Challenging Middle Management Interview Questions:

By March 15, 2020 No Comments

A middle manager is accountable for balancing the organization and department’s objectives and goals. Typical titles include Division, Regional, General, Branch, and other Department Managers. He/She will be responsible for delegating tasks, providing input into the overall direction, as well as managing daily operations for their entire department.

Here are some challenging interview questions to consider:




1. Tell me about a time when you were faced with a problem or opportunity that you knew would be best handled by a team. What did you do to select and guide the team?

2. Describe how you’ve worked with a team to set specific and measurable goals. Tell me about a time when you were successful in meeting those goals and a time when you experienced challenges along the way.

3. Describe the most effective techniques you’ve used to encourage team members to contribute their talents to the team’s function or goal. Give me a specific example of a time when you used one of these techniques.

4. Sometimes teams get off track when working toward a specific project or goal. Describe a time when this happened and you were able to help your team get back on track.




1. Describe a recent coaching discussion you conducted. How, if at all, did you involve the other person in the discussion (e.g., offer suggestions, listen to concerns, etc.)?

2. Describe what you’ve done to link organizational objectives to your direct reports’ objectives.

3. Tell me what you have done to identify and retain high performing employees.

4. Tell me about someone whom you found difficult to coach. Describe a specific situation. How did you handle this?



1. Tell me about a time when you were especially proactive about pursuing an opportunity.

2. Describe a time when you had to gain the trust of others in order to succeed.

3. How have you influenced employees to follow your strategic vision for the department/organization?



1. Tell me about a time when you were responsible for helping a group of people think about approaching a problem and/or an opportunity in a new way.

2. Describe the most significant change initiative you have led. Describe the steps you took to prepare for and execute the change.

3. People often feel threatened by change. Tell me about a specific situation and the actions you took to smooth the process of change for others. Which actions were successful and which were not?

4. Describe a time when change caused a problem for your department, business unit, or organization.




1. How do you decide when and how to communicate a new directive from senior management? Describe a situation when you applied this strategy.

2. What strategies have you employed to make sure a major new directive from senior management was carried out? Which strategies worked, and which did not? Give me a specific example.

3. Tell me about one of the most innovative strategies or methods you have used in implementing strategic directives created by senior management.

4. Describe a time when you recommended a plan of action in response to business/market trends. How did you come up with this plan?

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