To understand how, let's model stock-based compensation in two possible worlds: A CEO whose stock has followed the S&P more or less exactly and a CEO whose stock has remained steady over the same period. Assume both took the reins on January 1, 2007 and are still there. (If you want to follow along in Excel,
here's a spreadsheet.)
The first CEO, let's call him Thrill-a-Minute Tom, has had a wild ride. Using the S&P500 as a proxy, and setting the January 1, 2007 stock price at $100/share, Tom's share price at the beginning of each year is as follows: 2008 — $102; 2009 - $66; 2010 — $ 80; and 2011 — $90. Using the same indexing approach, the current stock price would be $94. So after a precipitous drop, Tom has led his company back to within 6% of the 2007 starting point. Most public company CEOs could tell a similar tale.
The second CEO, who we'll call Steady Eddie, was able to buck the market trend. He managed carefully and proactively and managed to keep the stock flat at $100/share from 2007 through to the present.
Who is the more valuable CEO? Whose compensation should be higher? Should it be Thrill-a-Minute Tom, who saw massive volatility and a net loss of 6% over the period? Or should it be Steady Eddie, who avoided ups and down, protected investors' capital and ended up 6% higher than Tom? Based on our current models of stock-based compensation, it's clear who will come out ahead. Tom leaves Eddie in the dust.
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As far as CEO compensation goes, under the current stock-based compensation model, it is unambiguously better to have your stock plummet and then partly recover than to have the stock stay steady over the same period. Though they wouldn't want to admit it, the crash of 2008 wasn't all that bad for the vast majority of big-company CEOs. With the exception of those few CEOs who were sacked, most had terrific air cover: "Our stock may be down 50% but so is everybody else. Really, I'm doing well, all things considered."
Even better, CEOs got tranches of options and/or grants at super-low prices — in some cases lots of them to keep the CEO in question from being depressed that his/her existing options were 'so far underwater'. As the market dragged their stock prices up with everyone else's, these CEOs made out like, well, bandits.