Exercise 2: The Evaluation Gap
Setup
Choose a piece of work in your domain — something you've evaluated before or something that exists (a report, a design, a proposal, an analysis, a strategy document). Choose something where you have strong domain knowledge and clear standards.
Before you look at it critically, write down what excellent looks like for this type of work. Be specific. What are the qualities of excellent work in this category? Don't edit yourself. Write what comes to mind.
The Work
Now evaluate the work carefully. Go through it systematically. Where does it succeed? Where does it fall short? Be specific about both.
Reflection Questions
After you've evaluated:
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Where does your written standard match your actual evaluation? Where do they diverge?
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What did you notice during evaluation that you didn't anticipate in your written standard? What does that reveal about the gap between your implicit and explicit standards?
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If you had to coach someone to improve this work, what specific feedback would you give? How does that feedback compare to your written standard?
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What would you do differently next time you evaluated this type of work, based on what you learned?
Module Deliverable: The Direction Brief
The Real Work
Pick a piece of work from your current role that you could realistically direct to an AI system or a junior colleague. Not a hypothetical. Not a thought experiment. A real piece of work that you actually do or would actually like to do less of.
Write a genuine direction brief for it. Not a description of what a direction brief is — an actual one that could be used to delegate the work.
Your direction brief should include:
Context: What's the background? Why does this work matter? What's the business or professional outcome you're trying to achieve?
Outcome: What, specifically, are you trying to achieve with this work? What does success look like? What would a successful output do or enable?
Constraints: What constraints apply? What's negotiable and what's not? What's the timeline? What resources are available?
Standards: What does good look like specifically? What are the qualities of excellent work in this category? What would make the output insufficient?
What to avoid: What are the specific failures or pitfalls you want to prevent? What would make this work wrong or unhelpful?
Scope and latitude: Where can the executor make decisions? Where do they need to check with you? What's the range of acceptable variation?
Evaluation criteria: How will you know if the work meets your standard? What will you look for when you review it?
The Discipline
Write this brief as if you're actually going to use it. Write it clearly enough that someone unfamiliar with your typical process could read it and understand what you want. Write it specifically enough that you could evaluate whether the output met your standard.
After you've written it, read it back. Did you discover anything about your own thinking? Did making your standards explicit reveal places where your thinking was fuzzy? Did you realize you care about something you hadn't articulated? Did you find conflicts in what you want?
This exercise is the single best way to develop the director's skill, because it forces everything: clarity about outcome, explicit standards, the ability to anticipate problems, the discipline of describing what matters instead of how to achieve it.
If you have the opportunity to actually use this brief to delegate the work, do it. The real practice of direction comes from writing the brief, giving it to an executor, evaluating the result, and learning what you would clarify or change next time.
How to Proceed
Complete Exercise 1 first. The Instruction-to-Direction Rewrite builds the foundational skill of outcome-first framing.
Complete Exercise 2 next. The Evaluation Gap exercise develops your director's eye and reveals the gap between implicit and explicit standards.
Complete the module deliverable last. Writing a real direction brief integrates everything: clarity about outcome, explicit standards, evaluation criteria, and the discipline of communication. This is the work that actually develops the director's skill.
All three exercises are most powerful when done in sequence, because each one prepares you for the next. Instruction-to-Direction makes you more careful about framing. Evaluation Gap makes you more aware of your standards. The Direction Brief integrates both. Do them in order.