How to Ask Your Boss for Help Without Looking Stupid

Have you ever felt this way?

I feel like I don’t know how to do my job well but I don’t know how to ask for help.

Feeling like you are struggling at work is scary. You might not know how well you are doing. You might think that your manager doesn’t have much faith in you. You want to ask for help but you feel like you might look stupid.

I want feedback from my boss, but she is incredibly busy all the time and I’m not sure what asking ‘How am I doing?’ would accomplish, especially if she says I’m not doing well.

Fortunately, you can ask for help and your manager will thank you for the conversation. I’ll show you how below.

Top value creators ask for help

Asking for help is what sets apart top value creators from everyone else. That guy in your office with the extra computer monitor writing Excel macros got that way by learning slowly and getting feedback from other people, although it might not look that way to you now.

Being unsure about your job performance is hard so don’t make it harder by not asking for help. Asking your manager about where you stand and how to improve is part of feeling more confident at work. It’s also part of your manager’s job to coach you to be your best, but you have to be proactive in asking for help. You and your manager are working toward the same goal, and the better you do at your job, the better your boss’s performance review will be. It’s her job to help you!

It’s a good idea to setup a meeting with your boss when you think you aren’t performing up to standard.

Know what you want to ask your boss

Before setting up a meeting with your boss or manager, think what you specifically want to know from your boss. Think about these questions:

  1. What projects are you working on now?
  2. Why are those projects important to the company?
  3. What are you doing well on those projects?
  4. What fears do you have for those projects?
  5. What areas do you think you need improvement in at work?
  6. What questions do you have for your boss about your job performance?

Set up a meeting with your boss

Now that you know how you feel about the projects, let’s write an email to your boss asking for a casual meeting to discuss how you can improve. It’s important to ask for a meeting before hand so it gives you boss time to prepare. You don’t want to march into your boss’s office and surprise her with this conversation. She needs time to prepare for it just like you do. Modify the email template for your own situation:

Hi [boss],

As you know, I am working on the cost report for the Acme project and I feel like collecting the data is going well. But I could use more guidance on how to present the data within the report. [Say something you are doing well so your boss knows you are adding value to the company. Then say something where you need a little guidance from your boss to lead into the main ask for help.]

Do you have 15 minutes to talk about the best way to present the data next week? I’d love your opinion on how to make this project successful. [Ask a simple question for a short meeting in the future. This puts off the pressure of clearing time in your boss’s schedule now. Then ask for your boss’s opinion which will be flattering that you value his/her opinion.]

I have a few ideas, but your ideas would be helpful. I feel like I still need to ask others in the department for help too often and don’t fully understand the big picture for the project. As a result, I’m not sure how well this project is going. [Tell your boss that you have ideas so your boss knows you are being proactive in learning your job. Then, be more general about the help you need. This gives him/her an opportunity to give you more general feedback about your overall performance.]

Can we set aside some time next week so I can get your feedback? [End with a yes or no question so it’s easy for your boss to reply with a yes response.]


[Your name]

Practice, practice, practice

Practice beforehand by running through the scenarios in your head. Think about the ideal outcome at the end of the meeting. For example, your boss might say that you are doing great so far and that the doubts you have are normal for someone with your level of experience.

Also think about how you will react if your boss tells you that you are under performing. Visualize yourself staying calm and explaining that you want to be a top value-creator 6 months from now by using the feedback from this meeting. Your boss will then know that you want to improve and can help you reach your goal.

Most importantly, remember that it is your manager’s job to support you and make sure you know how to successfully complete your projects. Your boss is on your side even if they don’t communicate that with you often. His/her performance review is based on how well you do. You and your boss are on the same team and working toward the same goals.

Take action

Take action now. Leave a comment below with your answers to the six questions above, then go to your email and write the message to setup a meeting with your boss. Good luck!

3 thoughts on “How to Ask Your Boss for Help Without Looking Stupid

  1. Pingback: How to Succeed in Your First Software Development Job | UpGrad Blog

  2. Bhuvi Kumar

    Worth reading this post! As we know that Manager has different qualities and sometimes it is difficult to cope with the situation. But this post is really appealing for those essential things that we need to practical to stay smart in front of our boss. Thanks a lot for this great share!


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