Paul Baltes has developed constructs for looking at wisdom and practical judgment that can help us develop both of these skills.

Wisdom Heuristic
Baltes explores wisdom as a complex integration of knowledge and understanding using the construct of a heuristic to help us grasp the automaticity inherent in wisdom. The PDF, Wisdom: A Meta-heuristic (Pragmatic) to Orchestrate Mind and Virtue Toward Excellence Link, by Baltes, Paul B. and Staudinger, Ursula M., describes the elements of the wisdom heuristic. Baltes’ ideas are further detailed and contrasted with other models of wisdom on the website, The Berlin Wisdom Model.

Konrad Banicki in the PDF, The Berlin Wisdom Paradigm: A Conceptual Analysis of a Psychological Approach to Wisdom, reviews the psychological nature of wisdom. Specifically, he looks at how the philosophical and the psychological views on wisdom have a considerable degree of correspondence that allows us to benefit from looking at both perspectives.

Select—Optimize—Compensate
Baltes has also developed an analytical system for making choices and behavioral changes. His model of Select, Optimize, Compensate (SOC), helps us set a focus, develop a strategy, and learn from the process to develop the next level of skill required.

Paul Baltes defines the SOC as:

“Select: Delineate the range of possible alternative options or ends (articulate, develop, and commit to a set of goals).
Optimize: Acquire and invest—apply means to achieve the ends or goals selected.
Compensate: When confronted with loss or other forms of blockage of previously available goal-relevant means, acquire and invest alternative means to maintain functioning or goal attainment.”

The basic constructs of SOC are outlined in the chapter titled, The Intermarriage of Wisdom and Selective Optimization with Compensation: Two Meta-Heuristics Guiding the Conduct of Life, By Paul Baltes and Alexandra Freund, in Flourishing: Positive Psychology and the Life Well-Lived.