1. Start with the work, not the software category
“We need WhatsApp” is too vague to be useful. What teams usually need is a better way to handle one of three things: campaign activation, support workflow, or a wider cross-channel conversation model.
2. Separate marketing from operations early
Some demos shine when they show broadcasts, journeys, and ads. Others shine when they show team routing, inbox control, and shared visibility. Do not assume one product is equally strong at both just because the UI feels polished.
3. Draw the daily flow you need to sustain
- Who starts the conversation?
- How many people touch it after that?
- Where should the history live?
- Which steps need automation and which need human review?
4. Ask about complexity cost, not just feature upside
A wider platform is not automatically a better one. Breadth has a cost: onboarding, maintenance, process design, and the burden of features the team may never use well.
5. Validate reporting, permissions, and governance
A sensible buying process should include questions about native reporting, approval flow, template handling, access control, and what happens when the team or the workflow gets more demanding.
6. Be honest about integrations
An integration only matters if it supports a process you actually run. If it only sounds good in a future-state story, it may be adding noise rather than reducing risk.
7. Close the shortlist with questions that can be tested
- What daily task becomes easier in the first month?
- What important task still sits outside the product?
- What team capability is required to make the tool work well?