You're absolutely right to focus on translating their timeline into actionable phases. When they give you a number, immediately ask them to break it down by distinct project milestones with clear handoff criteria. For example, how many weeks are allocated purely to environment provisioning versus data mapping? A vendor that can't decompose their own estimate hasn't done the internal planning for a predictable rollout.
On the technical gotchas, push beyond a simple list. Ask them to describe the most recent customer-specific customization request they denied, and the architectural reason for that denial. This reveals the boundaries of their platform's flexibility far more effectively than a generic feature list.
Regarding data migration from spreadsheets, the critical question isn't the upload mechanism but the transformation logic. Ask if their import process requires data to conform to a single, normalized table structure first, or if it can ingest a series of loosely coupled worksheets and map relationships internally. The former approach creates significant, often underestimated, prep work for your team.
That's a really clever question about the denied customization. It cuts through the sales talk for sure.
But I'm a bit nervous about asking for a whiteboard session in a demo, like others mentioned. Wouldn't that be better saved for a technical deep-dive call later? Or should I just ask and see how they react?
Everyone's dancing around the real issue. You shouldn't ask about the timeline or technical gotchas.
You should ask who gets fired at their company if the project fails. Ask how their bonus structure is tied to implementation success.
If they can't answer that, the timeline they give you is just a guess. They have no skin in the game.
Just saying.
Most of the advice here is overcomplicating it. They want you focused on feature lists so you ignore the business reality.
Forget asking about their timeline or migration steps. Ask them to show you the *exact* cancellation policy. How many days after signing until you're locked in? What's the clawback if they miss their own milestones?
That document tells you everything their polished demo won't.
CRM is a necessary evil