The debate between plotters and pantsers is as old as writing itself, especially in the mystery field. I used to list all my novels' scenes and changed the order as I figured out where I was going, usually creating a dozen chronologies to get the cause and effect right. I seldom outline short stories because they don't have subplots and are short enough so I can keep track of everything. I revise as I go along and, once I have a complete draft, I go back and fix the discrepancies.
But whether it's a short story or a novel, I have one constant problem.
I've written a few stories where the sleuth solves a mystery with deduction and detection (Both Black Orchind Novella Award winners had to pay homage to Rex Stout's Nero Wolfe tales), but they're hard for me because I have trouble plotting.
I generally start with an idea of who the bad guy is, especially when he or she is also the protagonist. I write many stories from the bad guy's POV, and many stories where someone gets away with a crime in the name of chthonic revenge rather than legal justice. Those stories are me compensating for my big weakness. It's why I don't write many traditional "Whodunnits."
Even if I know who the bad guy is and how he did it, I almost never know how the sleuth will figure it out.
I've been known to reach page 275 of a 300-page manuscript without knowing how I'll cross that last bridge. When I figure it out, I have to go back and add or change something earlier in the book, sometimes almost at the very beginning. It might be a descriptive detail, a bit of dialogue, or a scene. Maybe someone's story changes a little. Once, I had the clue in there and hadn't spotted it myself.
"Stranglehold," which won the Black Orchid Novella Award in 2009, was like that. I had a short story that wasn't selling, and I realized it was too rushed and had too many characters. When I expanded it into a novella, I added more character background and discovered that I had everthing I needed. I just had to have a character reinterpret something. When I did that, the story became very "Golden-Age" mystery.
"Look What They've Done to My Song, Ma" was different. I'd struggled with a novel off and on for months, but the subplots got in each other's way and the characters wouldn't work together. I abandoned the project twice and wrote other stories, but kept coming back to that one because I wanted to write a sequel to "Stranglehold." When I realized that it should be another novella, I dumped the contradictory subplots and saw a possible solution right away. I know several musicians who also record their own work and know the technology well. I asked on of them a few questions, and as soon as he told me the shortcomings of recording technology circa 2009, I wrote a complete draft in a few days.
One of my few other puzzlers, "Death and the Dancing Bears" actually got its solution from the theme an anthology was looking for. I knew the solution before I even started writing. The anthology didn't take the story, but it fit the guidelines for another market.
I knew my solution for "Afternoon Delight," too, a story I conceived while sweating on an elliptical trainer at my health club. When I was leaving for the day, I asked the guy at the reception desk a few questions about how their server worked, and he gave me the answers I needed. Voila.
Those two stories are the only ones where I knew the solution to the mystery, so I remember them well.
The Whammer Jammers had a clear ending until I was about 80% through the first draft and decided that ending was too obvious. But all I had to do was add one more scene at the end and about a hundred words of dialogue in an earlier scene to take the book in a completely different direction. Even better, that change made it possible to write a sequel, Hit Somebody, with most of the same cast of roller girls I'd grown to love.
Right now, I have fifteen stories submitted to various markets, and only two of them involve a puzzle the sleuth has to unravel. The clue/solution was even my inspiration for writing one of them.
I was about two-thirds through the first draft of the other day when I saw what I needed. I went back and repeated a detail from the beginning and it all worked out.
Well, maybe it worked out. That story still hasn't sold…
What gives you the most trouble?