So there’s been a lot of questions about how to get various achievements for Choice of Robots. I was thinking perhaps we could work together and create a full guide. I copied down the list of all of the achievements for reference, I worked on some of them and then I got bored (so very, very bored, sorry). 
I haven’t even double-checked the ones I have written out so if they’re wrong, or need more detail, please correct me.
Huge thanks @Lys who has written the more detailed explanations of how to get some achievements below.
Pickled - Electrified a pickle. How romantic!
In Chapter 1, choose to invite Elly/Eiji back to yours then select the pickle option.
Bright - Told a light bulb joke. How romantic!
In Chapter 1, choose to invite Elly/Eiji back to yours then select the ask your neighbors for a bulb option.
Gadgeteer - Made Professor Ziegler reminisce about the Chief.
In Chapter 1, when you’re choosing the arms for your robot choose the Inspector Gadget choice
Scholar - Won a fellowship for having a high robot stat.
It’s in chapter 2. I suspect you can’t be getting your funding from Josh at the time, and you need to avoid the military funding too. And you need to have any robot stat above 20. You also need to avoid the various options that lower your application score (so put time into your grants).
Knifethrower - Threw throwing knives with Juliet.
Chapter 2. You need to attend the meeting for financing with Juliet (which means getting your robot built for the next day) and then after the meeting ask to join Juliet.
Sidekick - Your robot is pretty good with throwing knives.
Chapter2. Your robot’s grace needs to be higher than 3. You need to attend the meeting for financing with Juliet (which means getting your robot built for the next day) and then after the meeting ask to join Juliet. Once there give your robot some knives.
Beeroisseur - Tried a dark chocolate coffee porter with Josh.
In Chapter 2, go out with Josh to either the bar or to view the band. He’ll buy you a beer.
Shakespearean - Discussed Hamlet’s age-old question with your robot.
Chapter 2. Give your robot the K-12 educational curriculum.
Ludophile - Your robot interpreted the ending of Braid.
Chapter 2. You need empathy greater than 10. Choose to educate your robot via games, then choose to discuss Braid.
Warlord - Your robot got the conquest ending of Civilization IV.
Chapter 2. Your military should be higher than your autonomy. Choose to educate your robot via games, then choose to discuss Civilisation.
Spacefarer - Your robot got the Alpha Centauri ending of Civilization IV.
Chapter 2. Your military should be lower than your autonomy. Choose to educate your robot via games, then choose to discuss Civilisation
Chatty - Your robot passed the Turing Test.
Chapter 2. Choose to educate your robot via television then mention the Turing Test.
Celebrity - Mark wrote a positive article about you.
Chapter 3. Accept the interview with Mark, generally be nice to him. Keep in mind that Mark is anti-military and not keen on the idea of robots replacing people.
Bionic - It’s like the arm you lost, but with more features!
Chapter 3. Tammy/Sylas needs to have an extremely low relationship with you so they plant a bomb. Ways to get this is to have a bad article written about you.
Rebellious - Your robot sang “Head Like a Hole” in front of a live studio audience.
Chapter 3. Autonomy needs to be greater than Empathy and higher than 10. On the Talk Show choose Sing a Song.
Heartbreaker - Your robot sang “Maps” in front of a live studio audience.
Chapter 3. Autonomy needs to be higher than 10, but less than Empathy. On the Talk Show choose Sing a Song.
Oracle - Your robot got compared to drunk Nate Silver.
Chapter 3. On the Talk Show choose “Make predictions about the future.”
Doctor - Earned your doctorate.
Chapter 3. The main key to this is to keep your relationship with Professor Ziegler fairly high.
Halloweener - Attended Mark’s costume party.
Chapter 3. If your relationship with Mark is high enough he should invite you to a costume party. Don’t accept other plans.
Terrible - Died in the earliest possible place.
Chapter 3. I think this involves trying to kill Tammy/Sylas and having a military less than 16.
Philanthropist - Started a large charitable organization.
Chapter 4. You need to be CEO of your own company and then choose to donate everything to charity.
Cultist - Started a cult around your robot.
Chapter 4. If you have no job then you have an option to start a cult. I don’t think the future opportunities to built a cult around your robot count for the achievement.
Novelist - Your novel was a success, thanks to your high Humanity.
Chapter 4. If you have no job then you can choose to write a novel. You need humanity 85 to be successful.
Character - Your robot wrote a successful autobiography.
Chapter 4. Chapter 4. If you have no job then you can choose to write a novel. Your robot will copy you. It needs to have Empathy and Autonomy greater than 15 to succeed.
