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Conversational Selling: The 5 Critical Questions That Will Help You Generate Sales Leads From The Traffic You’re Already Getting

I want to start this post with a quick question:

What is the highest-converting sales medium of all time?

I’ll give you a second to think about it.

(Cue the “Jeopardy” music…)

OK, time’s up!

The answer…is face-to-face selling.

And that makes sense, right?

After all, a real human salesperson—especially a GOOD one—has all kinds of advantages over mass medium channels like email, TV, and print.

For example, when face-to-face with a prospect, a real salesperson can see your reactions in real time. Ask you questions. Address your objections as soon as you raise them.

And, perhaps most importantly, they can create a sense of connection with you and make you feel like you’re talking to someone who truly cares.

I call that conversational selling, and it’s quite simply the single most effective way to sell a product or service in history.

Engineer more high-converting sales conversations from the traffic and leads you’re already getting.

So why do I bring this up?

(Especially on a blog that’s dedicated to digital marketing?)

I’m glad you asked.

Because the truth is, the way we sell products and services online is changing.

One-to-many marketing methods (things like banner ads and email blasts) are becoming less and less effective every day. At the same time, 1-to-1 marketing methods (things like Messenger marketing) are becoming more and more common—and more effective.

And by using some of these tools, we can actually start to leverage the high-converting power of conversational selling


And in this post, I’m going to help you do just that by showing you how to engineer more high-converting sales conversations from the traffic and leads you’re already getting.

But before we dive into that, there’s something you need to know first.

How Do People Converse Online? (AKA What Tools Should You Use?)

OK, so we’ve established that conversational selling is the highest-converting sales medium of all time.

In the past, conversational selling meant either face-to-face selling or selling over the phone. But we’re not talking about face-to-face or phone conversations here.

Instead, you’re going to learn how to leverage conversational selling in digital marketing.

But how do you do that?

Today there are 3 big tools you can use to leverage conversational selling online:

  • Email
  • On-page chat
  • Messenger chat

Later on, in this post, I’ll go over some of the specific tools I recommend for #2 and #3. But for now, I just want to talk about these tools in general.

And in order for this whole conversational selling thing to work, you can’t do what most people do—which is to use these 3 conversation channels interchangeably.

These are different tools and they have to be used in different ways to really generate sales with high-converting messages.

So, let’s dive into how you do that.

How to Start a Conversation Online (Strategically)

The first step in any conversation is—obviously—to start the conversation in the first place.

This is something you should spend some time thinking about. Because there’s a right way and a wrong way to do this, and the way you begin a conversation can have a big impact on that conversation’s outcome.

So, with that in mind, there are the 3 different ways to open your online conversations in a strategic way that tends to lead to more sales.

Conversation Starter 1: Page to Chat

When I say “page to chat,” I’m referring to those little chat windows that you see pop up in the lower-right corner of websites. Here’s an example:

A chat example in the right hand corner of the screen asking, "How can we help you today?"

Unfortunately, these chat boxes don’t really have much of a sales effect for the majority of companies who use them. And you want to know why?

Because they don’t do a good job of starting the right kind of conversation.

And to illustrate why that’s the case, I want you to go through a little exercise with me.

Pretend you walk into a department store and start browsing around in the clothing section.

And after a few minutes, a salesperson approaches you and says:

“Hi there, can I help you?”

We’ve all heard that question in a situation like this before. So, how do you usually respond?

Well, if you’re like most people then your response to that question will be:

“I’m just looking.”

Now, notice what happened there.

The salesperson asked you a question—they tried to start a conversation.

But the question they asked you was way too open-ended. There was no easy way for you to respond, so rather than make the effort to come up with a thoughtful response on the spot, you did what 99% of other people do: you politely refused their help.

Conversation attempt…denied.

And there’s an important lesson here for digital marketers.

If you don’t believe me, take another look at this chat window, and pay attention to the question they’re asking:

A chat example in the right hand corner of the screen asking, "How can we help you today?"

It’s the same basic question! “How can we help you today?”

Ask a binary question that leads the conversation in the right direction.

And I guarantee you it gets the same answer from the vast majority of people. That is to say…no answer at all.

People ignore this question on your website, just like they do in person.

Why? Because, once again, it’s too open-ended. It isn’t focused. There’s no quick and easy way for them to answer.

