{"id":2903,"date":"2025-08-26T11:00:00","date_gmt":"2025-08-26T11:00:00","guid":{"rendered":"http:\/\/www.coclea.org\/?p=2903"},"modified":"2025-08-27T16:02:12","modified_gmt":"2025-08-27T16:02:12","slug":"15-crucial-questions-to-ask-prospects-throughout-the-buyers-journey-according-to-hubspots-former-sales-director","status":"publish","type":"post","link":"http:\/\/www.coclea.org\/index.php\/2025\/08\/26\/15-crucial-questions-to-ask-prospects-throughout-the-buyers-journey-according-to-hubspots-former-sales-director\/","title":{"rendered":"15 crucial questions to ask prospects throughout the buyer\u2019s journey, according to HubSpot\u2019s former sales director"},"content":{"rendered":"
If you\u2019re still ignoring buyer journey questions, it\u2019s time to pause and rewind. I say so because sales is now an increasingly consultative profession. Success today is less about \u201calways closing\u201d and more about \u201calways helping\u201d as a knowledgeable, reliable person that buyers can trust.<\/p>\n<\/p>\n
Genuinely helping prospects demands providing them helpful and specific resources instead of stuffing irrelevant information down their throats. There\u2019s no other way to come across as someone they trust. But how do you know what\u2019s helpful for them? Asking the right questions for each stage across the buyer\u2019s journey<\/a>.<\/p>\n If you\u2019re wondering what questions to ask, you\u2019re in the right place.<\/p>\n Table of Contents<\/strong><\/p>\n <\/a> <\/p>\n I\u2019ve been harping for the longest time: The sales rep\u2013prospect relationship needs to cut both ways. As your prospects qualify you, you also need to qualify them back. How?<\/p>\n Source<\/em><\/a><\/p>\n This starts with asking the right sales qualification questions<\/a> at the right time. These questions will get you in the position to:<\/p>\n In essence, in my experience, buyer journey questions are the holy grail to successful sales outcomes. Now, let\u2019s review some of the most effective questions you can ask across the different stages.<\/p>\n This is the top-of-funnel stage where your prospect realizes they have a problem but struggles to articulate it precisely. In turn, they have little or no sense of how to solve it. The marketing team primarily handles such leads, and I suggest avoiding engaging heavily with prospects now. When you do, my best bet is to keep things light, with questions like:<\/p>\n This is a typical icebreaker question. I usually look through the company\u2019s CRM profile before I ask this. Doing so helps me determine what content the prospect engaged with or downloaded, and then I know I have to dig deeper from there.<\/p>\n Remember, like I said, this stage is about keeping it light, just a regular conversation about their needs. So, when you ask this question, try to get them to open up about their business pain and how the content they checked out relates to it.<\/p>\n Pro tip: <\/strong>Take everything they say about their problem early on with a grain of salt. Make your notes, but remember this can change. According to research, buyers can change their problem statement an average of 3.1 times<\/a> during complex purchases. We\u2019re just asking them this question to get them talking.<\/p>\n This question is my go-to for inviting prospects to discuss the root causes of their pain. I advocate asking it because it helps to understand the bigger picture, straight from the horse\u2019s mouth. Often, buyers themselves don\u2019t have clarity and asking this question helps them articulate it better. I\u2019ve seen that this information is eventually quite handy to tailor future conversations around the real issues<\/em> they care about solving. Also, not to discount, everyone likes a good pair of ears to their problem, right?<\/p>\n As a salesperson, I prefer having a baseline from which to work. Understanding their existing process with this buyer journey question gives me exactly that.<\/p>\n Do they rely on internal teams? Google? Industry forums? A competing product? Answers to this question reveal their resource preferences, level of expertise, and even their pain tolerance. Suppose they\u2019re patching things together with duct tape and spreadsheets. Then it is a sign that there\u2019s a clear opportunity to eventually offer a solution that might address the gaps or inefficiencies.<\/p>\n I often ask this awareness stage question when I\u2019m looking to shift the conversation toward their desired outcomes from focusing on the pain points. Once I know that, I try to understand what \u201cgood\u201d looks like in their mind. I\u2019ve seen that it makes it easier to position myself as someone who helps them achieve<\/em>, not just fix<\/em> at the right time.<\/p>\n I like to keep this question vague, as I prefer staying in educational mode during the awareness stage. I advocate asking it to let prospects know that you\u2019re there to help and that they can ping you whenever they have questions.<\/p>\n Pro tip: <\/strong>Be careful here and keep things low-touch when you ask this to avoid a prospecting mistake<\/a>. Remember, there\u2019s a fine line between helpful and pushy, and the way you ask this question may blur it.<\/p>\n By the time it is the consideration and evaluation stage, prospects better understand their pain points. This is the time when they\u2019re most likely internally setting budgets and priorities. I take this as the prime time to get my foot in the door as the pain-point solver.<\/p>\n Some great questions I swear by at this time include:<\/p>\n These are some of the classic BANT questions<\/a>, and I reckon, you must aim to cover all elements.