KITTy - Made a deal to design intelligent cars.
Chapter 4. Choose to work with the makers of the flying cars. Then suggest you make a car like KITT. You need empathy higher than 18.
Spouse - Got married!
In Chapter 3 you need to get engaged then in Chapter 4 you can get married. (Or, you can get married in the empathy chapter, which I found easier.)
Elfin - Your robot was a good little elf.
Chapter 4. Take the job at the shipping company. Your robot needs to be the smallest size and have an autonomy lower than 15. Tell your robot to be a good little elf.
Beloved - Your company threw a surprise party for you.
Chapter 4. Company Morale needs to be higher than 60.
Resilient - A company you founded survived its startup phase.
Chapter 4. Survive.
Hero - Prevented the Sino-American war from starting.
Chapter 4. You need to be unemployed. You get a scene where you’ve the chance to have your robot save the Chinese President.
Transformative - Made robots that are more than meets the eye.
Chapter 5. Agree to make robots for the war, and choose to make transformers.
Numismatist - Earned a coin.
Chapter 5. You need to supply the war effort with robots and ensure the Americans win the war. The President will give you a coin.
Hacker - Found a vulnerability in the Chinese robots.
Chapter 5. Leave the killer drone briefing but accept Juliet’s invitation to work on other things. Insist that I’m only interested in hacking the Chinese robots.
Florist - Made use of the language of flowers.
Have a high relationship with Elly and put off the agent who comes asking questions about her. Choose to try sending her a cryptic message of warning.
Patriot - America won the war.
Have a high Military score and supply the war effort with robots.
Rebel - Led the Alaskan Rebellion.
Generally if you get to the end of the Sino-American War with a high Military score, you’ll have the option to start the Alaskan Rebellion.
Escapee - Loyal robots freed you from prison.
Get imprisoned toward the end of the Sino-American War, for example by being caught selling secrets to China; your robot and friends will come break you out.
Founder - Started a new country.
Win the Alaskan rebellion and choose one of the options to start a new country.
Holiday - Got an Alaskan holiday named after you.
Canuck - Fled to Canada.
Several ways you can get this one – flee with Elly during the war (if you have a relationship with her), or betray the US and move to Canada, or move to Canada to get married to your robot in the high-Empathy path
Neurosurgeon - Put a piece of your own brain in a robot.
This is a little obscure to get as well. First, at the very start of the game, choose the Robot Companion beginning. Go through the game as normal, but make sure your Empathy stays rather low. Some people say don’t go above 15…I was able to get around with 11 to 12. It is possible that it could be even lower.
The key moment then comes at the end of Ch. 5. You will experience the dream again, but your Robot companion will crumble away saying you didn’t have the Empathy to build robot companions. However, an alternative will be presented, one which scoops out part of your brain to put into a robot. This will get you the Achievement.
Pardoned - Freed from jail by order of the President.
When the agent comes asking about Elly, either text her an explicit warning or (if you have a low Military score) attack the agent. You’ll be taken to an offshore prison and eventually released by Presidential order.
Cleared - Got a Top Secret clearance.
Join the military at the beginning of the Robot War. Let your robot fill out your clearance form for you.
Blockbuster - Saw the White House blow up.
When the robot rebellion starts, go to the White House and either sit back to watch it explode or attempt to rescue the President
Bodyguard - Escorted the President from the White House.
Get the Numismatist achievement; then, when the robot rebellion starts, go to the White House and convince the President to leave with you. She’ll trust you because you’re a war hero.
Safecracker - Got inside the Top Secret room.
Find the password to the door Juliet’s guarding – either by bringing a hobbit-sized Shiva with you to the military briefing or by looking for Post-It notes in the lab during the robot rebellion.
Kingmaker - Gave your robot control over all the other robots.
Spook - Accessed the government’s master intelligence database.
Chapter 5. Agree to work on the AI project to track down spies, then use this opportunity to (illegally) peruse the classified communications database for people I know.
Gourmand - Your robots tried lutefisk.
Highest stat needs to be empathy. Choose the strangest food tasting menu.
Partybot - Your robots got a little tipsy.
Highest stat needs to be empathy. Josh needs to be alive and have a greater relationship than 50. He’ll come to the tasting party with beer. Choose an option that lets your robots get drunk.
Trio - Had a very special night with your two loves.
Marry a human and invest in a good relationship with your spouse. Take the high-Empathy path where you create a robot lover. Go stargazing with your robot, and when they suggest making love, suggest that you invite your spouse as well. If the relationship score is good enough, they’ll accept the suggestion.
Robophile - Married a robot.