So, what should you do instead?

Rather than asking a difficult, open-ended question that could lead anywhere…

A smarter approach is to ask a binary question that leads the conversation in the right direction.

Here’s an example of what I’m talking about:

An example of chatbot from DigitalMarketer asking a binary question.

See how much easier that question is to answer? There’s really no thought involved. It’s super-quick and super-easy.

It also leads the conversation in the right direction!

Rather than bringing up an unrelated subject, the question leads very naturally to a conversation about agency/consultant marketing.

It’s just a better way to open a sales conversation.

So, that’s my first tip to help you open better sales conversations. Start by asking a binary question.

Now let’s move on to Tip #2, which is going to help cut down on the number of conversations with unqualified prospects.

And the way you do that is to throttle your conversations to filter out unqualified prospects.

When it comes to conversational selling, particularly with on-page chat boxes, more is not necessarily better.

See, most companies put their online chat widget everywhere: on every single page, including the homepage, for every single visitor.

That will lead to way too many conversations with way too many unqualified prospects.

Instead, I recommend throttling your page-to-chat conversations. Be more strategic about when and where you choose to display your on-page chat widget so that you’re starting higher-quality conversations with better-qualified leads.

And here are 4 ways you can do that:

Avoid the Homepage

Your homepage gets way too much general traffic.

When people come to your homepage, they aren’t ready to have a sales conversation. Instead, they’re just getting oriented to your site and trying to figure out where to go next. So, skip the homepage.

Trigger Chat on the Third Visit 

People often aren’t ready to buy right away.

They need some time to learn more about your company and your product or service. So, don’t try to rush things—wait until they come back after a few visits and are ready to take the next step.

Trigger Chat on Bottom-of-Funnel Content Only

Separate your content into top-of-funnel (TOFU), middle-of-funnel (MOFU), and bottom-of-funnel (BOFU) content.

People viewing your TOFU content aren’t yet ready to buy; they’re still getting acquainted with your product or service.

Instead, trigger your chat boxes on BOFU content that indicates the visitor is close to making a buying decision.

Examples of BOFU content includes individual product sales pages, trial or demo pages, pricing pages, and so on.

Another benefit of targeting bottom-of-funnel content is that the content can inform the conversation. For instance, if our visitors here at DigitalMarketer are visiting BOFU content about Facebook advertising, we might open a different conversation than we would with someone visiting BOFU content about Google Analytics. 

Trigger Chat on Pricing & “Thank You” Pages 

Another way of targeting BOFU content is to trigger chat on the pages that people tend to visit just before and after converting.

Throttle your conversations to filter out unqualified prospects.

Anyone visiting your pricing page is clearly considering a purchase. And anyone who visits a “thank you” page has just signed up for something, such as your mailing list—which means they’re often open to a conversation about making a bigger commitment with your company.

So, to recap, page-to-chat is a great way to open sales conversations with the traffic that’s already coming to your website. And 2 tips you can follow to start better conversations with those people are:

  1. Start by asking a binary question that leads the conversation in the right direction.
  2. Throttle your conversations to filter out unqualified prospects.

Conversation Starter 2: Email to Chat

OK, now we’re going to jump to a new medium: email.

And to many of you, it might not seem like email is really a conversational marketing channel. After all, isn’t email the same channel you use to blast out promos and deliver automated campaigns that never really involve any back-and-forth?

Well, yes. It is. But email can also be a really powerful way of opening sales conversations…if you’re strategic about it.

Here’s a 3-step process you can use to generate high-quality sales conversations through email:

Step 1: Use High-Intent Gated Content

It might sound obvious, but the first step to using email to generate sales conversations…

…is to attract the right email subscribers in the first place.

And to do that, I recommend using high-intent gated content. In other words, you ideally want the content attracting people to your email list to inform the conversation. To give you an idea about what that person is interested in.

So, at DigitalMarketer, we would NOT want to use gated content like: “How to be a better marketer.”

That’s way too general. It doesn’t tell us anything about what that person wants, except that they want to be a better at marketing. Very vague and nonspecific.

Here’s a much better example of high-intent gated content that has worked very well for us in the past:

An example of landing page from DigitalMarketer for a free online training

See how much more specific that is?

We know that the only reason someone would register for this is if they want to build an in-house marketing team.

