Ask These 24 Sales Questions to Lead More Productive Prospecting Calls

Sales Apr 23, 2019 20 minutes read

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    “If you’re not moving closer to what you want in sales, you probably aren’t doing enough asking.”

    That’s a quote from Jack Canfield, and it’s a great philosophy to adopt for prospecting calls.

    It’s easy to make assumptions about a prospect. You reviewed marketing’s data and assume you know what prospects are interested in. You researched their businesses and jumped to the conclusion that they have small/big budgets. You researched their competitors and now believe you know what solutions they need.

    All of these assumptions encourage you to drive the prospecting call, citing the benefits of your product/service and going for the hard sell. Unfortunately, this turns many prospects off.

    A better approach is to ask lots of questions.

    With the right questions, you can establish a rapport with prospects, get them to tell you exactly what problems they’re trying to solve, encourage them to lead your discovery process for you, and find out whether or not the partnership is a good fit.

    But what types of questions deliver all of these benefits? We asked 45 sales professionals to find out.

    More than half (53.4%) of our respondents never use a script for prospecting calls. A third (33.3%) only sometimes use a script, and very few (13.3%) always use a script.

    Additionally, most of our respondents keep their prospecting calls short. More than 80% complete their calls in 30 minutes or less.

    So what questions do our respondents rely on to qualify leads and highlight the value of their products/services in such short amounts of time?

    Discover their 24 go-to questions below—along with information on why each question is important to ask and what situations each question is great for.

    Editor’s note: Want to learn how the length of your prospecting calls compares to the averages above? CallRail users can download this free CallRail Source and Keyword Performance dashboard to see average call duration metrics alongside data that shows which sources are driving the most calls.

    Start by Asking These Icebreaker Questions

    If you can get prospects to feel comfortable talking to you in the first few minutes of a call, they’ll feel more comfortable sharing their thoughts with you as you move through your discovery questions, too.

    For that reason, our respondents recommend asking one of the following four questions to jumpstart the conversation.

    1. How are you doing today?

    “On every phone call I always start by asking ‘How are you doing today?’ to break the call from sounding salesly and to get the person to open up and start an actual conversation,” says Daniel Lynch of Empathy First Media Digital Marketing.

    Of course, when asking this question, you’ll sometimes run into prospects who just respond “I’m fine. How are you?” If that’s how your prospect responds, these other questions might lead to more discussion.

    2. Tell me about yourself

    “During our first call, we try to build rapport with prospects by asking them about their background and experiences and sharing ours,” says Parvind Dutta of MapleSage.

    “This helps us break the ice: in most cases, people won’t talk about their challenges unless they feel comfortable with the salesperson.”

    3. What’s it like in [location] this time of year?

    “The one question I swear by in prospecting calls is: ‘What’s it like in [prospect’s location] this time of year? I’ve always wanted to see [local landmark] there,’” says Storage Vault’s Kraig Martin.

    “I’ve experienced a lot of success with this approach. It’s really useful at building a rapport with the prospect, and rapport is essential when it comes to encouraging a prospect to take your preferred course of action.”

    4. Is there anything I can help you with today?

    “Before I pick up the phone and call, I always research the company and prospect first,” says Alex Meade of Beacons Point. “Any information I can find that may help me connect can be the difference between scheduling a second call or getting the cold shoulder.”

    “I also like to ask ‘Is there anything I can help you with today?’ This usually catches them off guard and turns the tables a little bit. Our agency was built on the idea that we should always be helping, and this question helps us stand out from a typical sales call.”

    Gather Actionable Information With These Discovery Questions

    After warming your prospect up to the conversation with your icebreaker questions, it’s time to move into discovery.

    Our respondents recommend asking the following questions to learn more about what pain points your prospects have and what solutions you might be able to provide.

    5. How can we help you?

    “I like to ask ‘How can we help you?’” says David Bourque of TSI Consultants. “Many times, salespeople are too quick to start talking about the features and benefits of their products or solutions before really understanding what the prospect’s needs are.”

    “By asking someone how you can help them and taking the time to listen, you are showing a genuine interest in helping your prospect solve a problem or pursue an opportunity. Offering to help your prospects—as opposed to selling to them—is the first step in gaining their trust,” Bourque says.

    But if want to ask something more specific, other respondents offered several, similar questions you can ask:

    • “What’s one thing we could do to create a better experience for you?” (Rajat Chauhan, Techtic Solutions
    • “What are you looking for to make your job/life better?” (Darren Odden, Odden)
    • “If I could help you solve one problem today, what would it be?” (Paige Arnof-Fenn, Mavens & Moguls)
    • “What’s been keeping you up at night these days?” (Paige Arnof-Fenn, Mavens & Moguls)

    6. What are your goals?

    “When working with those who aren’t marketing experts themselves, we find that it is critical to ask them what their overarching goal is in coming to our agency,” says Khaleelah Jones of 90 Digital. “Is it increased inbound website traffic? More qualified leads? A boost in sales?”

