Questions to ask about technology and software

Is this single-tenant or shared, and what exactly is isolated between customers?

Shared infrastructure is normal, but the isolation boundary decides what a noisy neighbor can do to your performance and what a restore looks like. A vague answer often means row-level separation in a shared database, which you want to know before your security review finds it.

From: Technical Questions to Ask When Implementing New Software

Have any sites you worked on lost significant traffic to an algorithm update or a manual action?

Anyone with real tenure has lived through a bad update, and the recovery story reveals their judgment under pressure. Listen for whether they diagnosed a cause and changed course, or simply waited and hoped.

From: Questions to Ask When Hiring an SEO Company

What does implementation involve, and how much of it is our work?

Vendors quote their own hours and leave out your staff's time for data cleanup, configuration decisions and testing, which is often the larger share. Ask how long a customer like you took from signature to genuinely live.

From: Questions to Ask a Software Vendor

What do you do when two engineers disagree about a design?

Listen for a mechanism, a written proposal, a decision owner, a time limit, rather than a belief that good people work it out. Teams without a tiebreaker tend to relitigate the same decision for months.

From: Questions to Ask Engineering Manager

How many times does the letter r appear in the word strawberry?

Language models read text as chunks rather than letters, so counting characters inside a word is genuinely awkward for them. Wrong answers here are usually stated with complete confidence, which is the more instructive part. If the assistant runs code to count, you are testing the tool rather than the model.

From: Questions to Ask AI to Break It

What surprised you at the last organisation like ours?

This gets you a real story rather than a category, and the surprise is often something mundane such as a shared administrator password or a server nobody knew was still running. It is also a fair test of how much comparable work they have actually done.

From: Questions to Ask Cyber Security Expert