Hey friend, Elias here—

Interface Design: Chatbots 💬

📝 this post was originally written for POP, a platform for launching messenger bots

I’m not Theodore Twombly and I don’t want a robot girlfriend, I just want to check the weather.

theodore twombly

My wife and I recently took a trip to the Republic of Ireland 🍀, and I decided to try out Kayak’s Facebook Messenger chatbot to see for myself just how practical the idea of a text-based conversational interface is when it comes to renting a car, a process that’s inevitably filled with nuance and a little confusion.

Before we get into it — the term ‘conversational interface’ is an umbrella under which two main forms of communication fall (there are probably others):


This would be Siri, Amazon Echo, Google Home, or anything else that you communicate with verbally or maybe yell at while running around your apartment because you’re late for work and need an update on the weather and traffic.


See Facebook Messenger integrations (like Kayak, BFF Trump), Slackbot, and many many more. These are all text-based or non-verbal conversations.

Anywho — let’s get into it, yes?

kayak chatbot

the process, more or less, in 4 screenshots

The process took longer that it otherwise would have if I were just doing it directly through the Kayak app or website.

But, that could be a good thing. The way the interface presents you with one clear question or prompt at a time could definitely help cut down on errors or making mistakes when choosing options you’re presented with. Almost as if you’re talking directly with a human and they’re posing one question at a time, unlike a web form where you’re traditionally presented with all your options at once and it’s up to you to work your way through the form. This single-question format helps the brain focus.

I can’t shake the feeling that using a chatbot to accomplish a task, regardless of level of importance, feels dystopian and inhuman.

It just feels bad & impersonal. I’ve had an inkling of this feeling before when I’ve ordered food through services like Postmates & Uber Eats, but not to this degree. I’ve gotten past it in that regard, because you always end up interacting with your delivery driver directly human-to-human. Something just feels different when it’s strictly human-to-machine interaction.

quickdraw with google

Broad strokes

Putting aside the great technological advances to bring conversational interfaces and chatbot functionality into the mainstream, I can’t help but feel like, right now, it just adds unnecessary steps to something that should otherwise be a 2 or 3 click task. Now, that’s a super broad statement. To clarify, I’m talking specifically about conversational interfaces outside of the home, of the chatbot variety. Being able to have Alexa or Google Home update you on recent news, tell you the weather, and play your Saturday morning spotify playlist all through verbal commands is quite useful.

But! That doesn’t mean that you should ever just rule out using a chatbot for anything until mainstream artificial intelligence reaches a critical mass. Quite the opposite, my friend. Chatbots are great for specific tasks like ordering food & building a march madness bracket.

Logically, I know that we’re in the awkward teenage years of artificial intelligence and the conversational interface, and this is an inevitable phase that we have to go through to reach a more mature point. Y’know with machine learning and all that. So for now, I guess I should keep trying to book flights with Messenger, draw raccoons with Google, and ask Siri difficult questions just to watch it flounder under the stress.

This project is maintained by eliasjulian