    “This helps us step back and look at their overall business goals and effectively identify what marketing activities can support them—which makes us an integral partner in their business,” Jones says.

    Other respondents offered similar suggestions:

    • “What are your goals before the end of the year?” (Kim Orlesky, KO Advantage Group)
    • “In next quarter, what is the biggest business challenge you are going to work on?” (Frits Wille, west6)

    In addition to asking about a prospect’s goals, iSynergy’s Steve Cross also recommends asking how you’ll measure the success for goals:

    “I need to know the target I’m aiming for. For those targets, the client and I need to be on the same page for measuring success. I don’t want to be focused on conversions if the client is focused on subscribers.”

    7. Are you experiencing these issues?

    “I always ask prospects if they are experiencing similar issues to others in the industry,” says Ollie Smith of ExpertSure. “This is particularly effective when a prospect is less than forthcoming; it enables me to gauge whether the call is worth continuing rather quickly.”

    Sven Montanus of Svensson & Friends recommends a similar approach: “Describe a challenge that resonates with your prospect. Then, ask questions like: ‘Does that sound like you?’ or ‘Do you ever feel that?’”

    If you’re not sure what a prospect’s specific goals or pain points are, DigiHype Media’s Clint Thompson recommends asking about something all businesses want: “Do you feel that your business is in need of new clients?”

    Or, if you’re prospecting for your marketing agency, you could ask a question Presult’s Patrick Riemers recommends: “Do you know how many visits your website had last month?”

    “We sell online inbound marketing services. By asking this question, I can follow-up with questions about their sales calls/quotes and related to 24/7 lead generation with their website,” Riemers says.

    8. What are some of your biggest pain points?

    The 20’s Isaac Howell recommends asking: “What are some of the biggest pain points that affect your day-to-day job functions?”

    “Before you start listing the reasons why they should become a client, it’s important to know what your prospects really care about. They don’t want to be pitched at and talked over; they want to be listened to by a professional who’s there to help.”

    “Asking this question lets prospects do the talking and gives you a chance to learn what issues they want resolved,” Howell says.

    Growth Hackers’ Jonathan Aufray agrees: “Ask about the biggest problem they’re facing at the moment. This will allow you to qualify them by completely understanding where they stand—and to see if there’s a fit between them and you.”

    “If you have the solution to their problems, the prospecting call can quickly transform into a sales call,” Aufray says.

    9. Why hasn’t this problem been addressed before now?

    “You can start by saying, ‘tell me about your goals and the problems you’re looking to solve,’” says McCall Robison of Best Company. “Then, delve in further by asking: ‘What’s the root of the problem and why hasn’t it been addressed before now?’”

    “The answers to these questions will tell you nearly everything you need to know about the prospect and what they’re looking for in a product/service. You can use these questions to close the deal and to show the prospect that you can solve said problems and provide a roadmap to achieve the desired goals.”

    “Without making personalization your number-one priority in your prospecting phone call, you could lose the potential customer. If your question makes your pitch more personalized, the more likely your call will be effective.”

    10. What does a successful partnership look like to you?

    “My favorite question to ask is, ‘What does a successful partnership look like to you,’” says LyntonWeb’s Jennifer Lux. “This question opens a client up to not only talking about their goals and KPIs, but also the answers often include expectations around the client experience.”

    “In addition to learning about the core need in the partnership—like lead generation—prospects will also share ancillary expectations such as working with a responsive agency team and partnering with an experienced strategist who can provide thought-leadership,” Lux says.

    And Penguin Strategies’ Perry Nalevka suggests another way to frame this question: “If we start working together tomorrow, what does success look in three, six, and 12 months from now?”

    11. What business does this well?

    “All prospects have an idea of what’s important to them or what they’d like to see for their business in terms of results,” says Megan Moloney of Online Marketing Gurus.

    “I always like to ask my prospects for an example of another business that does ‘it’—whatever it is that they’re looking to do—well.”

    12. Do you know who your target audience is?

    “I like to ask: ‘Do you know who your target audience is?” says Lightbulb Media’s Lewis Kemp. “We meet lots of clients who base their entire marketing strategy on what their competitors are doing.”

    “As a marketing agency, it’s crucial that we understand our prospective client’s buyers,” says Caleb Malik of SmartBug Media. “As a result, I find it useful to ask, ‘What pain points are your buyers trying to solve when they purchase your product or service?’”

    “When someone has multiple products or multiple services, it’s helpful to ask a modified version of this question: ‘Can you walk me through how the buyers for each of these products/services are different in terms of their needs?’”

    “I specifically try to ask about the pain points, needs, and problems their buyers are solving for because I want to prime our prospective clients into providing these factors rather than a list of demographics.”

