Interviewing the Interviewer: The Executive Company-Health Diligence Toolkit (Fillable PDF)

You'd never approve a multi-year capital commitment on a pitch deck and a pleasant dinner. An executive role is exactly that commitment — priced in years of your career, equity that may never clear the preference stack, and reputational exposure you carry into your next search.

This toolkit turns the interview loop into a structured diligence process. Built for VPs, C-level candidates, and senior leaders evaluating an offer, it gives you the exact questions, scripts, and scoring system to assess a company's culture, leadership, budget, and financial stability — before you sign.

Who this is for

Your last role looked great in the loop — then you inherited a frozen budget and a mandate that existed only in the job description. This is for you if you're a VP or C-level candidate who's been burned, or watched peers get burned, by companies that interviewed better than they operated. If you'd never approve an acquisition on vibes, stop accepting jobs on them — this is the diligence process.

Inside the 24-page fillable PDF:

• Module 1 — The Executive Evaluation Mindset: the stakeholder map (what the CEO, CFO, peers, and board each uniquely know), question sequencing across rounds, and the Ask-Three-Ways triangulation technique
• Module 2 — Culture & Operational Reality: 25 questions with "strong answer vs. weak answer" calibration for decision rights, operating cadence, turnover, and your mandate
• Module 3 — Financial & Budget Health: runway, burn multiple, revenue retention, preference stacks, and your approved budget — with a color-coded benchmark table
• Module 4 — Fillable Assessment Scorecard: a weighted 5-dimension scoring system with 72 form fields, an interview signal log, and 7 word-for-word scripts for sensitive asks
• Module 5 — Red Flags & Risk Matrix: a 20-signal catalogue, likelihood-impact grid, deal-breaker thresholds, and a risk-to-contract-term mapping
• Plus a one-page quick reference with 20 questions to carry into any loop

Fillable in Acrobat, Preview, or any modern PDF reader. Save a copy per company. Print versions work equally well with a pen.

50+ diligence questions. One weighted scorecard. Zero HR platitudes.

Instant download • US Letter • Edition 2026