29/07/2014 07:26 BST | Updated 27/09/2014 06:59 BST

The Curse of the Deputy

It was always Gordon Brown's problem. It's turned out to be Philip Clarke's as well over at Tesco. And, despite his recent runs for England, it may well be Alastair Cook's too.

But why are deputies so often such failures? Why, when they have spent years planning their accession and have been positively groomed to take over, do they invariably make such a hash of the top job?

All of the above individuals were destined to suffer similar fates because their predecessors cast such all-enveloping shadows long after they departed. Brown's earnestness was never a match for Blair's flair, Clarke could never escape the fact that it was Sir Terry Leahy who turned Tesco into such a formidable business, and Cook was deemed the 'safe' choice to build on Andy Flower and Andrew Strauss's dominant England cricket team.

More importantly, all three felt it was their turn - and their colleagues, disastrously, agreed. It was as if they were engaged in a self-fulfilling prophesy, little anticipating that the very best deputies rarely make accomplished leaders of the same teams they inherit.

I have no doubt Cook would be a wonderful captain of Essex, Clarke would probably excel at running a company like Poundland, for instance, and Brown could be an inspirational leader on a multi-national think tank.

But earmarking an internal candidate to inherit the top job is often a doomed enterprise. For deputies are appointed because they have two key qualities - they are do-ers or they are nodders, and the best deputies are both. They have an enviable ability at simply getting the job done, following orders to the letter, allowing the boss to delegate and not worry. And they are skilled sycophants - unthreatening ego-massagers whose lust to succeed is well-recognised by the boss who thus demands total obedience in return for subsequent patronage.

The irony, of course, is that those who determine not to play by the rules should be the real candidates for promotion. The ones who aren't afraid to do things differently, to shake things up even if it means tinkering with their gilded inheritance. The ones who are brave enough to appoint deputies that are willing, like them, to answer back and question the modus operandi.

I have won and lost jobs on the back of my (occasional) inability to be an obsequious yes-man. I won a job in a powerful publishing empire because I dared to speak my mind in a room of conformity, at precisely the moment the boss was changing his. The next day, my honesty was rewarded with a full-time contract.

And then I lost a job because I spoke my mind. Obviously I always did what was asked of me but, again in a room of conformity (though this time one in which the boss visibly reddened and shifted uncomfortably if there was debate) I spoke my mind if I felt my opinions would contribute to better decisions.

The arenas of politics, business and sport are littered with the corpses of new bosses who mistook demanding slavish agreement for good leadership. They fear opposition so surround themselves with unthreatening yes-men and women. Cook is a prime example - he jettisoned his most gifted player, Kevin Pietersen, because of his maverick outspokenness. If only Cook had made him vice-captain he'd now be hailed as a visionary leader.

More than 2,500 years ago, the same scenario was played out in the marbled halls of Greece, a fact memorably noted on by Socrates who warned its leaders: 'Think not those faithful who praise thy words and actions, but those who kindly reprove thy thoughts.'

Part of the reason we got into such a financial mess was due to individuals in banks not standing up and saying 'this is wrong'. Creative industries are stymied by ingratiating wannabes who never rock the boat. Our sports teams are trounced because governance is predicated on the need for people to fall into line - mavericks not allowed.

The higher we are promoted, the more likely we are to be ingratiated, the more our egos require servility. It is at this precise moment then, that leaders - especially new ones - should seek counsel from people who don't use flattery to further their careers.

That way, the mistakes they make will not stem from the cursed fear that accession engenders in deputies, but from the desire to be their own leaders.