After constructing the grid, cluing is the most daunting task facing a constructor. Constructor Robin Stears readily confessed, “Writing the clues is the most time-consuming process of puzzle construction, especially for common words that appear in many puzzles. Crossword Compiler allows me to keep a database of words and clues, but I try not to use the same clue twice.”

Constructor and puzzle archivist David Steinberg: “When writing clues, it’s important to strike a balance between original clues and clues that exist in databases. For entries that appear frequently and/or have a limited number of cluing possibilities, such as ALAI (traditionally clued as [Jai ___]), I feel it’s best to go with a database clue. In the case of ALAI, almost all clever cluing possibilities, such as [Half-court game?], have been exhausted.

“Original clues for such an entry often end up feeling strained or wordy and/or rely on a less common usage of a word, which solvers generally don’t appreciate as much.”

Constructor Ian Livengood also stressed finding a balance between creativity and accessibility: “Keep you clues relatively short, especially if you’re creating puzzles for outlets with strict line counts. But don’t just use one-line clues for everything, since that will bore solvers. Try to toss in some fun trivia, wordplay, etc. that seems interesting to solvers.

“And, like filling the grid, make sure you clues are appropriate for the intended day of the week. [High line?] for ELEVATED TRAIN works well for a tough puzzle, but would only fluster new solvers in a Monday puzzle. [Above-the-street transportation] is easier and more welcome for beginners.”

Constructor Robin Stears reminds you to utilize the many resources available: “Personally, I use a number of websites to help me write clues: Wikipedia, Wolfram Alpha, The Free Dictionary, Crossword Tracker, Internet Movie Database, Reddit, and Google. In the old days, I used to spend hours in the reference section of the library, but nowadays, it’s much easier to search the Internet. There’s a wikia for almost everything.”

When it comes to determining the difficulty of a clue, constructor Doug Peterson suggests doing a bit of research: “My best advice is to solve lots and lots of puzzles of varying levels of difficulty. It won’t take long for you to get a feel for what types of clues are found in what types of puzzles. And it’s OK to have a few hard clues on a Monday or a Tuesday. Just make sure their answers don’t cross.”

Los Angeles Times Crossword Editor Rich Norris and assistant Patti Varol touched on how cluing can set a puzzle’s difficulty: “With the right grid, a talented, creative editor can transform an expert-level puzzle into one that any newbie can solve (and that an expert would still enjoy). Every editor has his or her own ‘familiarity test,’ which is the educated guess we make to determine if a clue or an entry will resonate with or be recognized by our solvers.

“It’s subjective, sure, but there are also pretty straightforward guidelines. If an entry is not in most major dictionaries and only gets 10K or so Google hits, well, that’s pretty obscure and probably shouldn’t be used at all. The editor needs to know the solving audience and needs to know how to balance current and older pop culture references -– much of what the Millennials find easy will completely baffle the Boomer solvers, and vice versa.”

They were also kind enough to offer an example of how cluing a given word can affect clue difficulty:

“Take the entry SMITH, for example. Will SMITH and Ozzie SMITH are arguably more famous than Patti SMITH, who is arguably more famous than Matt SMITH. Plain clues — [Actor Will], [Baseballer Ozzie], [Singer Patti], [Actor Matt] – tend to be hard. Ozzie is the exception in this example, because Ozzie is such an unusual name in baseball that even nonfans are likely to word-associate their way to the correct answer.

“What information is added to those semi-naked clues is key. Thus, [“Men In Black“ actor Will] is an easy clue for SMITH because “Men In Black” is a popular movie franchise and having the first name narrows down the potential answers. Compare [“Just Kids” memoirist Patti]. Even with that first name in the clue, it’s a tough clue — more solvers know Patti Smith as a singer than as a writer, and the title of her memoir doesn’t even hint at her singing career. For a nonfan, [Hall of famer shortstop Ozzie] is about the same difficulty as [Baseballer Ozzie], but, alas, it’s likely only a Doctor Who fan will recognize any clue for Matt SMITH.

“There’s Kate SMITH, and Bessie SMITH, and Agent SMITH of the Matrix movies. Each one resonates with a different solver. The easiest kind of clue for SMITH is, of course, the generic kind: [Common alias] or [Popular surname] or [Suffix with lock or gun]. And then there’s the fun, inferable kind: [Surname that comes from an occupational suffix].”