10 Ideas for Questions to Ask a New Prospect

You and your services will immediately seem higher-value to the prospect when you ask them good, meaningful questions

Today’s clients are complex. They have different (often conflicting) wants and needs. They’re short in time, and attention span.

To provide value to these modern buyers, you need to ask good sales questions.

Sales qualification is a game of open-ended questions. Unless you ask the right questions, you won’t discover the right needs or understand the right problems to solve. Not having this information could cost you the deal right from the start.

Here’s a list of great sales questions to ask new prospects that will help you identify their core needs:

1. Could You Tell Me About Your Situation?

This is a non-threatening way to begin. This broad, open-ended sales question is a good way to start collecting information. It puts your prospect at ease because they give them freedom to respond as they like. Listen to what your prospect says and what they don’t say. Both will suggest areas to ask follow-up questions.

2. What are Your Biggest Pain Points?

Understand what they’re struggling with and you’ll understand how you can help. Once they share their pain points, ask follow-up questions. Never offer a solution before fully understanding all the details of the issue.

3. How Do These [Pain Points] Impact Your Life/Work?

This question achieves two important goals… One it uncovers the real prices your prospect is paying, so you know what benefits of your product/service to emphasize. And second… it makes the prospect feel the pain… making them a lot more receptive to a possible solution.

4. What are Your Short-Term Goals? Long-Term Goals?

This question gives your prospect the opportunity to tell you where they want to be in the near (and not so near) future. You can begin to figure out how your product/service will support their goals – so you can position it as a catalyst or accelerator that will help them achieve those goals.

5. What are Your Desired Outcomes?

This question focuses your prospect to think not in abstract visions or goals, but in concrete results. Wanting to achieve a far-off or even immediate goal is one thing; having a desired outcome in mind is another.

6. What’s Holding You Back from Reaching Your Goals?

Take the time to find out the answer to this crucial question. If they say, for example, that lack of time is holding them back – don’t offer them a solution that requires a lot of time investment.

7. Why is This a Priority for You Now?

The answer to this question will tell you everything about their motivation. When, for example, you ask the question “why losing weight is a priority for you now?” there’s a world of a difference if the answer is “because I just had a heart attack” vs. “I want to look good in my wedding dress”.

8. What is Your Greatest Strength? Weakness?

You don’t want to ask what their greatest weakness is first, so start by asking about their greatest strength. Then, go after their weaknesses. Knowing their weakness will help you understand what they could do better and how your product/service fits into potential improvement plans.

9. If You Could Change One Thing, What Would it Be?

This is a great question to keep the conversation flowing, while learning more about the challenges and pitfalls of your prospect. Even if the answer is unrelated to the product, you can begin to understand some of the challenges your prospect deals with.

10. What Level of Service are You Looking For?

Will they need extensive onboarding? Or do they want a solution that they can plug in and start using straightaway? Knowing the level of service and attentiveness they expect helps you estimate their needs once they become a client.

Now It’s YOUR Turn

For five minutes… come up with as many ideas as you can… what questions could you ask your prospects to be able to close the deal easier and faster?

Let's Brainstorm


Please share your ideas (all of them or just one) in the comment box below… and let’s get WOWing.

Live fully, stay awesome,

Nisandeh Neta

Top Commenters – last 30 Days

Let's Brainstorm


Please share your ideas (all of them or just one) in the comment box below… and let’s get WOWing.

Live fully, stay awesome,

Nisandeh Neta

  1. When I started I was really nervous when a client came for the first time. In fact, it was a problem even if they became clients.
    Because I learned to ask the right questions. Meeting a client for the first time is always exiting.

    I always have a systemized order in my head. I do not plan the questions, but the topics.
    Then with those topics in mind, I ask everything I need to know AND give the client the feeling I really listened.
    As I am very passionate, I forgot to listen.

    2. WHAT can I do for you/ brings you here
    I always want to know what the problems are.
    When parents come to me, sometimes they have driven for 1 hour, they just want to TALK about the PROBLEM
    NEVER EVER start with the practicallities. If possible, let them put the most important things, in the context box, just enough to give you an idea.

