Conservation translocations, including reintroductions, are practices that are vital to restoring biodiversity and ecosystem function within conservation schemes globally. Sadly, population translocations have had a poor success rate historically. At a time where biodiversity is constantly decreasing, improving translocation success is vital for future conservation schemes. Often, to improve success, the selection of individuals is based on genetic characteristics and behaviours linked directly to survival. Further development to improve selection is proposed within this paper using animal personality. The study took place opportunistically to test how personality, in particular an animal’s boldness/timidness, may influence a population restoration of red squirrels into the Ogwen Valley, North Wales. Despite frequent translocations, data on how boldness and timidness may affect the establishment of this species are low. Testing was performed on key survival behaviours and boldness/timidness pre-release. This was performed via video data collection and identification of key behaviours that could be used to identify boldness or behaviours that could be linked to reduced fitness once released. Encounters at different distance intervals were monitored post-release via camera trapping to identify if boldness/timidness may change the furthest encounter distance of focal animals away from their release site. Relationships between the period for an individual to reappear post-threat was significantly linked to boldness, with other behavioural results and the encounter distance also showing trends of a potential relationship. Our results indicate that bolder individuals have a higher chance of expressing behavioural traits that will increase exposure to risks and, therefore, reduce the likelihood of successfully establishing populations. However, the small sample size of this study means that further research is needed. We suggest that during early stages of conservation translocation programmes, personality testing for boldness should become common practice, and we recommend selecting timid individuals for an initial release to improve population establishment, with bolder individuals utilised later to expand population distribution.