The interplay of conductivity and friction in layered materials such as graphite is an open area of investigation. Here, we measure local conductivity and friction on terraces of freshly cleaved highly oriented pyrolytic graphite via atomic force microscopy under ambient conditions. The graphite surface is found to exhibit a rich electrical landscape, with different terraces exhibiting different levels of conductivity. A peculiar dependency of conductivity on scan direction is observed on some terraces. The terraces that exhibit this dependency are also found to show enhanced friction values. A hypothesis based on tip asymmetry and the puckering effect is proposed to explain the findings. Our results highlight the non-triviality of the electrical and tribological properties of graphite on the nanoscale, as well as their interplay.