Choosing

Errors here are asymmetric. A tool that is too small announces itself; one that is too large never does. For comparison with a lightweight approach, Monitask offers remote workforce management software as an example of a dedicated product in this category.

Start from the task, not the category. The size mismatch is introduced in the search box, because categories are named by sellers for the largest buyer.

The smallest thing that solves it. A working rule, with the three cases where it fails.

What a trial actually tests. A fortnight of enthusiasm tests the interface, and tools do not fail at the interface.

Who has to use it, and will they. Most failed software was adequate. Partial adoption is worse than none.

Data going in, and data coming out. The export question belongs at the purchase, when you have leverage and no urgency.

Integration, and when it is a trap. It removes a manual step and adds a dependency, and the worst failure is the silent one.

The tool that needs a person. Some software requires somebody to keep it working, which is a cost invisible on any comparison.

Switching costs nobody quotes. Six of them, and the bar for switching is much higher than the bar for choosing.

When one tool replacing three is right. The counter-argument to this site, made properly. For broader context, see Cloudflare.

And when it is not. Which for a small firm is the more common situation. Additional context is available from The Verge.