Better Questions Tell Better Stories

[AI Prompts for Jobseekers]

Change is rarely tidy…

And if you’re navigating a new chapter in your career, you’re probably carrying equal parts hope and hesitation.

The noise is also real: job boards, advice threads, “must-do” lists.

In that swirl, one thing consistently cuts through: CLARITY.

Those who move fastest aren’t always the best connected or the most polished. They’re the ones who ask better questions. Who knows how to ask in ways that surface evidence, reduce uncertainty, and nudge action.

They use curiosity like a compass, and make sense of the messy middle by inquiring, not guessing. Using questions that cut through uncertainty, open doors you didn’t know existed, and help you see the game you’re playing in a completely different way.

"A good question doesn’t just get you an answer, it changes how you see the problem."

And now we have a tool that will answer almost anything we ask: AI.

The catch? The quality of your answers depends on the quality of your questions.

When the Job Search Feels Like a Guessing Game

Perhaps you’re sitting at your desk, staring at yet another job description. It’s vaguely interesting, but is it really for you?

You tweak your resume, attach the same cover letter you’ve used three times before, and hit send. You skim the company website, click “About Us,” and absorb a handful of statements that could belong to any company in the industry. You rehearse interview answers in your head, but there’s a nagging feeling: If they ask something specific about the company… will I even know?

Networking feels awkward. You send a generic LinkedIn request to the hiring manager and get… silence.

It’s not that you’re doing nothing, it’s that you’re doing the same things as everyone else. You’re playing a high-stakes game with the same moves, the same information, and the same level of preparation as the hundreds of other people applying.

The Moment Everything Starts to Click

The turning point often comes in a moment of frustration…

Maybe you’ve had three interviews that all ended in “We’ve gone with another candidate.”

Or maybe you’ve applied for twenty roles and heard nothing back…

“It’s not just about getting answers, it’s about asking better questions.”

Generic prompts produce generic answers.
Vague outreach gets vague replies (or worse, none).

But precise, purposeful, context-rich questions change everything.

Here’s the difference:

• Prompt: “Tell me about this company.” → You get a Wikipedia summary.

• Prompt: “Summarize this company’s mission, core services, and recent news from the past six months using their website and trusted press sources.” → You get a strategic briefing you can use to shape your resume, cover letter, and interview plan.

This is when you realize: AI isn’t just a search tool. It’s a job acceleration tool, but only if you feed it the kind of questions that make you stand out.

A Mini-Framework for Better Questions

Use this rubric to design prompts that return decision-ready answers:

• Intent: What decision will this answer help me make?

• Context: What inputs am I providing (resume, job description, company URL)?

• Constraints: Timeframe, sources, length, tone (e.g., last 6–12 months; cite sources; ≤200 characters).

• Structure: Ask for a role/persona + output format (e.g., “act as a researcher,” “return bullets/table”).

• Challenge: Which assumption should this surface or test (e.g., “flag gaps or uncertainties”)?

Question Archetypes You’ll Use

• Diagnostic: What’s true right now? (baseline)

• Comparative: How does option A differ from B? (delta)

• Counterfactual: What would change if X weren’t true? (what-if)

• Constraint-led: What’s best under limits A/B/C? (practical)

• Leading indicator: What early signals predict success here? (forward-looking)

• De-risking: What could fail, and how would I know? (pre-mortem)

You’ll see these archetypes naturally appear in the prompts below.

Turning Curiosity into Career Strategy

At its core, a well-crafted question does three things:

1. it provokes thought,

2. uncovers insights, and

3. guides decision-making.

This is the kind of question that doesn’t just seek an answer but opens entirely new paths for exploration. And when AI is involved, these questions become even more valuable; they peel back the layers, revealing not just what we think we know but the areas we haven’t even considered.

Let’s follow Alex as he transitions from a scattered approach to a focused, confident, and ultimately successful job hunting strategy.

Use AI as if it were public. Don’t paste your full contact block or home address; don’t upload internal docs or take-home assignments; and always check the original sources before you repeat any “facts.” Keep placeholders where details aren’t public, then personalize offline.

Step 1: Company Research – From Blindfold to X-Ray Vision

Instead of passively reading a company’s homepage, Alex asks AI:

I'm interviewing at [Company Name] for the role of [Job Title].

Please act as a corporate researcher and provide:

1. The company's mission and vision;

2. Its key products or services; and

3. Major news, milestones, or developments over the past 6 months (using their website and trusted news sources)

Structure the response clearly and include sources or citations.

In minutes, Alex has a briefing that moves beyond “We strive to innovate” into:

• The CEO’s recent statement about expanding into new markets.

• The company’s latest product launch and the customer feedback it’s generating.

• Their sustainability initiative that aligns well with Alex’s values.

That context changes how Alex positions himself. It also gives him hooks for his resume, cover letter, and interview questions.

