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Courageous Career Conversations

I've found that leaders often mis-assume that having a career conversation involves mapping out your entire career plan. It's somehow been engrained in many of us that progression means moving up "a career ladder" reaching dizzying heights of seniority along the way. Instead, an analogy that I’ve found helps leaders to imagine a different approach is helping your team define and climb a “career climbing wall.” There may be steps sideways, or even downwards before climbing up. Higher is not always better.

Meet Kelly, who heads up a Design team for a tech company. Through coaching she figured out how to tackle her uncertainty around each team member's level of long term engagement and performance. She realized it was time to initiate a different kind of career conversation. She designed an approach that made it possible for her team to be honest with themselves and her about their internal motivation so that together they could explore the connection between what their current role and what matters to them as individuals.

She initiated focused 1:1s with the express purpose of "career dreaming" and asked her directs to come ready to share reflections with her. She approached the conversations asking open questions under three core categories. Past, Present and Future. The goal was to establish themes that would then help them identify "what could your next growth step look like?"

Past A helpful way to set future focus is to reflect on the path you have come along.

  • Reflecting on the past {six months}, when have you felt most engaged?

  • What have you been most proud of?

  • What setbacks have mattered most to you?

Present It's important to calibrate with their current reality, both what's working well and what's not.

  • What aspect of your current work is most fulfilling?

  • When do you feel like you are in your element?

  • What's draining you right now?

Future When looking ahead to imagine the future remember it's not always about finding the next best role, but can also be evolving an existing role or responsibility.

  • “Where do you hope to become an expert?”

  • “What aspect of our team’s work would you like to expand?”

  • “Where would you like more ownership?

As Kelly listened carefully to her team's responses they were able to co-create a personalized growth plan for the year ahead, broken down by priority themes that they revisited every quarter. As a result team measures of engagement and performance have improved and one person is now thriving in a new role in a different department. How can you use courage in your next career conversation?

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