So, the content itself is attracting the right kind of people for the sales conversation we ultimately want to have. And the content informs that conversation, so we know exactly what to talk about when we email them.

Step 2: Send Emails That Ask For Replies (Not Clicks) 

Most emails ask for a click. They want you to click through to a blog post, to a registration page, to a sales page.

But remember that email isn’t just a one-way communication channel! We can also send emails that ask for a REPLY.


And if you want to use email to start a sales conversation, that’s exactly what you need to do.

Here’s an example of a few emails that do that, including my all-time favorite, “the magic 9-word email”:

3 examples of sales emails that start a convesation

That 9-word email, in case you can’t read it, is:

“Are you still looking to grow your marketing team?”

And you can use this formula for just about anything. The formula is: “Are you still looking to,” and then add the desired end result you know the person is after.

  • “Are you still looking to grow your marketing team?”
  • “Are you still looking to lose 10 pounds before that wedding?”
  • “Are you still looking to drive a golf ball 10 yards farther with every swing?”

The frame of “Are you still…” is a great way to open a conversation because it tells the person on the other side that you know exactly what it is that they want. (And you know this because of Step #1—because you used specific, high-intent gated content.)

And if you do both of those things, you’ll begin to open the right kind of conversations with people via email. And the final step is to…

Step 3: Actually Respond! 

Now that the conversation is rolling, all you have to do is keep it going!

It sounds like a simple thing, but it’s actually becoming rare these days. Because so much email is purely automated, you’ll stand out from the pack by simply being a human being and responding to people.

Your prospects notice that. And they appreciate it.

Prospects responding to emails and Ryan responding back.

You can also use these conversations to increase sales and even to sell different products!

For example, here’s an email we received back from a prospect. In this email, the person wasn’t a great fit for the service we were originally marketing…

But because we started a conversation and listened to them, we were able to sign them up for a different service instead—one that made more sense for them.

An example of an email chain between a DigitalMarketer sales rep and a customer

Tip: you can use email to open conversations in other channels, too.

Here’s another example of an email we sent asking for a reply. And in this email, we gave people 3 ways to respond:

  • Reply to this email
  • Give us a call
  • Click a link to chat with us on Messenger

An email DigitalMarketer sent asking for a reply. And in this email, DM gave people 3 ways to respond

I was surprised at the results of this email.

The highest percentage of people (about 50%) chose to chat with us on Messenger. About 35-40% responded to the email, and 10-15% gave us a call.

So, remember that you don’t have to view these channels in isolation. Use them together and give people the freedom to contact you in the way that’s most comfortable for them.

Conversation Starter 3: Ad to Chat

The third and final way to open a conversation online is through an ad.

The first 2 conversation starters (page-to-chat and email-to-chat) were mostly about starting conversations with the traffic you’re already getting. The people who are already on your website, already subscribed to your email list.

But once you reach the point where you’ve maximized your sales conversations from the traffic you’re already getting, you’ll probably want to go out and start new conversations with even more highly qualified prospects.

And a great way to do this is with Facebook ads.

Facebook has 2 ad units that allow you to jump immediately into a conversation—the person doesn’t even have to visit your website at all.

And those 2 ad units are:

Lead Ads

Lead ads give you a really easy way to build your subscriber list and start conversations with people through email.

This is a really low-friction way to start more email conversations at scale.

To succeed with Lead Ads, you’ll want to offer some type of high-intent gated content (see Conversation Starter #2 above).

And when people click on the button in the ad, they’ll be prompted to enter their information:

A DigitalMarketer Facebook ad that leads to a form page once it's clicked on.

Once they click “Submit,” they’ll be added to your email list and the conversation can begin. I recommend going back and following the strategy laid out for Conversation Starter #2.

This is a really low-friction way to start more email conversations at scale.

Facebook Messenger Ads 

The other way to start a conversation straight from a Facebook ad is to use Facebook Messenger ads.

Facebook Messenger is one of the newest marketing channels, and it’s growing really fast.

And with these new ads, now you can create Facebook ads that lead to an immediate Messenger conversation:

A DigitalMarketer Facebook ad that leads to Messenger once the ad is clicked

In most cases, you won’t want this to trigger a live conversation right away. Instead, you’ll start by letting people interact with your chatbot first.

