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The Whipp

Wisdom, humour and insights for professional peeps — delivered weekly. Archive below.

Contacts vs. Context (Why Nobody’s Calling You Back)

I read a passage from Keith Ferrazzi a few weeks ago that has stayed with me. Ferrazzi has spent two decades coaching and writing about relationship-building. The core of his work in Never Eat Alone and beyond comes down to a single distinction: The people who are best at relationships, he argues, are not the … Continued

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Things fall apart again

is week I was working with a young professional I’ve been coaching for about a year. He’s bright, hardworking, and deeply thoughtful about the impact he has on others. Over the past year I’ve watched his reputation grow the way the best ones do—through consistent effort and genuine care for the work. Recently he was … Continued

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The Higher You Climb, The Farther You Can Fall

I heard this from a client recently, and it captured something I remember feeling myself at a certain point in my career: “I thought once I got to this level, I’d feel more secure.” We follow this invisible blueprint: work hard, prove yourself, earn the promotion, earn the bigger title, earn the bigger pay cheque, … Continued

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When Nothing Is Wrong and Leaving Is Right

Many years ago, I was in a really good relationship. He was kind, thoughtful, emotionally, and professional stable. He was the kind of partner many people would consider a catch. But inside I was struggling. He had children from his first marriage, which was accompanied by a “been there, done that” attitude whenever the topic … Continued

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The Power of ‘Anticipatory Intelligence’

I was on a call recently with a client who was feeling frustrated after a series of hiring decisions that hadn’t worked out. He was trying to figure out how to screen more effectively going forward so that he could avoid repeating the same mistakes. We started, as most people do, by listing the traits … Continued

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Is Your Team Holding Back Their Best Thinking?

Recently, I had two meetings with two C-suite executives from the same company during the same week, discussing the exact same body of work. I walked out of each room realizing how profoundly leadership shapes what people are willing to contribute.   Meeting One: Explanations I’m sitting across from a senior executive I work with … Continued

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The Real Cost of Keeping a Toxic A-Player

There’s a particular kind of leadership conversation that almost always happens behind closed doors. It’s the one about the high performer who is wreaking havoc on the culture. They deliver results. They have skills the organization values. They might hold critical client relationships, deep institutional knowledge, or insights pulled straight from a competitor. On paper, … Continued

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Did anyone else hear this during Carney’s speech?

I was listening to Mark Carney speak last week, and somewhere between his discussion of global economics and the fragility of power, I had a visceral aha moment. He wasn’t just talking about current leadership dynamics across the globe, he was describing dynamics I’ve seen in many organizations I’ve worked in—and many I still work … Continued

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Stop Hitting Snooze on This Important Problem

I was coaching a CEO this week who is sitting at a pivotal moment in her business. This year’s sales performance will be a major determinant of the company’s future. The stakes are real. The pressure is on. And the person she has in the sales leadership seat is, on paper, outstanding. Deep industry knowledge. … Continued

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