Leveraging Leadership

Nailing Curveball Interview Questions for Chief of Staff Jobs

• Emily Sander • Season 1 • Episode 190

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A listener preparing for final Chief of Staff interviews asks how to handle unexpected or tricky questions. Eric shares strategies like expecting curveballs, using them as a way to show problem-solving skills, and shifting interview conversations to a more natural tone. He gives examples such as reframing the question or asking for more details, and reminds listeners that not every question has a simple, right answer.


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Who Am I?

If we haven’t yet before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want. 

 

Time Stamps:

01:14 Expecting the Curve Ball
01:58 Turning Challenges into Opportunities
03:06 Shifting the Interview Tone
04:46 Engaging in Natural Conversation
06:59 Handling Complex Questions
08:20 Recap and Final Advice

emily-sander_2_05-28-2025_110439:

It is my favorite day, and you know what that means? It's listener question day. Arlene C has a question. She says, Hey Emily. I'm in final rounds for a chief of staff role, and I'm so excited. I really want this job. The first rounds went great and everything I'm hearing about the company and team has me even more fired up. My next round of interviews are with members of the leadership team, who would be my future colleagues. One of them invited me out to a more casual coffee chat, and the other seems like it would be a more traditional interview. I've done my research. I've prepped like crazy, but I'm nervous about getting hit with a question. I haven't thought of something that throws me off and makes me freeze. I'm scared I'll get stuck or sound unsure. How do I keep my cool? Stay confident and put my best foot forward, especially when I know they might throw me a curve ball. Arlene. Good question. Very common question. First thing I would say is expect to get a curve ball. I'm, I don't mean to scare you, but expect to get a curve ball. Expect to get a question that you're like, I don't know how to answer that right away. What that does is take a little bit of the edge off of the dread of like, I hope I don't get a curve ball question. I hope I don't get a question I don't have an immediate answer to. And instead of going, oh no, you go, I expected that to happen and look, here it is, I'm a genius. So expect it to happen.'cause it will happen. It will happen in the interview for a chief of staff role and it will absolutely happen in a chief of staff role where you will get curve ball projects and requests and like what the. Flying Heck is this. You will get those. Second thing. Instead of seeing these as like, oh no, let me like give an answer and then get off this question as soon as possible. I would see this as a golden opportunity. I would be like, yes, I got this type of question. This is perfect because it will allow you to demonstrate a key skill of being a chief of staff. This is like a hallmark skill of being a chief of staff. You get random crap thrown at you and you figure it out. You ask good questions. You figure out what's important to the person that's requesting it from you. You figure out what's important to the company overall. You ask some reframing or some framing questions that help people see it in a different perspective. You ask good probing questions. All these different things come into play here and you get to showcase this in your interview. You will absolutely be doing this in the chief of staff role, and you get to showcase this. And demonstrate, not just tell someone, but you get to demonstrate how chief of staffy you are, if you wanna put it like that. Okay. So we are expecting the question instead of dreading the question and resisting it, we're saying yes. Okay, perfect. this is, this is my jam. This is the money shot. This is the money question. Here we go. Rock and roll. One other thing you can do here when you get this question is, Shift the tone. And what I mean by that is many people, both people in an interview kind of go into like their interview roles and like they're playing a part. And we all, we all kind of do this where it's like, okay, I'm going into an interview and I'm being interviewed, so I act this way. And the other person is like, all right, I have to interview someone today. I'm the person interviewing someone else. And so I kind of act like this. and people kind of fall into interview speak where it's like, tell me about yourself. And you're like, well, here's my background in a short recap, and here's my skillset and here's why. Be an asset to your company. I. Okay. And, um, can you tell me about your experience around this specific thing? I sure can. Here's my canned answer to this. and like you go into the interview speak and it's all well and fine and everyone does it to a certain extent and everyone plays their part, so that's fine. Use these. Curve ball questions or these golden opportunity questions to drop the conversation into more of a normal conversation, more of a normal tone where like you're talking to someone like a human and possibly very possibly the coffee chat setting helps to do that. So that would be a good