What Makes a Winning Personality?

Apr 13, 2022

It’s likely that many of you reading this blog are in the process of transitioning away from the workplace. Some of you may have already made the move into retirement, but are still anxious to continue in a consulting role or similar. Whatever your work status, just remember that if needed later on, you can always rely on the knowledge and experience that made you a success.

Those qualities, along with good character assets, don’t wither and die as we age. On the contrary, they can still come in handy in a wide range of social and semi-professional situations in which you may find yourself after leaving work.

The bottom line is, retirement isn’t the end of the road anymore. And having a ‘winning personality’ will enhance whatever endeavours you may wish to pursue.

A What? Yes, a Winning Personality!

If you Google the expression “winning personality” you’ll come up with a vast range of definitions and descriptions, some based on psychological insight, others on less conclusive information. Whatever way you want to look at the phenomena, having one will help you no matter what you do if it didn’t already.

The classic text on the subject is, of course, Dale Carnegie’s book, How to win friends and influence people. Though originally published in 1936, it’s still widely regarded as one of the most masterly self-help books of all time.

A recent Bartleby commentary in The Economist put the issue in corporate management terms, explaining that “the modern manager has to play the role of coach in charge of their team. And that requires an understanding of the different personality types they may be managing, and indeed the role their own personality may play in the way they manage.”

There are, even in retirement, situations where you may still find yourself encountering similar challenges. For example, if you’re working alongside other people and it’s your job to get the best out of those folks—be it at your social club, while doing volunteer work with others or maybe collaborating as a board member of your homeowner’s association. Having a winning personality will certainly influence how these relationships pan out.

Introverts, Extroverts & Ambiverts

Bartleby cites the work of Karl Moore, an associate professor at McGill University in Quebec, who has written extensively on the role of different personality types in business and in life in general.

Mr. Moore identifies three such types:

  • Introverts (40%)
  • Extroverts (40%)
  • Ambiverts (20%)

While the distinctions between personality types are easy to establish, predicting the relative success of each one is tougher. The assumption that extroverts go further in business is muddy, because the chain of causation is unclear. Writes Bartleby: “It is possible that working in a high-paid job makes people more confident and outgoing, although personality traits tend to develop early in life.”

To that point, we may want to ask ourselves, “Am I successful because my upbringing was positive and prosperous? Or is my success attributable to my ability to overcome and rise above an upbringing that wasn’t?”

Writes Bartleby: “Introverts should not give up hope of climbing the greasy pole. A study in 2017 – A winning personality: The effects of background on personality and earnings – found that introverts were slightly more likely than extroverts to surpass the expectations of boards and investors when appointed as chief executive.”

And let’s not forget ambiverts – those who possess a balance of both introverted and extroverted qualities in tandem. Mr. Moore believes that this often-ignored group tend to display unanticipated strengths – they are good listeners but are not afraid to be outspoken.

Masters of Strategic Disguise

The most successful people among us, as it turns out, are masters of strategic disguise, being low key when necessary (pipe down and listen) and outward-going when required (deliver a rousing speech).

Identifying Types of Personalities

Knowing who you’re dealing with helps – but the trouble is, people don’t have labels on their foreheads. So, you’ll have to discover what kind of personality they have. Sometimes people make it obvious (like the old joke “How do you tell if people went to Harvard?” “They’ll soon tell you”).

But that means managers must spend time chatting to, and observing, their team members before deciding how best to get them motivated and inspired.

Concludes Bartleby: “Managers need to be less like Henry Ford, and more like Sigmund Freud.”

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