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To me they mean two different things. "Upskill" tells me he wants the people on his team to develop better writing skills. "Improve" means he wants the writing to be better. A concrete example of the difference is that you can hire contractors to edit and publish the team's writing, which wouldn't necessarily make better writers of the members of his team, but it would improve the team's technical writing.

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And writing something like improve my team's writing skills is just too many words to countenance?

Off the top of my head, I don't know. I don't know what the character limit is for titles. That aside, one isn't clearer than the other -- at least not to me. And clarity is the most important part of technical writing to me. Sometimes jargon helps, sometimes it hurts, sometimes it is neutral.

"improve my team's writing skills" wouldn't sound quite so pretentious.

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