Conversational Content & Chatbot Strategies | EWR Digital

May 7, 2024

<a href="" target="_self">Matt Bertram</a>

Matt Bertram

Matt Bertram is a award-winning marketing consultant and SEO Expert. He is the lead digital strategist at EWR Digital. Host of the Best SEO Podcast and Co-Host of the Oil and Gas sales and marketing podcast.
Image of a person conversing with a robot on a couch, showing the use of chatbots and AI in modern communication


Let’s talk about how “conversational content” can and should be the ultimate secret weapon when it comes to connecting with your audience and your customers in a personalized and human way. If you think about it, the internet is made up of two types of communication: one-way and two-way content.


One-way content is the slow and boring informational (blog post or podcast), visual (infographic or video), promotional (sales email or banner ad), or entertaining (memes or viral videos). Two-way content has existed since the internet began — just think back to bulletin board systems, IRC servers, instant messenger, and now WhatsApp and Discord.


When we talk about the “conversational” content to apply to your business today, we’re focusing specifically on chatbots, social media interactions, and interactive quizzes. Conversational content is relevant when we’re dealing with possibly small screen sizes (mobile phone screens), visitors with short attention span or perhaps in a hurry, or those who aren’t technologically savvy or familiar with your interface.


If you’ve ever helped a “non computer techie” navigate a specific piece of software, you’ve experienced the frustration of “menus.” Click this tab, that’s not it, go back, try that button. Compare that to a time you were on a web page, unsure what to click, and opened a chat bubble. Maybe you were able to type in your problem or question, in natural language, or step through a few micro-decisions, clicking through a few simple choices, to get to your solution.


A chatbot can be very valuable and powerful because it requires no interface, or at least, a minimal interface. 88% of customers chatted with a bot last year and only 10% of those rated their experience with the chatbot as negative. Just last week, I had to respond to a transaction within my PayPal account, so I logged in and used their chatbot. I then needed to submit documents to my H&R block accountant, so I used their chat-based app. I sold a domain name on GoDaddy’s Dan marketplace, and the process involved answering a few questions from a chatbot.


Humans are naturally used to conversations. It’s no coincidence that OpenAI used the chat-based model of ChatGPT to make its interface accessible to the public. Anyone can understand how to ask a question or provide an answer — there’s no coding SQL or formatting JSON. Because of the magic of no-code integrative tools like Zapier, you can connect this to your existing data warehouse or query your system.


You can add chat functionality to your existing frontend or backend system within minutes. Consider the AI chatbot, help desk, and live chat tool Intercom. You could use Chatbase to load a custom GPT with your organization’s knowledge. You can use the ChatGPT Plugin for WordPress to add chat to your website.


When implementing a chatbot to help your customers, consider:


Purpose, Goals, and Scope. You can create a chatbot for customer service (order look-up, ticketing), sales (frequently asked questions and objections), appointment booking, and more. In a famous “fail”, a Chevrolet dealer in Watsonville, California added chat to its site. Pranksters were able to get the sales agent to solve complex chemistry problems and get the bot to agree to sell a car for $1, simply because the bot had not been setup with any bounds (limitations). Although a chatbot can potentially handle any question, what specific use cases do you want to limit it to?


Simplicity with Clear Navigation. The point of a chatbot is to provide speed and ease-of-use. About 90% of customer queries are resolved in 10 messages or fewer. Your chatbot should speak in short, simple sentences. It should ask only simple questions from your users (i.e. ask only for their email address in one question, then continue, instead of asking for multiple contact details at once). Limit multiple-choice options to three options or fewer, when you can. Also consider finer details such as “Yes/No” buttons — can you re-word those buttons so it is 100% clear what “yes” or “no” means?


