Why You Should Tell Your Boss the Truth

Last Updated Apr 1, 2010 7:08 AM EDT

A recent study of CEOs revealed that the number one worry of the job -- besides fear of losing the corporate jet, of course -- is a growing sense of isolation. No surprise, really. If you were constantly surrounded by people whose paychecks you signed, who would you turn to for unvarnished feedback and data that hadn't been fluffed?

In olden times a king would be flanked by his courtiers, the usual obsequious parasites and leering, fork-tongued politicians. (I know that actually sounds pretty cool, but believe me, it gets tiresome after a while.) Only one individual was authorized to deliver what are now called "difficult messages," and that was the court Jester, or, as he was more affectionately known, Fool. Fool had a special template for delivering unflattering memos. They were encrypted, either through verse, ditty or humorous quip. So if the king had toilet paper (or the medieval, metaphorical equivalent) stuck to his royal footwear, Fool would telegraph that critical information to His Highness as he entertained him. No one else had impunity to address the throne with such frankness, including those of superior status. Anyone who dared to would have met the dungeon...or worse.

To a large degree management consultants have filled that role in contemporary business, assuming they are smart and colorful enough to get away with it. Somewhere in the past decade, though, consultants became as salesman-like as the rest of the boss's entourage. And a CEO who can no longer rely on outsiders for a dose of tough reality could easily misplace his compass and map.

Here's an opportunity for an energetic up-and-comer, maybe a younger person who doesn't have the universe to lose: Be the person your boss trusts. Earn that trust by saying the hard thing, the thing that nobody else has the insight or courage to say. Let your boss feel that she's received something more valuable than a token pledge of loyalty.

It's true, bosses can be fragile. And you can probably guess that the bigger the ego, the more delicacy is required. But tact doesn't mean avoidance of difficult messages. It means expressing your ideas in a caring diplomatic fashion. You'd want someone to tell you if you had ketchup on your tie, wouldn't you?

So consider letting the emperor know when he's not wearing any clothes. Gently and privately, of course. You may just find that a lowly member of the court is the obvious choice to be his most trusted advisor.

  • Mark Jaffe

    As President of Wyatt & Jaffe, Mark Jaffe has been called one of the 'World's 100 Most Influential Headhunters' by BusinessWeek magazine. His firm, Wyatt & Jaffe, works with a select list of financial services, high-tech and consumer companies worldwide and has been called one of the 50 leading retained search firms in North America.