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Five Questions To Ask Your Boss When They Offer To Help Your Career

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If you are lucky enough to have a boss who shows an interest in your career development, don’t squander the opportunity . One reader froze up when her boss asked her what she wanted next. This finance professional didn’t like her job and hadn’t given much thought to what would make it better.

Even if you don’t like your job as it is currently, the fact that your boss takes an interest in your next step is a positive sign. Build on this offer of support to improve your situation – at the very least, you make like your job better, and you may even refashion your role into something you love.

First and foremost, thank them enthusiastically for offering to help you. Not every boss is so supportive, so this really is going above and beyond. After showing due appreciation, here are five questions to ask your boss when they offer to help your career:

1. What would you recommend for me?

Ideally, you have your own ideas, and I would definitely be prepared to share these. But don’t be so quick to roll out your own wish list since additional feedback from your boss might change what you end up asking for . You may only be thinking about other roles within your group, but maybe your boss knows about opportunities in different subsidiaries, cross-functionally, or even abroad. You may only be thinking about a promotion but your boss knows of some lateral moves which might be more suitable or enjoyable.

2. Who should I know?

In addition to thinking about next steps you can take – e.g., responsibilities, projects – you also want to expand your network and your visibility. Ideally, you also have ideas on specific groups and/or people you’d like to get more exposure to. Your boss can build on this list and advise you on how best to proceed.

3. What keeps you up at night?

Your boss will love it when you show an interest in helping them. This is also a good question to get insight into issues, goals, or projects that your boss might not have shared in the team meeting (if you even have these on a regular basis). Getting a deeper understanding of key goals – even just those of your immediate boss – can help you prioritize your work better. If you aspire to management, knowing what is required of your boss gives you a heads-up on the types of issues you will face.

4. What do you think of [INSERT DESIRED PROJECT/ CLIENT]?

When you do share your own wish list, formulate your request so that it leaves an opening for your boss to help you shape it. Of course, you should do your own research into upcoming projects (or clients you wish to serve), what these projects entail, and how you might get considered. Doing the advance work shows your boss that you are genuinely interested and have already done some of the foundational prep work. However, a supportive boss can provide nuance into projects that can mean the difference between getting on a plum project or landing on a minefield. Your boss may have nuance into the decision-making process that can mean the difference between getting what you and not.

5. What is the best next step for [INSERT DESIRED ROLE]?

Instead of or in addition to a specific project, you might have a role in mind – e.g., to manage a team or direct report, to lead a project, to own a budget. A new role is likely a multi-step process, and you may need to develop additional skills or get visibility to additional decision-makers in order to make this happen. A supportive boss can outline the process for you and tell you where you are in that process. They can help you get resources to close any gaps. Perhaps they’ll pay for classes or coaching. Perhaps they’ll sponsor you for company mentorship programs or leadership training. Perhaps they’ll give you an opportunity to present at an upcoming leadership meeting, giving you visibility in front of additional decision-makers.

Turning your boss’ offer of career help back into additional questions for them isn’t about shirking your own responsibility to manage your career. You need a ready wish list in order to make the most of the above questions. However, by giving your boss the opportunity to help you shape and refine your next career moves, you enroll them even more deeply into supporting you. You’ll want this ongoing support whether you stay in your current group or move onward.

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