Could a potential boss be a great boss? Questions that can help you find out

02.19.2019

Toxic bosses are responsible for lots of workplace stress. In fact, career coach Jill Hugget discovered a phenomenon she calls Post Bad Boss Stress Disorder (PBBSD). She writes about working with former employees who’ve had their confidence stripped due to abusive, micromanaging, intrusive bosses.

If you’ve tried coping with a bad manager like Hugget describes, you know how stressful that can be. That’s why getting to know your potential boss before accepting an offer can be crucial. Sure, it’s important to come prepared with questions about the company’s culture, organizational values, and growth opportunities, but what about questions for your potential boss? Planning ahead and asking the right questions early on can clear up stressors and make way for creative pathways and success. Consider these four questions as you get to know your potential boss — before taking the job.

How would your employees describe you as a manager?

“In three words, how do your coworkers and friends describe you?” It’s a question often asked during interviews. Employers want insight into your self-awareness, confidence and demeanor. Turn this question around and ask your future boss how their employees would describe them.

You want to work for an authentic boss. One who strives for greatness, but will probably end up making some mistakes. Jim Whitehurst, president and CEO of Red Hat, wrote, “I’ve found that leaders who show their vulnerability, and admit that they are human, foster greater engagement among their associates.”

Look for authentic answers. Your boss isn’t perfect and will probably make mistakes, just like everyone else.

Tell me about an employee who became successful as a result of your leadership.

A good boss can push employees to grow and stretch themselves, which fosters collaboration and productivity. Dig in a bit deeper to learn how this prospective boss might push and coach you to success. Is he a mentor? Will she give you challenging projects with helpful guidelines? Is he around when you have questions? It’s one thing to have a fun, relaxed boss, but it’s another thing to have a boss that believes in you and pushes you to do your best.

This is a good place to bring up mentorship. In today’s ever-changing work places, mentoring has become an important opportunity, helping seasoned employees find fulfillment and new employees find direction. Learn how your boss feels about mentorship and how that could help you find success in your career.

How do you handle performance issues?

The best bosses understand that their employees are human and will make mistakes. Look for clues here to give you an idea of how performance issues are handles. Will he give you clear expectations so you can succeed? Will she set specific objectives for the future? Will he handle any issues swiftly and honestly?

Amazon founder Jeff Bezos says, “I find as soon as I identity an issue, and make the first phone call, or send off the first e-mail message, or whatever it is that we’re going to do to start to address that situation — even if it’s not solved — the mere fact that we’re addressing it dramatically reduces any stress that might come from it.”

This is a good place to bring up a time when you’ve handled constructive criticism well. Explain that you’re upfront and honest about any mistakes or confusion.

How do you provide or deliver feedback?

Identify whether your manager provides feedback in frequent, scheduled meetings or by informal conversations in the hallway. Do they expect a list of projects you’re working on or do they just want a brief chat?

Kelli Thompson, life and leadership coach, writes, “I found myself working for a boss that preferred to communicate differently than I did. I worked for a department that didn’t have a strategy as clear as I thought it should be. There were silos, too many meetings, and people were swerving into each other’s lanes,” she writes. “However, those weren’t problems — they were simply — reality.”

Workplaces are constantly influx and never perfect. But, the larger question to ask is, can you grow and thrive in these, albeit, imperfect circumstances?

You’re not asking your future boss these questions to ensure that your prospective workplace will be perfect. Because as Thompson writes, “If everything were perfect, where would I add value?” Your goal is to find out if you can see yourself interacting well with your future boss and thriving in this new workplace.