Notice the cost of the workaround
A spreadsheet or off-the-shelf tool can be the right answer for a long time. Custom software becomes worth investigating when repeated manual steps, disconnected systems, or brittle workarounds create a measurable operational cost.
Describe the workflow in concrete terms: who uses it, how often it occurs, what errors look like, and what the current process prevents the team from doing.
Compare the full cost of ownership
A build is only one part of the cost. Include hosting, security, integrations, support, future changes, and the time needed to train people. Compare that total with licensing and process changes available through existing tools.
A small prototype can help test the riskiest assumptions before a large commitment is made.
Keep the first version focused
Start with the smallest workflow that creates a meaningful improvement. Clear ownership, a realistic maintenance plan, and feedback from actual users matter as much as the technology choice.