kind of catalyst and environment to, elicit that type of conversation. But even if you're in a coffee shop, a coffee setting, or even if you're in a more traditional setting, you can use. These types of questions and your tone of voice, just a little shift in your tone of voice to drop it into a more of a, regular human sounding conversation. So an example of that could be something like, um, you get a question and you're like, you know, that's a good question. I actually saw your guys' press release you put out yesterday, and it's really exciting that we're merging with X, Y, and Z. And it sounds like Jason would be on point for the integration internally. Is that right? And then your team would feed this type of info to Jason. Just be like, and just ask a curious question and be like, I saw this happen. You've told me that Jason, or it sounds like Jason is in charge of this internally. And then I'm wondering how what you've said is connected to that. Like, is that why you're asking? Another one could be, a lot of times in order to answer the question best, you would need to get more information. So ask, ask for that information.'cause it helps them see your thought process it shows them how you would ask. Clarifying questions or questions that help them get to a better answer or think about it in a different way, all of which is a chief of staff job. So it could just be, you know, that's a great question. I'm wondering how much of the process is automated today and how much is still manual data entry? And they can be like, oh, well, like so and so does the manual data entry. We've tried to automate this like couple different times and it just keeps not working. For whatever reason, it keeps backfiring. But I would love to have this fully automated. I would love to just have like set this in motion and forget about it each time. Okay. that drops it into a normal conversation. It also gives you some additional information and data points about what's important to her. if you're speaking to someone and. Getting this fully automated and getting it to the point where she doesn't have to think about it once it's kicked off is important. If you have. Actual solutions for that, for like, oh, well we use this tool in previous places I've worked, would that work here? Or, okay, here's some ideas for how we could, approach automating that in a step-by-step fashion over the next six months. Any kind of conversation and ongoing dialogue off of what she has said is positive and just drops you into that normal natural conversation. So you can do this with both the content of your words. But also the tone and just like drop it into like real, real life speak. By the way, there are questions that have the answer in quotes. The answer like two plus two is four. Got it. Um, what should we do with our go-to market strategy for the next 18 months that doesn't have like a, obviously it's blah, blah, blah. It's like there's multiple opinions and there's multiple factors and it's multifaceted and it's dynamic and it's all these things. And so there's just always know that there's the concrete answers. Where it might be, Emily go research tools and apps that do this and find the most cost effective one. The price point is the most important factor to me, so just do your research and find me empirically the one that costs the least. there is an answer to that question. There's like a concrete answer to that question for many other types of questions that a chief of staff will get. There is not a set concrete answer. Okay, so recap for you Arlene. Number one, I would expect an answer that you don't expect, and when it happens, go, hooray. I'm a genius. I predicted this and now it's coming true. Number two, I would be like, this is a golden opportunity. Thank goodness that I got this in the interview, because I get to showcase how. Chief of Staffie, I truly am. And how you would be lucky to have me as chief of staff'cause I can help you solve this problem. I can help you get more clarity on this question, or I can help you get some different perspectives or different ideas that maybe this person hasn't even thought of around this question. All of those things can happen. I would try to drop it into a different tone of conversation, and I would remember that. It's okay not to have the answer to certain questions.'cause some questions don't have a concrete answer. And if you try to jam one in there, you're actually you're not answering it appropriately. It's like, certain tools are like used for certain things, If you're trying to like pound a nail in, you wanna hammer. If you're trying to eat something, you don't wanna eat with the hammer. So I would switch gears into like, oh, okay, now I get to kind of play around with this and ask some questions and use kind of a different part of my brain for this type of q and a. So Arlene, hopefully that helps. I'm super excited for your final rounds, please, please, please do drop me a note and let me know how it goes.'cause now. Now I'm interested and now I'm invested in, in how these final rounds go. But um, hopefully that's been helpful to you and hopefully it's been insightful to all the other listeners. And I will catch all of you next week on leveraging leadership.