30-Day Checkup: Share and Compare with the Boss


Use these tips to help you and your boss reflect on the first 30 days of your new job.

Reflect on the first 30 days of a new job with your boss

It’s time to find out if everyone is on the same page.

Book time with your boss – at least 20 minutes – maybe as much as an hour– at the beginning of the day or during lunch.

Ask your boss if the two of you can review the first 30 days – what went well and what could go even better. Perhaps your boss could start first? Then you can share and compare your experiences and observations. Start with the positive things. If there are topics of concern, put them in the middle. And then wrap up with the more good things.

Here is an outline of a presentation you can use:

• Ask your boss to review your performance.

• Ask questions to clarify your understanding.

• Share what you like about the job, the organization and people.

• Share what your questions and concerns are.

• Share your goals and aspirations for the future.

• Ask how your boss sees your future.

Seek understanding between you and your boss. Hopefully the two of you are on the same page. Then ask about your boss’s recommendations and availability on training and development that will help improve your performance now and prepare you for future responsibilities.

If your boss is not happy with your performance, then seek to understand the problems and what it will take to solve them.

If you are unhappy with the job, then share with your boss (and later on, the human resources representative). Seek ways to make the situation better. Perhaps the problem is the job, possibly the boss or the organization.

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