Niles is a Slack bot that learns your team’s questions and answers them so you don’t have to

Most chat bots are dumb. No one wants to message a soulless stack of if-then statements just to order a pizza when a half-decent app or website interface can do the same job in half the time.

Chat assistants are a different matter. Rather than actively bugging you for information in a back-and-forth no one enjoys having, chat assistants lurk in the background of the conversations you’re already having and glean little details that might help later. It’s the approach Google is taking with their aptly named Assistant.

Niles, a company in Y Combinator’s Winter 2017 batch, wants to be your company’s chat assistant — an alternative to that internal wiki that every company has and no one uses. It sits in Slack and tries to learn the answers to the questions that your team is tired of hearing for the billionth time.

The basic premise:

  • Any user in a slack room can @ Niles a question. If Niles knows the answer, it’ll cough up the answer. If not, it’ll ask for help from the rest of the team. If someone gives Niles an answer, it’ll remember it for next time.
  • Over time, the team says, Niles will learn to parse common questions without being directly asked.
  • If an answer to a question is no longer correct, the user can flag it — Niles will then flag the question and ask whoever it thinks might know (like the person who answered last time) to provide up-to-date information.

Something like this requires a good amount of language processing, allowing Niles to answer a question without you having to ask it in a pre-set concrete way. It’s not perfect, yet, but it’s something they’re focusing on improving.

Most interactions with Niles — including editing answers, flagging those that need updates, or tagging topics (for quickly retrieving everything Niles knows on a subject) — happen within Slack, with the Niles team having figured out a few clever hacks to avoid having to boot you into an external interface.

But Niles can also reach outside of Slack by way of its Google Drive integration. Want it to check how much your team sold last month? Connect Niles to Google Drive through OAuth, point it at the relevant spreadsheet, and say something like “@Niles How much did we sell in February?” It can tap into your Salesforce data, too — though that currently requires a little more assistance from Niles’ support team to get working.

One challenge I see Niles facing here is the same one that pretty much “assistant”-type thing (be it one in your chats, like Google Assistant, or one in your living room, like Amazon’s Alexa) faces: privacy. You’re putting a good amount of faith in these things, both in their creator’s intent and their ability to keep any information it logs secure.

In this case, Niles logs the conversations in any room it’s a part of and stores it an encrypted AWS instance, with each team’s data silo’d individually. It needs that data to figure out what any given team’s common questions are and answer them down the road. The Niles team was quick to clarify that nothing is logged in rooms where Niles isn’t deliberately included as a member nor in direct messages, the logs are encrypted both in transit and at rest, and that they “take great care to make sure the data is stored securely” while still allowing the concept to work. It might not be something all organizations are comfortable with, but the team is at least being open about it when asked.

As someone who has worked at the same company for many a year, I’ve both answered the same questions a hundred times and helped build wiki-esque things as an alternative, so I can deeply appreciate what they’re going for here.