If you are a flight instructor, then you already know how to fly the airplane, helicopter, or whatever, and now you have to show others how to do it. Here are some resources that you may use with your students -- particularly when you are trying to improve their pilot judgment.
Australian Civil Aviation Safety Authority Advisory Publication 59.1 - This publication was designed to provide practical guidance on how to teach and assess single pilot human factors (HF) and threat and error management (TEM).
Judgment Training for Instructors & Judgment Training for Student Pilots -- These two manuals were produced as part of a cooperative effort between the FAA, Transport Canada, and the General Aviation Manufacturers Association. Lots of good ideas on how to teach and assess judgment. There is also a Pilot Judgment Evaluation form that may have been part of that effort. All of the other manuals produced by the FAA that dealt with Aeronautical Decision Making are also available here.
Teaching about weather. These are the responses from a a group of Certified Flight Instructors who took part in an FAA-sponsored survey. The instructors were asked to describe: (a) Ways in which they taught weather-related decision-making to their primary student pilots. (b) Ways in which they assessed the weather-related decision-making of their primary student pilots. You may find their approaches to those two instructional problems enlightening. (Here is the complete report on the CFI survey.)
Pre-flight risk Assessment This is a form that you may use with your students to help them evaluate the risks before a flight. Feel free to add or modify the form to make it more useful. Think of it as a starting point for a discussion of the flying risks and what the student can do to manage them.
Teaching and evaluating pilot judgment. Here are some ideas on how to conduct a standardized Biennial Flight Review (BFR) based upon a multi-year research program to assess objectively the skill retention levels of pilots. It includes guidance for Certificated Flight Instructors (CFIs) on the selection of specific maneuvers to be performed based upon pilot characteristics such as total and recent experience, ordering of maneuvers, standardized grading procedures based upon the FAA practical test standards, and procedures for the assessment of pilot judgment. It addresses both ground and in-flight assessment.
In years past, the FAA maintained an extensive collection of PowerPoint presentations, available for download by the public. Unfortunately, those presentations no longer seem to be available anywhere on the FAA web site. Luckily, I copied all the presentations before they disappeared, so you can access and download them from here.
In addition, I have found a large number of PowerPoint presentations created by NASA and other organizations. Some are great and some are not. But, if you need to give a class or just get smart about anything from METAR/TAF to ditching your aircraft, this would be a good place to start.