Start with the work
Ask who experiences the problem, how they handle it today, where time or confidence is lost, and which part of the process genuinely needs to change. A tool should answer a specific constraint—not a general desire to modernise.
Look for the informal systems already carrying the work: spreadsheets, messages, personal checklists, and people who translate between teams. They reveal both the unmet need and the adoption challenge.
Make the trade explicit
Every new platform introduces another model to learn, another integration to maintain, and another source of truth to negotiate. Compare that ongoing cost with the value of the behaviour it enables.
The right decision may be to buy, build, simplify, or remove. Good technology strategy keeps all four options available until the evidence points clearly.