Tailoring Applications Fast

Why Tailoring Matters

In the previous lesson, we explored resumes that actually work. Now let’s build on that foundation. You’ve probably sent generic applications. We all have. It feels efficient.

But here’s what happens on the other side:

Recruiter sees: “I’m excited about opportunities at your company…”

Recruiter thinks: “This person sent this to 50 companies. Next.”

Tailored applications take more time. But they work dramatically better. The good news: AI makes tailoring fast.

The Tailoring Framework

Every tailored application answers three questions:

Why this company? (Shows you’ve done research)
Why this role? (Shows you understand what they need)
Why you? (Shows your relevant experience)

Generic applications skip questions 1 and 2. That’s why they fail.

Quick Company Research

Before tailoring, spend 5 minutes understanding the company:

AI: "Research this company for a job application.
I'm applying for: [Role Title]
Company: [Company Name]

Find:
1. What they do (2-3 sentence summary)
2. Recent news or achievements (last 6 months)
3. Their apparent culture or values
4. Challenges they might be facing
5. Why someone might want to work there

I'll use this to tailor my application."

Even surface-level research makes your application stand out because most people don’t bother.

Resume Tailoring in Minutes

You built a strong base resume in Lesson 2. Now tailor it:

Step 1: Identify top requirements (1 min)

AI: "From this job description, what are the
3-5 most important requirements?

[Paste job description]"

Step 2: Match your experience (2 min)

AI: "I'm applying for a role where the top requirements are:
[List from Step 1]

Here's my experience:
[Paste relevant sections of resume]

Which of my experiences best match each requirement?"

Step 3: Reorder and emphasize (3 min)

Move the most relevant experience up
Adjust bullet points to highlight matched skills
Add any missing keywords naturally

Total resume tailoring: ~6 minutes

Cover Letters That Don’t Suck

Most cover letters are either:

Generic garbage (“I’m excited about this opportunity…”)
Rehashed resumes (just repeating what’s already there)

Neither helps. A good cover letter adds something new.

The 3-Paragraph Cover Letter

Paragraph 1: The Hook (2-3 sentences) Why you’re excited about THIS role at THIS company. Be specific.

Paragraph 2: The Proof (4-5 sentences) One relevant story that proves you can do the job. Not a list—a narrative.

Paragraph 3: The Close (2-3 sentences) Why you’d be great for them specifically. Clear call to action.

Total length: Half a page. Maybe three-quarters max.

Writing Cover Letters with AI

Step 1: Generate first draft

AI: "Write a cover letter for this role.

Job: [Title] at [Company]
Key requirements: [Top 3-5 from job description]

My relevant experience:
- [Relevant accomplishment 1]
- [Relevant accomplishment 2]
- [Relevant accomplishment 3]

Why I'm interested in this company:
[Your genuine reason—be specific]

Keep it to 3 paragraphs, under half a page.
Don't use generic phrases like 'I believe I would be
a great fit.' Be specific and conversational."

Quick check: Before moving on, can you recall the key concept we just covered? Try to explain it in your own words before continuing.

Step 2: Make it sound like you AI drafts are a starting point. Read it aloud. If it doesn’t sound like how you’d actually talk, rewrite those parts.

Step 3: Add something personal The best cover letters have one specific detail that couldn’t appear in anyone else’s letter. Maybe:

A specific project of theirs you admire
A genuine connection to their mission
A relevant anecdote from your experience

The “Why This Company” Problem

The hardest part: genuinely answering why you want to work there.

Weak answers (don’t use these):

“I’m impressed by your growth” (generic)
“I align with your values” (vague)
“It’s a great opportunity” (lazy)

Strong answers (specific and real):

“I’ve used [your product] for 3 years and have opinions about where it could go”
“Your recent [specific project] showed an approach to [problem] I haven’t seen elsewhere”
“I want to work in [industry] and you’re doing [specific thing] better than anyone”

If you genuinely can’t answer why you want to work there, maybe you shouldn’t apply. Or at least be honest with yourself that it’s just a paycheck—and don’t expect your application to compete with someone who actually cares.

Batch Application Workflow

When you’re actively searching, batch similar applications:

Monday: Research Day

Find 10-15 relevant job postings
Quick research on each company
Rank by interest level

Tuesday-Thursday: Application Days

Tailor resumes (10 min each for high-priority)
Write cover letters (15 min each for high-priority)
Skip cover letters for low-priority (if optional)

Friday: Follow-up Day

Track what you’ve sent
Follow up on applications from last week
LinkedIn connection requests to relevant people

When to Skip the Cover Letter

If a cover letter is optional, decide based on:

Write one if:

It’s your dream company
The role is highly competitive
You have a genuine story to tell
Your resume needs context (career change, gap, etc.)

Skip it if:

You’re applying to many similar roles
The company likely won’t read it
You have nothing specific to say about this company
Your resume already tells the full story

Time is limited. Allocate it strategically.

Exercise: Tailor One Application

Pick a job you actually want to apply for.

Spend 5 minutes researching the company
Identify the top 3 requirements from the job description
Match your experience to each requirement
Write a 3-paragraph cover letter with one specific detail

Time yourself. With practice, this becomes a 15-minute workflow.

Key Takeaways

Tailored applications dramatically outperform generic ones
Quick research makes you stand out—most candidates skip it
Resume tailoring: reorder and emphasize based on top requirements
Cover letters: 3 paragraphs, one story, something specific
Be honest about “why this company”—generic answers don’t work
Batch your workflow: research day, application days, follow-up day

Next: Deep company and role research for applications and interviews.

Up next: In the next lesson, we’ll dive into Company and Role Research.