Friendliness and Transparency. Do what you can to make your bot polite to your customer. However, don’t try to pass off your bot as a human. It’s annoying when someone believes they’re having a human interaction and getting repeated answers. Manage expectations! Additionally, legislation exists in some jurisdictions that require you to disclose the fact that your bot is an AI and not a human: California’s Bolstering Online Transparency (BOT) Act of 2018, and the US Senate’s Bot Disclosure and Accountability Act of 2019. There’s no doubt that lawmakers will continue efforts to regulate AI (especially chatbots) in the future, so it’s in your best interest to avoid human impersonation.


Easy Exit or Handoff to Human. We’ve all been there — you just want to talk to a real life representative. It’s possible that years ago, you navigated through a phone-based customer support menu (“press 3 for this department, press 4 if you are calling about that issue.”) Perhaps you were frustrated with the system, and when you called back once or twice trying to restart your navigation, it connected you with a human immediately. The universal language for such systems was to dial “0” or speak the phrases “Representative” or “Talk to Human” in order to default to a human operator.


All of this is to say that you should have several easy paths for a chatbot to lead to human interaction. The biggest advantage to a chatbot is the speed with which your end-user can get the answer to their problem. But if the chatbot is not helping, be sure your chatbot flow can lead to human interaction.


Part of an easy “exit” should also make it clear when the chat transaction is over. How can they close, and if the chat window has been sitting idle for several minutes, are both parties still online? Who is waiting on whom for a response?


Iterative Auditing, Improvement and Feedback. Just like with any system, you should look at raw logs (if privacy allows) to see how the chatbot is working. What does success look like to you? What is your chatbot’s success rate? How many seconds does it take to get to that success, and in how many steps? Are there any missing pieces, or can some complexity be removed?


Consider chatbots in your business to gain a deeper connection with your customers, and ultimately, establish a more approachable and relatable brand image.


Social media is all about two-way interactions and you are rewarded on any platform for delivering value. If you make posts that no one reads or views (they scroll right by and the algorithm notices), deliver little value, and get low engagement (likes, comments, shares) then that social platform is trained to show less of your content, in order to make room for more “effective” (addictive) content.


On the other hand, if your content proves to be engaging, they will show your content to more users on the platform in general, more of your own followers, and more of that “lookalike” type of social media user.


You should write the way you speak — in normal, plain, everyday language. Use short sentences and paragraphs, avoiding jargon whenever possible. Write in an active voice — “I ate the cake” instead of “the cake was eaten by me.” Use humor, especially self-deprecation, to be more memorable. People watch. Follow similar content and do your best to replicate what seems to be getting attention, while delivering your own uniqueness.


Use storytelling techniques: start with an attention-getting hook, relate to your viewer’s urgent and immediate problem, provide a quick solution, and direct them to a call-to-action. Consider asking a question or in some way directing your video viewer or blog reader to take a specific action after consuming your content.



You may have already heard about the “four C’s of social media” which are content, connection, communications, and community. This means you should post consistently. Always be posting something that’s new, interesting, attention-getting, and valuable. Pay attention to what your audience wants and do your best to get them to interact.


One of the most evergreen ideas with social media marketing is to go where the attention is — even if a social network is new, or not your personal choice, do they reward you for posting on their platform? When you share great content, do they give it lots of traffic?


Short form video content is extremely popular and an on-the-rise trend you should pursue. 73% of consumers prefer short-form videos to search for products or services. YouTube Shorts get 70 billion daily views. TikTok has 50 million daily users, 167 million views per minute, and the average TikToker uses the app 95 minutes per day. Keep in mind, that is an hour and a half watching and scrolling through videos, sometimes only a few seconds at a time!


That sounds great, but how do you get your own results from short form videos, especially with this 2-way conversational content?


Conventional logic will tell you to make it a habit of posting daily short form videos, onto multiple platforms, so that you can eventually amass thousands of short videos. This provides for thousands of opportunities (paths) for someone to notice you and find our more about your brand (company). Also consider that some random video you posted today may be the one that gets that ideal prospect to view the rest of your account, then they browse and they see many past weeks worth of videos, and they click on that reel 15 posts ago about intermittent fasting or mortgage refinancing, which is what really cements you as the authority in their mind.


