So one of the things I get asked all the time when people find out I own a trivia company is "How do you come up with the questions?" So I'm going to try and answer that for you.
First off there is no one way that works, but there are a few things that I do to help me come up with the things and there are some rules I try to stick by. By no means am I perfect so as much as I try to stick to my own rules sometimes I get off track and well bad questions happen even to good people. My hope is always to minimize the bad questions.
Bad questions come in lots of forms. First there are questions that are just flat out wrong or out dated. I was once at a trivia night where they asked the capital of Sri Lanka which used to be Colombo but has since been relocated to Sri Jayawardenepura Kotte which is located just outside Colombo. I knew they quiz master didn't write the question and I let them know there was likely an error in the question. Remember when there are mistakes it is often not the fault of the person reading the question but somebody like me who didn't research properly. It happens and the best thing you can do as a quiz player is to politely let the host know their is a potential error and ask for clarification and/or if they will accept alternate answers. Whatever the hosts decision remember this is pub trivia and if you don't agree with that decision it isn't the end of the world.
So outside of poorly researched questions there are also just bad questions. Sometimes a questions is bad because it is too easy although this is rare it can happen. Asking what color is Rudolph's nose is probably a question you want to avoid unless your audience is made up of 1st and 2nd graders. The opposite is true as well as a question that is too obscure is equally as bad. These are much harder questions to recognize as the difficulty level of a question depends on so many factors it can be hard to know for sure, but there are times when it shoud be obvious. One of the first questions I ever asked at a pub quiz and one of the worst was: How many Presidents were born in the month of February? It was part of a President's Day round I did. Of course we all know (or should know) that Washington and Lincoln were born in February and many people do know Ronald Reagan was born in February but who the heck knows only one other President was born in February? So the correct answer is 4 which nobody is likely to get without just making a lucky guess. What I should have asked is besides Washington and Lincoln there are two other Presidents born in february name either of them with a bonus point for getting both? Those who know Reagan have an easy get, those who don't have a chance to guess two presidents and maybe get lucky.
Another thing to watch out for are multiple choice questions. In general multiple choice questions are less fun then others. This is especially true of T/F questions or This/That questions. Asking a T/F questions is essentially asking people to play Heads/Tails with you as you flip a coin and well that's about as much fun as watching paint dry. I personally hate questions of this ilk and rarely if ever will I ask them.
One other important thing when writing questions is sourcing your information. Yes Wikipedia can be edited by anyone but it's not easy to update a Wiki Page if you don't know what you are doing and it is time consuming so not really worth it to make random updates, not to many all changes are monitored and errors are corrected pretty quickly. That said it is always good to get a 2nd source besides Wikipedia. Also when asking a question about information that is likely to be different depending on the source (box office totals, record or book sales, population statistics, etc.) cite the source in the question. So instead of asking the highest grossing Tom Cruise movie ask according to boxofficemojo.com what is the highest grossing Tom Cruise movie? Also with regard to box office questions it is always best to clarify if you mean domestic or worldwide totals and with population numbers specifying city proper vs. metropolitan numbers is always a good thing.
Another thing that is important to make clear is when asking about things like the Oscars or The Super Bowl is to be clear in the year. Asking who won the Super Bowl in 1986 is different than asking what team was the Super Bowl champs of the 1986 season. The Super Bowl is always played the year after the season in question so the Seahawks were the champs for the 2013 season but won the Super Bowl in 2014. Same is true of the Oscars. 12 Years a Slave won the Best Picture Oscar for 2013 but it won the award in 2014. A minor point but it can cause all sorts of confusion when you forget to clarify.
So keeping all that in mind how does one write questions? Well first off you want questions to not be too narrowly focused so everybody hopefully might know an answer or two. Don't ask who led the NFL in touchdowns scored in 2006, but instead ask What man charged his way into the endzone a record 31 times in the 2006 season? In doing so you have let people know it was a record and by using the word CHARGED some people may pick up on the fact he played for the Chargers and come up with the correct answer of LaDainian Tomlinson. There aren't always ways to give clues in the question but often times there are so instead of asking something like what is the 10th most populous city in America (city proper) you can ask Dionne Warwick once asked Do you know the way to this 10th most populous city in America? The question know references a well know song title which might help people come up with the correct answer of San Jose.
Lastly I will warn against asking too many questions from a particular era. I am a child of the 80's and early 90's that's when I grew up so stuff that happened between 1985-1995 is when I was most aware of what was going on in the world so questions from that era seem much easier to me than to somebody who is 10-20 years younger. One of the biggest and more bothersome complaints I get is from people who say "How am I supposed to know that I wasn't born or I was only 5." This is valid for some things like knowing about popular but not timeless TV shows from an era. Example I Love Lucy is timeless but My Three Sons is not. Asking a question about a show like Cheers or the Cosby show is fair even though some folks weren't alive to see those shows in first run they have lived on in syndication enough but asking about Night Court or Remington Steele as fun as those show may have been is probably unwise. Listen I understand if people don't know about Chad & Jeremy, Loggins and Messina or Robert Palmer, but I don't care how old you are you should know something about The Beatles, Led Zeppelin, Whitney Houston, etc. Certain shows, books, movies, and artists transcend time and are fair game. Others are more generational and while they can be asked about should be done so sparingly. As a question writer this was probablt the hardest lesson for me to learn beacuse well I loved Night Court and feel like everybody should know that Harry's favorite musician on the show was Mel Torme but alas I know that just isn't reality. At the same time as I've grown older it sometimes is hard to keep pace with what shows or movies stick with a generation. Wayne's World was a movie EVERYBODY my age saw in the theaters. MacGruber is a movie that people my age are proud to say they didn't see in the theater but I've found that people 15 years my junior love that movie for whatever reason. So from time to time I try and get outside my comfort zone and avoid the Night Courts and Robert Palmer's of the world and instead ask about Savage Garden or MacGruber.
In the end there is no perfect formula for writing questions and no matter how well you perfect the art of question writing you are going to write some duds. Best advice I can give anybody looking to write questions is try to know your audience and do your best to reference when needed and be clear about what is being asked for. Don't get too generational and avoid the multiple choice.