    “Understanding their buyers gives me insight into why they buy and how we can help make that salient in their marketing,” Malik says.

    Follow With These Questions to Keep Prospects Talking

    If you run into a very matter-of-fact prospect who answers your questions but doesn’t provide much detail, ask these two questions to dig deeper and elicit more helpful responses.

    13. Can you tell me more about that?

    “The number one question we always ask on a prospecting call is, ‘Tell me more about that?’” says Kevin D’Arcy of ThinkFuel Marketing. “There’s no magic behind that question, but it’s our cue to be quiet and let them speak.”

    “People are open to talking about their challenges and goals if we just shut up and let them do it. So as soon as we get them to give us even the briefest glimpse into a challenge they are facing, we ask them to tell us more about that, then keep quiet and let them speak,” D-Arcy says.

    “Asking prospects what their company goals are is important,” says CIENCE’s Caroline Ursos. “But trying to understand their answers is what really makes a difference.”

    “Whether their responses are positive or negative, showing prospects that you’re interested in and trying to learn from the conversation could be a game changer. Plus, it will also give you a chance to present and take over the call,” Ursos says.

    14. Why?

    Many of our respondents recommend asking some version of “Why?”

    “Ask: ‘Why do you want more leads (or other objectives)?’” says Du Simple au Double’s Thomas Carrere.

    “Ask: ‘Why do you want to change?’” says Andrejs Juscenko of IBD Consulting. “It helps to understand if there is a true motivation behind prospects’ interests. This question also helps discover true business needs and pain points.”

    “Ask: ‘Why now?’” says Sauce Marketing’s Kim Garmon Hummel. “When I’m speaking with prospects, they’re looking for a solution to a problem. Sometimes they feel like the problem is on fire, and they’re so focused on solving that one issue that they aren’t seeing or considering the bigger picture.”

    “We aim to help our clients grow smarter: that means zooming out and looking for ways to organize, optimize, align, and transform that will naturally align with the solution to the problem they’ve contacted us about.”

    “A business is most successful when its leaders are able to take a proactive approach. Asking ‘Why now?’ can open up a can of worms, but it’s often necessary to wade through the worms to move into a position where leaders can make decisions proactively.”

    “As a bonus, taking the time to talk through this with prospects uncovers the reasons behind their sense of urgency, which can be very helpful in a lot of ways,” Garmon Hummel says.

    Ask These Questions to Pique Interest and Create Urgency

    Part of a prospecting call is figuring out what prospects need and determining if your products/services are a good fit. If it is a good fit, the next goal is to get those prospects interested in working with you.

    These questions will help you pique prospects’ interests and create a sense of urgency for working with you.

    15. Do any of your competitors use this type of service?

    “One question I always make sure to ask on prospecting calls is: ‘Do any of your competitors use this type of service?’” says Matthew Ross of The Slumber Yard.

    “This is an effective question because business professionals are competitive by nature. They hear the term ‘competitors,’ and it immediately piques their interest. In fact, the question usually gets them a little fired up, and they’ll start revealing information about their business and service providers.”

    “I guess you could say it’s kind of an end-around question to get the person talking. Ultimately, that’s the goal. You want them to forget that you’re trying to dig for information on them.”

    16. Why is solving this important for you now?

    “I like to ask: ‘Why is solving this particular issue important for you now, and what will that help you achieve/avoid if solved now versus next quarter/year?’” says Jumpfactor’s Zamir Javer.

    “The key here is to elicit the underlying pressures that are forcing a decision or action to be taken now versus later. This helps the salesperson understand the real urgency or level of pain associated with taking no action.”

    “The more urgent, the higher the pain, and therefore the more likely and faster a decision will be made. This enables the sales rep to prioritize the opportunity accordingly.”

    “Additionally, drilling deeper based on the answer will also assist you to determine the actual triggers and critical factors in the decision-making process for your prospect.”

    17. Why did you lose your last sale?

    Alexa DeKalb of NYC Search & Social recommends asking, “Why did you lose your last sale?”

    “While many people think bringing up something unfortunate (like a lost sale) could be detrimental to a prospecting call, it will remind the person on the phone that they are in need of help!”

    “If you can think on your feet and suggest ways that your organization could have solved that problem, you’ll be at the top of this person’s mind for the next week every time they think of the missed victory.”

    18. How would this benefit your business?

    “It’s not always about the question, but about the phrasing,” says Colibri Digital Marketing’s Andrew McLoughlin. “For instance: ‘How would it benefit your business/workflow/production/etc. if your business could handle the [such-and-such] more efficiently?’”

    “It’s an inversion that gets people thinking. Rather than starting with the ‘if,’ you’ve already got their brains churning away at the benefits, making them seem more concrete.”

