Chapter 7 Exercises: Prompting Fundamentals

These exercises progress from foundational identification tasks to full prompt construction challenges. Work through them sequentially — each builds on skills introduced earlier. Allow 2–3 hours for the complete set.

Part A: Recognition and Analysis

Exercise 1: Prompt Component Identification

Read each of the following prompts. For each, identify which of the five components are present (Task, Context, Format, Constraints, Examples) and which are missing.

Prompt A: "Write a thank-you note to a client."

Prompt B: "You are a professional speechwriter. Draft the opening three minutes (approximately 400 words) of a keynote address for a nonprofit's annual gala. The audience is major donors aged 45–65. The theme is 'ten years of impact.' Open with a specific story, not statistics. Tone: warm, grateful, forward-looking. Do not use phrases like 'transformational' or 'making a difference.'"

Prompt C: "Explain machine learning to my team."

Prompt D: "Create a project status update using this format: one sentence on what we accomplished this week, one sentence on what blocked us, one sentence on next week's priority. Max 75 words total."

Analysis questions for each: - Which components are present? - Which are missing? - What assumption does the AI likely make to fill each gap? - How would the output quality differ if the missing components were added?

Exercise 2: Specificity Ladder Mapping

For each prompt below, identify which rung of the specificity ladder it sits on (1 = vague to 5 = fully specified). Then explain what would need to be added to move it up one rung.

  1. "Write something about sustainability"
  2. "Write a report on our company's carbon footprint reduction progress for the board of directors, summarizing Q3 data and recommending two areas for Q4 focus, in formal report format with an executive summary"
  3. "Draft an email about the project delay"
  4. "Summarize this article"
  5. "Create social media content about our sale"

Exercise 3: Failure Mode Diagnosis

Each of the following prompts contains one of the five structural failure modes: Buried Lede, Assumption Gap, Vague Imperative, Wall of Text, Over-Constrained. Identify which failure mode is present and explain how you would fix it.

Prompt 1: "We are a healthcare technology company. We have been in business for 12 years. We work with hospitals and health systems. We recently won a major contract with a regional hospital network. We have a team of 200 engineers. Our CEO is Dr. Sarah Chen. Our headquarters is in Boston. Write a press release."

Prompt 2: "Improve this report."

Prompt 3: "Write a 250-word product description that is exciting but not salesy, detailed but not overwhelming, professional but not stiff, creative but not confusing, and memorable but not gimmicky."

Prompt 4: "Write a client proposal using our standard methodology, following the WRS process, and making sure to address the three-tier stakeholder model we always use."

Prompt 5: "We need a comprehensive analysis of market trends. Include historical context. Also write an executive summary. And draft the Q4 forecast. Make sure the tone is right for the board. Also, one of the board members is skeptical about our growth projections, so address that. The analysis should be data-driven. Include charts if possible. Also write talking points for the CEO."

Part B: The Prompt Transformation Exercise

This is the core exercise of the chapter. Take each of the five weak prompts below and rewrite them as high-performance prompts. Your transformed prompts should reach at least Rung 4 on the specificity ladder and include at least three of the five components.

For each transformation, write a brief explanation (3–5 sentences) of the specific changes you made and why.

Weak Prompt 1:

"Write a cover letter."

Your task: Transform this into a Rung 5 prompt for a specific role, applicant background, and company. Create a fictional but realistic scenario.

Weak Prompt 2:

"Give me ideas for my team offsite."

Your task: Transform this into a fully specified prompt that would produce a genuinely useful set of recommendations.

Weak Prompt 3:

"Explain blockchain to me."

Your task: Transform this for a specific audience (choose: a 60-year-old retail banking executive, a 22-year-old marketing intern, or a 45-year-old software developer who knows networking but not cryptography).

Weak Prompt 4:

"Write a performance improvement plan."

Your task: Transform this with appropriate context, constraints (especially around tone and legal language), and format requirements.

Weak Prompt 5:

"Make this email better."

Your task: Transform this assuming you have a specific email in front of you. Describe what "better" actually means with at least four specific criteria.

Part C: CRAFT Framework Application

Exercise 4: CRAFT Deconstruction

Take the following high-performing prompt and map each sentence or clause to its CRAFT component:

"You are a financial services copywriter who specializes in plain-language communication. Our company provides retirement planning services to first-generation wealth builders — people aged 35–55 who grew up without financial guidance and are the first in their family to have significant savings. Draft a 250-word introduction for our new client welcome email. The intro should acknowledge that managing money can feel overwhelming when no one in your family did it before, validate the client's achievement in reaching this point, and introduce our advisor relationship as a partnership. Do not use financial jargon. Do not be condescending or oversimplify. Tone: warm, peer-level, not patronizing."

Map each element to: Context / Role / Action / Format / Tone

Exercise 5: CRAFT Construction from Scratch

Build a complete CRAFT prompt for each of the following tasks. Write out all five components explicitly before combining them into a single prompt.

Task A: A LinkedIn post about a product launch - Choose your own fictional product, company, and audience - Fill in all five CRAFT components before writing the final prompt

Task B: A policy memo about a new expense reimbursement process - Choose your own fictional company (industry, size, culture) - Fill in all five CRAFT components before writing the final prompt

Task C: An explanation of a complex concept for a specific non-expert audience - Choose: quantum computing, GDPR compliance, compound interest, or A/B testing - Choose your audience (who they are, what they already know, why this matters to them) - Fill in all five CRAFT components before writing the final prompt

Part D: Constraint Design

Exercise 6: Constraint Mapping

You are a communications manager at a pharmaceutical company. You need AI to help draft public statements. For each scenario below, write at least five specific constraints that must be included in the prompt.