If I were to give you the three best pieces of advice about making the most of short form conversational video content, it would be this:


Principle #1: Get into a daily posting habit. The only way you will improve and create a huge library of content is to create a little bit every day, adjusting every time based on what you see your peers posting, and what feedback (engagement, such as video watch time) from your audience.


Principle #2: Think about your video’s structure. The basic template when making a statement is to, “Tell them what you’re about to tell them, then tell them, then tell them what you just told them.” Consider what two or three talking points you will state in your video, and possibly decide what your first and last spoken sentences will be.


Principle #3. Boil down your video ideas into the simple and then advance into the more complex. After several weeks of creating and posting content, you will have to overcome your own resistance about repeating yourself. Repeat away! Just think about your favorite thought leader expert (or motivational speaker) and the number of times you have heard their memorable phrases in different contexts. Take your own ideas and figure out ways to make them extremely simple and stripped down for short form video, then later create other helpful 60-second videos helping a beginner get to expert status in your industry.


I would say there are three types of short form 60 second TikTok videos: talking head selfies, podcast reels, and out-of-the-box content.


When most people think about a TikTok video, they imagine a camera in selfie mode, pointed at a thought leader expert (you), delivering a quick piece of advice.


Keep in mind that a “complete” sentence is about 5 to 10 seconds, so in a 1-minute video you will only have about 7 sentences to deliver your message in a structure like this:

  • Hook: 3 seconds. Capture attention with a strong statement, surprising fact, intriguing question, or surprising image.
  • Introduction: 10 seconds. Get to your topic, problem, setup.
  • Body content: 35 seconds. Either tell the story or explain the steps. Use quick cuts when possible, and maintain high energy.
  • Call to action: 10 seconds. Prompt your viewer to like, comment, follow, subscribe, or share. Direct them to other videos or next steps to take. If necessary, deliver one last sign-off and leave a lasting impression.

The goal is to reduce the number of decisions to make about creating your content down to zero. When you don’t know what your video will be about, you have an unlimited number of decisions to make. Choose the focus of your topic, apply it to the above structure, you now have 50-100 small decisions to make about what you will say and do in your video. You tap the record button and speak the first few sentences, and there are only 10 to 20 possible ways the rest of your video can progress. Finally, you’ve finished recording and are ready to publish that video, with very little overthinking on your part.


Using a template (structure) means you can create your video content predictably and consistently. Repeating this activity leads to intuitiveness, and before you know it, you have achieved “unconscious competence” and can record a new helpful video almost automatically.


The next method to create short form content that you can perform very consistently and repetitively at scale: repurposing (slicing up) longer content into short “reels.” If you have presented a 30-minute stage speech or 90-minute webinar, you are almost guaranteed to have 15 viral-worthy soundbyte clips you can post to social media.


There are many reasons to have a podcast, but the one that excites me the most right now is this: I can schedule a conversation with a thought leader in my industry, have a 30-minute conversation with them, and stumble upon some unpredictable “viral” moments that we use for LinkedIn, Facebook, Instagram, YouTube Shorts, and TikTok. My podcast guests can consistently create unique and helpful content for me.


Then I only have to use a tool such as Veed or Opus to quickly extract short videos (reels) from our longer form content.


The final type of short form content that you should really consider are “outside the box” videos. Perhaps you are at a networking event, you meet someone, and  you want to record a quick video together, perhaps promoting the person’s business or sharing a helpful tip from them. Maybe you show some behind the scenes activity in your business. Do you have a fun and helpful moment you can capture for social media?


As attention spans dwindle, your brand should leverage video to capture and retain your audience interest. Short-form videos on platforms like TikTok and Instagram Reels are more popular every year, while live streaming continues to offer an authentic and real-time connection with consumers. To drive customer engagement, integrate video into your marketing strategy.


