The Right Questions to Ask Your Boss in Your Next One-on-One Meeting

Modis Posted 28 May 2019

Your next one-on-one meeting with your boss is set. What now? Stop fearing your shortcomings, and start shifting your mindset to find ways in which the meeting can benefit you. Performance check-ins and one-way meetings are a thing of the past: in nowadays' global, collaborative work environments, being successful is all about aligning your goals with those of your employer and its upper management.

A one-on-one meeting then becomes the best way to get intelligence on your boss's objectives, as well as on the company's direction. Keeping those in mind, you can better find ways to achieve your personal development goals, all while adding value to your work. What's more, the meeting is also a great chance to assess your boss's and the upper management's perception of your work, which will provide further insights on how to strengthen and grow your standing within the company.

meeting with boss

Still worried? No need to panic: with mid-year reviews coming up, we put together a list of questions to ask your boss in your next one-on-one meeting.

  1. What are my best skills, and which ones do I need to improve? Yes, we know this is a tough question to ask, but better to be upfront and identify inevitable areas of improvement right away. Maybe you're a master of details, but your time management skills are lacking. Or you're doing great when it comes to teamwork, but you could get more done by improving your assertiveness. While it may feel like a double-edged sword, this question brings to the table two key pieces of information - first, what your main assets are in your boss's opinion, which may differ from yours, and secondly, how critical your weaknesses are. Listen as actively and objectively as you can, and you might be in for some pleasant surprises. Maybe your lack of punctuality is not that important compared to your strong drive, which brings every project to fruition. With this added knowledge, you may want to focus on strengthening the latter rather than patching up the first.
  2. What are your goals, and how can I help you achieve them? Let's be honest, from a personal perspective it's easy to complain about your employer just nothelping you achieve your personal development goals. Instead, try flipping your thinking to focus on your boss's goals. By knowing what those are, you can find ways to help achieve them, all while advancing on your own. By asking this question, you may find that your manager would benefit from you learning a certain skill, and they might even offer training for you to do so. Or that one of their new projects requires a skill you gained on a previous job – and could engage you immediately, eliminating the need for more headcount.
  3. What perception do other senior leaders have of me? More than ever before, our jobs lead us to cross-team interactions, presentations and workshops. Senior managers also have to review headcount on a year-to-year basis in year-end performance reviews – which means that they will end up hearing about the employees in their division. By asking how other senior leaders see you, you will immediately know which areas to focus on during future interactions to increase your visibility and improve your image.
  4. How can <insert personal development goal> be integrated into my work? It may seem such an easy question for you, but it's not. Here, you need to be very tactful and focus on one or more goals that are both vital to you, and in line with those of your management. Choose well, and the answer may surprise you - maybe your boss would benefit from you becoming a people manager, and put you in charge of a virtual team, or hire an intern to assist you. The key to dealing with the ensuing conversation is to gracefully prioritize your manager's goals over your own. You can brag about your personal development with your friends after the meeting.
  5. How do you feel about this year? By choosing to end with an easy question, you will dispel some of the inevitable tension pervading the meeting and close on a good note. At the same time, listen carefully to the answer in order to gauge your manager's stress levels and identify problematic areas. This crucial information will allow you to find ways to simultaneously help your boss, grow your skillset and become even more valuable to the company.

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