The Question I Ask Every New Report
When I take on a new management role, whether it’s through a reorganization, succession, or stepping into a new organization, I make it a priority to ask this question in my first 1:1 with each direct report:
- Who was your best manager, and what made them great?
- Who was your worst manager, and what made them difficult?
This question may seem out of ordinary. I know. Maybe even a little intimidating especially during a first meeting. But I’ve found it to be an incredibly effective way to set the stage for a positive, long lasting relationship. It helps me understand what matters most to my team, signals my willingness to adapt, and establishes trust from the get go.
I first came with these questions because I changed jobs and went to a new org knowing nothing about people I would manage. In previous roles, I knew everyone around so I didn’t think much. In retrospect, I should have used these questions back then too. Well, you live and learn.
Now, why do I think this is useful? Let me break it down.
1. It Prioritizes Empathy and Emotional Intelligence
When stepping into a new team, it’s easy to assume that the dynamics and preferences will align with your past experiences. That’s rarely true. Every person is unique in their cultures, values, and histories. Hence, you need to understand where they’re coming from. And that requires empathy.
Daniel Goleman defines empathy as the ability to recognize, understand, and manage emotions in yourself and others. Asking about their best and worst managers helps me tap into the people’s emotional landscape. What motivates them? What frustrates them? When I hear their past experience, it allows me to lead in a way that resonates with their needs and motivations.
For example, if someone tells me their best manager always offered constructive feedback and clear goals, I know they value structure and development. If another says their worst manager micromanaged them, I know to offer more autonomy.
2. It Builds Trust Through Vulnerability
When you come as a leader to an org, there’s often an unspoken expectation of perfection. But the truth is, you have many questions on your own and you don’t have many good answers. So, pretending to be a guy who knows it all can create distance between you and your team. Vulnerability is the antidote.
When I ask about the best and worst managers, I’m implicitly acknowledging that I might not immediately live up to their ideal manager. You know what, I’m willing to try. This act of vulnerability signals humility and openness. In her book Dare to Lead she explains that vulnerability is not about exposing weakness; it’s about showing humanity.
By asking these questions, I try to create an environment where it’s okay to be honest and imperfect. I’m not just their manager but someone they can partner with.
3. It Creates Psychological Safety
Psychological safety is the belief that you can speak up, ask questions, or admit mistakes without fear of judgment or retaliation. Amy Edmondson has done a great deal of research on it. She says psychological safety is one of the most important factors in high-performing teams. Without it, people hold back their ideas, concerns, and feedback. I hope at this point you have been into a company which actually cares about it and tries to teach it to their leaders. If not, read a few books and articles. It’s worth your time.
Going back to the topic, starting my relationship with these questions sends a clear message: This is a safe space for honesty. I’m not looking for the “right” answer; I’m genuinely interested in their perspective. By asking them to share openly about their past experiences, I create an opportunity to build trust and show that their voice matters. Obviously, hold your horses. It takes a bit of time for someone to open up completely.
For example, if someone feels comfortable sharing that they struggle with unclear expectations because of a previous manager, they’re more likely to approach me when they need clarity in the future.
4. It Helps Me Avoid Assumptions
I think one of the biggest mistakes a new manager can make is assuming that what worked for them in the past will work for others. Remember the saying treat people like you want to be treated. Well, not quite. Treat people the way they want to be treated. I have been there, done. In the past, I assumed everyone would like to push to the next promotion or project by definition. Well, that’s not true. People have different priorities. Thus, leadership isn’t one-size-fits-all.
When I ask these questions, I avoid projecting my preferences onto the people in the my group. Instead of assuming they’ll appreciate the same leadership style I’ve used before, I let them tell me what they need. This approach aligns with the principles of situational leadership which emphasize adapting your style based on the needs of your team.
For instance, if someone tells me they value frequent check-ins, I know to schedule regular touchpoints whether it’s face to face or just quick check in through slack. If another says they thrive on independence, I know to give them space to work autonomously.
How This Plays Out in Practice
This is the last part of my first 1:1. I will first tell them about myself and what I did before. I ask them what to introduce themselves. After a while, I try to find a good point to ask my question. When I ask these questions, I make it clear that there are no right or wrong answers. I listen intently, take notes, and reflect on what they’ve shared. Patterns often emerge. I always see people have a common frustration with micromanagement.
In consequence, these questions work because they tap into fundamental human needs: the need to be heard, understood, and valued. By asking these questions, I demonstrate that I care about their experiences and I also care about what they need. I think It’s a small act with a big impact.
If you’re a leader, what’s your go-to question for building relationships with your team? Have you ever asked your team about their best and worst managers? If you found this post useful, too, please share it.