Identifying and managing weak scenes during planning
I structured my plot, designed the path to the climax, listed my characters and even outlined some scenes. Then halfway through I got stuck: one minor transition scene just did not make sense. The characters in it couldn't possibly behave like I initially thought.
This was due to some nuances of the story that I developed while writing. I thought they would be harmless and rather adding some color. In hindsight, this scene was probably a weak link. To solve the impasse, I had to plan a different plot route at the last moment.
How could have I identified and managed weak scenes during planning? I don't mind spending extra time planning, but it breaks my flow to halt writing to re-plan one scene en route.
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Understanding your characters is definitely important. I know that there are some authors who take specific events from main characters' lives -the types of events that shape who they are as people- and write a short blurb of that event. This not only helps them find the characters' voice, but it also allows them to become better acquainted with who the character is.
Once you write these blurbs, when you are thinking about your story while standing in line or driving you can use the knowledge you gained from the blurbs to walk the characters through the plot as you currently understand it. If you hit on something that the character just wouldn't do, you are more likely to notice it. That is the benefit of knowing someone so well. You know if it would take a very specific set of events to get them to do what you think is necessary, or it could force you to use your resourceful skill to find another way.
Like most things in life there is still a small possibility that your flow will be broken by something else, but knowing your story elements intimately will help greatly.
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I'm a discovery writer (no plan!) and I seldom have this problem. I would suggest actually writing less on the plan.
The issue, which discovery writing takes care of automatically, is that main characters tend to grow throughout the book. That is what happened to you, in your own "discovery" phase of writing (some scene) you embellished and created some personality traits.
That is a good thing, a natural thing, and readers find it entertaining to gradually discover character traits. But it is very difficult to plan out in an outline. Many plotters have the problem of their characters growing and then straining against the leash later in the story, they don't want to say and do what you planned for them to say and do. It is no longer in their organically developed character, and feels awkward, or cardboard, or forced, when the time comes to write it. That is what happened to you.
The way around it, if you feel like you must have a plot, is to skeletonize the plot. Do not put so much detail in it. Write only the turning points, things you can remember while actually writing the early parts. This will leave you the room you need to improvise new character points while writing, and to then improvise when you get to the scenes.
Examples:
1) The team decides they have to go to Chicago.
2) In Chicago, Mike hooks up with Alice. Consensual, but she regrets it. He knows it.
For (1) In your head, from the beginning, you know they have to decide to go to Chicago, but don't write in all the emotions or dialogue of WHY, leave the character arguments and motivations for when the time comes.
For (2), From page 1 you know Mike and Alice have to hook up; consensually. So you won't give either of them a trait that would sabotage that hook up or make it implausible. But wait to write the emotions and motivations until the time comes. At that time, you may also go back and insert incidents that foreshadow the event, or make it more plausible.
That is how I work as a discovery writer, there are big things I do know about the relationships but I intentionally develop the characters as we go along, by letting them do and say whatever comes into their head. Or to be more exact, they do, think and say what I think that character-so-far would most likely do, think or say in the developing situation.
So my recommendation is to write less in the outline, stick to the bare bones of plot turning points, and let your characters become people in your mind. There are many ways to decide you have to go to Chicago. Some characters may like the idea, others may hate it. Good, that creates conflict and tension.
There are many ways for Alice to have a disappointing sexual experience with Mike. That could be Mike's fault, or Alice's, or the environment or demands on their attention making it a rushed experience which did nothing for her.
You know when you are writing that is how it has to be to serve the plot, let the characters figure it out when you get there.
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