You are not
evaluating the software.

Every product in this category demonstrates well. During a demo you are evaluating a presentation about it, not the thing itself.

Why demos do not work

Every product in this category demonstrates well. The demonstration is built from clean data, by someone who uses the product daily, along a path chosen to avoid the parts that are awkward.

You are not evaluating the software during a demo. You are evaluating a presentation about it.

Bring your own data or learn nothing

The single highest-value thing you can do is insist that any evaluation uses your book, not their sample. Your household with accounts at two custodians. Your client with the concentrated legacy position. The account that transferred in with incomplete cost basis.

Vendors who resist this are telling you something. Vendors who agree and then take three weeks are telling you something more specific about implementation.

Questions that change the answer

• After we sign, who does the work? A screen or a named person. Everything downstream follows from this.
• Which system owns each number a client sees? If the answer takes more than a sentence per number, you have found your future reconciliation problem.
• Where is access enforced — in the data or on the screen?
• What does it cost to leave, and what does the export contain?
• What is billed separately from the headline number? Modules, seats, reports, data extracts, onboarding, support tiers.
• What happens when something is wrong? Who owns a billing error, and is it in the contract or in a sentence someone said in a meeting.

Reference calls, done properly

References supplied by the vendor are pre-selected and will be positive. Take them anyway, and ask three questions that are difficult to coach: what surprised you after signing, what took longer than they said, and what do you still do manually.

Then find a firm that left. Ask the vendor directly for one. The response to that request is data whether or not you get the call.

The contract details that matter later

Notice period and renewal terms, including auto-renewal windows that quietly remove your ability to leave. Price escalation. What happens to your data at termination and in what format. Which obligations survive termination. Whether support levels are contractual or aspirational.

The test nobody runs

Ask to speak to the person who would actually handle your account, not the person selling it. In firms where those are the same people, you learn that immediately. In firms where they are separated by three layers, you learn that too — and it is the more useful finding.