An employee asked me for advice on how to approach something with their manager. When he was done, I asked a few questions:

  • If you were the manager, what would you think of that request?
  • Have you made a pros/cons list for how your manager would view granting the request? Not pros and cons for you but thinking from your manager's perspective.
  • How has your performance been the past 30 days compared to your entire tenure? Past 60 days? Past six months?
  • If you get what you're asking for, will that make other people on your team want the same thing?

Asking for things before exercising empathy and giving it real thought is an emotional exercise, and this applies to all professionals at all levels including executive leadership and the C-suite.

Emotions can result in rash decisions. Take the time to reflect and think through the conversation. Write out your thoughts and emotions. It will go a long way towards helping you not make rash decisions that may have negative impacts on your career (and life).  As E.M. Forster once said, "How do I know what I think until I see what I say."

And after you write it down, role play the conversation. Play out different scenarios of what the feedback could be. What happens if you don't get what you want? What are you willing to give up in order to get what you need? Practice this conversation out loud to yourself and then with someone you trust.

Whatever you're asking for, be ready to explain how it will help you improve in your role, and never compare yourself to someone who has what you're seeking. That will work against you. Also have enough EQ and self-awareness to weigh what you're asking for against the health of the organization.

Regardless of the conversation, good, bad or otherwise, it's always good practice to take a few minutes and write out your thoughts, mapping out what you want to address. Rarely does something great come from being underprepared.

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