"What Do You Look for in a Boss?"
During a job interview two weeks ago, I was asked one of the most thoughtful and impactful questions I’ve encountered: “What do you look for in a boss?” This wasn’t a run-of-the-mill inquiry—it came from the director of the organization during my final interview after multiple rounds over the previous month. The question struck a chord with me, not only because it revealed the director’s genuine curiosity about the people who might work directly for him but also because it provided an opportunity to reflect on my career and leadership experiences.
These are some of the lessons I’ve learned from almost 30 years of working under both excellent and challenging leadership. I hope these insights help someone else prepare for similar questions and to approach their interview with greater confidence.
My Response:
I began by emphasizing that I prefer a management style that is collaborative, with open communication and transparency on both sides. Leadership is about building trust and working together to navigate challenges, and I’ve found that a boss who is approachable and values input from the team fosters a far more productive and engaged environment.
Acknowledging the inevitable ambiguity in any role, I shared that I appreciate knowing when my boss is also navigating uncertainty. When leaders admit they’re facing unknowns, it creates an opportunity to collaborate as a team and find solutions together. This honesty builds trust and strengthens the working relationship.
I also highlighted the importance of having clear objectives paired with a degree of autonomy. While boundaries and expectations are critical, I value the freedom to explore innovative solutions within those parameters. It’s a balance between guidance and independence that leads to meaningful outcomes.
Finally, I spoke about my appreciation for constructive feedback and a supportive partnership that fosters growth. A boss who invests in my development and offers actionable feedback creates an environment where both individuals and the team can thrive.
The Director’s Reaction:
To my surprise, the director responded: “Wow. Most candidates just say they don’t want to be micromanaged. That’s the best response I’ve heard. You can expect a call from HR.”
It was a validating moment. Shortly after, I received two offers for Lead Technical Product Manager roles with the Center for Program Integrity at the Centers for Medicare and Medicaid, US Department of Health and Human Services, which was an incredible outcome, even though circumstances beyond his control eventually canceled both opportunities when the new administration announced a hiring freeze.
Lessons From 20+ Years of Leadership Experiences:
Reflecting on 20 years of military service and almost nine in civil service, I’ve learned that you can gain valuable insights from every boss you work under. Here are a few of my key takeaways:
Good Bosses Build Confidence: A great boss encourages you to take ownership of your work while providing support when needed. They celebrate successes and treat mistakes as learning opportunities.
Bad Bosses Teach Resilience: Challenging bosses can still teach you what not to do. Whether it’s poor communication or micromanagement, these experiences can help you define the leadership style you want to embody.
Authenticity Matters: The best bosses I’ve worked with have been honest about their limitations, fostering a culture of humility and collaboration. When leaders show they’re human, it’s easier to work as a team.
When preparing for an air assault in Afghanistan, ensuring mission success and the safety of everyone involved was paramount. We made sure the entire team received the same level of detail about the plan. Everyone knew what frequencies were being monitored by the attack aircraft supporting us, how to request help from the quick reaction force orbiting above, and the time of flight to the nearest role 3 hospital. Just as in agile development, each team member was asked to provide honest feedback and a confidence score on the plan. This level of transparency and shared understanding fostered trust, minimized confusion, and allowed the team to operate cohesively in high-pressure situations.
Preparing for This Question:
Keep a notebook handy, write down the question(s), and quickly outline some bullet points you want to get across. If you’re asked what you look for in a boss during an interview, here are a few tips to craft a response:
Reflect on Your Values: Think about what has helped you thrive in past roles. Is it clear communication, autonomy, or mentorship? Use these insights to frame your answer.
Be Authentic: Avoid generic responses like “I don’t want to be micromanaged.” Instead, share specific attributes of leadership that resonate with you.
Show Alignment: Tailor your answer to the organization’s culture. If collaboration is a core value, emphasize your appreciation for teamwork and open dialogue.
Highlight Growth: Mention how constructive feedback and support from leadership have helped you grow in your career. Employers want to see that you’re coachable and invested in professional development.
Final Thoughts:
This question was a highlight of my interview experience, and I’m grateful for the opportunity to reflect on it. Leadership is one of the most important factors in job satisfaction, and being clear about what you value in a boss not only helps you succeed in an interview but also ensures you’re aligning yourself with an organization where you can thrive.
If you’re preparing for interviews, take some time to reflect on this question. It’s not just about impressing your potential employer; it’s also about finding the right fit for your career and growth.
What do you look for in a boss?