<\/p>\n Source<\/em><\/a><\/p>\n Why? Many times, I\u2019ve seen a prospect seem like a fantastic fit on paper, but not in reality. Reasons could be: They may not have the budget, their leadership isn\u2019t considering vendors, and so on. So, ideally, you don\u2019t want to waste too much time on such prospects. If you do, you can even risk souring your relationship by pushing them to act before they\u2019re ready.<\/p>\n Remember, you can\u2019t help someone who doesn\u2019t want you to, and the most competent salespeople don\u2019t try to.<\/p>\n Since prospects generally weigh various options during consideration, I advocate asking this one to pin down what truly matters to them, and not what I think matters to them.<\/p>\n I\u2019ve seen firsthand how transparency helps to better focus on the must-haves rather than spending time harping about the nice-to-haves they don\u2019t care much about.<\/p>\n This is one of my go-to questions to personalize a sale. Whenever I\u2019ve asked it, most prospects have answered \u201cyesterday\u201d to this one \u2014 and your prospects would perhaps say the same, too. Take my word for it: When you ask this, get such an answer and follow up correctly, that\u2019s where the magic starts to happen.<\/p>\n When you ask, get specific with them about their process, goals, and timeline. What are they hoping to accomplish, and when must that happen? By personalizing the sale this way, you can get your prospect thinking about their purchase in terms of the benefits, how their specific pain points will be addressed, as opposed to things like features or price.<\/p>\n Pro tip: <\/strong>Remember, your product becomes valuable to customers when they start seeing benefits, not when they purchase it. So, focus on the solution, not the purchase; this move will make your product look more attractive.<\/p>\n I\u2019ve always found it helpful to know beforehand who (or what) I compete against. This buyer journey question is my shot at hearing that directly from the prospects.<\/p>\n If you ask this question, you will understand how seriously they\u2019re shopping and whether they\u2019re already leaning in any particular direction. This will guide you to go back to the right strategy deck to determine why your product is better than the ones they\u2019re considering, where it falls short, and use it to tailor the conversation in your favor. I\u2019ve saved a ton of time with this one.<\/p>\n I personally love this question, since it hits two targets with one stone. First, I\u2019ve seen it surface any objections early. Knowing the obstacles at the right time makes them much easier to handle. Second, asking it also signals that you\u2019re not just pushing a sale; you want them to feel confident in their decision.<\/p>\n This question offers an excellent avenue to show empathy and build trust. Asking it signals you\u2019re not just there to close a deal but to truly partner with the buyer. I tend to ask this to appear empathetic and set myself apart from pushy, transactional sellers.<\/p>\n I normally acknowledge that buying isn\u2019t always easy: There are approvals, paperwork, comparisons, and risks involved to connect with them better. In fact, nearly every time I\u2019ve asked this question, I\u2019ve seen the prospect share some hidden blockers, internal hurdles, or decision-making preferences that I might not have uncovered otherwise.<\/p>\n In my experience, it has also opened the door for collaboration. Sometimes, all they need is something as simple as a one-pager for their boss, a demo for their team, or just more time. By asking this question, I\u2019ve been able to provide them that, build goodwill, and chalk out a roadmap to move the deal forward with less friction.<\/p>\n Once you move past the awareness and consideration stage, you\u2019ll know whether your product fits your prospect well. You\u2019ll also probably understand what needs to happen for a deal to close. Now is the time to hold their hand and help them cross over, making them feel they\u2019re in the driver\u2019s seat. This is when you need to ask buyer journey questions like:<\/p>\n I know what you might think: How could such a generic question do anything for you this late in the game? And as you can probably assume, this question isn\u2019t some secret, magical, \u201chiding in plain sight\u201d deal-sealer. In all honesty, I use this question to gauge my prospects\u2019 trust in me, where I stand, and if I\u2019m talking to the right person.<\/p>\n Buying a new product isn\u2019t traumatic, but risks are still involved, right? Sales is the art of building trust within a tight window. How a prospect answers this tells me a lot about where I stand with them:<\/p>\n Quite often, it so happens that the person we\u2019re speaking with isn\u2019t the ultimate decision-maker.<\/p>\n Research shows that 80% of deals<\/a> in B2B sales require multiple decision-makers. Moreover, the average buying group has grown to include at least 10-11 stakeholders<\/a>, and the final decisions require alignment from at least five key stakeholders.<\/p>\n In light of these facts, asking this question immediately lends perspective on who\u2019s involved in the buying committee. I\u2019ve seen firsthand how this can be a tremendous advantage in addressing everyone\u2019s needs and concerns, and not just the person in front of me. So don\u2019t skip this one.