How to evaluate software in an hour: a due diligence checklist

Most software is judged from a distance: a landing page, a deck, a demo video, a review. All of those are made by people who want you to like the product. The only source that cannot spin is the product itself.

Here is the routine I use when I look at a tool, as a buyer, as a user, or as someone deciding whether a business is worth a closer look. Call it software due diligence for one hour, with no spreadsheet. I will run it on AwaCut as I go, because I would rather be judged by it than by my own copy.

1. Install it on a machine you care about

Not a VM. Not a throwaway account. The real thing, on your real computer. Installation is the first interaction and it tells you what the team thinks of your time.

What to watch: Is the installer signed, or does the operating system warn you? Does it ask for permissions it has no business asking for? How big is it, and does the size make sense for what it does?

AwaCut: the installers for macOS, Windows and Linux are linked from the product site. The macOS and Windows builds are signed. The download is large for a utility, because the AI model ships inside the app rather than living on a server. That is a real trade-off, and a sign of the design, not a bug.

2. Give it your own data, not the sample

Every demo works on the demo files. The question is what happens with yours.

Pick ten real files, including at least one awkward case: a photo with hair, a transparent object, a busy background, a very large image, a format you are not sure is supported.

AwaCut: drop a folder, not a file. Include an iPhone HEIC if you are on a Mac. Include a 20 megapixel image. Look at the edges of the cutouts at 100%, not in the thumbnail. The first ten photos are free, so this test costs nothing.

3. Turn off the internet

Then try again. This single step separates “software you have” from “software you are renting”.

What to watch: Does it still open? Does it still do the main job? Does the trial or licence check fail closed?

AwaCut: it is built to pass this test. The model, the processing and the trial counter are all on the machine. If it does not work offline for you, that is a bug and I want to know.

4. Find the limits before the pricing page does

Read the pricing page last, after you have formed your own view of what the thing is worth. Then check the fine print against what you saw.

What to watch: credits, quotas, watermarks, per-device limits, “fair use” clauses, and whether the free tier is actually usable.

AwaCut: there are no credits and no per-photo limit; the pricing is a yearly licence for a fixed number of computers. The current price and the exact terms are on awacut.com, not here, so that there is one page to keep correct.

5. Break something, then ask for help

Feed it a corrupt file. Fill the output folder’s disk. Close it mid-batch. Then write to support with a real question and see how long the answer takes and who writes it.

What to watch: Does the app fail loudly and specifically, or silently? Is the support address a person or a form? Does the answer address your question or paste a help article?

AwaCut: support is an email address, answered by me. The app is meant to tell you which file failed and why, and to keep the rest of the batch going.

6. Look at how it changes

Open the changelog. A product’s release notes are the most honest document a company publishes, because every line is a thing that was wrong or missing.

What to watch: frequency, specificity, and whether the notes are written for users or for investors. “Improvements and bug fixes” is a flag. “Fixed: HEIC photos from iOS 18 opened rotated” is a team that is paying attention.

AwaCut: the changelog is on the product site and lists each version with what changed. Read a few entries and decide for yourself whether it reads like a real product.

The checklist, and why it matters more than the pitch

A pitch is optimised for a room. A product is optimised, or not, for a desk. When I spent my day in San Francisco the thing that moved the conversation was not the slide about the market. It was people dropping their own photos into the app and watching the backgrounds disappear with the Wi-Fi off.

Install it on a real machine, use your own files, cut the internet, read the pricing last, break something and ask for help, read the changelog. That is the whole checklist.

So when someone shows you software, ask to open it. And when I show you AwaCut, I would rather you open it too.