The questioning page of the Managing Your Opportunities workbook opens with a thought from the writer Madeleine L’Engle: that the moment we begin to think we have all the answers, we forget the questions. It then sets out two boxes, one for open questions and one for closed questions, each asking for a definition, examples and when to use them.
It is one of the most practical pages in the workbook. The kind of question you ask shapes the kind of answer you get, and in customer conversations, answers are everything. This article fills in those boxes and goes further: how to combine question types, how to sequence them, and which questioning habits to avoid.
Why questions matter so much
In a sales or customer conversation, questions do several jobs at once:
- They gather information you cannot get any other way: needs, priorities, constraints, worries.
- They show interest. Thoughtful questions signal that you care about the other person’s situation.
- They help the customer think. A good question can help someone clarify a problem they had not fully articulated, even to themselves.
- They guide the conversation without dominating it.
- They check understanding, preventing the illusion of communication discussed in the previous article.
A conversation in which you ask good questions and listen carefully is usually more persuasive than any presentation, because the customer arrives at their own conclusions.
Open questions
Definition
Open questions invite a full, free answer. They cannot be answered with a single word. They typically begin with what, how, why, tell me about or describe.
Examples
- “How do you handle maintenance scheduling at the moment?”
- “What prompted you to look at this now?”
- “Tell me about the last time this problem caused trouble.”
- “What would a good outcome look like for you?”
- “How will you decide between the options?”
- “What concerns you most about making a change?”
When to use them
- Early in a conversation, to understand the situation and build rapport.
- When exploring needs and priorities, where you want the customer’s own words.
- When you hear something important and want to learn more.
- When uncovering concerns, which people often do not volunteer.
- When you want the customer to do most of the talking, which in early conversations is almost always.
A note on “why”
“Why” questions can be powerful, but they can also sound accusatory (“Why did you choose that supplier?”). Softer alternatives often work better: “What led you to choose that supplier?” or “What did you like about that approach?”
Closed questions
Definition
Closed questions invite a short, specific answer: yes or no, a number, a date, a choice between options.
Examples
- “Is the 14th still the date you need?”
- “Do you have budget allocated for this year?”
- “How many sites would this cover?”
- “Would you prefer the standard or extended warranty?”
- “Shall I send the revised quote today?”
When to use them
- To confirm facts and details: quantities, dates, specifications.
- To check understanding: “So the main issue is downtime on line two, is that right?”
- To narrow down options once the broad picture is clear.
- To agree next steps and gain commitment: “Shall we book the site visit for Tuesday?”
- When time is short and you need specific information quickly.
The two together
Neither type of question is better. They do different jobs, and good conversations use both. A useful general pattern is to open wide, then narrow:
- Open questions to understand the situation broadly.
- Probing questions (follow-up open questions) to explore what matters most.
- Closed questions to confirm details and check understanding.
- A closed question to agree the next step.
This pattern is sometimes called a funnel of questions, echoing the sales funnel discussed earlier in this series.
Probing questions
Between open and closed questions sit probing questions: follow-ups that dig deeper into something the customer has said. They are where much of the real insight emerges.
Examples:
- “You mentioned the team is frustrated. Can you tell me more about that?”
- “What happens when that occurs?”
- “How often does that happen?”
- “What’s the impact on your customers?”
- “What have you tried so far?”
- “And what made that not work?”
Probing questions show that you are listening, because they build on the customer’s own words. They also move the conversation from surface symptoms to underlying causes and consequences, which is where the real need usually lies.
A sequence for a discovery conversation
Here is an illustrative sequence for a first conversation with a prospective customer about a workflow problem. It is a guide, not a script.
| Purpose | Question | Type |
|---|---|---|
| Context | “Tell me a bit about how your team works day to day.” | Open |
| Problem | “What’s the most frustrating part of the current process?” | Open |
| Probe | “What happens when that goes wrong?” | Probing |
| Impact | “Roughly how often does that happen, and what does it cost you?” | Probing / closed |
| Urgency | “What’s prompting you to look at this now?” | Open |
| Attempts | “Have you tried to fix it before?” then “What happened?” | Closed, then open |
| Outcome | “If this were solved, what would be different?” | Open |
| People | “Who else would be involved in deciding on a change?” | Open |
| Confirm | “So the priority is reducing rework on custom orders before the busy season. Is that right?” | Closed |
| Next step | “Would it be useful if I came and saw the process on Thursday?” | Closed |
Questioning habits that undermine conversations
Leading questions
Questions that push towards a particular answer (“You’d agree that faster delivery would help, wouldn’t you?”) feel manipulative and produce unreliable answers. People often agree just to be polite.
Multiple questions at once
“How do you schedule work, who’s involved and what software do you use?” Customers answer one part, usually the last, and the rest is lost. Ask one question at a time.
Interrogation
A rapid series of questions without acknowledgement or reflection feels like an interview. Mix questions with summaries, comments and genuine responses.
Asking without listening
Asking a question and then talking over the answer, or moving straight to the next prepared question regardless of what was said, signals that the questions were a formality. Listening is covered in the next article.
Answering your own questions
“What’s your biggest challenge? I imagine it’s probably cost…” removes the customer’s chance to answer. After asking, wait.
Too many closed questions too early
A conversation that starts with a string of closed questions (“Do you have a maintenance system? Is it software? Are you happy with it?”) feels like a survey and produces thin information.
