another insight: great high tech strategies are also by definition unique. Otherwise everyone would have already thought of them -- again, no advantage. So it's not just failure you have to get used to, it's also the fact that most people will view an effective strategy as unconventional -- and will probably resist it. People tend to buy the same strategy everyone else does, even though in high tech "popular strategy" is an oxymoron.

That strikes me as the core of the strategy communications challenge: to convince stakeholders why killing off most strategies early is a good idea and that an unpopular strategy might be worth a try.