First, some context. The latest from the US justice department saying that they will be focusing on finding "ANTIFA leaders" is incredibly troubling for anyone involved in leftist groups. I foresee a lot of good activists, regardless of how far left they actually are, arrested on trumped up charges in order to squash opposition.

Organizing is essential to resist fascism. This is made more difficult by the pandemic, as in person meetings bring a huge, almost unacceptable risk. As such, many orgs have been turning to platforms like Slack instead. Trouble is, Slack logs are not encrypted and I am certain that as a business based in the US Slack will not put up a fight to keep user data safe if the feds come calling.

I'd like to collect a decent list of alternatives. Important factors include encryption, ownership, open source status, ease of use, federation, scalability, hosting, cross platform, and anything else you can think of.

Input wanted for an article.

Let's say that your company is considering the purchase of an expensive new application to help in the company's software development. The demo looks great, and the feature list makes it sound perfect for your needs. So your Management arranges for a proof of concept license to find out if the software is worth the hefty investment. The boss comes to you to ask you to be in charge of the PoC project.

I'm aiming to write an article to help developers, devops, and testers determine if a given vendor's application meets the company's needs. The only assumption I'm making is that the software is expensive; if it's cheap, the easy answer is, "Buy a copy for a small team and see what they think." And I'm thinking in terms of development software rather than enterprise tools (e.g. cloud-based backup) though I suspect many of the practices are similar.

Aside: Note that this project is beyond "Decide if we need such a thing." In this scenario, everyone agrees that purchasing a tool is a good idea, and they agree on the baseline requirements. The issue is whether this is the right software for the job.

So, how do you go about it? I'm sure that it's more than "Get a copy and poke at it randomly." How did (or would) you go about designing a PoC project? If you've been involved in such a project in the past (particularly if the purchase wasn't ideal), what advice could someone have given you to help you make a better choice? I want to create a useful guide that applies to any "enterprise-class" purchase.

For example: Do you recommend that the PoC period be based on time (N months) or workload (N transactions)? How do you decide who should be on the PoC team? What's involved in putting together a comprehensive list of requirements (e.g. integrates with OurFavoredDatabase, meets performance goals of X), creating a test suite that exercises what the software dev product does, and evaluating the results? ...and what am I not thinking of, that I should?