<\/p>\n I swear by this question nearly every time. Why? It shows how much hand-holding and education there is left to do. If your prospect has undergone a similar process, you can expect to put in less legwork to get them to cross over. If they haven\u2019t, the help you offer your prospect can make or break the sale.<\/p>\n I always offer to walk my prospects through a first-time decision-making process. After all, I\u2019ve done this a million times and understand how to help get executive-level buy-in.<\/p>\n Pro tip: <\/strong>I occasionally offer a \u201cGodfather.\u201d By that, I mean a senior executive at the company who will check in with a customer once or twice a year to ensure things are going well. I\u2019ve made this offer hundreds of times, and only a few customers have taken advantage of it. I\u2019ve seen how simply offering this is often more valuable than the actual resource. Prospects start feeling that their risk is reduced if they know help is just a phone call away.<\/p>\n This is my bet to uncover hidden hesitations. Each time I\u2019ve asked it, I\u2019ve seen how it gives prospects the space to voice any last-minute fears or logistical blockers. The input gives me a final chance to address them before they stall.<\/p>\n Buyer journey questions have been among my most valuable pawns throughout my sales career. Asking the right questions has helped me open up honest conversations, uncover what prospects truly need, and build trust that closes deals, without feeling pushy or scripted.<\/p>\n In case you\u2019re wondering, no, asking these questions won\u2019t <\/em>magically seal every deal. But take my word, they will<\/em> give you insight, credibility, and momentum. In a world where buyers are more informed and skeptical than ever, trust me, that\u2019s your competitive edge and path to success.<\/p>\n Stay curious, stay helpful, and stay focused on serving first. The results will surely follow.<\/p>\n Editor’s note: This post was originally published in March 2023\u00a0and has been updated for comprehensiveness.<\/span><\/p>\n If you\u2019re still ignoring buyer journey questions, it\u2019s time to pause and rewind. I say so because sales is now an increasingly consultative profession. Success today is less about \u201calways closing\u201d and more about \u201calways helping\u201d as a knowledgeable, reliable person that buyers can trust. Genuinely helping prospects demands providing them helpful and specific resources […]<\/p>\n","protected":false},"author":1,"featured_media":2905,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[16],"tags":[],"class_list":["post-2903","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-featured"],"_links":{"self":[{"href":"http:\/\/www.coclea.org\/index.php\/wp-json\/wp\/v2\/posts\/2903","targetHints":{"allow":["GET"]}}],"collection":[{"href":"http:\/\/www.coclea.org\/index.php\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"http:\/\/www.coclea.org\/index.php\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"http:\/\/www.coclea.org\/index.php\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"http:\/\/www.coclea.org\/index.php\/wp-json\/wp\/v2\/comments?post=2903"}],"version-history":[{"count":2,"href":"http:\/\/www.coclea.org\/index.php\/wp-json\/wp\/v2\/posts\/2903\/revisions"}],"predecessor-version":[{"id":2911,"href":"http:\/\/www.coclea.org\/index.php\/wp-json\/wp\/v2\/posts\/2903\/revisions\/2911"}],"wp:featuredmedia":[{"embeddable":true,"href":"http:\/\/www.coclea.org\/index.php\/wp-json\/wp\/v2\/media\/2905"}],"wp:attachment":[{"href":"http:\/\/www.coclea.org\/index.php\/wp-json\/wp\/v2\/media?parent=2903"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/www.coclea.org\/index.php\/wp-json\/wp\/v2\/categories?post=2903"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/www.coclea.org\/index.php\/wp-json\/wp\/v2\/tags?post=2903"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}<\/a><\/p>\n
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Why Buyer\u2019s Journey Questions Are Essential<\/strong><\/h2>\n
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Instead of assuming what matters to the prospect, asking buyer journey questions lets you hear it straight from them.<\/li>\nCrucial Questions to Ask Prospects Throughout the Buyer\u2019s Journey<\/strong><\/h2>\n
Awareness and Education<\/strong><\/h3>\n
<\/p>\n
1. What were you looking for help with?<\/h4>\n
2. What challenges prompted you to start looking for a solution?<\/h4>\n
3. How are you currently handling this issue?<\/h4>\n
4. What would success look like for you?<\/h4>\n
5. Is there anything else I can do to help you right now?<\/h4>\n
Consideration and Evaluation<\/strong><\/h3>\n
<\/p>\n
6. Where are you in the budget-setting process? \/ Are you looking for proposed solutions now? \/ Is there a timeframe for finding a solution to your problem?<\/h4>\n
<\/p>\n
7. What features or services are most important to you?<\/h4>\n
8. When do you need to achieve [X] goals by? When do you need to implement the solution by?<\/h4>\n
9. Have you considered other solutions or providers so far?<\/h4>\n
10. What concerns do you have about moving forward with a solution?<\/h4>\n
11. How can I make this process easy for you?<\/h4>\n
Decision and Purchase<\/strong><\/h3>\n
<\/p>\n
12. How are you doing?<\/h4>\n
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13. Who else will be involved in the final decision?<\/h4>\n
14. Have you gone through a similar purchasing process before?<\/h4>\n
15. Is there anything holding you back from moving forward with us?<\/h4>\n
Lead with curiosity, close with confidence.<\/strong><\/h2>\n
<\/p>\n","protected":false},"excerpt":{"rendered":"