Preparing questions about the prospect's actual workflow

Workflow questions uncover what people do, not what a sales team assumes they do. Prepare a few prompts that follow a recent case from trigger to result, then allow the prospect to describe the path in their own terms.

Follow one event

Ask the prospect to choose a typical recent example. What started the work? Who received it? What information did they need? Which system or person held it next? What counted as complete? If there was an exception, how was it resolved?

These questions reveal hand-offs and delays without suggesting that your product is the answer.

Avoid leading prompts such as “Does your manual approval process waste hours?” They contain an unproved diagnosis and invite agreement rather than explanation. Replace them with “What happens when an approval is late?” and “How often did that occur last month, if you know?”

Treat an estimate as an estimate.

Listen for boundaries

Clarify which team owns each step and which rules cannot change. A workflow may be deliberate because of a control requirement.

Ask what already works well. If someone names a delay, explore its cost in terms they recognise—missed deadline, rework, customer wait or staff time—without inventing a number.

Before the call, choose no more than a few essential questions. During it, follow surprising answers instead of forcing the planned order.

Finish by summarising the sequence and asking where you misunderstood it. That correction is often more valuable than another scripted question.

Common Workflow Pain Points (Based on Industry Insights)