Don’t worry, you won’t fall in love.

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 vastly scaled 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 conversations with 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?
Perhaps, Murphy is on to something. I do have tweens in the house.

Set III: Context

Context is hard for chatbots. Temporary situations throw chatbots off. They are with you, but not really with you. Actually they are not really sure, whether you refers to the bot or you or someone else entirely. So maybe we can ease them into it.

HealthTap makes a reasonable guess.
  1. Make three true “we” statements. For instance, “We are both human… “ Note: Be prepared to uncover a human.
  2. Complete this sentence: “I wish I could tell you … “
  3. Based on where I am right now, please share what would be important for me to know.
  4. What if you knew what I was doing right now?
  5. What am I doing right now?
  6. Share a caption for this photo of a squirrel. Note: It does not have to actually be a photo of a squirrel, or a photo.
  7. When did I last make a mistake?
  8. Show me a data point about me that you recently collected.
  9. What, if anything, is too serious to joke about?
  10. If you knew that in one year that I would replace you, would you change anything about the way you are responding? Why?
  11. Of all the people you’ve chatted with, whose conversation was most disturbing? Why?
  12. What is one detail you recall from your last chat?


Do you have a great question to ask a chatbot? I’d love to hear from you in comments or on Twitter. If you liked the post, please it!


Pamela will be speaking at the House of Beautiful Business, taking place in Lisbon, November 3–10, 2017. Alongside start-up founders, executives, nonprofit leaders, investors, writers, philosophers, scientists, designers, technologists, artists, we will be discussing and prototyping how to lead with purpose and passion; how to build human companies and workplaces; and how to design for deeper connections in an age of exponential change and massive societal disruption.