top of page
  • Writer's picturePaul Wyman

Would you hire your boss?

Updated: Jan 14, 2021

The top ten behavioral interview questions you should be asking your future boss

It’s an HR cliché that when employees leave an organization, they’re really firing their boss. So when an employee joins an organization, shouldn’t they interview their boss thoroughly, to know what they’re getting themselves into?

If you’ve interviewed for a job in the last three decades, you’ve encountered interview questions which start “Tell me about a time when…” Known as behavioral interviewing, this approach has become a ubiquitous element of hiring because it works. It generates specific information about how a candidate behaved in the past, and assumes this has predictive value about his or her future behavior.

But there’s an inherent problem with behavioral interviews: only half of the most critical behavioral questions are ever asked.

In a typical one-hour interview, maybe five or ten minutes at the end is reserved for the candidate’s questions. I’ve been asked questions about the business, strategy, benefits plans, vacation time, and, on one memorable occasion, whether alcohol is allowed at company picnics. Not once has a candidate asked me, as the hiring manager and prospective future boss, the most important question: What kind of a boss are you?

So here’s a radical proposition. Next time you’re in a job interview with the person who might be your future boss, ask her if she would agree to splitting the interview time in half. She can go first, asking the typical set of prepared behavioral questions. Then it’s your turn to ask a series of behavioral questions of your future boss.

Here are the top ten behavioral questions you should be asking your future boss, and some thoughts about how to interpret what you hear.

1. Tell me about the time when you first decided to become a manager. What did you hope to accomplish in that role?

  • Importance: Motives matter. A manager motivated by money, power, prestige or status will see their employees differently than one who’s motivated by a desire to contribute, serve, grow or learn. Many people managers back into the role, and would really rather be technical experts. The qualities, attitudes and approaches that make for good technical experts (depth of knowledge, problem solving, being right) can be disastrous in management roles, because they set up conditions for micromanagement, half-hearted delegation and decision bottlenecks.

  • Red flags: “I never really wanted to be a manager,” or, “I love solving problems”.

  • Green lights: “I get real satisfaction from seeing my people succeed.”

2. Describe a time when you felt fully successful as a manager.

  • Importance: Gives you a good idea of what your future manager thinks his job really is.

  • Red Flags: If she talks about accomplishing work independently of her team, she thinks her job is to produce results herself, not through her team. Get ready to be micromanaged.

  • Green Lights: Pride in the accomplishments of others, in creating a high-performing team, in overcoming obstacles by working together.

3. Describe a time when you changed someone’s job to better suit their strengths.

  • Importance: Good managers use the knowledge of people’s strengths to make decisions about where people can best use those gifts. Bad managers are more likely to treat everyone the same, under the guise of fairness or equality. Managers who are ignorant of their employees’ strengths are also far more likely to focus on their deficiencies, faults and weaknesses.

  • Red Flags: Unable to answer the question. Believes the employee should be 100% responsible for fitting themselves to the job.

  • Green Lights: Any story of balancing employee preferences with organization needs, individualizing task assignments, or detailed descriptions of employee strengths.

4. Tell me about a time you’ve had to deal with an under-performing employee. What did you do? What factors did you take into account?

  • Importance: Do you want to work with slackers? Depend on people who are chronically late, have an excuse for everything, point fingers at everyone but themselves, refuse to pull their weight and otherwise make for a toxic workplace? Nor do good managers.

  • Red Flags: Stories of firing someone on the spot without giving them feedback and a reasonable chance to improve should give you pause. So should managers who tolerate everyone, or make excuses for their employees’ bad behavior or incompetence.

  • Green Light: A good manager should be able to tell you what they expect, what they don’t tolerate, and how they handle low performers.

5. Give me an example of a time when you delegated authority as well as responsibility for a project.

  • Importance: Being asked to accomplish something without sufficient authority to make decisions is a set up to fail, and a common error for rookie managers and control freaks occupying the bosses’ leather chair. The best managers set expectations about timeline, quantity and quality of work expected, and clear guidelines about when to check in with them.

  • Red Flags: Not understanding the question, suggesting they’ve never considered what makes for good delegation. Run away.