I’ll go into more detail on how we do this in just a minute.

The 5 Critical Questions that Lead to High-Converting Conversations

If you follow my advice above, then you’re going to succeed in starting a lot more conversations.

If you ask these 5 questions, it generally tends to result in a sale.

So…now what?

The next step is to keep the conversation going.

Now you don’t want to chat about just anything here; you want to lead the conversation in the direction of a sale. But at the same time, you want to make sure you do this in a way that feels natural, not forced, and helps build a relationship with the prospect.

At DigitalMarketer, we instruct our salespeople to do that by asking the following 5 critical questions. If you ask these 5 questions, it generally tends to result in a sale.

When used correctly, these questions will help you to have a “warm handoff”—an easy transition from conversational marketing to conversational selling.

Question 1: “Are you [insert market/avatar]?”

Most often, this question is asked by marketing as part of the conversation opener.

It’s a good way to start because it makes sure you’re talking to the right person. Someone who’s a good fit for your product or service.

You can also use this to subtly qualify your prospects. If you want to make sure you’re talking to a decision-maker in a business, your question might be:

“Are you a marketing manager looking for a better way to train your team?”

Question 2: “Tell me more about yourself/your business.”

That’s great! Tell me more. Do you specialize? What do you do?

In this question, you’re just digging a little deeper. Showing some genuine interest.

There’s no ulterior motive. You aren’t taking notes to segment these people for some kind of automated follow-up.

You’re just taking a minute to learn a little more about them and have a normal human conversation.

Question 3: “What brought you here today? What are your goals? What are you hoping to accomplish?”

Now we’re starting to steer the conversation toward your desired end, the sale. And the best way to do that is to ask what they’re hoping to achieve today.

Keep in mind, a lot of people won’t necessarily have a great answer ready for this question. So, if that’s the case, here’s what I recommend.

Take the biggest 3 benefits that your company can provide to your customers, and list those benefits out. Then ask the person which of those benefits they’re most interested in.

This gives them an easier way to answer this question and keep the conversation moving forward.

For example, when speaking to an agency prospect we might say:

“Here at DigitalMarketer we’re really good at helping agencies to (1) attract more clients, (2) scale and systematize their business, and (3) increase their retention and recurring revenue. Between those 3 things, is there 1 that really fits in with your goals?”

Question 4: “What do you know about [your product/company name]?”

Asking someone what they know about you is a great question that continues to help move the conversation forward. It’s also a way you can discover hidden objections so you can overcome them.

So, for example, if they say something positive like, “I’ve heard great things about your product…” Then you can transition pretty seamlessly into the sale.

But if they say something negative, that’s OK too! Because the fact that they’re there, having that conversation with you, suggests that they’re still open to being sold.

And now you have the opportunity to respond to that objection. If they mention that they’ve heard bad things about your customer service, you could reply with: “Yeah, we’ve had our growing pains in the past. Luckily, we’ve got that all sorted out now, and we’re in a great position to help you get more clients…”

When you’re asking this question, look for opportunities to refer back to those 3 big benefits from Question #3.

And once your prospect indicates that they want to achieve one of the big benefits that your product/service/company can provide—once you know what they want—the last thing you need to do is ask:

Question 5: “Do you want some help with that?”

This is the highest-converting close I’ve ever used.

It’s super simple. Really non-intimidating.

This is the highest-converting close I’ve ever used.

And if you’ve followed along with Questions 1-4 already, then making the sale at this point should be pretty easy!

They want a benefit. You know what that benefit is. You also know that your product or service can provide that benefit.

So, at this point it just makes sense.

And if their answer is “Yes,” then you’ve made the sale!

3 Conversational Selling Tips

Now that we’ve covered the process of how to engineer high-converting sales conversations, here are a few more tips to help make this process even more effective.

Tip 1: Try Out These Recommended Tools

Earlier in this post, I told you the 3 channels through which you can use conversational selling online:

  • Email
  • On-page chat
  • Messenger chat

For Channel #1, email, there are a ton of options and I’m sure you’re already familiar with them. MailChimp, AWeber, ActiveCampaign, InfusionSoft, etc. Take your pick.

