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You should set aside a 1:1 per quarter to walk through career conversations with your direct reports. The goals are to make sure it’s 1) a priority for you and your direct report and 2) you don’t wait until the annual reviews to have a conversation about what they are thinking about for the future.
Remember that most reps don’t want to stay on your team forever! They will want to get experience moving up market and supporting larger companies, they might want to explore another team like success or market, or they might want to move into leadership. If you don’t explore these possibilities at your company, you might risk losing an employee to another company that has a role that’s a better fit.

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