How can I create stricter boundaries around dinner-time business meetings on work trips

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Conversations about the day and what we could’ve done better should be happening during work hours, especially because I can strategize better when I’m not exhausted at the end of the day

My boss and I take work trips once a month to pitch new business to potential clients. We’ll usually go out for dinner after the day is over, during which he’ll always debrief about the day and talk about what we could’ve done better. I think these are conversations that should be happening during work hours, especially because I can strategize better when I’m not exhausted at the end of the day.

With this strategy, you can turn a potential “me versus you” dynamic into a positive conversation where you’re on the same side, looking at ways to improve the status quo together. First, consider acknowledging the value of the debriefing process for both of you. Then, communicate how, while your boss may feel energized after such pitches, you feel like your energy is spent. Share how having some downtime after work is important for you, so you can give your all at work the next day.

Be proactive and bring some win-win solutions to this conversation, factoring in your boss’s working style too. For example, perhaps you can have a 15-minute re-group after a new business meeting is done, while the pitch is still fresh in both of your minds. Then, as a standard process, pre-book a follow-up meeting for the next morning to dive deeper.

A plan like this could take both of your needs into account and show your boss that you are committed to bringing your best self to the job, so you can build more business together.with ‘Nine to Five’ in the subject line. Emails without the correct subject line may not be answered.

 

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