Questions CS Leaders Should Ask in the Interview

Interview the company before you take the CS leadership job, and make the decision based on what you heard.

Most CS leaders who end up in the wrong role saw the warning signs in the interview. They just didn't ask the question that would have made them impossible to ignore, and six months in they find out they're accountable for net retention with no say over headcount, pricing or who Sales signs.

This workbook gives you 105 questions in 16 categories, from budget and runway to why the role is open, with 34 marked must ask and a suggested person to ask each one. Record what each company said, mark every answer green, yellow or red, and the Summary tab scores up to three companies side by side, weighted by what matters most to you. It tracks your non-negotiables too, and tells you whether to walk away, keep asking or decide. The interview is the moment you have the most power in this relationship, so use it.

What's included

• Questions CS Leaders Should Ask in the Interview workbook in Excel, plus a make-a-copy link for Google Sheets

• 4 tabs: Start here, Questions, Evaluate and Summary

• 105 questions in 16 categories, with 34 must-ask questions, who to ask and what each category reveals

• Scoring for up to three companies side by side, with a weighted fit score, your non-negotiables and a clear read on where you stand

• A step-by-step PDF guide with the five questions that matter most, how to read the answers, red flags to listen for and a Steal This offer readiness check

Who it's for

Heads of CS, Directors, VPs and Chief Customer Officer candidates interviewing for their next role or weighing more than one offer.

How it works

Digital download. Your files are ready right after checkout. Open the Excel file, or use the link included with your download to make your own copy in Google Sheets. No physical item will be shipped.

Bundle and save

This template is part of the New CS Leader Bundle: 8 templates for $79, about half the price of buying them one at a time. Want everything? The Complete Architect Collection has every template in the collection for $299.