We spend so much energy preparing to answer questions in job interviews—polishing our resume stories, rehearsing strengths and weaknesses, trying to sound impressive but not rehearsed. What we don’t always talk about is this: interviews are also your chance to get the real story behind the role you’re walking into. Especially when it comes to the people you’ll be working with every day.
And I don’t mean just the team. I mean the person who signs your performance review, sets your deadlines, shapes your growth, and quietly impacts your daily peace of mind more than almost anyone else—your future manager.
So how do you figure that out in one short conversation—when everyone’s trying to put their best foot forward?
That’s where smart, thoughtful questions come in. And not the recycled ones like, “How would you describe your leadership style?” (You’ll get fluff. Trust me.) The real insight lives in the in-between. It’s in how they describe team dynamics, how they make decisions, and what they default to when things get hard.
1. “How do you typically support new team members during their first few months?”
This question does double duty: it gives you insight into their onboarding process, but more importantly, it tells you how hands-on or hands-off they tend to be.
You’re listening for:
- Whether they have a structured onboarding process (or expect you to “figure it out”)
- If they mention regular check-ins, mentorship, or feedback
- How they balance independence with guidance
If they seem surprised by the question or vague in their answer, that might be a red flag. Support during the ramp-up period says a lot about how much they invest in people.
It also reveals whether they lean more toward coaching or control. Are they empowering? Do they trust their team? Or do they expect perfection on day one?
2. “Can you share a recent example of how you helped someone on your team grow?”
This is one of my favorites. It cuts past surface-level answers like “I love developing people” and gets into actual behavior.
You’re not just listening to what they say—they might pull from memory or speak off-the-cuff. You’re watching for:
- Did they offer tangible support—like stretch projects, training, or visibility?
- Do they seem proud of their team’s growth—or do they take credit for it?
- Is their example recent, or years old?
If they stumble here, it doesn’t mean they’re a bad manager. But it may suggest development isn’t a priority. The best leaders often light up when asked this—because helping people rise is part of what keeps them going.
3. “What’s your approach to giving feedback—especially when something isn’t working?”
A good manager doesn’t avoid conflict—they handle it with clarity and care. This question will show you how they communicate in tough moments.
Look for clues around:
- Do they give feedback early or wait until reviews?
- Are they direct, passive, or overly cautious?
- How do they handle mistakes?
Bonus: if they mention specific methods like weekly check-ins, 360 reviews, or growth-focused feedback, that’s often a sign of emotional intelligence. Feedback style matters, especially if you’re someone who thrives on communication (or has been burned by vague criticism in the past).
According to Harvard Business Review, employees whose managers give regular, strengths-based feedback are more than twice as likely to be engaged at work.
4. “How do you typically handle competing priorities or shifting deadlines on your team?”
This question opens a window into their decision-making process under pressure. Every workplace has busy seasons. What matters is how your manager reacts when things get real.
Are they calm or chaotic? Do they help the team refocus, or expect everyone to “just get it done”? Do they redistribute work, adjust expectations, or ignore burnout?
You’ll learn whether they advocate for their team, communicate changes clearly, or expect flexibility without support. And if they mention collaboration—looping in the team for input—that’s a sign they lead with their people, not above them.
5. “What does success look like in this role after six months?”
This one might sound like a performance question—and it is—but it also reveals what your manager values most.
Are they focused on output or process? Metrics or learning curve? Do they expect you to be fully autonomous in half a year, or still evolving?
Their answer will tell you:
- How realistic their expectations are
- What skills they prioritize
- How they define “value” on their team
It’s also a great way to manage your own expectations. If their six-month vision aligns with what you want to build, you’ve likely found a good match.
6. “How would your team describe your management style?”
This one’s deceptively simple—but the way they respond can be telling. Most managers know how they see themselves. But self-awareness comes through when they can imagine how others see them, too.
Listen for:
- If they speak with humility or defensiveness
- Whether they mention both strengths and areas of growth
- If they’re in touch with how their team actually feels
If they say something like, “You’d have to ask them!” and stop there, that might be a missed opportunity. But if they say, “I’ve heard I’m structured, but fair,” or “I’ve worked on being more available during crunch times,” that’s gold. Self-aware managers make better leaders, period.
7. “When someone on your team disagrees with you, how do you typically respond?”
This one goes straight to the heart of psychological safety. The best leaders expect disagreement and encourage it—because they know great ideas (and better decisions) come from diverse perspectives.
If they seem rattled or resistant to the question, that’s a red flag. But if they say:
- “I welcome pushback—I want people to challenge my assumptions.”
- “We try to make room for open discussion, even when it’s uncomfortable.”
- “I may not always agree, but I try to understand their why.”
You’ve probably found someone who leads with both confidence and humility.
The Daily Essentials
- You’re interviewing them, too. That’s not a slogan—it’s a mindset. Step into that room like you’re choosing a relationship, not begging for a seat.
- Write your questions down. Bring a notebook. Refer to it. Thoughtful is memorable—and professional.
- Avoid generic questions. Get specific. The best insights live in the details, not the job description.
- Watch their body language. How they answer matters just as much as what they say. Trust your gut.
- Follow up afterward. If a manager said something that stood out, reflect it back in your thank-you note. People remember that.
The Clarity Check
You don’t have to interrogate your future boss to get to the truth. You just need to ask questions that reveal who they are under the surface—and who you’ll get to be when you work with them.
Because it’s not just about landing the role. It’s about finding the right rhythm, in the right environment, with someone who doesn’t just manage—but mentors, supports, and sees you.
The best interviews aren’t about performance. They’re about connection. And with the right questions, you can get that clarity faster—and make better choices because of it.
So go in calm. Go in curious. And go in with the confidence that you’re allowed to ask for what you need—not just in a role, but in the person who helps shape your experience of it.
