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Aim: To develop a substantive theoretical explanation that makes sense of the decision‐making process that clinical instructors use to place students on a learning contract. Background: Clinical instructors are challenged with the task of objectively evaluating students using subjective tools such as anecdotal notes, diaries, unstructured observations and verbal feedback from other nurses. Clinical instructors' assessment decisions have a considerable impact on a variety of key stakeholders, not least of all students. Design: Grounded theory method and its heuristic tools including the logic of constant comparison, continuous memoing and theoretical sampling to serve conceptualisation were used in the process of data collection and analysis. Methods: Seventeen individual semi‐structured interviews with clinical instructors in one university in Western Canada were conducted between May 2016–May 2017. Data were analysed using open, axial and selective coding consistent with grounded theory methodology. The study was checked for the Standards for Reporting Qualitative Research (SRQR) criteria (See Appendix S1). Findings: Three subcategories, "brewing trouble," "unpacking thinking" and "benchmarking" led to the study's substantive theoretical explanation. "Gut feeling" demonstrates how clinical instructors reason in their decision‐making process to place a student on a learning contract. Conclusion: Placing a student on a learning contract is impacted by personal, professional and institutional variables that together shift the process of evaluation towards subjectivity, thus influencing students' competency. A system‐level approach, focusing on positive change through implementing innovative assessment strategies, such as using a smart phone application, is needed to provide some degree of consistency and objectivity. Relevance to clinical practice: Making visible the objective assessments currently being done by clinical instructors has the potential to change organisational standards, which in turn impact patient and clinical outcomes. [ABSTRACT FROM AUTHOR]