Executive public leadership in Danish municipalities takes place under complexity and turbulence, with social acceleration as the temporal background. At the political-administrative apex, the mayor and the municipal CEO work with strategic issues whose direction, consequences, and conditions are not yet fully grasped. However, the concept of strategic readiness offers a practical solution for the dyadic systematic, coordinated, and collaborative strategizing. The three dimensions concern continuity, alignment, and the joint development of interpretations, possibilities, and direction. Four strategic horizons specify how this strategizing is oriented through the relation between future knowability and issue-specific organizational readiness. A theoretical causal argument links leadership training to change in strategic readiness through shared orientation, repeated practice, reflection and adjustment, and application in municipal practice. The argument is operationalized in a dyadic-based, practice-near, cumulative, and horizon-oriented training program in which dyads work on strategic issues during and between training sessions, using strategic cases, modules, touchdowns, feedback, and diary work. Three respondent-specific measures operationalize one systematized concept of strategic readiness: strategic readiness reported by the dyad, perceived by directors, and perceived by city councilors. The measures distinguish self-ratings from observer ratings of the dyad’s strategizing. A comparative study in twelve Danish municipalities examines leadership training in a difficult-to-access elite-level municipal field. Questionnaire-based measurements before and after the training period provide the basis for comparing changes in training and no-training municipalities. Strategic readiness brings the joint strategizing of mayors and municipal CEOs into focus as a subject for concept development, leadership training, measurement, and empirical inquiry.