How to tell if your boss is good or great


In 2007, a year before the Italy-born vintner Robert Mondavi died, scores of his former employees queued up for a long time after dinner with him just to say hello to the 94-year-old man who had given California's Napa Valley wines credence internationally.

Earlier, in 2005, Mr Mondavi's family had been kicked off the board of the wine company he founded, and the business was soon sold off. Still, almost all of his former employees retained a "profound respect" for him, recalls management don Sydney Finkelstein, who teaches at Dartmouth College's Tuck School of Business and is also director of its Centre for Leadership. Professor Finkelstein, who was at that 2007 dinner, mused in his book Superbosses: "When I am in a wheelchair, will everyone line up to greet me?"

Such reverence, Prof Finkelstein found from some 200 interviews with leaders over 10 years, is reserved for three types of exceptional leaders, whom he calls "superbosses".

The first is what he refers to as iconoclasts such as the late jazz musician Miles Davis, who was always itching to change the status quo, and approached everything new, with a "beginner's mind" of openness and curiosity.


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The second type, he says, is the "glorious bastard", who is overbearing, perhaps even a bully, discompassionate, selfish and focused entirely on winning first and mentoring later. Oracle Corporation co-founder Larry Ellison is named as one such superboss.

Then, there is the glorious bastard's antithesis, the "nurturer", like fashion legend Ralph Lauren and cosmetics queen Mary Kay Ash.


1  The difference between a good boss and an extraordinary one is that the former behaves like he works for someone else, whereas the latter behaves like he owns the organisation he commands.

2 You have a superboss if he has a clear vision of how to make a difference to others; is always thinking up new ways to do things; is always fearless in trying to convert dreams into reality; is very competitive; and likes to coach colleagues regularly and informally. The superboss is also invested in the well-being of all who work with him.

3 Such a superboss will continue to be successful only if he is also true to his beliefs, ideas and values.

4 Learn to read your boss because if he turns out to be a superboss, much of his know-how and wisdom will be yours for the taking.

5 Superbosses want people who are like them, that is, highly intelligent, endlessly creative and extremely flexible. Someone with these attributes would, for instance, have something refreshing to say on issues that matter; solve problems such that superbosses learn something new from that; and be ready to switch from, say, writing about food to covering politics.

6 Superbosses are not fazed by churn or constant employee turnover, if that is the price to pay for demanding strong performances and hard-to-fulfil standards of those working for them.

7 Such leaders are so secure in themselves that they may tweak the way their organisation works to accommodate the quirks of top talent.

8 The surest way to keep top talent is to convince them that what they do counts and that they have their boss' attention in their endeavours.

A version of this article appeared in the print edition of The Sunday Times on April 30, 2017, with the headline 'How to tell if your boss is good or great'. Print Edition | Subscribe