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Interviewing Your Future Boss

I’m sure you have been asked if you have any questions during interviews. A few things come to mind. Often, we think we need to impress the other party. Nevertheless, tough questions are the ones you want to ask, especially to your future boss. We all know that switching teams or starting a new job is a significant decision. You need to understand your future manager’s leadership style and approach before signing up. You should have an idea of how they handle team dynamics, support growth, and maintain accountability. You can even ask for a pre-joining call to ensure that. Getting paid is important, but choosing the right boss might be even more so. Here are some important questions to consider:

  1. What Are Your Team’s Ways of Working?
    • Purpose: Understand the team’s work methods and culture.
    • What to Look For: Description of work processes, collaboration tools, meeting structure, flexibility, and alignment with your preferred work style.
  2. How Do You Challenge Top Performers?
    • Purpose: Discover how they provide challenges and opportunities for growth.
    • What to Look For: Examples of meaningful projects, recognition strategies, and continuous learning opportunities.
  3. Can You Share an Example of When You Had to Let Someone Go?
    • Purpose: Understand how they handle tough decisions and maintain team culture.
    • What to Look For: Their approach to difficult conversations, fairness in the process, and how they protect the team’s integrity.
  4. What’s Your Approach to Supporting Team Members Who Are Struggling?
    • Purpose: Gauge their empathy and coaching ability.
    • What to Look For: Methods for identifying issues early, willingness to offer support and resources, and their coaching style.
  5. How Do You Ensure Accountability Within the Team?
    • Purpose: Learn about their methods for setting expectations and promoting responsibility.
    • What to Look For: Clear communication of expectations, regular feedback mechanisms, and how they handle accountability.
  6. Who Have You Recently Promoted and Why?
    • Purpose: See if promotions are based on merit and how they develop their team.
    • What to Look For: Criteria for promotions, examples of recent promotions, and the development opportunities provided.
  7. Who Are You Preparing to Take Over Your Role?
    • Purpose: Understand their commitment to leadership development and succession planning.
    • What to Look For: Evidence of grooming future leaders, their own career aspirations, and how they plan for team continuity.

I know it sounds like you are almost interviewing your potential boss. As a manager, I would appreciate these questions. There’s no reason to be upset about them. In fact, it means the candidate really cares and has something to offer to my team. If you get a negative response to these questions, do not take that job. That speaks volumes about the workplace. We talk about similar topics in our book, Software Engineering Handbook. Get your copy today!

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