Buyer's guide
Twelve questions, asked in the same order, of everyone on your list. The pattern in the answers tells you more than any single answer does.
Print this. Ask every firm on your list the same questions in the same order, and write down what they say. The pattern matters more than any single answer.
| Ask | What a good answer sounds like |
|---|---|
| After we sign, who does the billing run? | A named team. If the answer describes a screen, you are buying software. |
| Who places the trades? | Either answer is fine — but know which one you are getting before you sign, not after. |
| What happens on a Tuesday when a client needs cash raised? | A process that does not require you to open anything. |
| Ask | What a good answer sounds like |
|---|---|
| What is the all-in number, including everything? | One figure, or a clear reason why it depends and what on. |
| What is billed separately? | A short list, volunteered. A long list you had to drag out is the answer. |
| Which of your pricing structures would be cheapest for my firm? | A recommendation, even when it is not the one they prefer. |
| Ask | What a good answer sounds like |
|---|---|
| How many hours of my time? | A number. Weeks of their effort is not an answer to this question. |
| What makes a transition run long? | Held-away assets, unreconciled history, undocumented fee schedules. If they say nothing goes wrong, they have not done many. |
| What was your longest one, and why? | A specific story. Vagueness here is the single most useful red flag on this page. |
| Can I stop if the parallel run does not match? | Yes, in writing, with nothing owed. |
| Ask | What a good answer sounds like |
|---|---|
| What is the contract term and the notice period? | Short term, short notice. Multi-year lockups tell you how confident they are. |
| If I leave, what do I take and who helps? | Everything, in standard formats, with a named person running the exit. |
You are not scoring features. You are looking for two things: whether the answers were specific, and whether anyone volunteered something that cost them. Specificity means they have done this often enough to know. Volunteering a weakness means they expect the relationship to outlast the sale.
Questions this did not answer? Ask them directly — that is what the twenty minutes is for.
Book 20 minutes with KyleQuestions we get asked
Five questions do most of the work. Who actually performs the operational work after signing. Which system owns each number a client sees. Whether trades are generated per mandate or allocated afterwards. Where access control is enforced — in the data or on the screen. And what it costs to leave, including whether your data comes back whole.
Broadly three: build the operation in-house and hire for it, assemble best-of-breed software and accept that someone at your firm becomes the integration layer, or outsource the operation to a partner. Each is defensible. The failure mode is choosing the second while believing you chose the third.
For most firms it is measured in weeks rather than months, and the long pole is rarely the software — it is the quality of the history being carried across. Firms with clean data move quickly. Firms whose custodian retained only a few years of history take longer, because reconstructing the rest is real work.
Almost nothing, when it is done properly. Accounts stay at the same custodian under the same account numbers. What changes is that reporting gets better and arrives on time, under your brand.