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Connecting with colleagues outside of work can be a tricky endeavor, especially for leaders. On the one hand, it can be a swift means of creating more personalized relationships and stronger bonds: Studies show that connecting outside of work can help leaders and employees thrive in their work and improve team performance. On the other hand, leaders (rightly!) see that blurring the lines between work and non-work boundaries poses real risks. In the wrong setting, these encounters can lead to uncomfortable interactions that tarnish work relationships or potentially jeopardize a professional image that’s taken years to build.