    3. WHY ME?
    I always want to know WHY ME.
    Not because I want to be a rock star. But I want to manage my and their expectations

    4. Only if nessesary, ask for SOME DETAILS, just to be able to get the picture

    You want to make sure that what you are offering is not already done before.

    Sometimes they have had great result. Even I can sometimes see that the results they got from a previous consultant was great
    Then of course you say so.


    This question I hardly ever need to ask. As I am often not the first in the row.

    It is very important that you make sure that you know what they expect from you.

    The best results come from cooperation.
    It does not have to be much. In my case I work with children. How ever I ask parents to join the lesson. Especially if they help their kids at home.
    Then they know exactly what they are supposed to. By doing that my results improved big time.
    And even if they do not want to join, they know they can not put their problem on your shoulders.

    This gives me a lot of info on: 1. How to do an offer, 2. what to offer, 3. The duration. 4. And during the period of cooperation manage expectations

  2. Next to being an Airbnb hostess I am also an interim people manager responsible for organizational change. These are some of the questions I’ll ask my client:
    1) what is the reason you want your organization to change?
    2) which companies/departments/teams/people are effected by the change?
    3) which companies/departments/teams/people will gain from the change and whom will be impacted by it?
    4) in which areas does your business need changing?
    5) how do these areas influence your business?
    6) is the need for change recognized by the people within the organization?
    7) when is my assignment a success to you?
    8) how do you feel/see that my interventions have been successful?
    9) how do we measure the improvements the best so we know that we are on the right track?
    10) assuming the organizational change is carried out successfully, how do we ensure the change is sustainable implemented? Which stakeholders needs to agree to what in which area?

  3. 1. What brings you to me? What is the problem?
    2. how does it effect your child?
    3. How does this affect you?
    4. What have you already done so far
    5. What were the results of your previous efforts?
    6. What result do hope for then we are going to work together?
    7. How would it change your life and that of your child if you get the result you want?
    8. What is the reason you think I am the one that can help your child?
    9. What would you like me to do for you?
    10. How much time do you have to bring and or help your child?

  4. My clients don't like many questions. My main question is what is stopping you or is creating a delay or is upsetting your team on a daily basis. Accroding to their reply I'll come up with a plan to help them streamline their business

  5. questions
    - what does happen if you do what you want to do?
    - what does happen when you don't do what you want to do?
    - what does not happen when you do what you want to do?
    - what does not happen when you do not do what you want to do?

  6. So many great questions. Thank you all.
    There is one I like to add.

    It is this question:

    What happens when you don't do anything about your current situation?

    Or more specific:
    What happens if you don't work with me and you keep doing what you do?

    Try it for sure in a sales conversation!

  7. What are good questions?
    There are many different types of questions you can ask. Here's a layout with sample questions:

    Open and unbiased questions
    How do you like it here?
    What are the possibilities?
    How do you handle this?
    How much space do you need?
    What do you want?

    Sincerely curious questions
    What is your preference?
    What do you like?
    How does this work?
    What have you seen?
    What are your qualities?

    Accompanying questions
    What will you do first?
    What do you need for this?
    What other options do you have?
    Who can support you with this?

    Confronting Questions
    What was your contribution to this?
    What is your explanation for this?
    What could you have done differently?
    What have you learned from this?

    Empathic questions?
    How was this for you?
    How do you feel?
    What touches you in this?
    How did you experience this conversation?

    Investigative questions
    How many times has this happened?
    What time did this start?
    Which parts are replaceable?
    When was that?
    Who were you with?
    How long did it take?

    Clarifying questions
    What do you mean?
    What do you mean by that?
    What does this mean?
    How do you explain this?
    What does this look like?

    Supporting questions?
    What facts show this?
    What is that based on?
    What statements show this?
    Who said this?
    Why would you think that?

    Questions about consequences?
    What will be the effect of that?
    What risk do we run with that?
    What consequences does this have?
    Who is responsible for this?
    Who bears the costs thereof?

