How to Turn Common Conversational Marketing Mistakes into Great Plays

By Sammi Reinstein


Everyone has that one thing they absolutely nerd out about. For me, it’s chatbots ?

I know this sounds a bit strange, but hear me out. They’re pretty amazing. And I know I’m not alone in this – just check out this collection of really good chatbot examples from these fine people who love chatbots as much as I do.

I love building out bots and optimizing experiences, which is a good thing because it’s literally my job. I recently joined Drift’s Professional Services team, which means I get to take my love of chatbots to the next level and help build and enhance playbooks for customers.

On my mission to become a master in conversational marketing, I’ve been observing and researching different bots across a ton of organizations and industries. For the most part, the bots I’ve seen are engaging, personalized, and best of all – real (aka they don’t sound like a form).

However, I’ve also seen people fall into a few traps that make the experience feel buttoned-up and “sales-y.” The good news? All of these mistakes can be turned into great plays that can increase CQLs and drive more revenue.

Keep reading for three common mistakes you may be making with your chatbots and how you can turn them into wins today?

Common Mistake #1: Using A Qualifying Question As Your Hook

This is something I’ve seen in a lot of bots. In the hook, or the preview text, there is a qualifying question, such as “Hey, welcome to the site! What’s your role?”

Seems innocent enough, right? But the problem with doing this goes back to a theme we talk about a lot here at Drift – no one wants to be sold to. Asking a qualifying question right off the bat makes it seem like all you want to do is get information, not have a quality conversation with your site visitors.

Don’t get me wrong. Drift is a great tool to qualify leads, and you should ask qualifying questions. But that step comes later in the flow. Because it’s not how anyone would start a conversation in real life.

Imagine you’re at a tradeshow. You walk up to a booth and someone starts talking to you and says, “Hey there! What’s your current role at your company?” Not only is this a strange way to greet a stranger, but from the very beginning, this kind of greeting lets you know you’re in a transaction – not a conversation.

How To Fix It: Show What You Can Do For The

If I’m going to give you my email, I first want to be shown the value of your product or the content you’re sending over.

So the best practice (and the best way to boost your conversion rate) is to have a great hook that shows the WHY of your company. How do you help customers? How are you different? The hook should also be interactive (people should want to click on it) and be low lift for the customer.

There are great examples of hooks that show value off the bat all over, but I want to highlight this one from Marketo.

There are a few things about MarketoBot that I want to call your attention to. First, it starts off with an awesome hook. By asking, “Is your MarTech stack strong enough to help you reach your marketing goals this year?” MarketoBot is both acknowledging a known challenge and enticing the customer.

Then comes the second key part of this flow. After asking the prompting question, MarketoBot then delivers the value proposition, which informs the customer and shows the functionality of the tool. Finally, and only after the bot has shown what Marketo is all about and had a conversation with the customer, it then goes into the flow of qualifying questions.

So, does this work?

Marketo has had 8,000+ conversations and generated 2,500+ CQLs using Drift (not to mention a 10% increase in total pipeline generated) ?

Common Mistake #2: Routing Sales Into Chat Too Soon

I understand the eagerness to connect a salesperson to a prospect. However, here’s the issue with jumping into a chat before someone has expressed intent – they get scared off.

Part of creating a great experience for customers means you need to meet them where they are.  So having a person routed into the chat before someone has gotten the chance to see your value prop creates an assumption that they’re ready to buy, which for a first time visitor or someone just browsing, is almost always not the case. For marketers, the goal is to nurture leads down the funnel. If a lead isn’t ready to talk to a salesperson, then we don’t want to make that their only choice.

Personally, when I’m connected with a salesperson and I’m not ready, I often leave the chat or even close out of the site. And this is really the worst part. Because you’re losing quality leads and increasing bounce rate.

How To Fix It: The “Just Browsing Net” Play

So what’s the solution? We call it something called the “Just Browsing” play… and it works really well.

By adding this net, you’re able to continue a conversation with someone who is still in the discovery phase, but not quite ready to talk to sales. There are a few ways to do this. One is to have the bot nurture the lead and get an understanding of who they are and why they are interested in your company.

The other is to have a CDR (a conversation development rep) introduce themselves with a goal of getting to know the prospect and their challenges, not to directly sell to them. Doing this helps create a real relationship with prospects – and you may even get to a place where people are coming back to your site just so they can talk to one of your CDRs, like this visitor who came to Drift asking to talk with one of our awesome CDRs, Matt.


This play takes the pressure off and allows your prospects to choose an option that is low stakes. At this stage, the customer may be looking for more information about your product, so be sure to identify their pain points and further educate them on who you are and what problems you can fix for them.

To get the most out of this play, you should end the conversation with a great CTA, like a highly-trafficked blog or eBook.

? Remember: this is a way to continue the conversation, so if someone says they are just browsing don’t say “thanks for chatting ?” – find out more about them and why they are on your site.

At Drift, we added a “Just Browsing” play to our welcome bot, and we increased our leads captured by 13% in less than 1 month.


Common Mistake #3: Being Unwilling To Iterate

Okay, I get it. You’ve worked hard on your bot and have meticulously set up the flow, picked your hook, and narrowed down your qualifying questions. At this point, you don’t want to touch the bot any further – your masterpiece is complete ?‍?

But here’s the thing. Your work doesn’t stop once the bot is live. Optimizing is a key piece of the playbook process. Your bot won’t reach its full potential unless you’re willing to iterate on the process and enhance the customer experience.

If you notice customers are getting stuck in the flow, or you aren’t hitting your benchmark metrics – it’s time to optimize.

How To Fix It: Optimize, Optimize, Optimize

There are a few great ways to identify where you need to optimize your playbooks. The first is monitoring conversations.

Take some time to sit in your chat inbox and see how people are moving through the flow of your playbook. Where are you seeing drop-off? What are some common trends in the flow that are leading to frustration? Are people typing in questions you aren’t optimized to answer? As you observe, take note of where you can make changes. And be sure your bot is following the criteria of a “healthy” chatbot. The beauty of the technology is these updates can be made right away.


Another way to identify where you can improve is by talking to sales. Ask your reps if you’re using the right qualifying questions or if what you’re doing is providing them with good leads. If sales is getting a lot of support questions – it’s time to optimize and make sure you’re sending these inquiries elsewhere. If sales is getting leads from countries you don’t support – update the playbook to exclude these countries or have a condition that sends content to“bad leads” so they can self-educate.

Reporting is another great way to see what you’re doing well and where you can improve. If you see a high engagement rate but a low meetings-booked rate, this means a lot of people are engaged but they drop-off before a meeting can be booked. What can be added there to make sure customers get through the whole flow? This may mean it’s time to take out some qualifying questions – and the best practice is to ask around two or three.

Optimizing your playbooks will ensure your customers are getting the best experience possible, and not to mention, get you more quality leads and more meetings booked.

What have you done to flip a mistake into a great play? Email me here – I’m always down to chat about bots⚡️

Want more conversational marketing examples you can steal right now? Click here.