How to Plan a Line of Questioning
Decide what you need to learn and how you will get there before the conversation starts. Define the learning goals, prepare a broad opener, sequence from broad to specific, and map where key answers would take you next.
Developing
Start here. Build the foundation.- 1
Before a planned conversation, create a note for it and list the two or three things you must understand by the end. Write the learning goal, not the agenda topic. You know it worked when you can check afterward whether you actually learned each item.
- 2
In that same note, draft your first real question and make it wide open, something that invites a few minutes of talking. Have it ready before you sit down, so the other person sets the framing before you steer.
Proficient
Build consistency and rhythm.- 3
When you have several questions on a topic, lay them out so the open, exploratory ones come first and the narrow, confirming ones last. You collect the person's spontaneous account before you start checking specifics.
- 4
For your most important questions, note where you will go depending on how the person answers. Planning two or three branches keeps you following the answer instead of reading the next scripted question.
Mastered
Operate at the highest level.- 5
For conversations the team runs again and again, such as discovery calls or interviews, build a shared guide: sequence the questions, note the intent behind each, and store it where colleagues can find it. It is working when they run sharper conversations because they picked it up.
Common Pitfalls
Avoid the common failure modes.- Treating the meeting topic as the goal. You discuss the subject but never learn what you needed. Write the learning goal, not the agenda topic, in your notes.
- Writing a long, flat list of questions. You ask the narrow ones first and bias the answers. Sequence from broad to specific before you start.
- Over-preparing to the point of reading questions off a page. You miss what the person actually says. Keep the plan to three learning goals and one broad opener.