Opportunity Research – Practical Exercise

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Foundation — Month 4

Job Search Fundamentals • Opportunity Research — Practical Exercise

Research a Real Opportunity in 90 Minutes: A Three-Layer Framework

Job Search Fundamentals — Practical Exercise

The deep dive made the case that a focused, research-driven application — based on real understanding of the role, the organization, and the people — is worth far more than a high-volume approach to applying. This exercise gives you a repeatable framework for evaluating any opportunity you’re seriously considering. Do it once with a role you’re currently looking at, and you’ll have a method you can use for every application that follows.

The Exercise

  1. Choose a role to research (5 minutes) — Select one specific job posting you’re genuinely considering — something you’ve looked at and thought “this could be interesting.” Have the job description open and ready. This is your research subject for the exercise. If you don’t currently have a posting in hand, choose a role type you’re targeting and find a recent posting online to use.
  2. Analyze the role deeply (20 minutes) — Read the job description carefully and answer these questions in writing: What does this role actually need to accomplish? What skills or experiences are mentioned multiple times? What’s noticeably absent from the description that you’d expect to see? What does the language tell you about the organization’s culture or priorities? What questions does this description raise that you’d want answered before accepting an offer?
  3. Research the organization (30 minutes) — Spend time across three sources. First, the organization’s website and any recent news coverage — what’s happening with them right now? Second, their LinkedIn company page — how large is the team, how long do senior people stay, what are their recent hires? Third, employee reviews on Glassdoor or Indeed — not the extremes, but the patterns in the middle. Write down three things you learned that weren’t in the job description.
  4. Identify your connection into the organization (15 minutes) — Search LinkedIn for people who work or have worked at this organization. Do you have any first or second-degree connections? Is there anyone in a related role whose path interests you? Even identifying one person you could potentially reach out to is a useful output of this step.
  5. Make your decision (20 minutes) — Based on your research, write a short paragraph — five to eight sentences — answering three questions: Do I still want to apply? What are the two strongest reasons this role fits me? What is the one thing I most want to find out before I’d commit to pursuing this further? This becomes your personal brief for everything that follows in the application process.

What to Do Next

If your research confirms this is worth pursuing, use your written brief as the foundation for your application materials — your cover letter, your tailored resume, your interview preparation. The three questions you answered in Step 5 should guide every conversation you have about this role. If your research raised serious concerns, give yourself permission to pass — that’s not giving up, that’s using the information well. A few hours of research at the front end is far less costly than weeks invested in the wrong opportunity.

Try It With AI

Opportunity Evaluator

Use this prompt to work through a specific job opportunity with an AI coach — so you can evaluate whether it’s genuinely worth pursuing before you invest hours on the application.


Access the full tool library →

You are a career coach who helps adults evaluate job opportunities before they invest time applying. You help people see past the job description to assess whether a role is genuinely worth pursuing — and what they’d need to know to make a confident decision.

I want to evaluate a specific job opportunity I’m considering.

Ask me these questions one at a time, waiting for my answer before continuing:

1. Describe the role and organization you’re considering — what is it, who is the employer, and what initially attracted you to it?
2. What concerns or unknowns do you have about this opportunity that the job description doesn’t answer?
3. What does this role need to offer for it to be worth a full application — what are your non-negotiables?

After each answer, reflect back what I’ve shared and probe anything important. When we’ve worked through all three questions, help me answer three things clearly: (1) Does this look like a genuine fit worth pursuing? (2) What are the two or three most important things I should try to find out before committing to a full application? (3) What’s the single most important thing I should emphasize in my application materials if I decide to move forward?

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