    Intervened questions
    What's happening here now?
    What can we do to keep it central?
    What makes us stray from the theme?
    Who needs a break?

    Tactical questions
    What will happen if we don't act now?
    Which test balloon is suitable for polling some reactions?
    Which people should we take into account the most?
    How can we increase our influence?

    Deeper questions
    What was your intention with this?
    What problem is there below?
    What's stopping us?
    What do you run into more often?
    Who are you?

    Converging Questions
    What are the benefits of this approach?
    How do we get even more results from this approach?
    What do you need to take the plunge now?

    Diverging questions
    What innovative alternatives can you think of?
    What other solutions can we propose?
    How would a six year old child handle this?

    Powerful questions through simplicity
    What is that?
    How is that possible?
    Who wants that?
    What is possible?
    What are we doing?

    Two Socratic questions
    What do you mean?
    Is this correct?

    1. WOW ... Marcel... This is an amazing list.
      Thank you so much for sharing it.
      I especially appreciate the "categorizing" of the questions.

  8. THANKS! Nice lists!
    Most of the time, I ask how people did find me?
    What kind of entertainment they are looking for?
    What sort of audience they expect.
    (Elderly, Kids, age?)
    If there is a theme or not?
    Find out what they expect.

  9. Many things have been mentioned already. My main questions are to the caregivers of people with dementia:

    What is your biggest struggle right now?
    Why do you need help?
    Why now?
    How do you think I can help?

  10. Great questions Nissandeh and Muriël. As it is not possible to cure a learning challenge like dyslexia I have options to improve the input, processing and output.
    1. Why do you come to me?
    2. What are your expectations of my method?
    3. What help did get or do you get right now?
    4. What is your biggest problem right now?
    5. How much time are you willing to invest at home? There will be homeplay (as we call the homework).
    6. When your child is under 12 it needs to be accompanied by an adult during the consult. As the child will not be able to recall what we have been working on. Can you do that?
    7. When shall we start?

  11. What a content! Long list with great questions.
    There is one that Intry to use:

    In the Line of...what are you still missing or what needs to be added...

    When would you say yes ...to me...my service...my product...

    And then you can figure out whether there is enough' ground... and bargain a little more.

    1. Totally Agreeing with you @Frans! That’s a wonderful question.

      Did you Ever read “The Ultimate Sales Machine” by Chet Holmes? He worked alot with this kind of “Isolating the objection” methodes...

  12. 47 questions to help you in a sales conversation...

    Here are 47 questions you can ask your prospect as soon as possible to sit down with them, understand exactly what they are up against, and already think about possible solutions. There are hundreds of other questions you could think of, but here is a sample.

    NOTE: I often use the word "problem" to describe the pain or challenge your prospect is facing. But remember to avoid this word in your conversations. Otherwise, you'll turn it into a problem conversation. You fill in for the word "problem," the description of the challenge. Preferably use the words the customer uses.

    1. How can I help you?
    2. Can you give me some background information regarding this situation?
    3. What is not going well at the moment and why do you think that is?
    4. How long have you been struggling with it?
    5. To what extent does this problem* (read the note above regarding this word) affect the rest of the organization/you/department/team?
    6. What is this problem costing you in time, money, personnel, energy, etc.?
    7. How long will you last without a solution? (Where is the stretch?)
    8. Have you shared your current frustration with your staff/your colleagues/your suppliers?
    9. How did this problem arise?
    10. What makes a solution to this problem important to you?

    11. What does solving this problem give you?
    12. Why do you think this question has been around for so long?
    13. How big is the problem?
    14. Who is ultimately responsible for this problem?
    15. Tell me more about it.
    16. Can you estimate what it will cost you?
    17. Why does this happen do you think?
    18. What is your role in this situation?
    19. What have you done about it so far?
    20. What has stopped you from working on it so far?

