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Ask 6 Powerfully Revealing Questions to Identify a Bad Boss

As all areas of the US economy continue to show improvement, more and more people will be making moves to new jobs. As such, the chances of working for a new boss increase, and unfortunately so do the chances of working for a bad boss. Whether you are one of the millions who will interview for a new role or one who will be working for a new boss in the coming weeks and months, you may not know how to determine if your new boss fits into the category of boss from hell. There is some good news. Social media and other technology based tools and resources make it a lot easier to conduct your own form of background check.  But a few old fashion questions are some of the best tools you can deploy to get a peek inside your boss’ mind. Here are 6 questions you should ask any potential new boss as they can reveal some traits that may just be the wrong fit for you.

Question #1: Of all the people who’ve worked for you, how many have been promoted and how did you help them get promoted?

You want to work for someone who has a history of developing people. A great boss will have many examples of helping former employees take on larger roles and responsibilities and get promoted. If the potential manager talks in general terms and provides very little details about anyone s/he has helped, it may be a warning sign that s/he doesn’t develop employees.

Question #2: Tell me about a time there was a disagreement with your team and another team. What was the situation, and how did you help to resolve it?

Conflict and collaboration go hand in hand in every organization, and the key is to try to determine how healthy the organization’s ability to collaborate is. Bad bosses will be dictators with their own staff and often will stay away from putting themselves directly in the middle of any conflict that could damage their careers. Listen for their involvement (or lack thereof), and ask probing questions based on the story that is shared.

Question #3: In what ways do you and the organization support ongoing employee development? Are there formal mentoring and coaching programs? What resources do you typically support for your employees?

Do your homework first and ask your HR representative(s) about the employee development programs available to employees at the level you’re working at or the level you’ll be entering into the organization. Then ask the hiring manager how s/he supports these programs. If the hiring manager appears to have little knowledge of the programs and cannot provide specific examples of how s/he has developed employees, this would be a clear sign that employee development may not be a priority.

Question #4: Where did the last person in this role go?

Just by asking this very open ended question and closely watching the hiring manager’s body language, you will glean a great deal of information about the past. Listen and watch for signals indicating success – the previous employee was promoted internally or accepted a new role at a different company. Good bosses will speak with pride that someone in their team moved on to bigger and better opportunities. On the flip side, if there are signs of an unpleasant ending to the previous employee’s tenure, it would be extremely important to carefully ask follow up questions to assess what the current state of perception is about the role. Horrible bosses and high turnover rates go hand in hand, and it might behoove you to seek more information about the role and the manager’s contributions to the role’s vacancy.

Question #5: What are three expectations you have of the candidate who fills the job?

Horrible bosses will talk in very vague terms when responding to this question. The key would be to ask a follow up question seeking specific details of the expectations stated. For example, if the hiring manager states, “demonstrate trust and respect” or “live our values”, ask for more specific details and watch the verbal and non-verbal signals. If you see clusters of the top 10 potential signs of deception, it might be a good idea to reconsider taking the job.

Question #6: How would you describe your preferences for getting work done?

Listen for signs that would indicate preferences that don’t match yours. Also ask the follow up question, “How do you deal with people whose preferences are different from yours?” If the hiring manager’s responses are fairly generic, this should be a sign of concern because a good manager would be able to tell you very specifically how s/he values diversity and uses it to achieve better results.

By taking the time to ask the right types of questions and to look for the clues that your new manager may not be a good fit for you, you can dramatically decrease the potential for having a very bad employment experience. And in the new, normal economy where competition for great jobs is extremely high, working for a boss who effectively supports your development has become a critical competitive edge for sustainable career success.

If bad bosses are destroying productivity and causing high turnover in your organization or if you want more strategies for detecting bad bosses, email me today at

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There’s a couple of questions there that I might tweak and use with potential new clients! Very well written and insightful Blog post Sardek, thanks. C

Thanks Cris! And as a leading and highly SUCCESSful global sales expert, please feel free to share any experiences using the questions w/ your clients in the UK and abroad as that would be very insightful information for our readers indeed.


I should have known better. The last person in my job was fired. I was told it was because he was doing freelance work on the side. Soon after I started work, another woman was fired (for making too many “mistakes”). Sadly, I got sucked into my current bad boss situation. I should have know, but at the time I really needed a full time job.

Your comments reaffirm the unfortunate experience many people have with bad bosses. If there is a silver lining in having such a poor work experience, it comes in the fact that you’re wiser and more aware of what to look for in the future to avoid or minimize the chances of working for the wrong person. Thanks for the comments! They are very sincerely appreciated.


I employed questions #4 an #5 during a phone interview last week. While I couldn’t see the body language, I did get quite a pause and somewhat evasive tone with question #4 that set off some red flags for me! You see, I actually had a phone interview with this same company about a year ago for a similar position (but a different department). Worse, I did not get a direct answer to #4, only that the were “looking for someone that would be more detail-oriented.”

I don’t want to repeat my mistakes and end up in a worse situation than I am in now. While I don’t want to rule out this company completely, I am being very wary. Any thoughts?

Thanks for using the questions from my blog article and for your follow up questions after using them! Vague answers to question #4 and #5 should send warning signals to you. Most managers are very unprepared for question #4 because very few have been taught how to handle such a provocative and very bold question, especially if the previous person in the role was terminated or left under not so great circumstances. So it is no surprise you received pause and evasion. The key now is to try to get a better understanding of the manager’s management and communication style. This is where you can flip the script so to speak and use behavioral interviewing techniques to ask for examples of management and communication preferences. That is why question #6 is so important – it effectively serves as the natural follow up question to #5. Good managers can easily tell you what they expect because they tell you what success looks like. So when the manager was vague and stated s/he was “looking for someone that would be more detail oriented”, you could ask, “What examples can you share that would be signs of success in the role where detail orientation are important?” That should elicit responses that provide specific examples of tasks where the previous candidate may have failed OR tasks that are critically important for the new hire to be able to consistently do successfully. So you don’t have to rule the company and opportunity out – just be much more diligent in asking questions that help you determine whether or not the role and the style of management is a good fit for you. I encourage you to also read my blog article on trust entitled “How to Know If You Can Trust Someone: 4 Guaranteed Ways to Know” as it provides 15 questions in 4 categories that allow you to assess trustworthiness. Some of the 15 questions would be very applicable to the interviewing process. Good luck, don’t hesitate to ask more questions, and thanks for reading and engaging with me on the blog! I look forward to your continued contributions as they add great value for other readers of the blog.

Best Regards,


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