Don’t take on a management job without asking these two questions

Taking on a new management role is a big step. It can accelerate your career if it’s right or set you back if it’s not. Before you say yes to any leadership position, make sure you will actually succeed in the role. One of the best ways to assess this is by asking two questions during the interview process. These questions will uncover the culture, expectations and leadership styles that are most valued at your potential employer, helping you determine if the environment is compatible with your personal approach.

Why leadership style matters

Organizations are defined by the leadership styles that drive their goals, shape their culture, and ultimately influence how they treat their people. Essentially, most leaders will fit into one of four styles: pragmatist, idealist, administrator, and diplomat.

We know from the millions of adopters of “What is your leadership style?” tests that each style offers unique strengths, but also comes with specific weaknesses and limitations. So before you can discern whether a particular management job is right for you, you need to understand your approach.

Pragmatists: Pragmatists are goal-oriented leaders who push themselves and their teams to meet high standards. They often thrive in ambitious, high-stakes environments that prioritize results and rewards. Pragmatists excel in environments where growth, market disruption, and ambitious goals are top priorities, but their relentless drive can also overwhelm teams if not managed carefully.

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-minded, collaborative, and deeply invested in fostering a positive and inclusive work environment. But sometimes they can struggle to set firm boundaries or give harsh feedback.

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

Diplomats: Diplomats are relationship-focused leaders who value harmony, collaboration and teamwork. Acts as the glue that holds teams together, especially during times of change or conflict. Diplomats excel in environments where collaboration is critical to success. However, diplomats may have difficulty enforcing deadlines or pushing people beyond their comfort zones when high performance is required.

Understanding these leadership styles isn’t just about defining your own approach; these styles provide a framework 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?”

The company’s current management style tells you a lot about what it takes to succeed there. Let’s say you’re considering a position with an ambitious, high-growth startup with a disruptive vision for the market. In this case, a pragmatist leadership style that emphasizes results and bold risks might align well. On the other hand, if the organization focuses on incremental improvements and operational stability, it might prefer Stewards—leaders who excel at creating a structured, predictable environment where teams can thrive without constant change.

Ask this question: “Can you tell me about a leader here who truly exemplifies the company’s values ​​and goals? What did they do that stands out?”

The answer to this question can reveal not only the dominant leadership style, but also the true values ​​of the company. Hearing the stories of other leaders provides insight into the qualities and behaviors the organization values. For example, if you are told of a leader who consistently achieves ambitious targets and takes bold risks, you may be looking at a culture full of pragmatism. Alternatively, if the answer emphasizes teamwork and conflict resolution, it is likely a diplomat-style environment that values ​​harmony and collaboration.

“Which attitude best fits the culture?”

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 job success, with studies showing that almost half of new hires fail within 18 months, mainly due to attitudinal mismatches rather than skill deficits. If a company’s culture is fast-paced and risk-tolerant, they will appreciate leaders who embrace change and push boundaries. Conversely, a company that prefers stability and cautious growth will gravitate toward leaders who value structure and consistency.

Ask this question: “Think of someone who hasn’t been successful here. But didn’t their attitude or approach work?”

This question does more than probe for a generic cultural fit; discover specific attitudes that clashed with the company’s environment. For example, being told about someone who failed because they pushed for rapid change could indicate a culture that values ​​stability over innovation. Conversely, if they struggled because of a reluctance to take risks, the company is likely to value a more entrepreneurial attitude. Knowing what doesn’t work can help you assess whether your approach and attitude will fit the organization.

Taking the time to ask these two questions in the interview process can help you avoid unnecessary frustration and ensure that your leadership style and attitude are compatible with the company’s values. Success in a new role depends on more than having the right skills – it’s about making sure your leadership approach aligns with the environment and culture you’re entering. Remember, if the company prefers a leadership style and values ​​that match yours, you are much more likely to thrive and succeed in the role.