The Aftermath
Last week, I had to let go of people I respect deeply—skilled, creative, generous team members who didn’t do anything wrong, but who found themselves on the wrong side of forces outside their control.
It was one of the hardest weeks I’ve had recently as a leader (I published a bit of a rant about the experience here.)
And as I sat with the weight of those conversations, one thought kept coming back: we spend so much of our careers building momentum—when one moment stops it cold, how do we reclaim momentum?
This week’s Red Thread is about what happens next.
It’s for anyone who’s been laid off, let down, or left wondering what their next move should be.
While you can’t control the market, the org chart, or the budget cuts—you can control how you respond. You can be more than a job seeker. You can be what Madeline Mann refers to in her book Reverse The Search as a job shopper—evaluating, qualifying, and designing your next role with focus and intention.
And in that process, AI can be your partner—not just to write your resume, but to sharpen your strategy, clarify your story, and help you regain your footing.
This issue is for anyone in transition—and for those who want to support them.
Let’s dive in on how to use the tools we have to build something better from here.
How to Job Shop with AI
Instead of approaching your job search like you’re auditioning—approach it like you’re evaluating. Like you’re shopping. That’s the core idea behind Madeline Mann’s Reverse the Search strategy: stop chasing jobs, start qualifying them.
And here’s where AI comes in.
Use it not just to write cover letters, but to:
- Research company culture through tone analysis of execs’ LinkedIn posts.
- Map career pivots by comparing your skills to real job descriptions.
- Refine your positioning by training AI on your best testimonials and turning them into a brand narrative.
AI can be your:
- Market analyst
- Resume stylist
- Networking scriptwriter
- Interview role-play partner
You’re not just “applying.” You’re designing a better next move.
Try this: Use tools like ChatGPT, Claude,orPerplexity to turn your career narrative into a strong, story-led elevator pitch. Upload your resumé or LinkedIn profile and ask it to summarize your last role, based on what you provide, in the tone you want to be known for.
Supercharge Your “Job Shopping” with These 5 Prompts
Copy + paste the prompts below into ChatGPT, Claude, or Perplexity, to help you land your next gig.
1. Discover if You’re a Proactive or Reactive Job Seeker
Prompt:
Act as an experienced career coach. Ask me 5 questions, one at a time, to help me understand if I’m a proactive or reactive job seeker. At the end, rate me from 1–10 based on my responses (1 = very reactive, 10 = highly proactive). Then, for each area, share one specific strategy to improve and become a more proactive job seeker.
2. Reverse Engineer Any Job Description
Prompt:
Act as a recruiter with deep experience writing job descriptions. My goal is to land an interview by uncovering what the company really wants. Read the job description I paste below and answer the following five questions for me:
- What’s the role?
- Who’s the company?
- What’s the salary?
- What are the main responsibilities?
- What are the 3 most important skills mentioned?
Then, bold each skill, give a real-world example of it in italics, and share one actionable way someone could learn that skill if they don’t have it yet. Here’s the job description: [paste job].
3. Rework Your Resume into a Results-Driven Document
Prompt (a):
Act as an expert resume writer with 30+ years of experience helping candidates land top jobs. Highlight the 5 most important responsibilities in this job description: [paste job description].
Prompt (b):
Based on those responsibilities, help me rewrite my resume bullets. Use this format: “I accomplished A by doing B, which led to C.” Each bullet should include a clear action, measurable result, and relevant keyword. Avoid jargon, do not make information up, and stay under 60 words. Here’s my resume: [paste resume].
4. Prep Like a Pro for Behavioral Interviews
Prompt:
Act as an expert interview coach and former hiring manager. I’ll give you my job description and resume. Then, help me build a table with 10 interview stories—one for each of these topics: Leadership, Teamwork, Challenges, Problem Solving, Communication, Decision Making, Initiative, Organization, Time Management, and Ambiguity.
For each, write a question and a “STAR” response (Situation, Task, Action, Result) using keywords from my resume and the job description. Keep it clear, specific, and conversational.
5. Simulate a Real Salary Negotiation
Prompt:
Act as an expert recruiter and negotiation coach. I want to role-play a salary negotiation using the following job offer details:
- Name: [insert name]
- Job: [insert job]
- Company: [insert company]
- Location: [insert location]
- Offer: [insert salary]
- Target: [insert desired salary]
- Market Rate: [insert market rate]
Play the role of the recruiter. Ask me up to 10 tough negotiation questions. Wait for my response before continuing. At the end, rate my performance from 1–10 and give clear feedback on how I could improve next time using proven negotiation tactics. If I say “end simulation,” wrap up with key takeaways.
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