My boss is asking me to “reconsider” the way I approach a client… I am in charge of this annoying corporate maintenance thing that we do for a client (I.e., making board of directors meeting to comply with some regulatory reporting required. I always end up missing deadlines. How would you reply?

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I’m not sure what the context of “reconsider” is, but “always end up missing deadlines”? Doesn’t sound too good. Are you not putting them on the calendar? Sounds like a low hanging task to me!

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1. Always write client emails in the most cordial, polite way possible. 2. If they don’t reply, check in and remind in the most gentle way possible. 3. When deadlines are super near, pick up the phone. 4. Try to give clients some mini deadlines within the bigger work steam. 5. I also send reminders like 1 month out. 1 week out. 1 day out. (For tasks they just need to do (would take them a few hours). Adjust the reminder timing according to the type of work stream and task. If you need to work with them on something for a couple days and finish by Monday, don’t send reminder on the Thursday before. Earlier would be appropriate

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Just insert corporate niceties in your emails.

“Kindly following up…”

“With apologies for the [evening/weekend] interruption…”

“We would greatly appreciate if you could please…”

Etc

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Hard to say. Is he asking you to be tougher, nicer, bill more hours?

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