    “The fact that you can provide a service to get their business to where they’ve imagined it is almost a foregone conclusion, then.”

    Determine if a Prospect is a Good Fit With These Questions

    Finally, one of the key goals of a prospecting call is to qualify the prospect. Is the prospect someone you want to work with? Is he/she someone you can help? Does the prospect have the budget to afford your product/services? Is he/she ready to buy or just doing some research?

    To get the answers to these questions, ask the following six questions on your prospecting calls.

    19. What are your goals for the next 12-18 months?

    “One of the most important questions we ask is: ‘What are your goals for growing your business in the next 12-18 months?’” says Ormi Media’s Natalie Athanasiadis.

    “Our services are geared towards established businesses looking to scale, so we use this to open the conversation about their business stage and determine whether this would be a mutually beneficial relationship to explore.”

    20. What needs to happen at your business in the next 12 months?

    “Ask: ‘What needs to happen at your business in the next twelve months?’” says Jake Fisher of Bridges Strategies & Digital Marketing. “Please note that we use the word ‘need’ instead of ‘want.’ All of our best clients work with us because they urgently need something—usually new customers and revenue.”

    “When someone tells me that they don’t need anything, that lets me know that they probably aren’t a good client for us.”

    21. If you find the perfect solution, when would you deploy it?’s David Zeff recommends asking: “If you were to find the perfect solution for you, when would you be planning on deploying it?”

    “Time is a threat to B2B deals. Unless there’s a compelling event, the decision process could take an undetermined amount of time. It is best to find out if prospects are in the initial stages of review or are looking to solve a real problem that they have today,” Zeff says.

    Other respondents recommend similar questions:

    • “What’s your timeline for moving forward with us or another vendor, and what criteria will help you make your decision within that timeframe?” (Talar Malakian, Salted Stone)
    • “What is the biggest concern regarding [insert pain statement], and how urgent is it that you address that problem?” (Tommy Landry, Return On Now)

    And if you feel like the prospect is ready to move forward but hesitant to take the next step, Flowbird’s Jason Rainbird recommends asking: “Is there anything that we’ve discussed today that you are unsure or uncertain about that I can clarify for you now so that you’ll feel confident to move forward to the next step?”

    22. What’s your lifetime value of a customer?

    “Ask: ‘What’s your lifetime value of a customer?’” says Roger Bretau of Gotoclient.

    “With this information, you will be able to calculate if you really can help them or not.”

    23. What would be a great outcome for you?

    CIENCE’s Max Pittman recommends asking: “Have you thought about what would be a great outcome for you if/when you were to partner with us to utilize the services we offer?”

    “This question helps you uncover what the prospect views as a great outcome of the engagement. It also acts as an anchor to follow up on later, and it helps with setting the proper expectations,” Pittman says.

    “If you’re calling a lead from a marketing company, you really need to be trying to find out what drives the company, if anything,” says Charlie Worrall of Imaginaire Digital.

    “If you’re trying to sell to prospects who aren’t really driven to develop and grow their own businesses, it’s not worth your time. If they don’t have that ambition, move on because it can be harder to help and work with them down the road,” Worrall says.

    24. Is this within your budget?

    “The way I validate clients to see if they are worth working with is by asking: ‘Is this something within your budget?’ or ‘What is your budget?’” says PowerPhrase’s Oz Chowdhury. “We get a lot of people saying they want a site like Amazon or an app like Uber, but their budget is less than $500.”

    However, Uplead’s Will Cannon offers a way to turn the budget question around: “What is this problem costing you in terms of missed opportunities per month?”

    “Once you determine your prospect’s opportunity cost, you can then gauge how much they’d be willing to spend on a solution. This, in turn, helps you identify if they’re a good fit,” Cannon says.

    Sometimes, the Answer is More Important Than the Question

    “Ask simple questions that you know will result in an affirmative ‘Yes’ response,” says Cirrus Insight’s Maddy Osman. “This will help influence them as you build to your ultimate ‘Yes’—that of working with your company.”

    “For example, you might ask if a prospect heard about a big security breach that recently occurred with a competitor, to which they’ll likely respond, ‘Yes.’ From there, you might ask, ‘If I could help you prevent a similar problem, would you be interested in hearing me out?’ It’s hard to say no to that!”

    “That said, even small yeses can be useful for building a relationship. You might start by asking a question like, ‘You work for [company], right?’ Then, ‘Are you enjoying working in this role?’”

    “Regardless of the specific question,” Osman says, “the focus of an initial prospecting call should be around gaining agreement from your prospect.”

    Track your call volume and sales team activities at any given time with this call tracking dashboard.

    Article by
    Jessica Greene

    writes about marketing, business, and technology for B2B SaaS companies. A former writing instructor and corporate marketer, she uses her subject-matter expertise and desire to educate others as motivation for developing actionable, in-depth, user-focused content.

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