Conversational sales: 5 questions to get right if you want to boost your business growth in 2021


If you’re looking to build a conversational sales strategy that’s equal parts memorable as it is useful, then you’ve come to the right place.

Conversational sales is nothing new. It’s more popular now than ever before. Customers are looking for genuine conversations and personalized online shopping experiences to engage with on their customer journey.

We’re seeing more conversational sales strategies emerging in both B2C and B2B industries, which means conversations, and automated interactions, need to be more stand out and authentic than ever.

In this article, we’ll explore five questions you need to be asking people to build relationships, affirm trust, and ultimately encourage that site visitor to purchase with your business.

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Five questions every conversational sales strategy needs

There are a few areas you can implement a conversational sales strategy. It largely depends on your resources and the platforms your ideal customers are most comfortable using. Before you even consider your conversational sales questions, you need to identify your personas and your marketing channels first.

Once you’ve got those down, then you’re ready to start on your conversational sales workflow and start mapping out conversations that convert customers and building personalized sales funnels that will have better results.


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1. “What brought you here today?”

This is a big question, so you may be better off providing multiple choice answers for it. What brought you here today helps you do a few things:

Firstly, this question helps you understand someone’s business problem. By understanding their problem, you can better align your product to provide a solution.

This outlook will also enable your conversational flow and your sales team to provide a more intimate, tailored experience for your customer. Plus, when they get there, it will help inform your customer success team to provide the most accurate onboarding experience possible.

Secondly, this question enables you to understand your marketing efforts and apply a lead acquisition ROI to your marketing channels—especially if you don’t have a tag manager set up.

Someone can go down the solution-orientated route to answer this question. For example, ‘I need to convert more leads, but I need to manage them better.’ Or, someone can take a very literal approach to your question. For example, ‘I saw a Facebook ad and got curious.’

Either way, from this discovery call, you’ll be able to determine how educated they are, how ‘hot’ they are, and where you can attribute their knowledge to.


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2. “What’s your role at your company?”

Before you get into any of the nitty-gritty, it’s still important to get our introductions out the way. Understanding whom you’re talking to will do the rest of your conversation and sales journey a world of good. Plus, introducing whom your customer is talking to will help build trust and loyalty to the conversation at hand.

If you’re using smart tools, then the chances are you’ll already have someone’s name—or can garner that information further down the line. We’ve typed our name out enough times in various forms over the years; we don’t want to do it again. However, we’re still happy to talk about our role and our company. These types of questions rarely get asked, but can provide tremendous benefits.

By understanding someone’s role, you can determine if you’re speaking to the decision-maker or if decisions come from higher up. You’re ultimately deciding if the person you’re talking to has the cash disposable or not.

If they are the decision-maker, then great, you won’t need to go anywhere else. If they’re not, then don’t stress. It just means your content sales strategy will have to be slightly different after this question.

Although this person cannot say yes or no to buying your product, they can fight your case for you and be your internal brand ambassador. It’s your job to win them over and provide them with the resources they need to make their case for a budget proposal.

Lastly, by identifying the role of the person you’re speaking to, you can tweak your language and product positioning further down the line. Content Marketing Managers will be looking for different things than a CMO, for example, yet your product may be able to answer both roles’ needs. Showcase your product and your brand tone accordingly.

3. “How do you think we can help you?”

This is another fundamental question that enables you to understand and manage expectations. By getting a hold of what someone thinks you can do or hopes you can do, you can better align your future sales process to fit.

That’s only one half of the question though. The other half helps you work on positive business growth.

When you ask this question, you gain an insight into the content and product messaging someone has already seen. By this point, you may also know from which acquisition channel they’ve come from. It’s an opportunity for you to understand if your product messaging is on point and communicating what your product does clearly. It will also help you know if your messaging and targeting are attracting your ideal personas or are not quite hitting the mark.

If someone has an accurate idea of what your business can do for them, then you can give yourself a pat on the back and let your marketing team know you’re thankful. However, if they’re coming this far in the customer journey and still don’t have an accurate grasp of what your product does, now’s the time to figure things out and tweak top of funnel messaging.

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4. “Would you like to see how we can help?”

This question is more about the psychology behind whether a person is open to your sales process or not. If someone feels like they volunteered themselves to your sales team, rather than your sales team imposing upon them, then they’ll be more willing to buy from you. They will feel like the power and decision-making is entirely in their hands.

This is also a make or break question for your potential customers. Do they want someone to make an effort and give them a product demo? Or are they just browsing? This question is the first opportunity someone has to exit the conversation. That’s the reason it’s coming so late in the conversation—after someone has put in a certain amount of time and investment.

The truth is, you’ll likely get quite a few drop-offs at this stage in the conversation. But, that’s okay; trust the process. At this point, you don’t want to send leads to your sales teams that are not deemed as sales qualified (SQLs.) By placing this question here and filtering it down to those that are genuinely ready to invest it’s the most time-efficient thing you can do for yourself, your potential customer, and your team.


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5. “What’s the best way we can show you?”

Conversational sales is all about scalable personalization. You automate conversations and processes and always provide a variety of customer-facing flows. In doing so, you create on-brand, personalized conversations and sales funnels that people (and their persona types) can relate to. In all, building trust and confidence in your business, and making more sales.

This last question is a giant step towards a tailored sales experience, as you begin to understand a user’s communication preferences and learning style. Do they want a 1-1 product demo? Do they want to join a webinar? Would they prefer a phone call or talk to someone via email?

Once you understand how someone wants to communicate, you can be flexible toward them from here-on-in. Plus, you can get any contact details you haven’t already got. If your product is on point, then this question almost guarantees a sale; it’s just up to you to determine how big of a sale it is.


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Wrapping up conversational sales

“The key to conversational sales is to build a rapport. Each time you speak to somebody, the challenge will be different but the at the heart of the relationship is trust. You have to be natural, confident, and honest. Listen to the dialogue and focus on their needs. Listening is equally as important as talking in these conversations.” Matt Janaway, MarketingLabs

Remember, the questions you ask are more than just determining how to sell to the respondee. They can do more than build relationships and trust. The questions you ask can inform other areas of your business. From product design to customer success, marketing to business development, these first few questions with an MQL can be critical information to work from and use to evolve elsewhere.

Ask smart questions, gain valuable data, and build a conversational sales strategy that helps your business grow.