We’ve all been there. The interview’s wrapping up, and you hear the familiar, “What questions do you have for us?” Before you reach for your notes, your brain sparks with all the things you wish you’d said- examples, insights, that one perfect story to show you’re the valuable new addition to the hiring manager’s team.
But here’s the truth: success in interviews isn’t just about how prepared you are. It’s also shaped by how prepared your interviewer is and what questions they ask you.
What if the questions had been broader and more thoughtful?
What if they were designed to bring out your full potential, instead of boxing you into what’s missing on your résumé?
In this post, we’re highlighting questions candidates wish they’d been asked. Our goals are simple:
- Equip job seekers with ideas and confidence to ask great questions of their own and feel empowered in the process.
- Encourage hiring leaders to reflect on the purpose and impact of their interview questions.
We asked current job seekers, some anonymous, some not, what they wish executive leaders had asked them during interviews. Here’s what they shared.
1. “How does your field experience translate to leadership, strategic planning, and standard operating procedures?”
This candidate’s reflection hits a common frustration: interviews that stick too closely to scripts, especially in panel formats.
Instead of inviting the candidate to connect their background to the role, interviewers defaulted to résumé gaps, which shuts down potential and vulnerability in one go.
A question like this could have opened the door to a rich story grounded in lived experience.
Takeaway: Curiosity matters. It shows you’re not just looking for a fit, you’re looking for someone’s why.
2. “What’s a student story that has stuck with you?” – Christopher Gause, Alfred University
This one is simple but packs a punch, thank you to Christopher Gause, contributor to this piece.
Chris’s question invites the candidate to share a moment that reveals who they are, not just what they’ve done.
Especially for folks in education or mission-driven work, questions like this surface empathy, impact, and values.
They also help candidates connect past work to future goals, like stepping into leadership while staying grounded in purpose.
Takeaway: If you want to know what drives someone, ask them who they’ve helped.
3. “What is your communication style preference?”
It’s surprising how rarely this comes up. Communication is the backbone of collaboration, yet it often goes unexamined in interviews.
This question does two things: it shows how a candidate operates and offers a window into how the team functions. It’s a small ask with big returns.
Takeaway: If you want to understand how someone adds value, ask about how they connect.
4. “What’s one thing you want to do more of? What’s one thing you’d like to do less of?”
A two-for-one special. This question is refreshingly personal, giving candidates a chance to reflect on what fuels them and what drains them. For hiring managers, it’s a glimpse into how to set someone up for success and how they might complement the current team. It also opens the door to creative role-shaping and better long-term alignment.
Takeaway: Great hires start with knowing what energizes people and what burns them out. If you want to know what drives someone when the going gets tough-ask them this question.
5. “How do you see yourself contributing to our team’s mission?”
Candidates- This is your big break. It’s an opening for you to clearly state your unique value, rooted not in titles or credentials, but in lived and learned experience. You are 1 of 1, and this is the question to tell the team that you are the person for the job. Just don’t forget to tie it back to the job itself!
The best responses connect the candidate’s personal strengths and motivations to the team’s goals. This signals that the candidate understands the job, sees the bigger picture, and knows exactly where they could add value.
Hiring leaders- you gain great perspective here too! It’s a chance to see how much research they’ve done and how deep they’re ready to dive into the mission, vision, and values of your organization.
Takeaway: Begin with the end in mind- the mission is an organization’s North Star and knowing how someone makes meaning of that in their day to day will provide clarity for all.
6. “What do you need from our organization or from me to be successful in this role?”
For candidates, this question signals care and trust. It reinforces that their voice matters before they’ve even joined the team.
For hiring leaders, it’s a fast track to understanding what support a candidate might need and how ready they are to articulate it.
Takeaway: Asking what someone needs builds trust and clarity before day one. If you want to build a strong foundation before day 1, ask this question.
Themes & Threads
Across all six responses, a few clear themes stand out:
- Person-first leadership: These questions reflect care, empathy, and a desire to understand the human being behind the résumé.
- Curiosity over scripted communication: Great interviewers ask thoughtful, open-ended questions, not just ones that check the box.
- Two-way fit: These prompts help candidates assess alignment, not just prove worth. They foster real conversations, not one-sided auditions.
- Powerful storytelling: They invite lived experience, not rehearsed talking points, making space for connection and nuance.
For Hiring Leaders
Interviews aren’t just about evaluation. They’re about invitation. The best questions unlock insight and trust. As you prep your next round, ask yourself:
- Does this question help me understand who this person really is?
- Am I inviting the candidate to connect to the work, not just recite qualifications?
- Would I want to be asked this question?
For Candidates
Don’t wait for the perfect question. Bring your stories with you. Look for moments where you can pivot to your strengths, values, and lived experiences. And if you’re not being asked great questions, ask one yourself. You deserve to leave an interview feeling seen, not squeezed into a template.
TL;DR
Success in interviews isn’t just about preparation. It’s about connection.
These six questions highlight what’s missing in too many interviews: curiosity, care, and context.
Whether you’re hiring or interviewing, the right question can unlock a better answer for everyone.
