Low-Power Wide-Area Network (LPWAN) technologies such as Long Range (LoRa) are emerging that enable power efficient wireless communication over very long distances. LPWAN devices typically communicate directly to a sink node which removes the need of constructing and maintaining a complex multi-hop network. However, to ensure efficient and reliable communication LPWAN devices often provide a large number of transmission parameters. For example, a LoRa device can be configured to use different spreading factors, bandwidth settings, coding rates and transmission powers, resulting in over 6720 possible settings. It is a challenge to determine the setting that minimises transmission energy cost while meeting the required communication performance. This paper is the first to present a thorough analysis of the impact of LoRa transmission parameter selection on communication performance. We study in detail the impact of parameter settings on energy consumption and communication reliability. Using this study we develop a link probing regime which enables us to quickly determine transmission settings that satisfy performance requirements. The presented work is a first step towards an automated mechanism for LoRa transmission parameter selection that a deployed LoRa network requires, but is not yet specified within the Long Range Wide Area Network (LoRaWAN) framework.