In a special edition of Good Question, we’re sharing an excerpt from When Harvey Didn’t Meet Sheelagh: Emails on Leadership. The book is unconventionally co-authored — through an exchange of emails — by Harvey Schachter, a management columnist, and Sheelagh Whitakker, a board member and retired CEO (notably, the first woman CEO of a TSX listed company). The pair have never met, but through emails share what they have learned over the years while challenging conventional wisdom on notions of ambition, success, ethics, getting communication right, gender at work, and legacy. In Chapter 10, they both explore a very good question: can contradictory personality traits combine to become a superpower? You can use the same exercise to meet your oxymoronic self — and perhaps discover that your contradictions aren’t self-defeating.

OUR EXPERT:

Sheelagh Whittaker
Retired CEO, board member, and author.

Sheelagh Whittaker loves to laugh. A savvy strategist and CEO, shrewd observer of the zeitgeist, and engaging storyteller — imparting wisdom from her invariably humorous stories — she rose to corporate top echelons back when people thought the glass ceiling was an observation deck. She has served as CEO, board member, and mother in Canada, the US, Britain and Australia. Her co-author, Harvey Schachter, is the dean of management column writers. Specializing in leadership, management and workplace issues, Harvey curates and synthesizes business how-to books and missives full of purported insights, and directs the reader to those worth consideration. Trenchant and practical, his delivery is sensitive to his reader’s need for insights delivered in small doses.

Hi Sheelagh,

Journalist Stewart Alsop called Bill Gates a “practical visionary.” That’s an odd combination, an oxymoron. But if he had just been a visionary without that practical side, he may not have been as successful as he was. If he had just been practical, there would be no Microsoft powerhouse today. The oxymoronic combination of traits was critical.

Walmart founder Sam Walton embodied not one but three critical paradoxes. He was relentlessly focused on winning but totally flexible and willing to try anything that seemed reasonable. He was creative but also willing to copy anything that worked well elsewhere. And he was an excellent motivator, willing to give people space to try out their own ideas but he also checked up on everything anyone did.

That comes from a 1997 sleeper book I loved, Paradoxical Thinking by Jerry Fletcher and Kelle Olwyler, which argues “the route to sustaining high performance is to consciously and actively encourage yourself to be paradoxical.” 

To find your core personal paradox, they suggest listing your personal qualities and characteristics – at least twenty – such as the types of actions you like to take, roles you like to play, and words that might be used to describe you. Then combine those into paradoxical pairs using oxymorons. For example, in one workshop they unearthed the following from participants:

• attack sheep
• lazy do-it-all
• spontaneous planner
• ruthless helper
• creative imitator
• passionate robot
• hesitant risk-taker
• velvet jackhammer
• insecure tower of strength
• ambitious slowpoke

Look for combinations of words on your list that are already opposites. You may, however, need to invent a phrase to describe yourself. The authors note that names of animals can be helpful – shy and timid making you a mouse, powerful and fearless turning you lion-hearted.

You’ll probably be uncomfortable with some of the characteristics you’ve named. “If one side of your core personality paradox seems like a limitation, you probably have felt for much of your life that you ‘shouldn’t’ act that way or you would be ‘better off’ if you were different. It is likely that you have tried to suppress or eliminate that quality of your personality. Yet this is not the direction to go,” they insist. 

Instead, reset your perceptions by listing the positives and negatives of the preferred and disliked sides. From those, develop a high-performance oxymoron combining the best of both sides, and a negative oxymoron combining the not-so-goods. In an example in the book, a woman defines herself as a “self-doubting overachiever,” liking the overachiever but disliking the self-doubting element. However, when she completes the self-examination, her high-performance oxymoron is quite helpful: “Thoroughly prepared expectation exceeder.” The nightmare scenario, though, is when she becomes a “hopeless wheel-spinner.” She has to try to be the former and not the latter.

Enough!

When I first read the book and for many years afterwards, I considered myself a “gentle tiger.” I still do, but recently I have focused more on a newer oxymoron: “rebellious loyalist.”

What about you? 

Hi Harvey,

I’d be interested in understanding your loyalties.

Meanwhile, I had a lot of fun with performance oxymorons. Right off I tried on “likeable bitch” with a good friend of mine who responded quickly but kindly, “Sheelagh, we are who we are. But maybe there are other ways to phrase it.”

Undaunted, I experimented with “irrepressible?” and came up blank. I guess I am simply irrepressible.

Other ideas included:

• insightful boss
• feminine feminist
• ambivalent disciplinarian
• effervescent recluse

While playing with performance oxymorons I was reminded of a very clever job category that existed in EDS – that of EDS Fellow.

EDS Fellows could be described as corporate individual performers. Early on, someone (maybe Ross Perot himself) recognized that we needed to attract and nurture brilliant mathematical and operations research minds to help us stay ahead of the game. Clearly, we did not want these people to spend their time managing others. We could handle that; we wanted them to spend their time experimenting and coming up with new ideas. 

A career path entitled Individual Performer was created, to which a very special class of IT artiste could aspire to be promoted. An EDS Fellow had the status, salary and perks of a vice president and no mundane day-to-day responsibilities. It was a brilliant solution to a motivation and retention problem and the EDS Fellows were revered by the organization.

I’ve got it – “irrepressibly curious.”

Hi Sheelagh,

You never follow the rules, do you?

But maybe you’re, as they say, aligned! Unlike me.

I’ve always worried my contradictions hinder my leadership, compared to others who are not as divided within themselves. The book offered me hope that maybe my contradictions aren’t self-defeating. You may be the model I need to follow. Together, we are probably an oxymoron.