1. What exactly is broken today?
If the team cannot describe the failure mode in one or two sentences, the evaluation will drift. Are leads being missed? Are handoffs weak? Are several inboxes hiding the same customer history? Name the breakage first.
2. Which channels matter enough to centralize?
Not every channel deserves equal complexity on day one. Focus on the channels that genuinely drive acquisition, support volume or commercial risk.
3. Where should the source of truth live?
This is often the decisive question. If the messaging platform and the CRM both seem to own the same data, your implementation will likely become fragile. Decide where the durable record belongs.
4. What is the minimum successful workflow?
Do not begin with the most ambitious automation map. Begin with one clear use case, one routing path and one clean handoff. Success should be visible within a simple operating flow.
5. What should the trial prove?
- That a real message can enter the system cleanly
- That ownership can be assigned with confidence
- That the CRM or downstream workflow stays coherent
- That the team can actually operate the new setup without friction
6. Which assumptions still need vendor confirmation?
This is where official documentation matters most. Pricing details, channel constraints, support scope and feature behavior should be verified with current vendor materials before a final decision.