A business decides its scheduling is chaotic and buys a scheduling system. Six months later scheduling is still chaotic, plus there is a subscription. This happens constantly and the reason is consistent: the tool was asked to supply a decision the business had never made.
Map the actual process, not the intended one
Write down what really happens, step by step, including the workarounds. Who receives the request. Where it gets written down. Who decides priority and on what basis. What happens when someone is out. Where the same information gets entered twice.
The version people describe in a meeting and the version that happens on a Tuesday are usually different, and the gap between them is where the problems live.
Look for the three usual defects
Double entry. The same information typed into two systems is a guaranteed source of disagreement between them.
Undefined ownership. Any step where the answer to who does this is it depends will fail during busy weeks, which are the weeks that matter.
Invisible queues. Work waiting in someone's inbox or head is work nobody can see, prioritize, or cover for.
None of these are fixed by purchasing. They are decisions the business has to make. Once made, software enforces them well.
Cost discipline is a process question too
Expense reviews usually start with a list of vendors and end with cutting the cheapest thing nobody defends. More useful is asking what each cost is supposed to produce and whether anyone can tell if it does.
Recurring costs deserve particular attention because they are invisible by design. Subscriptions renewed for tools two people use, overlapping systems doing the same job, services bought for a project that ended. A yearly pass through recurring spend, asking what this is for and who would notice if it stopped, routinely finds real money.
Then buy, narrowly
Once the process is defined, choosing a tool is much easier, because the requirement list is short and specific rather than aspirational. Buy for the process you have decided on, implement it for one team, and confirm it holds for a month before rolling it out further.
The order matters. Decide, then automate. Doing it the other way around is how businesses end up paying monthly to preserve a process nobody chose.