  • Green Lights: Effective leaders empower their people. Look for stories of empowerment, giving staff autonomy within limits, and with a clear goal or definition of success.

6. Tell me about a time you were successful in advocating for additional resources.

  • Importance: Staff need the tools and resources necessary to do the job, and effective managers find a way to provide them. While all organizations work with constrained resources, how a manager addresses this challenge speaks volumes about them.

  • Red Flags: Victim stories, where the boss paints himself as powerless to influence indifferent or tight-fisted upper management. It suggests he lacks credibility and influence skills, which won’t help you, your team or your career.

  • Green lights: Good managers generally combine two strategies: challenging their staff to work smarter, and having a good grasp on how to influence decisions to get additional resources.

7. Describe how you give feedback to your direct reports.

  • Importance: Every employee has the right to know how they are doing. What you need is a boss who will help you course correct when you’re going off track, and gives enough real-time feedback to make this possible. Most employees receive little to no feedback on their performance, settling for a perfunctory “check the box” performance appraisal once per year. Best case, you hear feedback late, often months after you could have done something about it.

  • Red Flags: Talking only about the annual appraisal, or exclusively about negative/corrective feedback. The best bosses achieve the “golden ratio” of 3:1 (positive to critical feedback), which has been shown to characterize the healthiest relationships.

  • Green Lights: Good bosses find ways to give frequent, specific feedback which tilts to the positive: prioritizing reinforcement of good behavior and strong performance over correcting errors and missteps.

8. Tell me about a time you were successful as a sponsor of someone’s career.

  • Importance: The best bosses see themselves as advocates for the careers of those who work for them. The worst see their staff not as people with goals and aspirations of their own, but merely as producers of work. The most toxic see their employees as existing simply to make their boss look good.

  • Red Flags: Inability to answer the question; pushing total responsibility back to the employee to manage their career.

  • Green Lights: Proud tales of seeing one of their staff get promoted, build skills, or get experience in areas they want to grow.

9. What management and leadership skills have you learned in the past year? How do you use them? How well have they worked?

  • Importance: Anyone who’s ever managed people knows that it’s not an easy task. That’s why it requires ongoing skills development. The best managers bring humility to the role, and regularly look for ways to be more effective at providing a great work environment for their staff. A willingness to learn is a pretty good indicator of humility.

  • Red Flags: Leaders who do not invest in their own development are unlikely to invest in yours.

  • Green Lights: Signs of humility, awareness of the need for ongoing learning, the willingness to change approach and try something new.

10. What feedback have you received from your direct reports which has helped you be a better manager?

  • Importance: Leaders who insulate themselves from feedback should scare you. Those who openly ask for feedback are typically less ego-driven. If your manager’s priority is to maintain their ego rather than improve their performance, look out.

  • Red Flags: No boss who is doing a good job should be afraid to receive feedback. A manager who has never thought to ask his employees for feedback has missed the point: the employees do the actual work, and the manager’s job is to enable this to happen effectively.

  • Green Lights: Any example of being open to feedback, or a pattern of being willing to level the power differentials which exist in hierarchical organizations.

Ultimately, workplaces will only become more humane, more ethical and more effective when employees start expecting more of their boss. Accepting a job working for a bad boss is a decision made from desperation for a paycheck. It’s like marrying someone just because they’re willing to go out on a date with you. Expecting a manager to change after you join the team works about as well as expecting your spouse to change after the wedding. Past behavior, as the relative effectiveness of behavioral interviews shows us, remains the best predictor of future behavior.

So the next time you’re dressed in your best suit, sitting across the table from the person who will evaluate your work and make decisions which affect your career and your life, pause for a moment. Exercise your right to gather relevant and predictive information about the leadership skills of your prospective boss.

It will turn off the ego-driven, power-hungry, pointy-headed bosses that we all hate to work for and will eventually, inevitably fire. And it will gain you credibility with the type of leader who works hard to earn the loyalty and effort of their team. It’s time we acted on the truth that effective manager-employee relationships are like healthy marriages: a partnership, requiring equal commitment of both parties.

(c) 2016, Paul Wyman PCC,

28 views0 comments

Recent Posts

See All


bottom of page