Another exercise you can do is role playing. If you’ve ever gone for an interview, you’ve probably tried this before in front of a mirror.
Create a list of as many possible questions and refutes that someone might have to your requests and follow the two steps as mentioned above.
Do your homework, come up with simple, realistic actions that you truly believe in and would do in order to refute any comebacks. To make it even more realistic, have some fun with it and get your partner to really get into character.
Ask him or her to try asking as an angry boss, a sarcastic boss or a sneaky boss. Ask them to try to give reasons that are as unreasonable as possible to prevent you from teleworking and refute those reasons clearly and calmly.
Take this a step further by getting into your office clothes or arranging a room to look like your bosses office. The goal here is to train yourself to feel as comfortable and as confident as possible when you approach your boss.
Once you’ve mastered this exercise, you’ll have the habit of being able to think before you speak and assess the situation properly before providing ideas.
Remember, you only need to make this work once, so do everything you can to ensure you are maximally prepared emotionally and mentally when approaching your boss to request teleworking.
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