Ensuring you will personally compatible with a new boss starts with thorough research and strategic communication during the interview process. Begin by learning about their background, work style, and values through their professional profiles and any available interviews or articles. Look for common ground in areas such as problem-solving approaches, leadership philosophy, and communication preferences.

During the interview you’re looking to uncover several things to determine if you’re are a good fit for the role and your boss. In this lesson we’ll focus on the first three.

  • Your Boss’s Management Style.

  • Your Boss’s Approach to Professional Development and Growth.

  • Your Boss’s Expectations of You.

  • Corporate Direction and Culture (Described in the previous lesson).

  • Challenges Facing Your Team. (Described in the next lesson).

Management Style: Start by asking your potential boss to describe their management style. This question can reveal much about their behavioral tendencies and how they interact with their team. Pay close attention to their response to uncover key characteristics. You’re not judging whether their style is right or wrong, just your comfort level with what is discovered. Things to look for, or to ask about if missing from the answer:

  • Do they collaborate or act unilaterally when making decisions?

  • Are they empathetic, respectful, transparent, when communicating?

  • Do they empower, or do they micromanage when delegating?

  • Do they inspire and motivate, or primarily give orders?

  • Do they provide constructive, positive, feedback on a regular basis?

  • Do they encourage dialog, or do they avoid confrontation?

Professional Development: Ask your potential boss to describe their approach is to professional development and career growth. The response should align with your career objectives. Things to look for:

  • Do they advocate for training and support continuous learning?

  • Do they help create career development plans?

  • Do they encourage advancement or are they protective of their resources?

  • Do they provide new opportunities, challenges, and projects aligned with employee aspirations?

  • Do they offer mentoring and feedback considerate of employee growth?

Your potential boss may need organizational support to fulfill some of these items and may respond as such. In that case you could be learning about the company’s commitment to employee development.

Expectations of You: You need to understand and be comfortable with the expectations for your role. Ask your potential boss for all goals that will be assigned to you. After the interview, assess the goals using the SMART technique to ensure each goal is well defined and easily understood. Specifically, ensure that each goal has clarity in the following areas:

  • Specific: The goal must be precise regarding expectations, and the outcome is not vague.

  • Measurable: The goal must state how success will be judged; the metrics used must be clear, and milestones should be defined for protracted goals.

  • Attainable: You have the skills, staff, tools, and time required to succeed.

  • Relevant: The goal makes sense for your role and should aligned with departmental and organizational objectives.

  • Time-bound: The goal has a documented start and end.

Document any discrepancies, clarify areas of confusion, and address all disagreements before you take the job. If you've been objective when reporting goal discrepancies, your boss should be able to mitigate your concerns. If you can't come to terms, then you need to understand why.

  • Document your boss's reasons for disagreement, then take time to review and understand these reasons.

  • Maybe you didn't correctly assess the expectations of the job, or perhaps you made unreasonable requests.

  • It’s critical that you fully understand and agree on the goals you’ll be assigned before you take the job

Metrics, are an essential indicator of your boss’s maturity regarding oversight of performance.

  • All roles have measurable output, so there should be a set of benchmarks used to evaluate performance.

  • These metrics should be tied to your goals, and you should ask how the data is sourced.

  • If no such benchmarks exist, reflect upon how your boss or even the organization evaluates success. This could be an area for concern.

If you're applying for an existing position, goals must exist with some set of measurements.

  • Lack of goals for an existing role is a huge red flag, ask your boss why this is the case.

  • Metrics may be handled somewhat informally, but the lack of clear measurement is also a warning sign.

  • Maybe there's an explanation for a lack of goals and/or metrics, but this seems like an organization and/or boss low on the maturity scale. These are red-flags.

If the goals failed SMART criteria or caused other concerns, you should have been able to agree on adjustments.

  • If you've been fair and realistic, there's no reason why mitigation would be difficult.

  • Failure to rectify may indicate a compatibility issue with your new boss.

If some goals are well outside your expectations or otherwise unacceptable, you need to ponder why such a disconnect exists.  

In the following downloadable survey you’ll summarize what you discovered during the assessment by placing a weight on each concern that was raised.

This exercise is to help you visualize the concerns, it can’t recommend a direction, one way or the other.