User-generated content (UGC) transforms the way brands like yours build trust and authenticity. Rather than relying solely on traditional advertising, which may often feel impersonal, leveraging UGC allows you to tap into the genuine experiences and endorsements of your users. This approach not only deepens trust but also fosters a strong community around your brand. By actively promoting and showcasing real-life stories and testimonials, you enhance your brand’s credibility and drive deeper engagement and stronger connections, making every customer interaction more meaningful and impactful!


Engaging with your audience through interactive content is more crucial than ever. Quizzes offer a unique way to interact with users, providing valuable insights while simultaneously educating and entertaining them. Whether you’re looking to segment your audience, reinforce knowledge, or simply increase engagement, quizzes can be tailored to meet a wide range of objectives. This guide explores the different types of quizzes you can implement and outlines best practices for designing quizzes that captivate and educate. Also, tools like ChatGPT can streamline the creation process, ensuring your quizzes are not only effective but also fun and engaging for participants.



  • Survey: This type of quiz involves a poll with no right or wrong answers, ideal for gauging opinions or preferences. Use tools like ConvertKit for email tagging to categorize respondents into beginner, intermediate, or expert sections on your blog, helping tailor subsequent content to match their expertise level.
  • Exam: Designed as a pass/fail assessment, this quiz type can offer rewards such as gifts, certifications, or freebies to incentivize participation and completion. Exams are great for educational platforms or any scenario where demonstrating knowledge or competency is beneficial.
  • Score: These quizzes provide a numerical score based on responses, similar to calculating a body mass index, mortgage payment, or financial savings estimate. Score-based quizzes are useful for engaging users in personal assessment and reflection.
  • Diagnostic: Offering scores in specific categories (positive or negative), diagnostic quizzes are particularly effective for segmenting users based on their needs or characteristics. Results can trigger specific actions, such as adding the user to a tailored campaign or a CRM call sequence, enhancing personalized marketing efforts.


  • Define Clear Goals: Determine whether your quiz aims to educate, market, entertain, or engage. Each goal might require a different approach in terms of quiz content and structure.
  • Maintain Interest: Utilize various question types, including true/false, multiple choice, and visual media (images or videos), to keep the quiz dynamic and engaging.
  • Optimize for Attention Span: Design quizzes that can be completed in 5 minutes or less, comprising 5-10 questions that flow logically from one to the next.
  • Provide Incentives: Enhance completion rates with incentives such as access to more content, entry into a giveaway, or a discount code, provided on a thank you page or through strategic redirects.


Let’s say you had an existing blog post, whitepaper, short report, transcribed webinar (or video) — you could paste its contents into a ChatGPT window, followed by a prompt like this:

Use the above content to create an engaging and informative quiz. The quiz should consist of 10 questions, each with 5 multiple-choice answers. Formulate 10 questions based on the content of the podcast. Each question should test knowledge or understanding of the key points or interesting facts mentioned in the material. For each question, generate 5 possible answers. One should be the correct answer, and the other four should be plausible but incorrect options that are related enough to challenge the quiz taker. Present the quiz in a clear format, listing each question followed by the options labeled A to E, with the correct answer indicated.

You could take the output, manually modify it according to your needs, and build a quiz using Typeform or Jotform.


You could have ChatGPT craft a compelling introduction that explains the quiz’s value and what the user stands to gain by completing it. Further ask ChatGPT to write a personalized congratulatory message that acknowledges the user’s effort and achievement upon completing the quiz. Even offer customized advice or recommendations based on their possible score ranges.


By integrating these structured elements and utilizing AI tools like ChatGPT, you can create quizzes that engage, entertain, drive meaningful interactions, and gather valuable data from your audience.


You can understand how these three “conversational content” ideas connect. You create a helpful chatbot, perhaps referring to your knowledge base or frequently asked questions to provide support. These insights feed your content creation machine, and you can use your information to craft lead quizzes, diagnostic quizzes, and so on.


The point is to be creative with what you think of as content. It doesn’t have to be a boring PDF or YouTube tutorial — it can be two-way, conversational! You can make your interactions count and you can stand out by applying these social and content engagement strategies to grow your brand!