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Difficult Employees (and How to Handle Them)

Published on: 2025-07-17 14:28:28

👋 Howdy! Claire here, Founder & CEO of Canopy. Welcome to my weekly newsletter on leadership, “Views from the Canopy”. If you’ve been enjoying my writing (and illustrations!) recently here, do please make sure you’re subscribed so you can receive a fresh piece each week, and consider sharing with a friend or colleague who you think might enjoy as well. Now, onto this doozy of a piece: A guide to difficult employees… “What in the world is happening here? I remember the words running through my mind, almost a decade ago. A team member sat across from me, masterfully spinning a web of excuses about missed deadlines while I wrestled with a crucial question: How do you coach someone to success when they won't even acknowledge reality? Luckily, I kept my cool. I stayed steady and calmly explained where I thought there was a gap between expectation and performance and what they could do better. They relented, and we were able to find a way to move forward, at least in that moment. Eventu ... Read full article.