The Elder Scrolls V: Skyrim Special Edition

Helpful Console Commands for this one:

Press ~ to open Console.
Upgrade all of the Speech perks: player.advskill speechcraft 999999
Fast Travel to Markarth: coc markarthorigin
Money for Bribe: player.additem f 999999

There are plenty of opportunities to meet the requirements for this achievement just playing through the game however I wanted to mention the way I use that gets all 3 in just a few minutes at the very beginning of the game and seem to be guaranteed successes at both persuading and intimidating regardless of Speech skill.

This method requires going through the first 2 Dark Brotherhood quests, Innocence Lost and With Friends Like These...

1. Travel to Windhelm and talk with Aventus Arentino and he'll send you to Riften.
2. At Riften either Persuade, Bribe or Intimidate the gate guard. Persuade and Intimidate options are not guaranteed to work. Once inside you'll be stopped by Maul, Bribe him. Complete Aventus' task and return to him.
3. Sleep in a bed somewhere other than Riften.
4. You'll wake up in a cabin, go through a bit of dialogue and have the option to question 3 people. They each have a Persuade and Intimidate option that seem to have a 100% success rate regardless of Speech skill, though you'll only be able to pick 1 option per person. Once you've used the Persuade and Intimidate options the achievement will unlock.

If there is any way that I can make this solution better please don't hesitate to let me know.

For speech level 100 and coins for bribing:
Open console commands with the "~" key
advskill speechcraft 9999999
player.additem f 9999999
Upgrade the right side path of the Speech skill tree, (unlock Bribery, Persuasion, Intimidation)

Input these CCs:
coc WinterholdTheFrozenHearth
resetquest da01 (only necessary if you have already started or completed "The Black Star" Daedric quest)
setstage da01 10
setstage da01 20

Speak to Nelacar - The dialogue option "I'm looking for the Elven mage who studies stars"
Choose the (INTIMIDATE) option, click through his dialogue ("Don't change the subject", "Get to the point")until the quest objective updates

If you wish to also bribe him, exit conversation and type these CCs again
resetquest da01
setstage da01 10
setstage da01 20

Otherwise it is just as simple to get caught pickpocketing or stealing from the market in Whiterun
coc WhiterunOrigin

Get caught stealing by guards until you are able to successfully Persuade and Bribe. They do not always offer both of these dialogue options, so keep trying until you get them.


Although Nelacar offers the Persuade option, I was NOT able to successfully persuade him after 15 or so attempts. It may not be possible but let me know if you have any luck with that.
If you end up failing the intimidate on Nelacar or something else goes wrong, make sure you click through his dialogue fully until the objective updates. Otherwise he will not give you the option to intimidate him again even after resetting the quest data.