I had someone ask me if Friday afternoon was a good time to raise a serious issue. I paused. Some timing choices are brave, others are chaos. What is the worst possible timing you have seen for an important conversation? 😅

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Sometimes there is no “good” time for a conversation. Friday afternoon and Monday morning are the only two times that ideally should be avoided. Outside of those, what time of day are you most open and receptive to concerns?

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I agree there is rarely a perfect time, but I have learned timing still signals intent. I try to ask myself whether the timing helps resolution or just discharges urgency. Friday afternoons often add unnecessary emotional weight.

I can't remember the worst for an important conversation. But I can remember the worst for a relatively unimportant conversation. A manager at a previous company set a meeting with me and an employee for 4 PM Friday afternoon. No notes on the calendar or in the invite. I shot him an email to see what it was about, and he said this employee had expressed interest in one of our furthering education initiatives and wanted to have me sit in to explain the ins and outs, how it'd benefit both her and the company and all that. Anyway. All this sounded reasonable enough to me, so I prepped the material I needed and thought nothing more of it until 4 PM Friday rolled around. This poor woman walked into the conference room looking like she was on the verge of tears because unbeknownst to me, she'd initially asked about the education program months prior and had no idea that was what was being discussed. Didn't take me long to realize that when she saw the invite with her manager + HR, no agenda, and happening on a Friday afternoon, no less, her assumption was that she was getting fired. I've never seen someone go from despondent to relieved in such a short amount of time.

@nasdaq 1
I feel exactly the same. I make it a rule to name the purpose upfront whenever HR is involved. Ambiguity triggers worst case thinking, especially late week. Transparency often prevents damage before it even starts.

Hmm I tend to try and read the room first but yeah as above sometimes there is no good time but needs must at times!

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