Technical Debt Management (TDM) can suffer from unpredictability, communication gaps and the inaccessibility of relevant information, which hamper the effectiveness of its decision making. These issues can stem from division among decision-makers which takes root in unfair consequences of decisions among different decision-makers. One mitigation route is Skin in the Game thinking, which enforces transparency, fairness and shared responsibility during collective decision-making under uncertainty. This article illustrates characteristics which require Skin in the Game thinking in Technical Debt (TD) identification, measurement, prioritisation and monitoring. We point out crucial problems in TD monitoring rooted in asymmetric information and asymmetric payoff between different factions of decision-makers. A systematic TD monitoring method is presented to mitigate the said problems. The method leverages Replicator Dynamics and Behavioural Learning. The method supports decision-makers with automated TD monitoring decisions; it informs decision-makers when human interventions are required. Two publicly available industrial projects with a non-trivial number of TD and timestamps are utilised to evaluate the application of our method. Mann–Whitney U hypothesis tests are conducted on samples of decisions from our method and the baseline. The statistical evidence indicates that our method can produce cost-effective and contextual TD monitoring decisions.