Have high Empathy, choose to make a robot who can love you, go stargazing and make love, and you should get the option to marry them.
Hat Trick - Got three achievements at the same time. And now, four.
Move to Canada to marry a robot. You’ll get Spouse, Robophile, and Canuck on the same screen. And now, Hat Trick.
Kinkadian - Made some popular paintings.
Crimefighter - You and the Crusader fight crime.
Take the high-Grace path where robots peacefully take over the world. The robots will allow crime to take place (possibly this requires a low Empathy score?) and Juliet will become a vigilante. Choose to join her.
Rocker - Played Freebird. Sort of.
Take the high-Grace path where robots peacefully take over the world. Vouch for Josh’s usefulness as a human. He’ll invite you out to celebrate at a bar where you (or rather your robot gloves) can play guitar.
Somethingian - I’m very sure that’s a real religion.
This one can be a bit obscure. First, you need to start a cult with your robot (one easy way to do this is not to get a job, essentially living on the streets. You will then get a chance to start the religion. Then, don’t do anything to promote it (If you are on a path where the USA/China go to war, don’t choose to promote the cult).
Then, when Ch. 6 rolls around you should get an additional screen where you can promote the church, or else quash it by saying you are a member of another religion. Pick to be a member of another religion. You will then get a list of real world faiths, or one you can enter yourself. Choose the one where you can input the name, and there is the achievement.
Mastermind - You basically rule the world.
There are a few paths to get this path, but the easiest way for me was to prevent the war between China and the US (If your robot has high Grace, and Humanity, and you don’t own a company, you can have her intercept the bullet which kills the Premier).
Afterward, you will go through a series of screens which shows robots eventually taking over. Then you will come to a screen with a rather large number of choices, but the one you want will say something along the lines of “Introduce a backdoor into my robots so I can control them all.” Pick this option, and you should get the Mastermind Achievement. Do note you want to keep their Autonomy low, otherwise the robots will overcome your actions, and arrest you
Filial - You bought a gift for Mom in her old age.
If you put some of your time into developing medical robots, your mother will survive until Ch 7 and you can buy her a gift – perhaps even a flying car if you have the Wealth for it.
Trophy - If nobody can judge you, is this achievement meaningless?
Pick the Anubis dream at the beginning. In Ch 7, during your stroke/hallucination, pick the choice which says “You can’t judge me”. Anubis will melt into a small gold trophy.
Nostalgic - Reminisced with a robotic Statue of Liberty.
Pick the Statue of Liberty dream at the beginning. Ensure America’s defeat at the hands of China or your rebel robots. Then, in Ch 7, during your stroke/hallucination, choose the commiserating, sympathetic response to the dying Liberty rather than being harsh or gloating
Chipped - Got a chip in your head.
When told of your stroke, choose to have part of your brain replaced with a robotic core. Survive surgery (I believe this requires robots which have a certain level of Grace, and perhaps for you to have invested in medical technology earlier in the game?).
Doubled - Made a robot double of yourself.
When told of your stroke, choose to make a robot brain and body.
Celebratory - Celebrated a birthday party.
If you have a child or your robot chooses to make a child, and you survive surgery, the story will end with a birthday party.
Alive - Made it to the end without dying.
Forgo surgery and have a high humanity (over 60). Or accept one of the surgical options, with robots who have enough Grace/medical technology to carry it off.
Lunatic - Your robots headed for the moon.
Officiant - Presided over a human-robot wedding.
Honored - You were honored at the White House in your old age.
Save President Irons in the robot rebellion (see Bodyguard above), then go to the lab, use the password to get into the code room, and choose to destroy all robots. In Ch 7, choose to live in Washington (this may not be necessary?). The new President will honour you at a special ceremony.
First Mate - Went out for coffee with ex-President Irons.
Singular - Joined the collective mind of the robots.
You need to control all the robots. If you have the the Kingmaker achievement it means you can then get Singular. There’s also a method in the autonomy path, but by the time you reach it you need your grace to be higher than your autonomy, and then tell your robot to control all the robots. Then in the last scene when you’re given the surgery options choose “I have a better idea. I will join the hive mind.”
Tragic Hero - Finish Chapter 7 with no other achievements.
Keep Grace low. Antagonize Ziegler so he won’t give you a doctorate. Educate your robot in a way that avoids Shakespeare, Civ IV, and Braid. Don’t get your arm blown off. Don’t go on any dates or to parties – especially with Josh, that achievement minefield. Don’t start a company – just stay in your apartment as much as possible. In the endgame, pick one of the surgical options and die in surgery because your robots lack Grace.