Open the conversation
“Before we discuss solutions, what would make this conversation genuinely useful for you?”
Use these prompts as adaptable structures, not rigid lines. Replace the bracketed language, stay present and make the conversation relevant to the person in front of you.
“Before we discuss solutions, what would make this conversation genuinely useful for you?”
“If this works exactly as intended, what changes in the next ninety days?”
“What is the practical cost of leaving this unresolved for another quarter?”
“Where does this sit among the other initiatives competing for attention right now?”
“Who else needs confidence in the decision, and what will matter most to them?”
“What have you already tried, and what prevented it from delivering the result you expected?”
“Which outcome or measure will tell you that the decision was worthwhile?”
“What concerns would make you hesitate even if the commercial case is strong?”
“Based on what you have shared, may I show you the part that is most relevant rather than everything we offer?”
“The reason this matters is that it helps you achieve [outcome] without [current friction].”
“How closely does that match the result you described at the start?”
“When you say the investment feels high, are you comparing it with another option or with the cost of doing nothing?”
“What would need to be true for this to become the right time?”
“Which part requires more confidence: the outcome, the process, the timing or the investment?”
“I can adjust scope or timing, but I do not want to remove the elements required to produce the result. Which variable is most flexible?”
“If we resolved that point completely, is there anything else that would prevent you from moving forward?”
“Shall we map the next three steps now so both sides know exactly what happens after today?”
“Do you have enough clarity to make a decision, or is there one final question we should address first?”
“Would the focused option or the complete option be the better fit for the outcome you described?”
“Since we spoke, I considered your point about [priority]. Here is the most useful way to approach it.”
“Has the priority changed, or would a simpler next step make it easier to continue the conversation?”
“To keep momentum, can we agree who owns each next action and the date it will be completed?”
“Who else in your network is facing a similar challenge and would value the same clarity?”
“What would make the next stage of our work more valuable than the first?”
“Whether the answer is yes, no or later, can we agree on the decision so neither side is left uncertain?”