Project Risk Prompt Generator

What this generator does

Draws a category of project risk to think about. Risk registers are usually written by asking what could go wrong, which reliably produces the risks the team already discusses — a category prompt reaches the ones nobody has mentioned.

What you'll get

This generator draws from a hand-checked list of 8 entries. Here is a spread of 6 of them, so you can see the style before you generate:

• What happens if the person doing the most critical work is suddenly unavailable?
• What assumption are we making that we haven't actually verified?
• What's the dependency most likely to slip, and what's our backup plan?
• What's the quietest warning sign we might be ignoring right now?
• What happens if the scope grows but the deadline doesn't move?
• What's the one thing that, if it went wrong, would be hardest to recover from?

A fixed sample of the list, not a live draw — your own results are picked at random from all 8, without repeating until the list runs out. Original authoring for Generate Random — general project-planning risk prompts.. Last reviewed 2026-07-18.

How to use this tool

1. Press generate for a question.
2. Discuss it with your project team.

Worked examples

Two of the eight

"What's the quietest warning sign we might be ignoring right now?" and "Who outside this team could derail this, and do they know they're involved?"

Common use cases

• Project-planning risk reviews
• Sprint-planning discussions
• Pre-mortem exercises

How this generator works

One question is picked whole from a fixed pool of eight risk categories, each phrased as a specific scenario — "What happens if the person doing the most critical work is suddenly unavailable?" — rather than the open "what could go wrong" that tends to surface only the risks already on everyone's mind.

Randomness and fairness

Categories are drawn uniformly with the browser's cryptographic random number generator, with no weighting by how likely a category is to matter for your project.

For how randomness is produced across the whole site, see how Generate Random works.

Limitations and good to know

• Eight categories is a small pool; running a pre-mortem with this generator alone will not cover every kind of project risk.
• This is a discussion prompt, not a risk-assessment methodology — it names a category to think about, not a probability, an impact score or a mitigation.

Practical tips

• Run through five or six categories rather than one; the value is in coverage.
• For each risk, write what would tell you it is happening. A risk with no early signal cannot be managed.
• This is a prompt for discussion, not a risk assessment methodology — use your organisation's own framework for anything formal.