Cassidy Williams

Software Engineer in Chicago

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5 Questions to Ask Your Boss

A lot of you are working a lot. When you get a job, it’s always important to have good communication established with your boss. You should ask them these questions, not just as a student, but also in your future internships and full-time roles!

  1. What’s the most important achievement you hope to accomplish in your current role? In asking this question, you can see what your boss/manager’s short-term motivations are, which will give you a better idea about what your goals and motivations should be. If yours match theirs, you’ll be better positioned for success to them.

  2. What is the most important thing you care about? Chances are, your manager/boss reports to someone too. Unless your boss is the CEO. In that case, nice work, you’re pretty high up, bro. Anyway. asking this question will help you learn more about what higher-ups in your organization expect. Knowing these goals will help you better understand your own work, because you can see how you fit in the organization better.

  3. What can I do to make you more successful today/this week/this month/etc.? You should always be trying to make your boss successful, because in turn you’re making yourself successful. When you get a direct answer to this question, you’ll know where to focus your energy at work, because you’ll know exactly what take priority. Plus your boss will like you.

  4. How would you like to receive feedback and communication from me? Does your boss want you to respond to emails on weekends? Do they prefer phone, or email, or face-to-face? When you know how to deliver feedback, you’ll be more prepared to ask what you need, from deadline updates to project requests. If you get the insight, you’ll have a better sense of what to expect, and how you can handle it.

  5. Why did you hire me? Especially when you start a job, you should ask this. You are often so excited to get the job that you forget to ask things like this, but it’s important, and here’s why: You know what they expect you to deliver. If they say, “you seem organized,” you know that they want you to produce organized work. If they say, “you seemed well qualified with your Excel skills,” then you know they want you to focus your work on spreadsheets. When you focus your work well based on their expectations, you’ll be up for bigger and better jobs later on.

So, I hope this was helpful to you! Good luck at your job, you’re going to kill it. :)

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