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One weekend this Fall, I helped my mom sell her herbal teas at a craft fair in New Jersey (Shameless plug, but check out her teas). This was my first time selling anything at a Farmer’s Market, so I had no idea what to expect.

When the craft fair started, I noticed a weird tension between us and shoppers. They would look briefly at our booth, show mild interest but were cautious of talking to us. They didn’t want to be “sold.”

We had to engage them, enticing them into our booth and start a conversation to ultimately make the sale. I learned that jumping the gun and asking them if they wanted to buy teas was too pushy and most people said: “no thank you.”

Once I realized that you had to start soft and start a genuine conversation, asking questions like “do you like tea?” or “want to try some tea?” people started to come by and let their guard down, more often leading them to purchase.

I couldn’t help but notice how similar this concept was to the chat bot on our commercial website. People float around your website showing mild interest but hesitate to start a conversation or schedule a meeting.

Like the people at the craft fair, navigating these conversations can be tricky but can yield great results for your business when done right.

I wanted to share three strategies that I learned from Ryan Deiss’s presentation at Inbound 2018 on Conversational Marketing that helped us have more genuine conversations through our chat bot and increase the quantity and quality of meetings set.

Strategy 1: The chat bot is meant to qualify, not to sell

Qualifying is the process of asking questions to determine if a prospect is a good fit.

This strategy is more efficient for two reasons: you’re focusing on the prospect and scheduling meetings with the right people.

Conversations start by asking questions. When you ask questions that are focused on the prospect, they’re more likely to respond. Who doesn’t like talking about themselves? People tend to answer because you’re focusing on them, not just trying to push your product.

The added benefit of this process is you always ensure that you’re only scheduling meetings with prospects who are good fits. So many random people visit your website. Chatting with all your website visitors is inefficient. 

By asking the preliminary, qualifying questions ahead of time, you’ll ensure that you’re only hopping into conversations and booking meetings with qualified prospects.

To do this, make sure you ask all the anonymous traffic on your site the minimum amount of questions that can lead to a qualified lead to take an intro call.

Strategy 2: Start your chat bot with a binary question

A binary question is one that only has two answers.  These types of questions make it easier for a website visitor to answer and start a conversation.


As we know, humans have short attention spans. In fact, a 2015 study conducted by Microsoft revealed that we now have an attention span of eight seconds.  If we ask a question that is too complicated, they’ll bounce off the site.

However, once they start the conversation, they’re more likely to continue it. This is why it is important to get them started.

Here are some guidelines for your opening binary question:

  • Ask them a question about their identity: On Ryan Deiss’s website, his chatbot asks if they’re an agency or digital marketer. This helps his team understand how they should direct the conversation and if you’re not one of those roles, they probably don’t need to be talking to you.
  • Ask a yes or no question: Having them only have to answer yes or no takes the least mental energy possible.
  • Ask them a question that they can’t say no to: For example, if you’re a marketing agency asking a question like “interested in increasing the number of leads?” is a hard question for a marketer to say no to.


Think about your business and how you could ask an easy question that always qualifies your prospects at the same time.


Strategy 3: Have a salesperson jump into the conversation once they’re qualified.

We usually see our website visitors getting hung up towards the end of the conversation where they have to input their email address or schedule time on one of our reps’ calendars.

Sometimes website visitors need a little more information before scheduling a meeting that our website didn’t answer. Having a human hop into the conversation and answer their questions can make a difference in getting them to agree to a meeting.

Whatever the visitor said they were interested in learning more about, we come in and say we can send over some materials about that topic. This usually gets them to respond and either one of two ways:

  1. They ask us to send them more information:  we get their email and send it to them. We then have established a connection and follow up later.
  2. They usually give us a little more detail as to what they’re looking for or why they’re on the site. Then we can have an in-depth conversation about our platform. This usually leads to disqualifying the visitor or scheduling a meeting.

We have a dedicated Business Development Representative (BDR) hop into all these conversations. Once the prospect has answered the minimum amount of questions that tells them they’ve qualified our BDR hops in.

When we first started using Drift, we weren’t scheduling meetings with qualified leads.

We had our bot ask straight away how we could help today. However,  we weren’t getting people to engage with the bot and the meetings we set were not always qualified. Essentially, our bot wasn’t doing anything different than our demo request form.

The first thing we did was change the first question to ask an easy qualifying question, “Do you work for an Owner?” Since our software is best fitted for real estate owners, this question was an easy yes or no question for them to answer to get them engaged and the one qualifying question we need to know to continue the conversation.

We then switched our bot to qualify the visitor instead of trying to sell them on our services. Originally we would try to sell them on our product through the bot saying questions like “interested in learning why the largest real estate owners use honest buildings?” One this was very focused on us and two it was not conversational at all. Would you ever say something like that in a face-to-face conversation?

Once we started qualifying through the bot, not only did we ensure that we’re only talking to qualified people, but the questions were focused on getting to know the prospect. Focusing the conversation on the prospect makes them want to talk more to the bot because everyone likes talking about themselves.

Here are the three qualifying questions we’d ask:

  1. Are you an owner?
  2. Tell me more about you, what best describes your role?
  3. What were you hoping to accomplish on this site?

Once they tell us what they’re looking to accomplish, our BDR hops in and usually says something on the lines of that he can send over some material on the goal they’re looking to accomplish.

This strategy has resulted in a 500% lift in monthly opportunities.

Think about how you would normally talk to humans.

As you can see, this process is not much different than being at a craft fair because you’re still talking to humans. The same rules apply when trying to get them into conversations and keeping them engaged.

Being conversational and understanding your prospects’ needs will generate the most success for your business.