Scenario A: A statement responding to a news article that incorrectly reported side effects from one of your drugs Scenario B: A patient-facing FAQ about a drug interaction warning that was just added to the label Scenario C: A social media response to a viral post that misrepresented your clinical trial results

After writing the constraints, review them and check for: (1) any contradictions, (2) any that could be replaced with a positive instruction, (3) any that are too vague to be useful.

Exercise 7: Positive Reframing of Negative Instructions

Rewrite each negative constraint as a positive instruction:

  1. "Don't be too formal"
  2. "Don't include technical jargon"
  3. "Don't make it too long"
  4. "Don't be vague about the timeline"
  5. "Don't write in a way that sounds like an AI"

Part E: Format Specification Practice

Exercise 8: Format Specification for the Same Content

Take this brief: "Explain the benefits of async communication for remote teams."

Write four different format specifications that would produce four genuinely different and useful outputs for different purposes:

  1. A specification for a 60-second spoken talking point at a team meeting
  2. A specification for a one-page PDF handout for new remote employees
  3. A specification for a LinkedIn post from a thought leadership account
  4. A specification for a comparison table to be used in a manager training course

Write each format specification in full, then consider: how different would the outputs be, even though the underlying content is the same?

Exercise 9: Format Translation

You have an AI-generated output: a 500-word prose essay about the risks of overreliance on AI tools in creative work. Write three different format specifications that would reformat this content into:

  1. A 5-slide presentation structure (one sentence per slide, plus speaker notes)
  2. A Twitter/X thread of 8 posts, each under 280 characters
  3. A structured FAQ with 6 question-and-answer pairs

You do not need to produce the reformatted content — just write the prompts that would accomplish each transformation.

Part F: Advanced Integration

Exercise 10: The Audience-Aware Prompt

Write a single prompt that asks the AI to produce two versions of the same content for two different audiences. The content: an explanation of why your team missed a quarterly revenue target.

Version A: For the executive leadership team (investors and board) Version B: For the sales team (the people most directly involved)

Your prompt should specify: - The factual situation (create a plausible scenario) - What is appropriate to emphasize/de-emphasize in each version - Format and length for each version - Tone constraints for each version

Exercise 11: The Sequential Task Prompt

Many complex AI tasks should be broken into sequential steps rather than addressed in one giant prompt. For the task below, break it into four sequential prompts (each building on the previous output):

Overall goal: Create a comprehensive competitive analysis of two fictional companies in your industry of choice.

Write Prompt 1, Prompt 2, Prompt 3, and Prompt 4 in sequence, where each prompt feeds on the output of the previous one. Explain your sequencing logic.

Exercise 12: Prompt Debugging

The following prompt was given to an AI tool, and the output was consistently unhelpful — generic, too long, and pitched at the wrong level. Diagnose the problems and write a fixed version.

Original prompt: "I need help with content for my business. We do consulting work and I want to use AI to help create some materials. Please write content that will be useful for our target audience and reflects our brand values of innovation, integrity, and excellence. The content should be professional and high quality. We serve enterprise clients in multiple industries. Please make sure the content is relevant and engaging."

Write a detailed diagnosis (which failure modes are present, what assumptions the AI is forced to make) and then a fully revised prompt that would produce genuinely useful output.

Exercise 13: The "Test Before You Trust" Exercise

For one of your own recurring tasks at work (a report you write regularly, an email type you send frequently, or a document you create repeatedly):

  1. Write your initial first-instinct prompt
  2. Rate it on the specificity ladder (1–5)
  3. Identify which CRAFT components are missing
  4. Identify any failure modes present
  5. Write the revised, high-performance version
  6. (If you have access to an AI tool) Run both prompts and compare the outputs

Document your analysis in writing, noting what you changed and why.

Exercise 14: Cross-Platform Prompt Adaptation

Take this prompt: "You are a senior brand strategist. Our company, Helix Foods, makes plant-based protein snacks for fitness-conscious consumers aged 22–35. Draft a one-paragraph brand positioning statement (75 words) that emphasizes performance over health anxiety — we're for athletes, not dieters. Tone: confident, technical, aspirational."

Adapt this prompt for three different platforms: ChatGPT, Claude, and Gemini. Your adaptations should: - Use each platform's preferred formatting or instruction style where relevant - Note any features specific to that platform (Custom Instructions, XML tags, etc.) that you would use - Explain why you made each platform-specific adjustment

Exercise 15: Build Your Personal Prompt Library Entry

Choose a task you perform regularly that could be assisted by AI. Build a complete, reusable prompt for it:

Part 1 — Task Analysis: - What is the task? - Who is the intended audience for the output? - What does "excellent" look like for this task? - What are the common failure modes or output problems you want to prevent? - Are there any non-obvious constraints (things that are obvious to you but not to an outside reader)?

Part 2 — Prompt Construction: Using all the frameworks from this chapter (5 components, CRAFT, failure mode avoidance, clarity rules), write a complete, ready-to-use prompt for this task.

Part 3 — Reflection: Write 3–4 sentences explaining how this prompt would produce better output than your previous approach (or first instinct) for this task.

This exercise produces a real artifact for your workflow — a prompt you can actually use.

Reflection Questions

After completing the exercises, consider these reflection questions:

  1. Which of the five structural failure modes do you most commonly make in your own prompting? What is the root cause?
  2. Which CRAFT component is hardest for you to specify? Why might that be?
  3. When you compare your Rung 1 prompts to your Rung 5 prompts, what is the most important difference — not in the words, but in your thinking?
  4. Is there a task in your work where you have been getting mediocre AI output that you now suspect was a prompting problem rather than an AI capability problem?