Breakthrough the CEO Facade: Smart Questions to Ask Your Boss


A healthy relationship between employer and employee is important in building a positive work environment. Employees need to establish trust and mutual respect with their boss in order to achieve company goals. For many employees, it might feel difficult to approach employers, because their position of authority makes them seem less approachable. 

In order to create this positive work environment and advance in your career, it’s important to regularly connect with your boss. If you’d like to break through the perceived CEO facade, here are a few smart questions to ask your boss and set yourself apart from fellow employees.


“What is your vision?”

A great way to connect with your boss is to get to know what they want to accomplish and what their vision is for the future of the organization. Once you have learned their vision for the larger organization, ask if there is one for your department and your role.

“Is there something I can do to help?”

Whether it is a component of the company vision or another issue that needs assistance, step up to the task rather than wait. Offer your assistance before your boss asks. Not only will they appreciate your offer, they’ll feel more inclined to trust you. Your team members will be grateful for the assistance, and your boss will see you as a team player.

“Is there anything I can improve on?”

Every CEO has their own management style, but as an employee, asking questions and showing a desire to improve will impress your boss. You’re showing interest in long term goals and career success, which is going to speak volumes about your character. Even though it can be difficult, opening yourself up to regular feedback goes beyond typical employee initiative.


“Can I be considered for this assignment?”

If you show initiative, and signs of leadership potential, your boss is going to be impressed. Not all employees are open to taking on more responsibility. Even if you aren’t selected for the job, showing interest is a good first step.

Rather than delegate tasks to other employees, your boss might be willing to let you work on certain projects and assignments first. You’re not only creating trust between yourself and your boss but showing your ability to adapt and take on new projects.


“How are you doing?”

Sometimes, steering the conversation away from work is a great way to connect with your boss. Recognizing they might feel stressed or have other things going on outside of the office makes it easier to form a connection. Your boss will also appreciate the gesture, and over time you can create connections that go beyond small talk.


If you take the time to create connections with your boss and show initiative at work, these are just a few signs of leadership potential. Rather than wait, take a moment to assess your skills by reading a leadership film room, or order your 360 Leadership Assessment today. Together, we can take the next step on your journey to leadership.

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