Ask your boss these questions to get the most out of your next one-on-one

Is it almost time for a one-on-one with your manager? If so, you’ll want to make sure you get the most out of your conversation, making it a productive and constructive time for both of you.

In order for your manager to help you blossom, it’s important to ask the right questions and make space to receive answers that may not be what you want to hear—but instead, what you need to hear. This will not only display how engaged you are with your job, but it can also make a big difference in how you navigate your work with clear intentions and a better sense of direction, adding deeper value to the evolution of your career.

Heading into your meeting well-prepared and anxiety-free with specific talking points in mind will help both you and your manager close the session with a clear view of how to better move forward and up—and we’re here to help with just that!

So without further ado, here are 15 questions to consider asking your boss during your next one-on-one:

1. Can you tell me what’s going well?
   
2. Can you tell me what I can improve?
3. How am I doing with [this specific thing]?
4. Are there any particular “soft skills” you think I need to work on?
5. If I could improve one skill between this meeting and the next, which would you choose?
6. What resources can I be using right now to learn and succeed?
7. Who on the team needs help? How can I support them better?
8. What do you wish I took more ownership of?
9. Where do you think I should be focusing more of my attention?
10. How can my communication be improved?
11. What’s worrying you most? And how can I better support you?
12. What do you wish you could tell your past self when you were just starting out in your career?
13. What is one book you think everyone should read?
14. What's the best way to ask for your input and feedback?
15. Ask a question of your choice that helps you get to know them better
    

Start off with knowing where you stand:

Can you tell me what’s going well?
First and foremost, it’s important to get an idea of what you’re doing right. This will serve as a nice pat on the back before you get to the more critical part of the conversation.

Besides, decades of research by Gallup has shown that employees who are aware of their strengths and use them every day are six times more likely to be engaged on the job.

Can you tell me what I can improve upon?
It should go without saying, but becoming aware of the areas that need improvement is a crucial step in helping you shift from a place of potential stagnation to a place of conscious growth.

But remember, awareness is only the first step. Check out this awesome guide on how to learn from your mistakes.

How am I doing with this specific thing?
Go ahead and get specific, don’t be afraid to dig deeper. It’s all conducive.

There may have been a past conversation about opportunities for improvement, if so, this is the perfect time to follow up on that conversation with this question. It shows that you’re being intentional and actively working on the areas that need your attention.

If this conversation hasn't happened in the past, think of something you aren't sure you're doing right or doing well, to signal that you are looking for feedback or validation about how it's going.

Are there any particular “soft skills” you think I need to work on?
Working as a part of a team isn’t just about applying your technical skill set and calling it a day. A huge part of your success will be traced back to your soft skills; this includes how you communicate and interact with colleagues, how you solve problems, how you manage your work and time, your mindset, your work ethic, and more.

Then, transition to gauging what you need to do moving forward:‍

If I could improve one skill between this meeting and the next, which one do you suggest I focus on?
This is a good way to set a starting point for yourself that will give you some momentum. Taking small, actionable steps, or even just one, can be far more productive than aiming for too much at a time and becoming overwhelmed by placing unrealistic expectations on yourself.

What resources can I be using right now to learn and succeed?
After getting clear on where you stand, it’s good to get all the advice and information you need on how you can move beyond that and keep expanding. Taking a recommended course (or asking to be signed up for one) can catapult you in your desired direction; don’t sleep on it.

Who on the team needs help? How can I support them better?
Teamwork is not only an essential work skill but also a life skill. Your ability to work harmoniously as a part of a team is paramount to your path to success and shedding light on what your teammates need can help you put more of a conscious effort into developing your teamwork skills.

What do you wish I would take more ownership of?
Being proactive and taking ownership are key traits that you’ll need if you plan on stepping into a managerial role yourself in the future. Start now—remember, small actionable steps.

Where do you think I should be focusing more of my attention?
Another point to help you leave the meeting with a clear sense of direction.

Here, you can further elaborate on how this can help keep you aligned with your manager about your most important priorities, as well as how to best divide your time moving forward so that you're putting more effort into the things that matter most.

How do you think my communication can be improved?
Addressing communication specifically is beneficial because you’ll want to make it known that you’re intentional with your communication. It’s a big part of how successful you are at work, so best not to skip it.

Finally, move the conversation over to them:‍

What’s worrying you most? And how can I better support you?
Even those in the highest positions need support, and even just the act of receiving this question can be a welcome and much appreciated source of comfort. That’s what teamwork is all about, after all.‍

What do you wish you could tell your past self when you were just starting out in your career?
Get them to share their experience, and practice being a good listener while you’re at it. Chances are, their story will serve as a treasure chest full of golden lessons and insights you probably need to hear at this time.‍

What is one book you think I should read?
Books are the best teachers. Share yours, as well.‍

What's the best way to ask for your input and feedback?
Make sure you don’t miss this question. Even outside one-on-one’s, it’s always better to be receiving feedback instead of working with no sense of your performance. It’s like trying to read in the dark. Ask for feedback whenever you feel like you need it, but the best way to do this is to first establish a method of exchange that works best for the both of you.‍

Ask a question of your choice that helps you get to know them better.
This could be anything really; ask what their favorite dessert is, their favorite color, their favorite animal, or their dream destination. Get to know them outside of the roles you play at work. This will also be a fun and effective way to know exactly what to gift them when their next birthday comes around!

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