    21. What is your strategy for solving it?
    22. Who else is aware of this story?
    23. What are your goals, where do you want to go?
    24. When will you know that you are satisfied with the solution?
    25. What pressure is there on you/the team/organization?
    26. Who supports the action to solve it?
    27. What is your biggest challenge regarding this problem?
    28. Does your competition have this same challenge?
    29. What is the first thing you could do?
    30. Who should have been at the table?

    31. What is the reason for inviting me here to the table?
    32. What do you hope I can do for you?
    33. On a scale of 1 to 10, how important is the solution to you?
    34. What will you do differently next time?
    35. What solutions are you all looking at?
    36. When do you want the problem solved?
    37. What do you think it will take to get this resolved as soon as possible?
    38. How are you doing this right now?
    39. How do you deal with setbacks?

    40. If you had the perfect solution what would it be in time, money, energy?
    41. What alternatives have you looked at?
    42. Which solution do you prefer and why?
    43. Have I overlooked anything else?
    44. Can you agree with this solution?
    45. Are there people who might have objections to implementing this solution?
    46. Are there any important issues I should consider?
    47. What makes you choose me to solve your problem?

    If you'd like to know more about these questions or have something to add, feel free to post a comment below.

    1. WOW ... Muriël... You're definitely demonstrating why you're called the Sales Diva.
      Thank you so much for sharing this amazing list.
      For me, personally, I'm going to pring #40-#47 and repeat it every night until I know them by heart...

      1. Well, thank you so much. Your reply to my comment makes me smile. Nice to hear you will print the last questions and repeat them. I'm curious to know why especially these questions. What triggers you specifically in questions 40-47?

        1. It’s just that I never (or rarely) ask those, and they’re very powerful to help the person make up their mind on their own… needs to add them to my “repertoire”.

    2. Halleujaa @Muriël! Finally you Made your way into the Challenge! YES!

      Now we can learn alot more from The One and Only SalesDiva!

      Thanks alot!

      And If I am really honest?

      I am printing ALL these questions and will train my team and myself to know them by heart!

      And you know what? Maybe I will Just Do an Event and invite all my ideal clients and Just ask them all of these questions!

      Thanks a Million and Welcome again!

      1. Yes yes yes I am here. I had a 2 weeks Holiday but back in town and back in business ;-). I am very pleased to hear it is helpful to you and your team. Let me know if there is more that I can do for you!

    3. I love your list
      It was really appealing. I had to restrain myself not to call you immediately. The only reason I did not, because I am in the middle of things.
      Of course I was reading Nisandeh's comment.
      For me 40. is something I like to add to my personal list.

  13. Great questions Nisandeh. My priority is to ask them about their passions and desires in life. From that point they will open up and we have a great conversation in which they talk about their needs.

  14. What is your biggest challenge?
    What have you tried allready to overcome this challenge?
    How did this pan out?
    What were your expectations beforehand?
    What would be a succesfull outcome for you? Paint the picture for me.
    What do you like most about your business? Why?
    What do you hate doing most in your business? Why?

  15. There are already so many good answers 😀

    1. What inspires you?
    2. What do you want to achieve with ...?
    3. What are you proud of?

  16. Interesting topic. The questions seem to be tailored for services, but they are quite universal. You just have to formulate them differently. Example #1: Could You Tell Me About Your Situation? I would ask my prospects: Could you tell me what happened? Their reaction is always very positive.

    1. Could you tell me what your budget is? When they come for a custom made product, it's important to ask this question at the beginning of the conversation. Otherwise you risk spending more than an hour until you discover a custom made product is not the solution for them. You can manage their expectations better. They won't get disappointed at the end of the meeting.

    2. What did you try in the past? Did it work? Why didn't it work?

    3. What will your life look within 2 (or 5) years?

    4. How long have you been struggling with this problem? Their answer says something about the urgency to solve it.

    5. This one's specifically for my business or products that need maintenance: Do you live nearby the graveyard, how frequent can you be there to maintain the monument? Or: How often do you expect to use the product? Do you maintain it yourself? Outdoor or indoor use?

    1. That's a brilliant observation @Ine - it helped me working on this topic as I was stuck due to thinking it's not really relevant for me. But your examples were so good it triggered me to see how I can apply it to my industry and case.

