This paper discusses potential barriers to electric vehicle purchase in fleets and how these could be overcome by policymakers, fleets, and organizations with fleets. Fleets may face unique challenges to electrification and require different support than is provided to private consumers due to their variety of vehicle uses and applications. The paper is divided into discussions on purchase issues and those on operational issues. Purchase issues include ensuring plug-in electric vehicles (PEVs) are available across different vehicle types, creating educational campaigns for both decision-makers and fleet vehicle drivers, and tailoring incentives to the fleet context. Operational issues include factors such as creating post-purchase incentives, implementing low-emission zones and congestion charges, and facilitating utility support for fleet vehicle charging installations.