Last year, I introduced a weekly series called "CEO Gaffe of the Week." Having come across more than a handful of questionable executive decisions when compiling my list of the worst CEOs of 2011, I thought it could be a learning experience for all of us if I pointed out apparent gaffes as they occur. Trusting your investments begins with trusting the leadership at the top -- and with leaders like these on your side, sometimes you don't need enemies!

This week, how could I not turn my attention to William (Bill) Cobb, CEO of tax preparation company H&R Block .

The dunce cap
There were plenty of reasons to give Bill Cobb a longevity gaffe award long before last week. Over the past decade or so, his company has allowed Intuit to completely steal the show when it comes to tax preparation software. According to comScore, TurboTax accounted for 59.8% of all DIY tax preparation last year with H&R Block's 14.7% market share even coming in behind Blucora's (formerly InfoSpace) TaxAct, which notched 17.7% of all DIY tax-prep market share. H&R Block lingered too long onto its bricks-and-mortar locations which still act as a drag on its operational performance.


However, even before TurboTax toppled H&R Block, H&R Block was making shoddy decisions with its mortgage loan portfolio. One of the primary reasons its share price lost about half its value between 2007 and 2009 had to do with the poor quality of its loan portfolio. In fact, without the added interest income of its mortgage loans, shareholders have seen revenue dip every year since 2008.

With tax season ramping up into high gear, this is the time of year where H&R Block is expected to strut its stuff through fancy TV advertisements and newly improved DIY tax prep software. Only it didn't quite work out that way. In fact, we got word from the Internal Revenue Service on Tuesday that H&R Block's DIY software had forgotten to fill out a critical portion of Form 8863 for education credits, specifically the American opportunity credit. H&R Block confirmed these allegations later in the day that its software did indeed have an issue.

The end result is that, after waiting two extra weeks to file their returns this year, about 660,000 people (or 10% of the people who'll claim an educational credit in a given year) are expected to have their tax refunds delayed by up to six additional weeks!

To the corner, Mr. Cobb
But wait - there's more!

In addition to screwing up on practically the only thing consumers count on you for -- properly designed tax preparation software -- H&R Block had just the previous day in a press release via newswire touted the value of its tax professionals as compared to TurboTax, which it has filed a suit against for unlawful use and misrepresentation of the H&R Block brand name in its advertising. The whole purpose of its suit (and the press release) is to continue to tout the value of its bricks-and-mortar professionals and play up the mistakes TurboTax users make. Ironic, given that H&R Block's software just delayed 660,000 filings by anywhere from another two to six weeks.

So let's review: Do I think H&R Block's DIY tax prep software is going to gain ground on TurboTax or TaxAct this year? Uhhhhh, no. Did H&R Block blow yet another opportunity to outshine TurboTax in a transitional tax year when taxpayers are looking for help more than ever? You bet. Will I ever miss a chance again to poke fun at H&R Block's errors? You bet I won't.

Do you have a CEO you'd like to nominate for this dubious honor? Shoot me an email and a one- or two-sentence description of why your choice deserves next week's nomination, and you just may see your suggestion in the spotlight.

With so many of the big finance firms getting bad press these days, it may be a "greedy when others are fearful" moment. Not surprisingly, some of Warren Buffett's biggest investments are in the space. In The Motley Fool's free report, The Stocks Only the Smartest Investors Are Buying, you can learn about a small, under-the-radar bank that's too tiny for Buffett's billions. Too bad, because it has better operating metrics than his favorites. Just click here to keep reading.

The article CEO Gaffe of the Week: H&R Block originally appeared on Fool.com.

Fool contributor Sean Williams has no material interest in any companies mentioned in this article. He is merciless when it comes to poking fun at dubious CEO antics. You can follow him on CAPS under the screen name TMFUltraLong, track every pick he makes under the screen name TrackUltraLong, and check him out on Twitter, where he goes by the handle @TMFUltraLong. The Motley Fool recommends and owns shares of Intuit. Try any of our Foolish newsletter services free for 30 days. We Fools may not all hold the same opinions, but we all believe that considering a diverse range of insights makes us better investors. The Motley Fool has a disclosure policy.

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