create_labels.sh

#!/usr/bin/env bash

# Colours picked from https://robinpowered.com/blog/best-practice-system-for-organizing-and-tagging-github-issues/

###
# Label definitions
###
declare -A LABELS

# Platform
LABELS["ruby"]="BFD4F2"
# LABELS["rails"]="BFD4F2"
LABELS["javascript"]="BFD4F2"
LABELS["html-css"]="BFD4F2"

# Problems
LABELS["bug"]="EE3F46"
LABELS["security"]="EE3F46"
# LABELS["production"]="F45D43"
LABELS["admin"]="F45D43"

# Mindless
LABELS["chore"]="FEF2C0"
# LABELS["legal"]="FFF2C1"

# Experience
LABELS["copy"]="FFC274"
LABELS["design"]="FFC274"
LABELS["ux"]="FFC274"

# Environment
LABELS["staging"]="FAD8C7"
# LABELS["test"]="FAD8C7"

# Feedback
LABELS["discussion"]="CC317C"
LABELS["rfc"]="CC317C"
LABELS["question"]="CC317C"

# Improvements
LABELS["enhancement"]="5EBEFF"
LABELS["optimization"]="5EBEFF"
LABELS["documentation"]="5EBEFF"
LABELS["performance"]="5EBEFF"

# Additions
LABELS["feature"]="91CA55"

# Pending
LABELS["in progress"]="FBCA04"
LABELS["watchlist"]="FBCA04"
LABELS["in review"]="009800"

# Blocked
LABELS["blocked"]="000000"

# Inactive
LABELS["invalid"]="D2DAE1"
LABELS["wontfix"]="D2DAE1"
LABELS["duplicate"]="D2DAE1"

# On hold
LABELS["on hold"]="AFAFAF"

# Technical Debt
LABELS["technical debt"]="5319E7"

###
# Get a token from Github
###
if [ ! -f ".token" ]; then
  read -p "Please enter your Github username: " user
  read -p "Please enter your 6 digit two-factor-authentication code: " otp_code

  curl -u "$user" -H "X-Github-OTP: $otp_code" -d '{"scopes":["repo", "public_repo"], "note":"Creating Labels"}' "https://api.github.com/authorizations" | jq -r '.token' > .token
fi

TOKEN=$(cat .token)

read -p "Who owns the repo you want labels on?: " owner
read -p "What repo do you want labels on?: " repo

for K in "${!LABELS[@]}"; do
  CURL_OUTPUT=$(curl -s -H "Authorization: token $TOKEN" -X POST "https://api.github.com/repos/$owner/$repo/labels" -d "{\"name\":\"$K\", \"color\":\"${LABELS[$K]}\"}")
  HAS_ERROR=$(echo "$CURL_OUTPUT" | jq -r '.errors')

  if [[ (! -z "$HAS_ERROR") && !("$HAS_ERROR" == "null") ]]; then
    ERROR=$(echo "$CURL_OUTPUT" | jq -r '.errors[0].code')

    if [ "$ERROR" == "already_exists" ]; then
      # We update
      echo "'$K' already exists. Updating..."
      CURL_OUTPUT=$(curl -s -H "Authorization: token $TOKEN" -X PATCH "https://api.github.com/repos/$owner/$repo/labels/${K/ /%20}" -d "{\"name\":\"$K\", \"color\":\"${LABELS[$K]}\"}")
    else
      echo "Unknown error: $ERROR"
      echo "Output from curl: "
      echo "$CURL_OUTPUT"
      echo "Exiting..."
      exit;
    fi
  else
    echo "Created '$K'."
  fi
done

I agree with a lot of things all you guys mentioned. About our tool we have to remember that we are going to be forced to use milestones and this is also visible.
About the labels in the workflow, in issues and pull requests, the tool add labels to mark the process. But I think that we have to run one week with the new tool to check how the things are going to happen.
Shane I think that you should to implement the things discussed to test on the next week. 👍

Will do 👍

Awesome! @shaneog sumarized everything regading labels. Regarding PRs, I agree when you said labels aren't helping, also agree with [WIP] convention, not sure about :+1:, tought