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"speaking how" is not a correct and usable phrase in written English
If you are trying to ask a question, a more appropriate way to phrase this would be "in what way?" or "how?". For example: "Do you think this plan will be successful? In what way?"
Exact(40)
So, generally speaking, how do you feel about things lately?
QUESTION FROM ALISSA: Journalistically speaking, how would you have handled the WikiLeaks issue?
When he was running for mayor, a reporter asked him, "conservatively speaking", how many votes he expected to get.
It is hard to see, legally speaking, how that is really different from any other gift one private individual might make to another.
Two questions spring to mind: objectively speaking, how legitimate is the labelling of Trump as a "narcissist" by critics when compared to other candidates who have sought to become president?
That isn't, strictly speaking, how Lost in Showbiz remembers pregnancy – its overriding recollection is of nine months spent rigid with terror at its wife's hormonally driven mood swings, which meant that the simplest of queries ("Is this Location Location Location a repeat?") could somehow, bafflingly, lead to a night spent sleeping on the sofa.
Similar(19)
I realized, as I spoke, how important this moment was.
He can't really speak how he wants to speak.
To paraphrase the American spoken-word poet Kesha, we speak how we speak.
I never really tried to explain to them how to speak, how to act, how to identify with those times.
We spoke how this will help us grow as a side.
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Since I tried Ludwig back in 2017, I have been constantly using it in both editing and translation. Ever since, I suggest it to my translators at ProSciEditing.

Justyna Jupowicz-Kozak
CEO of Professional Science Editing for Scientists @ prosciediting.com