Super easy method for the achievement, but some context first.
After freeing Bean in Act 1, you will find friendly NPC's around the map with blueish-green "!" symbols above their head around the map. You need to speak to 10, and you'll unlock the achievement. This is the only missable achievement in the game; if you happen to find all areas or do everything 100%, they will disappear. However, you can unlock this in around 5-10 minutes if you wait until you have upgraded Expeditions at Rank II.
Go unlock (presumably) any outpost (for me, it was The Pantry Rank II so I can guarantee that one works). Once liberated, there will be a women in front of the barn with a "!" symbol (right next to the scavenge station). Speak to her to get 1 of your 10 chats with a scout. Then fast travel back to Prosperity, and immediately fast travel and she'll be back in the same spot. Even though its the same woman, she'll keep giving different advice and increase your progress by 10% each time. Rinse and repeat until you get the achievement.
I had 40% already, so I only had to do this 6 times. Just gets the only missable one out the way quickly