7 Questions For Spotting Employers’ Hidden Flaws On A Job Interview

A job interview isn’t always the best venue for uncovering signs of bad management, but asking these questions can help.

7 Questions For Spotting Employers’ Hidden Flaws On A Job Interview
[Photo: Piotr Marcinski via Shutterstock]

People typically leave their jobs for three reasons: they were offered a better one, they don’t see a growth path, or they don’t like their bosses. As a recruiter, I see all of these scenarios play out, but boss troubles are the most common by far–and they don’t always stem from employees’ direct supervisors. Sometimes it’s your boss’s bad boss who sets the tone for everybody, a problem that can be harder to detect as an outsider.


Fortunately, there are a few ways to find signs of faulty leadership even within the formal ritual of a job interview. And it all comes down to being prepared for the wrap-up portion where it’s your turn to ask the questions. Here are a few you may want to keep up your sleeve, whether you’re meeting with other team members (people you’ll work with), higher-level execs (your prospective boss’s boss), or the hiring manager for the role (your own soon-to-be boss).

1. How Are Organizational Decisions Made?

Warning sign to listen for: Organizational changes are made without managerial input.

I know a CEO who decided that engineering recruiting wasn’t happening quickly enough, so he moved all the recruiters into his office and had the whole team report to him. The entire team quit, as did the managers who only found out about the change after it had been announced. By asking this question, you can get some insight into the chain of command and how well it’s abided by–including the part of it that reaches above your own prospective boss’s head.

2. How Do Executives Interact With The Rest Of The Staff?

Warning sign to listen for: Executives micromanage direct or indirect reports.

Micromanagement is utterly miserable and demotivating for employees at any level. Too many mangers leer over employees’ shoulders, forcing them to spend more time defending and reporting on their actions than actually doing their jobs. Sometimes even mid-level managers can’t do much to curb overzealous execs (their bosses), causing an unwelcome trickle-down effect. Asking to hear how a hiring manager would describe the company’s executive management style can help you spot this red flag.

3. How Often Do Execs And Managers Meet?

Warning sign to listen for: Other managers get ignored by top brass.


The opposite of micromanagement is total avoidance. I knew one large company SVP who spent literally five minutes with the CEO during her first six months on the job. The CEO considered her role to be so unimportant that he denied her many meeting requests–until the meeting involved firing her. Sometimes the best way to see signs of this problem is to ask about the typical cadence of meetings between team leaders and their higher-ups–even if you won’t personally be sitting at the table. What are these meetings like? And how often do they get cancelled?

4. How Long Have You Known The CEO And In What Capacity?

Warning sign to listen for: There’s nepotism and personal patronage afoot.

Public and venture-backed businesses aren’t supposed to be family businesses. No one can compete with the CEO’s “brilliant” uncle, second wife, or childhood best friend. When underqualified friends and family are on the company payroll–run, don’t walk. You may find that the CTO lacks an engineering degree, for instance, or that the well-paid executive coach lacks real coaching experience outside the company.

It’s tough to be the outsider struggling to break into an inner circle sealed by blood or personal loyalty. So don’t hesitate to ask your interviewer how they first found out about the company and in what capacity they’ve known the CEO. You can also ask about vendors, especially coaches. Do some research to make sure any friends and family are qualified.

5. Remind Me Once More Which Qualities You Need Most For This Role

Warning sign to listen for: The manager wants a buddy, not a partner.

Beyond a kickass engineer, marketer, product manager, program manager, business analyst, or recruiter, what else does the hiring manager want? A drinking companion? A confidante? A yes-man or -woman? A bad cop? Adult supervision?


Ask the hiring manager to summarize the desired candidate’s qualities one more time before wrapping up. Then ask any other team members you interview with the same question, as well as when and where they interact with the manager outside of work.

This isn’t prying–it’s a way to suss out an organization’s culture. For example, maybe the only way into the manager’s inner circle is to play on his soccer team. And hey, maybe you love soccer. But maybe you need to leave by 5 p.m. and have no time for soccer–which has nothing to do with how well you’ll perform in your job anyway.

6. Does Your Manager Respond Well To Feedback?

Warning sign to listen for: Management won’t admit when they’ve made a mistake or don’t know what they’re doing.

This question is best to save for any team members you speak with, but it can help you better understand a hiring manager’s relationship to their own boss, too. No one is perfect, and first-time managers have especially steep learning curves. All the more so when the managers are young and have little professional experience in the first place. They’re going to make mistakes–and this is fine. What’s not fine at any age or experience level is a refusal to acknowledge those skill gaps and an unwillingness to learn.

7. What’s The Culture Like Here During Really Intense Projects?

Warning sign to listen for: Management doesn’t respect employees’ personal lives.

If you’re not looking to work 80-hour weeks, don’t take the job where you have to travel internationally every other week or regularly call in for 3 a.m. conference calls. Researching work-life balance is common sense. Being able to find out about it without looking like a lightweight is the challenge.


So ask employees to describe the work culture both on a day-to-day basis and during intense projects. After the interview, head over to LinkedIn, Glassdoor, or a similar platform and find at least one previous employee and ask the same questions. Previous employees will obviously be the most honest.

Life’s too short to be unhappy at work. Decide wisely–and to do that, ask the right questions.

Valerie Frederickson is founder and CEO of HR executive search firm Frederickson Pribula Li. Clients include Facebook, Pinterest, Twitter, Uber, Tesla, SoFi, Microsoft, HP, Genentech, and other technology leaders.