High-performance growth coach & trainer 💙 | The ultimate hub for revenue leaders & their teams 🚀 | Side effects include teams that brag & organizational WOW 😮 | Host of Books That Built Me – a podcast for leaders 🎒
Park that eye roll - here are career conversations that actually work!
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Most career conversations are awkward, uninspiring, and end with vague promises nobody remembers. We’ve all been there ... sitting across from a well-meaning leader as they ask: “So, where do you see yourself in five years?” Eye roll. Most people don’t know where they’ll be in five months, let alone five years. And even if they do know, they’re not about to say it in case it doesn’t line up with what the company wants to hear. That question is outdated. It’s lazy. And it kills energy instead of creating it. Why the 5-Year question failsIt assumes clarity when what most people need is curiosity. It puts pressure where what’s missing is possibility. When leaders ask questions that are too far ahead, people check out. When they ask questions that feel too small, people shrink. So, then, what’s the alternative? The 3-Step career conversation that actually works: Past → Future → PresentWhen Helen - a brilliant leader I coach - told me she dreaded having these career conversations with her team. “They just stare at me. It’s like they’re waiting for ME to tell THEM what to want.” We rebuilt her approach around this simple flow: 1. Start with the PastAsk: “What are you most proud of in the last year?” Why it works: reflection builds confidence. When people remember their wins, they see themselves as capable of more. It taps into what psychologists call the progress principle - the biggest motivator at work is making progress and noticing it. Why this works: people want to be seen for their past wins! 2. Jump to the FutureAsk: “Where do you want to stretch in the next 2 years?” Why 2 years? Because neuroscience shows we struggle to imagine our “future self” beyond 24 months. Five-year plans feel fake. Two years feels tangible, doable, energizing. Why this works: people want to choose where to stretch! 3. Ground it in the PresentAsk: “What gaps do we need to close now to get you there?” This is where ownership shifts. Instead of the leader handing over a plan, the employee builds the bridge from today to tomorrow. Why this works: people want to be supported in the present. Why this worksBecause people don’t want to be spoon-fed a career path. They want a conversation that's not a chore, but a catalyst. Nobody in history has ever walked away from the five-year question thinking: “Wow, that was inspiring. I can’t wait to spend the next 1,825 days proving myself to Karen.” Let’s retire it, once and for all. Try this in your next 1:1When you sit down for your next 1:1, don’t pull out the dusty HR template. Just ask: >> What are you most proud of? >> Where do you want to grow in 2 years? >> What gaps can we close today? That’s it. Simple. Science-backed. Human. Park that eye roll, this works! My best, always, Shar |
Shar Banerjee | ACCESS+ Leaders Inc.
High-performance growth coach & trainer 💙 | The ultimate hub for revenue leaders & their teams 🚀 | Side effects include teams that brag & organizational WOW 😮 | Host of Books That Built Me – a podcast for leaders 🎒
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