Top 6 Conversational Skills To Teach Your Chatbots

Mariya Yao
Sep 13, 2016 · 9 min read

1. Empathize With Emotions

Sadly, even most humans suck at this skill. This is especially true when a conversation gets heated with criticism or negative emotions. We often respond in these situations with defensiveness, denial, argumentation, or negativity.

2. Proactively Offer Guidance

Most chatbots are designed to be transactional or assist a customer in accomplishing a specific task, such as order coffee, change a flight schedule, or purchase flowers. Yet most fail to make their capabilities clear at the outset, leaving customers to guess at what’s possible.

3. Remember Personal Details

Imagine having a conversation with someone who instantly forgets your name and what you just told them in your last sentence. That’s what talking to most chatbots feels like.

Sure is bizarrely forgetful about your location despite being a local recommendation bot.

4. Don’t Be A Broken Record

Nobody likes being told the same thing over and over again, so why do chatbots keep doing it? Bots should detect when they’re about to repeat a previously given answer and switch strategies. If the answer didn’t resolve the user’s needs before, repeating it certainly won’t either.

5. Know When & How To Escalate.

Until genius visionaries finally come up with superhuman AI, chatbots will still need human intervention when things start going wrong. After all, even human agents have human supervisors to escalate to.

  1. The chatbot detects negative emotions such as anger or frustration based on the customer’s language, especially the use of expletives and insults.
  2. The customer specifically asks for more help /a human agent

6. Don’t Sound Like A Robot

Seriously? Who doesn’t understand the word “OK”?
  1. Use simple, colloquial, and natural human language
  2. Build in domain knowledge of small talk topics, such as weather, current events, etc
  3. Add personality to your bot using appropriate avatars, names, biographical background, and other humanizing assets
  4. Inject wit and humor when appropriate
  5. Don’t be afraid to use emojis or stickers if that fits your brand context
  6. Keep messages short, sweet, and readable
  7. Pace messages at human reading speed. If your bot blurts out too much text instantaneously, this can be jarring for users to keep up with


Chatbots offer an opportunity to service customers with all the benefits of a human touch and none of the drawbacks. Gone are long support wait times, rude or incompetent agents, or unnecessary high-touch interactions.

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TOPBOTS is the business leaders’ guide to artificial intelligence and bots. For the full experience, visit

Mariya Yao

Written by

Chief Technology & Product Officer at Metamaven. Editor-In-Chief at TOPBOTS. Read more about me here:



TOPBOTS is the business leaders’ guide to artificial intelligence and bots. For the full experience, visit