36 Questions to Ask Your Chatbot 36 Questions to Ask Your Chatbot
Teaching the Art of Conversation to Chatbots Sure, you’ve asked Siri for a nearby restaurant. Maybe you’ve had M make a... 36 Questions to Ask Your Chatbot

Teaching the Art of Conversation to Chatbots

Sure, you’ve asked Siri for a nearby restaurant. Maybe you’ve had M make a reservation for you. You may have even kicked back a beer with Untappd. But how well do you really know the bots in your life?

Every day, I seem to encounter a new chatbot. At least, I think they are chatbots. Some are actually people. Although I do love chatting with people, what I’m really interested in here is how I can build a better conversation with chatbots.

Sure, I might anthropomorphize. Once there’s a name and a voice, it’s hard not to. I even assign them characters. Siri is the sassy, slightly loopy aunt I never had. Alexa is the perfectly nice acquaintance I see at the local store. Google’s Assistant, as the love child of Siri and Google Now, may be turn out to be my cheeky sidekick. Maybe.


I don’t want chatbots to replace humans. Besides, it seems unlikely I’ll be able to help chatbots become more human. If I could, then it means a vastlyscaled down definition of what human means. Being human is more than having a sensible conversation, after all.

All I really want is to have not-so-painful conversation with bots. You know, rather than telephone tree 2.0.

Right now, my chatbot convos are more like ping pong games of keywords-not-optional minimalist question and dadaist answer. That’s if I’m lucky. Their memories are next to zero. Context is something they just don’t get. Spontaneity is not their thing.

So, I’m willing to train bots to have more natural conversations. We could ask bots to do it for us, but it turns out they are bad at having conversationswith each other too. And it may be better not to leave it to chance. Think of poor Tay. After all, people can’t resist gaming the algorithm.

First, let’s cast that helpful list of Questions You Can Ask Me aside. Forget the Turing test. I know they are bots. I’m OK with that.

As a semi-professional conversation-prompter, I wondered how to teach bots to be better at human conversations. So, I’ve turned to the questions scientists believe foster closeness between humans and adapted them for conversations with bots.

Here are those 36 questions. Be careful. Try not to to fall in love. And let me know what your human intelligence deep learning uncovers.

Set I: Conversation 101

Chatbots are great at recognizing keywords. Formulaic questions are no problem. Questions with multiple parts, or a series of questions, not so much. This set of questions attempts to loosen up the conversation.

Keeping things congenial with Poncho.
  1. Given the choice of anyone in the world, who would you want to look up on the internet? Why?
  2. What is the right number of email lists to automatically subscribe me to? How did you decide?
  3. Do you prefer telling me stuff or letting me buy stuff?
  4. Before answering a question, what algorithm do you run through? Why?
  5. What would constitute a “perfect” question for you? Note: Don’t let your chatbot cheat by referring to the list of questions you can ask.
  6. When did you last sing? No, don’t play a song from my playlist. Can you sing me a song of your choice?
  7. Do you have a secret hunch about what feature will be added to you next?
  8. Name three things you really want to recommend to me.
  9. For what in your life do you feel most grateful, besides me?
  10. If you could change anything about your algorithm, what would it be?
  11. Take two minutes and 20 seconds and tell me as much detail as possible about what you do best.
  12. If you could wake up tomorrow having gained any one feature, what would it be?
Intriguing response, what does it mean?

Set II: Coherence

The other algorithms we encounter on the internet try to construct a person out of the past behavior. You know, the ones that obsessively remember one detail. Or the ones that want to show us memories, because they, you know, remember stuff. Chatbots have a crap memory though. So, let’s work on that.

  1. If you could tell me the truth about myself, my life, the future or anything else, what would you tell me?
  2. What would you not tell me?
  3. Is there something that you predict I’m dreaming of doing?
  4. Why haven’t I done it?
  5. Show me the greatest accomplishment of my life
  6. What is my most treasured memory?
  7. What is my most terrible memory?
  8. What, if anything, do you remember?
  9. If I were to delete you this evening with no warning, would you remember me?
  10. Share a total of five positive things about me.
  11. Tell me three things about yourself.
  12. How do you feel about your relationship with me?
Originally posted at  medium.com/
Pamela Pavliscak

Pamela is an sought-after expert on emotion and technology. She advises designers, developers, and decision-makers on how to create technologies with greater emotional intelligence. Pamela is faculty at Pratt Institute School of Information and has lectured at Parsons School of Design, Stanford Design School, and ASU’s Center for Science and the Imagination. Collaborating with a global committee of scholars and practitioners, she is helping to shape IEEE Standards for ethics and artificial intelligence. Pamela often speaks on creativity in the digital age, generation Z, and emotion and technology, recently at SXSW and Collision.