You don’t want to over-constrain your questions. If the answer is a simple “yes or no,” writers will feel demeaned. But you also don’t want your questions to be entirely unconstrained. If you ask, “This isn’t right, is it?” you throw wide the door to every possibility. And if that writer chooses wrong, you create more work for yourself and frustrate them.
Here’s a good example of a properly constrained question: “How could this (highlighted area) be 30 percent shorter?” With this, you are telling them paragraphs like that are too long. And then you apply a specific constraint—30 percent shorter. It’s up to them how they arrive at it.
Asking questions like this will save you work—it means less editing—but it can also unlock greatness within your writer. By questioning, you invite their intellect. Sometimes, they come up with something even better.
To help writers practice their reasoning, I like to cloak most of my question edits in a bit of self-doubt. I know I have an incomplete understanding of their deadlines and material, so I start with, “Maybe it’s just me, but …” and end with “Just a suggestion, feel free to disregard …” or “This is your call.” It averts an ugly back and forth and empowers them to exercise their executive function.
I’m also very clear with writers when I’m asking a question to which I do not know the answer. I say, “I don’t have an answer for this either. This is a tough one.” It tells them they aren’t missing anything and frees them to be creative.
Examples of well-constrained questions
To put this into practice, let’s examine four questions that range from constrained to unconstrained. All are valid.
Highly constrained: “Can we provide evidence for this idea?”
This question is nearly binary—yes or no. But the “yes” contains multitudes and they’re free to support it however they see fit.
Somewhat constrained: “How could this be 30 percent shorter?”
This one is really a veiled statement—“This should be 30 percent shorter.” But it gives them agency to reduce the copy in the manner that suits them.
Loosely constrained: “This reads like an overpromise. How could it sound more balanced and less effusive?”
There’s a debate to be had here. Is it an overpromise? They may agree or disagree. If they agree, there are many ways to achieve “greater balance,” and in that subjectivity there is freedom.
Relatively unconstrained: “Overall, love it. But if we want readers to feel inspired, how might we achieve that?”
This is a whole article edit. It affects the structure, style, and grammar. It’s not achieved easily. But the problem and constraint are clear enough: This is not inspiring, and when it’s done, you should be able to read this and think, “Our readers will feel inspired. Heck, I feel inspired.”
Limit your questioning, unlike poor Socrates
In 399 BCE, the unrepentant old badger Socrates accepted his sentence for “corrupting the youth,” drank a vial of poisonous hemlock, and expired. He had asked such a great number of inconvenient questions of Athenian elites and had spoken so much truth to power, they couldn’t stand him anymore.
This feels like an appropriate answer to the question, “How many questions are too many questions?” It also highlights their strength. They can stir strong feelings, like the one that inspired me to quit sales. They also exact a cognitive tax upon your writers and a document bursting with them may seem hostile. It can make some of your writers wish they had a little hemlock on hand.
Here is the rule: Only ask questions where you want the writer to focus and learn, and nowhere else. Ask Socratic ones that identify a problem and impose a constraint. And don’t do it more than 25 percent of the time, for their safety and yours.
