Ryanair boss Michael O'Leary, perhaps misunderstanding the nature of a live Twitter Q&A, once infamously replied to a female questioner with: "Nice pic. Phwoaaarr!
Not that the outspoken chief executive was all that abashed by his faux pas.
And two years earlier, Kenneth Cole, boss of the eponymous clothing and accessories brand, tweeted this howler during the Egyptian revolution: "Millions are in uproar in #Cairo.
Rumor is they heard our new spring collection is now online..."
The twitterstorm that followed forced him to make a swift apology in which he admitted that his tweet had been "insensitive" and "absolutely
So perhaps it is no wonder only 10% of the chief executives running the world's 50 largest companies regularly tweet.
The risk of contracting foot-in-mouth disease seems just too high for many.
But Robert Glaesener, boss of Twitter analytics firm Talkwalker, believes the fact that most of them are aged 50-to-60 has more to do with it - they're simply too old to
understand social media fully, he says.
Even tweeting extrovert Sir Richard Branson, who has more than six million followers and epitomises the consumer-friendly, approachable boss, is prone to the occasional
His tweet on the day of the fatal Virgin Galactic crash last year began: "Space is hard - but worth it."
This was considered insensitive by some commentators and led others to question the legitimacy of his space tourism mission.
"There is a real danger that something that is well meant can end up creating cynicism on social media," warns Mr Glaesener. "While most of the responses to that tweet were
positive and supportive, there were also negative responses with people questioning his motives."
But leaving Twitter campaigns to your corporate PR team sometimes isn't any better.
When British Gas decided to hold a Twitter Q&A with customers on the same day it announced price rises of 9.2%, it led to a barrage of abuse hurled at the then customer
services director, Bert Pijls.
Top Twitter tips for bosses
Get training before using social media
Think hard before you tweet: what's said online stays said
Don't start tweeting then give up, but don't tweet for the sake of tweeting
Focus on a handful of issues, don't try to appeal to everyone
Be true to yourself and to your brand: authenticity rules
Train your employees how to use Twitter, too: they are brand ambassadors
Listen to your customers, but don't feel you have to respond to every tweet
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