Tools · tool stack
Shadow IT inventory interview guide
Find and rationalize: not shame.
What's stuck?
Type A
AI already sitting in the source tool
Fits when: most of the truth for “interview prompts to find tools teams bought under the radar” lives in one place.
Skip if: the inputs live in four places that do not agree.
Type B
A connector that builds the pack
Fits when: the hour goes to assembly, not judgment. Think automation you may already pay for.
Skip if: nobody will keep the connections alive.
Type C
A writing or structuring layer on finished inputs
Fits when: inputs already exist; the hour is the first draft.
Skip if: the inputs are still a pile of screenshots.
Say the stuck step out loud
If you cannot finish this sentence, pause buying: interview prompts to find tools teams bought under the radar.
Start with a map, not another tab.
For / Not for
For
- Finance finds tools after the card charge
- You can point at last week’s version of this work (a doc, a thread, a CRM view).
- A human still owns judgment, exceptions, and the send button.
Not for
- Punitive gotcha culture
- You have not named an owner for the workflow.
- You are shopping to avoid writing a one-page outline of the current steps.
- The current process is unclear to you. AI will scale the confusion.
- You are shopping to avoid naming an owner.
- You already have AI sitting inside a tool you pay for, and you have never pointed it at this stuck step: interview prompts to find tools teams bought under the radar.
- The pitch is a ranking list. Rankings do not know your stack.
- Someone wants you to rip out a working habit for a platform you will not administer.
This week plan
How to choose
- What is the output? Name the artifact you already produce. Buy for that output, not the demo.
- Where does truth live? If three systems disagree, a new AI layer will disagree louder. Name the source of truth first.
- What should a human still do? Usually: fit, exceptions, tone. Automate gather and first draft. Keep judgment.
- Will this run if you are out Thursday? If no, you bought a helper for yourself, not a workflow.
Named stuck step: interview prompts to find tools teams bought under the radar.