7 Questions That Ambitious Employees Should Ask Their Boss

One of the most important and influential relationships you have at work is with your manager. Along with being an example you can learn from (for better or worse), your manager has great influence over your salary, your responsibilities and your ability to get a promotion.

Hence, it obviously behooves you to form a strong relationship with him or her. And the key to doing that connecting with them in ways that transcend the traditional employee-manager relationship, by helping their career or by allowing them the opportunity to mentor you.

In his LinkedIn Learning class Building Business RelationshipsExecutive Advisor Simon Bailey encouraged employees to ask their manager these seven questions. These seven questions will help you form a better relationship with your boss, which will both make your day-to-day life better as well as improve the prospect of your career.

1. What are your main objectives and key concerns?

Too often as employees, we focus solely on our own struggles and challenges. But, if you want to form a better relationship with your boss and understand the business better, you need to better understand their challenges and objectives.

So ask your boss what’s pressing in their mind and find out what keeps them up at night. By understanding what they are trying to accomplish, and knowing how you fall into that, you'll both improve your relationship with your boss and help you work more strategically, Bailey said.

2. What can I take off your plate that you don’t enjoy doing?

Along those lines, there’s often things your boss doesn’t enjoy doing and that they are able to delegate to someone else. By taking those things off their plate, you show them this isn’t a one-way relationship and you are willing to help them, instead of them just helping you.

In his course, Bailey told a story of an employee who asked his boss this exact question. The boss was so impressed he put that employee in charge when he went on vacation, a clear sign of trust. The point is, by asking this question you show your boss you care about the company and want to do what you can to help.

One caveat – do not ask this question if you yourself are struggling with your current workload. Instead, only ask it if you can reasonably take on whatever your boss will throw your way.

3. Who are the people I need to form relationships with?

Your boss generally has a broader view of the organization than you do. That allows them to have a better idea of the key relationships you need to form to help you excel in your role, Bailey said.

While forming these relationships could be more work at first, they usually will result in more lessons learned, synergies between business units and ultimately a more efficient organization.

4. What is your preferred method of communication?

Relationships ultimately come down to communication. And, if you want to form a good relationship with your boss, you need to communicate in a way that they feel comfortable.

For example, in his course Bailey said he once had a boss who texted him. Bailey would call the boss back, but the boss would never pick up and not listen to the voicemail – he preferred to text. So Bailey soon realized texting was a much better way to communicate than calling.

Sounds simple, but this tactical question can drastically improve your relationship with your boss.

5. What do you most attribute to your success?

A boss is someone you can learn from. And often your boss is someone who came from a similar position as you and worked their way up, so they often have somewhat similar experiences to yourself.

Asking this question will give you valuable advice on how to advance your own career, as well as helping you better understand your boss, Bailey said. 

6. What skills do I need to know and sharpen?

Most bosses want to help their employees grow, they want to be a mentor. This is because people both innately like helping other people where they can and because if you get better, they look better.

So ask them what you need to do to become a better employee, Bailey said. 

7. What can I do to stretch myself?

Similar to the last question, ask your boss what you can do that you aren’t already doing, Bailey said. By taking on stretch projects you have no experience in, you learn quickly and quickly advance as a person. Additionally, it again positions your boss in the role of mentor, which builds a stronger relationship between the two of you.

Tying it all together

Your boss can either be your biggest ally or your biggest detractor. And, trust me, life is a lot easier if they are your biggest ally.

These questions help you accomplish that. They let you and your boss get past the normal confines of an employee-employer dynamic and build a lasting relationship.

Forming great business relationships is arguably the most important ingredient to success. Learn how in Bailey’s LinkedIn Learning course, Building Business Relationships .