In situations of conflict, it is commonly found that a leader’s communication style matters tremendously to deliver an intended message (Khan, Ismail, Hussain, & Alghazali, 2020). Especially in times such as pandemics, wars, industrial revolutions it is the leaders that are discussed the most (Vacharkulksemsuk & Fredrickson, 2013). One of the many topics discussed regarding this profile of leadership is the communication style that is used by the leaders, especially during trying times such as mergers, change in leadership positions, or changes at any level of an organisation (Pavitt, 1999). Drawing on an existing psychological theory that attempts to target the complex psychological aspect of communication developed by Dr Eric Berne (1961) known as, Transactional Analysis (TA), the aim of this study was to first, adapt TA from a psychological theory to a business training programme for leaders, to be applied at the workplace. This aspect of TA has been missing from workplace leadership training (Nykodym, Longenecker, & Ruud, 1991). Second, this thesis sought to evaluate the adapted training programme that is based on the theory developed by Berne (1961), to ascertain its validity in a leadership sample away from the theory’s psychological settings. Training evaluation is central to the successful implementation of training in the workplace (Farjad, 2012). While there are many types of evaluations, this thesis evaluated the TA training programme using a two-fold strategy. First, using the Johari Window (Luft & Ingham, 1955) to evaluate leaders’ insights into the process of communication. Second, using Kirkpatrick’s (Watkins, Leigh, Foshay, & Kaufman, 1998) four levels of evaluation i.e. 1. Reactions 2. Learning 3. Behaviour 4. Results. The participants completed a second evaluation of the training programme one week after the intervention using Kirkpatrick’s evaluation model. The training programme was conducted for 11 participants of various backgrounds with leadership and business work experience, for 60 minutes each day for four days, with the training programme being evaluated on the fifth day. The sample consisted of Masters of Business Management Students, Bachelor of Engineering, Master of Cyber Security, Bachelor of Animal Behaviour, and other such programmes offered by the University of Waikato. These participants were international students, who largely had leadership experience, who were completing a one year Executive Education and or Masters level course. Participants chose to attend the training programme either via online zoom calls or face-to-face. There were 4 online participants and 7 face-to-face participants in total. While most participants’ feedback was that the TA training programme was relevant, well delivered, and interesting, some participants suggested that improvements in the timing and depth of the topics covered in the training could be made. In terms of evaluation, using the Johari window, the study showed, overall, increased levels of positive introspection and improved communication. Evaluation via Kirkpatrick showed that in terms of 1.Reactions – TA training was received as largely positive. 2. Learning – evaluated to be mainly good 3. Behaviour – evaluated to be overall consistent, overall demonstrating that the training module was successfully adapted for leaders. A limitation observed in the thesis was small sample size. It is also recommended that a replication of this study and evaluation over larger and more diverse samples (for example workplace, not student leaders) would be beneficial. Furthermore, future research may want to increase the teaching time to more than 60 minutes and delve deeper into some of the concepts covered to enhance the programme. In summary, a training module adapted from Berne (1961) on TA was developed and taught to leadership students studying tertiary degrees. Largely the evaluation of this adapted TA training programme was that it was both well received and that it does bring positive changes for leaders.