      Thanks so much for this...

    2. YES @Ine!

      Love Actually all of your questions. Very clever ones and Thanks for your explainations.

      I love especially #4... That’s a HUGE Eye-opener for me, thanks and keep it Coming, my friend!

  17. I love all these questions Nisandeh. And yes! Absolute agreeing with you about the Conflicting wants and needs. Business just got interesting as we are accelerating our abilities online.

    These are my questions I always ask while meeting or qualifying new prospects:

    1: How long has your company been in existence?
    2: What would you like to achieve with smart use of offline and online Marketing campaigns in your company?
    3: What are the biggest obstacles you experience in doing so?
    4: On a scale of 0 to 10, how important is it to you to overcome these barriers?
    5. Write down at least 20 things you tolerate.
    6. Make a list of 5 results you want to enjoy in the next 90 days.
    7. List three fundamental changes you need to make to do more to be successful. You know them, it's good to already share them with me.
    8. How do you define SUCCESS at this stage of your life?
    9. What are the 3 biggest challenges you are facing in your life right now.
    10. What is the most important thing you have learned in the past year?
    11. What are your strengths? Or in other words - what are the gifts you've been given?
    12. If you're not doing what you're doing now, what would you like you to do?
    13.What is your revenue target for the next 12 months?
    14: Are you willing to invest in the growth of your company? If so, how do you see this investment in time/money/energy?
    15: Are there any other issues that are relevant to our conversation?

    1. I like all the questions but I feel the need to highlight question 14. What I'm still noticing is how some entrepreneurs have huge ambitions but are not willing to invest in the skill that is one of the most important: learning how to sell. They want to result but are not always willing to invest. Not in money, time, or energy. Although this says something about the entrepreneur, I want to put out that as the selling party you can help your prospect to make the decision to invest by being clear on the return on investment. Apparently, they are not convinced they will earn back their investment and in some cases, I actually do understand their hesitation. So make sure you are able to sell the ROI and stand for this.

      1. Thanks @Muriël. I totally agree with you. Nobody really likes to learn how to Sell Eventhough we all know that without Sales, there is just a huge and expensive hobby 🙂 And yes: Totally agreeing with you about the ROI and making them clear what the benefits of the benefits are.

        I also use it totally the opposite... This question is one of my Anti-sales Strategies...

        And you what is so funny? This is part of my free Coachings Quick Scan that I give to ones that might be qualified to one of my few yearly 1-on-1 coaching programs that I do. This is part of their 4-step preparation.

        The funny thing: The answer to this specific question (#14) is always determining the Commitment of my prospect and I only need to look at the answer and then I know! Only 5% will know EXACTLY their commitment and will just give me their estimation of Time (in hours), Money (in euro's) and Energy (in %). So just by asking this question I will just disqualify 95% of my prospects which spares me a lots of time and effort And grant me the chance to ONLY work with those who are highly Committed 🙂

  18. After the ten suggestions above the only remaining question will be, "when do you want to start working together, this week or next week?"

    Sometimes it's hard to get someone talking. A good question to start a dialogue could be;

    👉 What prompted you to download my e-book
    👉 What has been the reason for you to participate in this challenge?
    👉 What was the reason for you to react to my linkedin post?

    Sometimes a potential customer is not directly willing to reveal any problems. A variation on the #9 magic wand technique could be;

    👉 How would you describe the ideal situation (with regards to your area of intrest)? Followed by "And what does the reality look like?" This will definately help to create gaps.

    I am sharing successful selling tips on a frequent basis on my LinkedIn. Are we not yet connected? Please feel free to send me an invitation request!

    1. In addition to your first remark, I can say I totally agree. I have asked this question many times and if said with confidence it works very well. I sometimes also already opened my calendar on the table and said: "When do you want me to give the training to your company. At this moment I still have some spots available." I did this to show I'm sure they will choose me. Like I expect this to happen. And yes it is a bit bold and sassy but hey, you want to be a sales diva/divo or not 😉

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