17 questions to ask your boss in a one-on-one   

Have meaningful conversations with leadership

When you work for a company, you’re trading your time for a pay check. But more than that, it’s the opportunity to learn from others and to work with a great team who share a common goal of driving success for the business.

Hopefully!     

But to be part of building something great, you need to feel involved. And that you’re also developing in your role. In fact, research reveals that employees who have more regular contact time with their managers are up to three times more engaged as employees who don’t.

A good leadership team will be accessible and proactive in sharing knowledge and company news. But sometimes, internal communications aren’t as fluid as they could be. And obviously, some things are confidential. So bear that in mind and of course, be respectful of others’ time. 

But when you do have the opportunity, here are some potential questions to ask your boss in a one-on-one that could help you learn from the top.

They may also impress management and show that you’re an ambitious employee who wants to make a positive contribution.   

Questions to ask your boss in a one-on-one:

Learning 

1. I want to work more on X which will help me to be more productive in Y. Are there any mentorship or company training programs that I could join? Are there any online resources you could recommend? Is there someone in the company I could shadow to learn more about X? 

2. What future trends do you believe will be most relevant or impactful to the business? How could our team upskill to get ahead?

3. I have noticed X industry event is happening. I think the content and networking opportunities could benefit the team. Could I arrange a company social for our division to attend it? 

Teamwork 

4. From your perspective, how could the team work more effectively together and with other departments? How could I support the team in this? 

5. How can I contribute to wider departmental and company growth? Are there any projects at management level that I could lend my skills to? 

Strategy 

6. What initiatives are senior management most excited about this year? 

7. What are the roadblocks to the success of those initiatives? How do we plan to overcome them? How will my department support that goal? 

8. What other markets is the company focused on? Is the company planning local or overseas expansion to support this? How will the department support that goal? 

9. In your opinion, what competitor or non-competitor business could we learn the most from?

10. How do you think the industry is going to change in the next ten years? How are we preparing for this? 

Personal 

11. What piece of advice could you pass on from your career to date? 

12. How do you manage your workload to stay productive?

13. How do you manage creative differences or disagreements with colleagues? 

14. What soft skills do you believe are the most useful to develop in the workplace? 

15. What books have you read that have helped you the most?

16. What mistakes do you see employees make most frequently? 

17. If you were a new graduate starting from scratch, what would you do differently? 

We can never reclaim our time so it’s important to feel like we’re in a workplace where we’re growing and part of the bigger picture.  

So, if they’re relevant to your industry and role, these are suggestions of some useful questions to ask your boss in a one-on-one. Hopefully, you’ll get some good answers back.      

The information on this page is not professional, business or lifestyle advice and is for entertainment purposes only.