Diversity and inclusion are the latest buzzwords in corporate HR. Studies show teams perform better when developed with these considerations. However, how HR actually handles these issues can be very problematic, the need for anonymous interaction for LGB and especially transgender employees is clear but often overlooked. Employees who remain closeted at work do so for a variety of reasons and being unable to seek information about health care services, insurance benefits or the possibility of transitioning anonymously can be tremendously isolating and stressful, potentially triggering mental health issues. In this talk, I will speak about my experiences trying to navigate these waters in an environment where the diversity and inclusion is at the forefront of the company’s ethos. I will demonstrate how a few seemingly minor mistakes can actually push away the groups that companies are trying so diligently to serve and include. HR policies cannot be created in a bubble, those they affect must be consulted.