Don’t Take a Management Job Without Asking These Two Questions

Taking on a new leadership role is a big step. It can speed up your career if it suits you, or set you back if it doesn’t. Before you say yes to any leadership position, make sure you can actually succeed in that position. One of the best ways to assess this is to ask two questions during the interview. These questions will reveal the culture, expectations and leadership styles that are most valued by your potential employer and help you determine whether the environment is compatible with your personal approach.

Why leadership style matters

Organizations are defined by leadership styles, which define their goals, shape their culture, and ultimately influence how they treat their people. At their core, most leaders fall into one of four styles: pragmatist, idealist, manager, and diplomat.

We know from millions of customers “What is your leadership style?“Check that each style has unique strengths, but also certain weaknesses and limitations. Therefore, before you can determine whether a particular management position is right for you, you must understand your specific approach.

Pragmatists: Pragmatists are driven, assertive leaders who hold themselves and their teams to high standards. They often thrive in ambitious, high-stakes environments where results and rewards are prioritized. Pragmatists thrive in environments where growth, market disruption and ambitious goals are top priorities, but their relentless drive can also overwhelm teams if it is not carefully managed.

Idealists: Idealists are visionary leaders who focus on growth, creativity, and the long-term development of their teams. They value learning and innovation, often prioritizing employee engagement and a culture of curiosity. Leaders with this style are often open, collaborative, and deeply interested in creating a positive, inclusive work environment. But sometimes they find it difficult to set clear boundaries or provide firm feedback.

Stewards: Stewards value stability, structure and consistency. They excel in environments where accuracy, reliability and flawless execution are critical, such as in highly regulated industries or where operational efficiency is a key priority. Stewards are meticulous planners and detail-oriented leaders who bring order and predictability to their teams. However, sometimes stewards can resist change or struggle to innovate quickly when unexpected problems arise.

Diplomats: Diplomats are relationship-oriented leaders who value harmony, cooperation and teamwork. They act as the glue that holds teams together, especially in times of change or conflict. Diplomats thrive in environments where cooperation is critical to success. However, diplomats may find it difficult to meet deadlines or push people outside their comfort zone when high productivity is required.

Understanding these leadership styles isn’t just about identifying your own approach; these styles provide a basis for assessing the culture and expectations of a potential employer. By asking two specific questions, you can get a clearer picture of whether your style aligns with what the company values ​​most in its leaders.

“What leadership style thrives here?”

A company’s current leadership style says a lot about what it takes to succeed. Let’s say you’re considering a position at an ambitious, fast-growing startup with a disruptive market vision. In this case, a pragmatic leadership style that emphasizes results and bold risks can work well together. On the other hand, if an organization focuses on incremental improvement and operational stability, they may favor stewards—leaders who excel at creating a structured, predictable environment in which teams can thrive without constant change.

Ask this question: “Can you tell me about a leader who truly embodies the company’s values ​​and goals? What did they do that was so special?”

The answer to this question can reveal not only the dominant leadership style, but also the true values ​​of the company. Stories about other leaders provide insight into the qualities and behaviors that an organization values. For example, if you are told about a leader who consistently achieves ambitious goals and takes bold risks, you may be referring to a culture in which pragmatism prevails. Alternatively, if the response emphasizes teamwork and conflict resolution, it is likely a diplomat-style environment that values ​​harmony and cooperation.

“Which attitude best fits the culture?”

The skills are essential, but without the right attitude, fitting into a company’s culture can be difficult. Attitude has proven to be one of the strongest predictors of success at work, with research showing that Almost half of new hires fail within 18 months, primarily due to inadequacies in approach rather than skills deficits. If a company’s culture is dynamic and risk-tolerant, they will appreciate leaders who embrace change and push boundaries. Conversely, a company that favors stability and cautious growth will gravitate towards leaders who value structure and consistency.

Ask this question: “Think about someone who hasn’t made it here. What about their attitude or approach that didn’t work?”

This question does not simply explore general cultural fit; it reveals specific views that were contrary to the company’s environment. For example, if you are told about someone who failed because they insisted on rapid change, this may indicate a culture that values ​​stability over innovation. Conversely, if they were struggling due to risk aversion, it is likely that the company values ​​a more entrepreneurial approach. Knowing what isn’t working will help you evaluate whether your approach and attitude will be a good fit for the organization.

By taking the time to ask these two questions during your interview, you can avoid unnecessary frustration and ensure that your leadership style and attitude are compatible with the company’s values. Success in a new role isn’t just about having the right skills—it’s about matching your approach to leadership to the environment and culture you’re entering. Remember, if a company favors a leadership style and values ​​that align with your own, you are much more likely to excel and succeed in the role.