The power of silence
After a good open question, the most useful thing to do is often nothing. Many people find silence uncomfortable and rush to fill it, either by rephrasing the question or suggesting an answer. Allowing a few seconds of silence gives the customer time to think, and the answer that follows is often richer and more honest than the first thing they would have said.
Questions for difficult moments
Questions are particularly useful when conversations become tense:
- When a customer raises an objection: “What’s behind that concern?” or “What would need to be true for this to work for you?”
- When a customer is upset: “Can you tell me what happened from your side?”
- When a deal stalls: “What would help you move forward?” or “Has anything changed since we last spoke?”
- When you suspect hidden concerns: “Is there anything that would stop you from going ahead?”
These questions turn a confrontation into a joint attempt to understand the problem.
A worked example
Two salespeople visit the same small manufacturer to discuss scheduling software. This is an illustration.
The first opens with closed questions: “Do you currently use scheduling software? How many users? Are you happy with it?” The answers are short: “Spreadsheets. About six. It’s fine.” He moves into a demonstration. The customer is polite but unconvinced.
The second opens with: “Tell me about how a new order moves through the workshop.” The production manager talks for five minutes. She mentions, almost in passing, that rush orders cause chaos because nobody can see what is already committed. The salesperson probes: “What happens when a rush order comes in?” The manager describes an expensive missed delivery last month. Asked what would be different if this were solved, she says she would stop spending her evenings rearranging the schedule.
By the end, the second salesperson knows the real problem, its cost and its personal impact. His proposal addresses exactly that. The software is the same; the questions made the difference.
Questions across the four stages
The balance of question types shifts as an opportunity moves through the stages described earlier in this series.
| Stage | Main purpose of questions | Typical mix | Example |
|---|---|---|---|
| Identifying | Find out whether the person matches your ideal customer and whether there is a reason to talk | Mostly open | “What’s keeping you busy at the moment?” |
| Qualifying | Understand the need, its impact, who decides, budget and timing | Open and probing, then closed to confirm | “What happens if this isn’t solved before winter?” |
| Satisfying | Check that your proposal fits, surface doubts and agree a decision | More closed, with open questions about concerns | “Is there anything that would stop you going ahead?” |
| Solidifying | Learn how things are going, find improvements and new needs | Mostly open | “What’s changed in your business since we started working together?” |
A common mistake is to stop asking open questions once a customer has bought. The solidifying stage depends on continuing to learn about the customer, and open questions are how you do it.
Adapting questions to the person
People respond differently to questions. Some enjoy talking and will answer a single open question at length. Others prefer to be brief and may find a long series of open questions tiring.
- With talkative people, use summaries and closed questions to keep the conversation focused: “That’s really helpful. Just so I’m clear, the main priority is…?”
- With brief or reserved people, use specific open questions that are easy to answer (“What does a typical Monday look like?”) rather than very broad ones (“Tell me about your business”), and allow silence.
- With senior or time-poor people, ask fewer, sharper questions focused on outcomes and priorities.
- With technical specialists, ask detailed questions that show you understand their world.
Noticing how the other person responds, and adjusting, is itself a form of listening.
Other useful question types
Beyond open, closed and probing questions, a few other types are worth having in your repertoire.
Hypothetical questions explore possibilities: “If budget weren’t a constraint, what would you do?” or “Imagine it’s a year from now and this has worked. What’s different?” They help customers think beyond current constraints and reveal what they really value.
Scaling questions turn vague impressions into something more concrete: “On a scale of one to ten, how big a problem is this compared with your other priorities?” Follow up with “What would make it a ten?” or “Why not lower?”
Clarifying questions remove ambiguity: “When you say soon, do you mean this month or this quarter?” Many misunderstandings come from words like soon, expensive or a few, which mean different things to different people.
Reflective questions turn a summary into a question: “It sounds like reliability matters more to you than price. Is that fair?” They check understanding and invite correction.
Each has its place. None replaces the basic discipline of asking one clear question at a time and listening to the answer.
Practising better questions
Questioning improves with deliberate practice:
- Prepare three open questions before every important conversation.
- Review your notes after conversations: which questions produced the most useful answers?
- Notice your ratio of open to closed questions, especially early in conversations.
- Practise in low-stakes settings, such as with colleagues or in everyday conversations.
- Build a bank of good questions for different situations, and share it with the team.
Common mistakes
Talking more than asking. Especially early in a relationship.
Using only closed questions. They confirm, but rarely discover.
Never confirming. Open questions without summarising and closed confirmation can leave understanding vague.
Scripted questions with no follow-up. The value is in the probing.
Fear of the money question. Budget and decision questions are essential and, asked respectfully, usually welcomed.
Bringing it together
Open questions open conversations; closed questions confirm and commit. Probing questions, built on what the customer has just said, are where the real understanding comes from. Used together, in a natural sequence and followed by genuine listening, they turn a sales conversation into a shared exploration of the customer’s problem.
The workbook’s prompt to define each type, give examples and say when to use it is a good exercise to repeat with your own customers in mind. The next article looks at the other half of every good question: listening to the answer.
Topics and structure drawn from the Managing Your Opportunities sales workshop workbook (Charlie Pidcock); the explanations and examples are GoCore’s own. Examples are illustrations, not real cases. This article is general information, not professional advice.
