Context When developing software, it is vitally important to keep the level of technical debt down since, based on several studies, it has been well established that technical debt can lower the development productivity, decrease the developers' morale and compromise the overall quality of the software, among others. However, even if researchers and practitioners working in today's software development industry are quite familiar with the concept of technical debt and its related negative consequences, there has been no empirical research focusing specifically on how software managers actively communicate and manage the need to keep the level of technical debt as low as possible. Objective This study aims to understand how software companies give incentives to manage technical debt. This is carried out by exploring how companies encourage and reward practitioners for actively keeping the level of technical debt down add whether the companies use any forcing or penalising initiatives when managing technical debt. Method As a first step, this paper reports the results of both an online survey providing quantitative data from 258 participants and interviews with 32 software practitioners. As a second step, this study sets out to specifically provide a detailed assessment of additional and in-depth analysis of technical debt management strategies based on an encouraging mindset and attitude from both managers and technical roles to understand how, when and by whom such strategies are adopted in practice. Results Our findings show that having a technical debt management strategy (specially based on encouragement) can significantly impact the amount of technical debt related to the software. Conclusion The result indicates that there is considerable unfulfilled potential to influence how software practitioners can further limit and reduce technical debt by adopting a strategy based explicitly on an encouraging mindset from managers where they also specifically dedicate time and resources for technical debt remediation activities.