For nearly two decades, I’ve coached mid- to senior-level professionals and leaders, helping them identify and achieve their most rewarding goals. A core part of this work is guiding people to make key decisions that align with their values, build confidence, and allow them to have a meaningful impact. Over the years, I’ve seen countless professionals wrestle with this critical career decision: deciding whether the manager or leader they’re interviewing with is someone they truly want to work for.
Even experienced professionals often hesitate when making this choice. Perhaps past career decisions led to disappointment—supporting the wrong leader, joining a team that didn’t align with their values, or taking a job that ultimately was the wrong fit.
Other times, professionals struggle because they haven’t fully trusted their judgment or clearly defined what they value most in a manager and work environment.
Through my work with leaders, I’ve identified five common reasons that our decision-making processes can fail:
- Our choices didn’t align with core values. When our decisions conflict with what we intrinsically care about and believe in, we often feel dissatisfied or frustrated, even if the move we’re considering seems attractive on paper.
- Lack of clear communication or enforcement of the decision due to insecurity. Sometimes people make the right choice internally but fail to act decisively, leading to ambiguous or less-than-satisfactory outcomes.
- Decisions is made from fear or disempowerment rather than strength. Choosing a direction based on anxiety, fear or worry rarely produces long-term satisfaction.
- Decisions not fully vetted for real-world outcomes. Without careful consideration of how choices will play out in our daily work and lives, we can overlook serious misalignments.
- Focusing on the wrong problem. We often fixate on surface-level issues rather than the deeper challenges that truly matter.
In today’s fast-changing workforce and emerging new developments and challenges, it’s more important than ever to understand who and what we are choosing to support. A leader shapes much of our day-to-day experience, our ability to grow, and our long-term career trajectory.
Below are 10 questions to ask yourself during your interview process, to help you assess if the manager/leader you’ll be working with closely is someone you can thrive under:
- Respect & Alignment: Does this leader behave, communicate, and lead in ways you respect and feel aligned with? Beyond technical skills and experience, consider whether you can support their approach to leadership, problem-solving, and decision-making. Respect is foundational; without it, engagement suffers.
- Core Values and Congruence: Do they share your values and inspire you to bring your best self to work? A lack of congruence here often leads to frustration and ethical compromises. Ask yourself: Does this manager’s vision resonate with mine? Will supporting them allow me to grow authentically?
- Relationship Building: Can this manager build strong, supportive relationships that foster sustainable growth? Leaders who cultivate meaningful connections encourage collaboration, mentorship, innovation, and trust (and psychological safety) across teams.
- Equity & Fairness: Do they treat all employees as equals and act with integrity? A manager who favors some individuals over others—or who tolerates or fosters inequity—typically erodes morale and generates unnecessary conflict, pain and struggle within the ecosystem.
- Accountability: Can they accept critique and take responsibility without blaming others? Accountability demonstrates maturity and self-awareness, and ensures that challenges are addressed constructively rather than through deflection or punishment.
- Respect for Differences: Do they honor differing opinions and perspectives? Inclusive leaders value diverse viewpoints, which strengthens teams, decision-making and innovation.
- Emotional & Social Intelligence: Do they demonstrate patience, empathy, balance, and emotional regulation? Leaders with strong emotional and social intelligence maintain stability under pressure and model constructive behavior for their teams.
- Positive, Uplifting Communication: Do their public and internal communications reflect more positivity than negativity over time? Words truly matter. A manager who fosters a positive approach and communicates clearly, respectfully and openly builds trust, engagement, and energy. This uplifts the entire organization.
- Impact on Teams and Culture: Do their actions support the growth, safety, and success of the broader team—not just those they are personally connected to? Leaders who play favorites risk damaging both performance and culture.
- Bridge-Building: Can you honestly say you admire their approach to leadership because it reduces conflict and builds connections, support and respect across differences? The most effective leaders build cohesion, encourage collaboration, and create a culture where people feel respected and valued for what they bring to the organization, and feel seen, heard, and valued.
Sometimes, you won’t be able to answer these questions fully through your interview process only. In those cases, it’s critical to speak with current or former employees, assess outside reviews of the organization online, and assess the external communications of the manager. Do what’s necessary to gain candid insight into the manager’s style and the organization’s culture. Ask others about how the manager handles conflict, feedback, promotions, and day-to-day team interactions. These conversations can reveal patterns that interviews alone may not show.
If you find yourself answering “no” to many of these questions, that’s a clear signal: this may not be the manager—or environment—you want to commit to. Making a decision based on clarity and self-trust will serve you better in the long run than acquiescing to a role that is misaligned with your values, leadership preferences and ultimate goals.
Choosing the right manager is more than a tactical career decision; it’s a statement about the professional you want to be and the environment in which you can thrive. Professionals who flourish support leaders they respect—leaders who cultivate trust, growth, and success organization-wide.
Ultimately, the questions above are about more than just evaluating a manager—they are about clarifying your own priorities, understanding your values, and leaning into trusting your judgment more confidently. The leaders you choose to support, the teams you join, and the cultures you invest in will shape not only your career trajectory but also your longer-term growth, satisfaction, and well-being.
The most successful professionals I’ve worked with don’t just chase roles; they align with leaders whose approach inspires and expands their potential.
Kathy Caprino is a global career, leadership and performance coach, LinkedIn Top Voice, 2x author, speaker and host of the podcast Finding Brave, supporting professional breakthrough to new levels of success, impact and reward.