Pro tip: Don’t accept AI’s summary at face value. Click the sources. Validate. Explore.

Step 2: Resume Optimization – From List of Jobs to Targeted Marketing

Alex realizes his resume tells his story, but not necessarily in the way this company needs to hear it.

Instead of vague “resume tips,” Alex prompts:

I'm applying for [Job Title] at [Company Name].

Attached is my current resume. 

Please:

1. Review for relevance, clarity, and impact based on the job description;

2. Suggest specific improvements (keywords, skills emphasis, quantified achievements) to tailor it for this role;

3. Identify skill or experience gaps compared to the role's requirements; and

4. Recommend practical ways to close these gaps through online courses, certifications, volunteer work or personal projects.

Provide feedback in two parts:

(i) An optimized bullet-point version of my resume and an aligned Executive Summary; and

(ii) A gap-closing plan with resources and timelines.

Now, instead of a generic resume, Alex has:

• A skills section that mirrors the job description.

• Measurable achievements instead of vague responsibilities.

• A short-term plan to address his skill gaps as a buffer in conversation.

Step 3: Cover Letter – From Template to Tailored Story

With company research and an optimized resume, Alex now crafts a cover letter that makes him sound like an excellent fit for the company.

I'm applying for [Job Title] at [Company Name].

Job description: [paste here]

Resume or Executive Summary: [paste here]

Please write a one-page cover letter that:

1. Opens with a strong, personal hook that connects to the role or company;

2. Highlights my most relevant experience, skills, and achievements that align with the job requirements;

3. Explains why I'm passionate about working for this company, referencing their mission, culture, or recent work; and

4. Closes with a confident, friendly call to action.

The tone should be professional yet conversational, free of fluff, and use industry-relevant keywords, specifically tailored to this role and company.

Instead of a generic “To Whom It May Concern” letter, Alex has a story that:

• References the company’s latest campaign.

• Links Alex’s background to the company’s upcoming projects.

• Ends with an invitation to continue the conversation.

Step 4: Interview Preparation – From Nerves to Strategic Conversations

Alex used to walk into interviews hoping he could handle whatever came up.

Now he prepares:

I'm preparing for a [Job Title] interview at [Company Name] in [Industry/Sector].

Please provide:

1. Key industry-specific challenges and trends that are most relevant right now (last 12 months), with brief explanations;

2. How these challenges or trends might specifically impact [Company Name];

3. Practical ways I can demonstrate awareness of these topics during the interview;

4. Suggestions for potential solutions or ideas I could mention; and

5. A list of common interview questions for [Job Title] within [Industry/Sector].

Where available, include citations for further research.

Now, Alex knows:

• The three big market shifts reshaping this industry.

• How those shifts could impact the company’s strategy.

• Informed questions that show he’s done his homework.

Step 5: Networking – From Cold Outreach to Warm Conversations

Instead of blasting connection requests, Alex approaches networking with intention.

He asks AI for two tailored strategies, one for employees, one for hiring managers:

I want to network on LinkedIn to learn more about the [Job Title] role and the company culture at [Company Name].

Please provide:

Part 1: Employees

1. A concise, customizable LinkedIn connection request of less than 200 characters. Give me 3 variants to choose from (value-first, shared context, direct ask); and

2. A follow-up message template for after they accept, asking for insights about the role and culture in a friendly, professional, and conversational style.

Part 2: Hiring Manager

3. A tailored LinkedIn connection request of less than 200 characters; and

4. A follow-up message template to express interest in the role and open the door for further conversation.

Now Alex sends messages that are brief, warm, and relevant, which start getting replies.

What’s the most frustrating part about writing cover letters?

As we bring AI into the job search mix, the questions we ask become even more pivotal. They don’t just determine the quality of the answers but also shape how AI applies its knowledge.

When questions are vague, AI often defaults to providing something that “sounds” good rather than something truly useful. The danger here is subtle: a pleasing AI answer can feel like progress, but it might not move you any closer to your goal.

That’s why questions must be tailored not only to the role and industry, but also to how AI works, so they’re not just good questions, but the right questions for the moment.

How Better Questions Build Momentum

Alex is being invited to interviews, walking into conversations armed with specific details, and receiving referrals from connections he's intentionally built. And the difference isn’t magic, it’s the shift from “What do I need to say?” to “What do I need to ask?”

Because when you stop asking vague questions, you stop getting vague results. And in career change, clarity isn’t just helpful, it’s the bridge between where you are and where you want to be.

The most effective job seekers don’t just ask good questions; they question the answers, too. They challenge assumptions, test implications, and explore different viewpoints. They don’t accept responses at face value, whether from an AI system, a hiring manager, or a networking contact. Instead, they validate, dig deeper, and follow up. That’s how they move from surface-level information to the insights that create opportunities.

Sometimes, the shortest path to a new chapter starts with a single, well-aimed question.

Download your FREE copy of A Strategic Approach to Career Change.