Questions to ask at the end of an interview to figure out what’s *really* going on
how to ask about skeletons in the closet and still end the interview on a positive note
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Read time: 6 minutes
Asking the right questions at the end of an interview is a delicate art.
You want to know what’s really going on: team dynamics that could slow you down, political baggage, cultural challenges, etc.
But you also don’t want to end the conversation on a negative note. You don’t want to come across as skeptical or confrontational, and no one likes feeling interrogated.
Here are a few questions I ask, why I ask them, and what their answers tend to reveal.
1. “What's something you've been advocating for, that took longer than expected to gain support? How did you eventually move it forward?"
What I'm really asking:
How does change happen here? What kinds of ideas face resistance?
What I observe:
The types of ideas that are controversial
Whether resistance comes from above, across teams, or within the group
How much political capital and effort basic improvements require
What styles of influence are the most effective?
What I reflect on:
Would I find this type of advocacy work energizing or draining?
Do I have the skills and patience for the influence style that works here?
Are the controversial ideas ones I'd also want to champion?
Red flags: If their example required months of effort for something that should be straightforward.
2. "What are some unique opportunities you've had on this team that you might not have gotten elsewhere?"
What I'm really asking:
How does leadership actually invest in developing people? What doors do they open?
What I observe:
Concrete examples of the leadership team leveraging their social capital to open unique opportunities
Whether opportunities come from the manager's network, company relationships, or industry connections
Whether the opportunities are genuinely rare, valuable, and meaningful to me
What I reflect on:
Visualization exercise: Do I feel excited about these opportunities?
Do these sound more compelling than opportunities I could get elsewhere?
3. "What's your biggest dream for this team, and what's one thing that would help you get there faster?"
What I'm really asking:
What's the vision, and what are the real constraints?
What I observe:
Whether they have a clear, compelling vision or just operational goals
If constraints are about resources, skills, organizational support, or external factors
How realistic and ambitious their thinking is
What types of success are the most meaningful to this person?
What I reflect on:
That "one thing" might become the center of gravity for team energy—how would I feel about a significant portion of my time and mental energy going toward solving that constraint?
Does this vision excite me enough to want to contribute?
Are the constraints things I could help solve or would find frustrating?
Red flags: No clear vision beyond "doing good work," or constraints that suggest deeper organizational dysfunction.
4. "What's something you wish you could spend less time doing?"
What I'm really asking:
What are the daily frustrations and time drains?
What I observe:
Whether pain points are about bureaucracy, technical debt, or people issues
How much of their time goes to low-value work
What I reflect on:
Would these same things frustrate me, or do I actually enjoy some of them?
Do the root causes seem fixable?
Red flags: Needing to spend significant time on things that seem obviously fixable.
5. "What would make someone the best possible report (or teammate) for you?"
What I'm really asking:
What do they value in collaboration, and would we work well together?
What I observe:
If they want someone to contribute strategically, or simply execute their ideas
What strengths they think are complementary to their own
What I reflect on:
Do I naturally work in ways that would make them successful?
Would their ideal teammate description energize or exhaust me?
Are we compatible in terms of communication and collaboration styles?
Also, this gives me clues about what stories to share and what strengths to emphasize in future conversations—if they value strategic thinking, I'll highlight analytical projects; if they want reliable execution, I'll focus on delivery stories.
If you found any part of this useful or insightful:
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Share this post with someone who needs permission to dig deeper. You're not being difficult by asking thoughtful questions. You're being thoughtful about one of the most important decisions you'll make.
This was incredible — it gave me a lot of insight, thank you!