Your One on One Meeting With Your Boss is your Most Important Work Meeting - Here's How to Make it Count

Questions you must ask your boss in one on one meetings

Don't leave your work success and happiness to chance. These are the questions you MUST ask your boss in your One on One Meetings. The Boss-Employee One-on-One Meeting is your most important work meeting because this is your chance to:

  1. Get recognition for the hard work you've done,
  2. Find out if you're making career limiting mistakes,
  3. Grow yourself personally and professionally,
  4. Secure your promotions, bonuses & and increases and
  5. Improve your relationship with your boss and more

Right or wrong your boss is the biggest ingredient for your work happiness and success. Get this meeting wrong and you could be looking for a new job.

Don't leave it up to your boss to tell you what you need to know because bosses are busy, distracted, shy or just plain haven't been trained about what they should communicate to you.  Instead this article will show you the best questions to ask during one on one meetings with your manager. 



Good Boss or Bad Boss - it Doesn't Matter, Take Ownership for Your Destiny

Now most employees think that their boss is responsible for One on One Meetings with Employees. And in an ideal world that's true but the reality is that most bosses have zero management training. This means you can't rely on your boss. If you rely on your boss to do everything then you're not going to get your needs met. If you take a more active role in the meeting then you can use this meeting to get what you want from your job.

Super User Tip: Your One on One Meeting with Your Boss is one of those important life skills that no-one shows you how to do. This is why I made an online course to show you how to manage your boss, and you can get it here for free:  121s with your Boss.

You don't ask these questions every time. Pick the questions according to what you want to achieve:

Questions to Ask Your Boss in One on One Meetings: Checking in with Expectations:

The most important thing you need to know is what your boss thinks of you. If you're doing something wrong you need to know about it before it frustrates your boss and ends up costing you your bonus, or worse.

  • What am I doing that is working and why? Do you want more of this and how?
  • What am I doing that needs to change? Why and how?
  • What am I doing that I should stop doing?

Questions to Ask Your Boss in One on One Meetings: Growth: Personal Development, Career Progression:

Being in a stagnant job is boring and get's you no-where in life. But even a boring, low-paying job can be worth it if you're learning, growing and have great prospects.

PS: Growth is one of the agenda items you must cover in your one on one meetings with your manager. Get a One on One Meeting Agenda here.

Some bosses are great at developing their employees but others don't have a clue. Here are questions to ask your boss that will help you to create a better future:

  • What future roles do you see as suitable for my skill-set and career progression?
  • What skills should I develop to do my job better?
  • What skills should I develop to support my career progression?
  • What responsibilities can I take over as part of career development or building my network / experience?
  • Can you please give me X responsibility (because I think I can do a good job at it or it will develop my experience / network)? Some bosses prefer their employees to be proactive. If you want responsibilities ask for them
  • Can you please support me in learning about X? (via coaching or sponsoring training - see "9 Ways to Get Your Company to Pay for Your Training." If you want training, ask for it specifically and justify why it supports your boss's goals.)
  • What do you think my blind spots are that are holding me back?
  • What do you think are my strengths that I should focus on?
  • Are there any people I should develop a better network with and how? Would you introduce us or put us onto a project together?

Questions to Ask in One on One Meetings with your Boss: Aligning Priorities:

I can guarantee you that your boss has got different priorities to what you think is important. This means you're working on the wrong things. When you find out your boss's priorities you can do less work but still keep your boss happy. Conversely if you're not working on your boss's priorities, your boss is going to be unhappy with your performance. Even if you think that you're doing a great job.

  • What is highest priority to you?
  • What are lower priority items and what's the possibility of these being cancelled / postponed indefinitely?
  • Is there anything I need to know about you, the team or the business?

Not aligning your priorities is one mistake here are another 9 mistakes to avoid in One on One Meetings with your Boss.

Questions to Ask in One on One Meetings with your Boss: Resources:

Do you need resources like extra time, assistance, tools, training? You won't get unless you ask (but remember to justify it to your boss because your boss won't like being asked if your boss does not believe it's necessary)

  • I am trying to achieve X, can you please help me with Y because of Z

Questions to Ask in One on One Meetings with your Boss: Being Helpful / Being Awesome:

Wrong or right you are going to have more work happiness and success if your boss has a good impression of you. These questions will show your boss that you're on their side and want to make a contribution. But if that seems a little brown nosed for you, these questions will also help you to understand your boss better and build a better working relationship with your boss.

  • What can I help with?
  • What are you struggling with?
  • What are you trying to achieve?
  • How can I support you with your own boss?

Related Content


The Ultimate Guide to One on One Meetings with Your Boss

Did anyone show you what to do and say in your one on one meetings with your boss?

  • One on One Meeting Agenda,
  • 5 Tips to get the most from your One on One Meetings with your Boss
  • Downloadable One on One Meeting form for employees,
  • 9 Mistakes to avoid in One on One Meetings with your boss,

Don't let a bad boss get you down. Get all this and more in the Ultimate Guide to One on One Meetings with your boss (free, online course)


Next Steps:

If you're wondering what to say in one on ones with your boss then my tip is that your meeting is as much talking as listening. If your boss doesn't cover the topics that you need to cover, then you can keep the conversation going by asking your boss the right questions. Of course if you are the boss, do more listening and keep your employees talking with the right questions to ask your employees in one on ones.

So those are the best questions to ask in One on Ones with your Boss which will improve your work life. Self Leadership is about taking control of your life to achieve what you want regardless of whether you have a good boss or a bad boss. Find out what to say and do in One on One Meetings with your boss.  

My Story of One on One Meetings with my Boss

 Work took me far but it would've taken me further if I knew what questions to ask my boss in one on one meetings

Work took me far but it would've taken me further if I knew what questions to ask my boss in one on one meetings

When I had my first one on one with my boss, I was extremely nervous. I didn't know what to expect and I didn't know what to do. I didn't know what to ask my boss. As someone with high standards I was extremely worried about having my work criticized. I worked hard but I had no idea what my boss thought of me because we had so little performance communications. And I was nervous that my boss would realise that I had no idea what to do in One on One meetings because none of my prior bosses had had one on one meetings with me. 

Needless to say I wasn't very good, I must've looked like a fool and was very embarrassed. I also missed out on some great work opportunities because of it. Years later I've come to realise that the one on one meeting with your boss is your most important work meeting and that there is a best way to get what you want from these meetings. So you don't have to make the same mistakes that I made I've put together a collection of best practices so you can have a happy, successful career.


Next Steps: How to Manage Your Boss:

Did anyone train you what to say and do in One on One meetings with your boss? The One-on-One meeting with your boss is your most important work meeting because this meeting determines your

  • Work Relationships
  • Growth & Career Progression
  • Your Promotions, Bonuses & Increases and
  • Your Work Happiness & Satisfaction and more...

One on One's for Employees is the Ultimate Guide to making the best of this meeting. This is an important part of managing upwards. it's an online course that will take you less than an hour to complete but has the potential to change your life. If you've found the above article helpful, the course is packed with more of the same. And you can access it for free over here