For Channel #2, on-page chat, some of the tools you might want to check out are: 

  • HubSpot Sales Live Chat. Hubspot does a great job with all their sales tools. And if you use other HubSpot tools, like their database, then you can do some nifty things—like having your chat box appear only to people who are not already customers.
  • Drift. Drift calls itself “the world’s first and only conversational marketing and sales platform.” I don’t think you can call it the ONLY one anymore, but they were certainly one of the first (if not THE first) company to promote chat for selling.
  • Intercom. This is another popular option. Intercom was originally envisioned more for answering questions and providing support, but you can also use it for conversational selling using some of the techniques you learned above.

And for Channel #3, Messenger chat, there’s really only 1 tool I recommend:

  • ManyChat. Unlike the 3 tools above, which are strictly widgets that you add to your website, ManyChat integrates directly with Facebook Messenger. It supports both live chat and chatbots, so you have a lot of power and flexibility when setting up the conversational selling system explained in this post.

One great thing about ManyChat is that you can get started for free. So, there’s really no risk to giving this a try.

Tip 2: Check Out The Hubspot Academy

I originally presented this material on conversational selling in partnership with HubSpot.

And if you’re looking for more training to help improve your ability to drive new leads and sales with an inbound strategy, I’d recommend checking out HubSpot Academy.

They put out some great training that is sure to help you grow your business and/or take the next step forward in your career.

Tip 3: Leverage Chatbots

Lastly, I want to talk about chatbots for a minute.

You may be wondering if bots have a place in conversational selling, and if so, where they fit into the big picture.

And the short answer is that YES, chatbots can absolutely play a critical role in conversational selling online. But they can’t do everything.

In order to do this right, a human will need to take over the conversation eventually.

What you want to do is use your bot for filtering, not for closing the sale.

Then after your bot has filtered out all the unqualified leads and started a conversation with the good leads, it’s time to let a human take over.

So, if you look back at the 5 questions above:

  • “Are you [insert market/avatar]?”
  • “Tell me more about yourself/your business.”
  • “What brought you here today?”
  • “What do you know about us?”
  • “Would you like some help with that?”

Question #4 is where your bot needs to hand over that conversation to a human.

Here’s a quick example of what this might look like in practice. This is how one of our bots opens a conversation—you’ll notice that this is Question #1:

An example of a DigitalMarketer bot starting a conversation by asking if they're a consultant or a marketing agency.

After we get their answer, the bot moves on to Question #2—asking more about their business:

The DigitalMarketer bot moves on to Question #2—asking more about their business

Then we can use the bot to get a general idea of what this person is looking for, by stating the big 3 benefits we can provide:

The DigitalMarketer bot asking what their top priority is and giving several prompts to choose from.

Now after the person answers that question, it’s time to transition this conversation to a human salesperson. This lead is potentially ready to buy.

Here’s an example of one way you can do that:

The DigitalMarketer chatbot asking if they'd like to schedule a time to talk more

And there you have it: a simple example of humans and chatbots, working in harmony to open—and close—more sales conversations.

Remember: All Selling Is H2H

I want to wrap up this post by saying:

The future belongs to the companies who are willing to invest in real, one-on-one, human-to-human (H2H) interactions.

Remember that while we talk about selling with terms like B2B and B2C…all selling is really H2H. Human-to-human.

NOT the companies who automate every single step of the customer journey so they never have to talk to another customer again.

Remember that while we talk about selling with terms like B2B and B2C…all selling is really H2H. Human-to-human.

It’s a person on the other end you’re talking to. Not a lead, or a number, or a blip on your analytics dashboard. It’s a person.

And people are relational beings! We like to feel connected with each other. Understood by one another.

And when you treat your prospects like real people, they appreciate that. They feel it. And they enjoy it much, much more than the experience of being crammed down a one-size-fits-all marketing funnel.

So, keep that in mind when you’re thinking about how you’re going to market and sell your product or service in the future. And just remember that it’s never bad advice to be willing to invest in real human interactions.

Ryan Deiss

Ryan Deiss

Ryan Deiss is the Founder and CEO of and Founder and Managing Partner of, a digital media and ecommerce group that owns dozens of properties. Ryan has been called one of the world’s leading digital marketers by Shark Tank star, Daymond John. A best selling author, founder of multiple companies collectively employing hundreds around the globe, and one of the most dynamic speakers on marketing in the United States today, he is undeniably a recognized expert on the digital era. Connect with Ryan on Twitter.

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