Skip to main contentA logo with &quat;the muse&quat; in dark blue text.
Advice / Succeeding at Work / Work Relationships

11 Surprising Things Your Boss Wishes You’d Talk About

Whether it’s taking a sick day or dealing with a task you don’t love, employees can be hesitant to discuss certain aspects of their job with their bosses.

But that’s often to your detriment. In fact, there are probably a lot of things you think are taboo, but that you really should be talking about with your boss.

Need some proof? We spoke to 11 entrepreneurs from Young Entrepreneur Council (YEC) to find out what they wish their team members would tell them, but typically don’t. 


1. What You Really Enjoy Doing

I wish my employees were more vocal about what they actually enjoy doing at the company as opposed to the usual vocalizing about what they don’t like doing. Then I can ensure that those positive things continue as part of their day-to-day in a proactive way.

Rameet Chawla, Fueled


2. What You Find Boring

I wish my employees would tell me what they find boring. I am always interested in how they think the workplace could be made more fun. It’s not something many employees are comfortable talking about, but I encourage the discussion to build a better work environment.

Simon Casuto, eLearning Mind


3. Your Ideas for Automation

No one likes repetitive tasks, but most people don’t even think of ways to automate certain processes to make themselves happier and more productive. I’ve encouraged my team to actively brainstorm ways to make their jobs easier with technology so they can work smarter, not harder. This is a win-win for everyone when they recognize opportunities to streamline workflows.

Firas Kittaneh, Amerisleep


4. Your Feedback and Goals

Employees usually don’t talk to me about the help they need to reach their goals and follow through on commitments. They probably don’t because they believe they’re not living up to our expectations. As a company, we have a strong “get it done” mentality, which can intimidate some.

Mark Samuel, Fitmark


5. Your Knowledge Gaps

Employees tend to hide any knowledge gaps they have in fear they will appear incompetent to their employers. This is unfortunate because offering the opportunity to help employees learn and fill in these knowledge gaps is every employer’s responsibility. Not knowing what these gaps are prevents employers from helping employees grow, which causes undue stress and poor performance.

Phil Chen, Systems Watch


6. What You’re Thinking

I wish my employees would talk to me more about questions or ideas they have. We have an open door policy, so I wish more employees would stop by and be candid, direct, and assertive with me about what they’re thinking. I think they don’t because they’ve been taught you should just conform and do what you’re told. They might have it ingrained in their head to not ask questions or speak up.

Dan Price, Gravity Payments


7. Your Issues With Other Employees

It can be difficult to create a culture of positivity and helpfulness while still remaining open to constructive feedback and grievances about other employees. I find that my team doesn’t want to “tattle” and talk badly about others. While this is generally a good thing, it can be a challenge when you’re trying to get a clear picture of an employee’s true performance within the team.

Laura Roeder,


8. How the Company Has Influenced Your Perspective on Life

I want my employees to share with me their thoughts on how the company changed their outlook on and approach toward life. I believe work should add meaning and value to your life, and understanding how my company accomplishes that for employees is extremely important.

Kevin Xu, Mebo International


9. What Isn’t Working

It’s really hard to get someone to tell you what doesn’t work. But surely not everything is perfect! Get people to tell you a few things that are wrong and make some effort to fix them so they know they can come to you with bigger things.

Jessica Richman, UBiome


10. When You’re Taking Time Off

I run my company mostly remotely. I’m based in Denver, but I travel quite a bit, and a lot of my team members live in other cities. I find that in this situation, sometimes employees are timid to say when they’re traveling or working from another city. I don’t know why this is; perhaps it’s something that’s been programmed in them from previous jobs.

Rob Fulton, Exponential Black


11. Your Career Progression

I’m often surprised when employees don’t ask about what’s next when it comes to the progression of their career. Unfortunately, many get comfortable in the details of their current role and forget that it’s important to continually push forward. This is important for their own career advancement and helping the company grow to the next level. If employees remain stagnant, so will the company.

Brian Honigman,

Photo of people talking courtesy of Shutterstock.