First of all and most importantly, happy FRIDAY!

Keeping this one short, because the market feels like it is catching fire again and I have picked up three new searches in the last seven days, all of which are listed below in the Hot Jobs section.

Which is great news. It also means I should be sourcing right now.

But I had to pause and write this, because as I have been screening candidates and running these processes, I have heard some version of the same few answers enough times this week that it felt worth addressing in real time.

All with love. Slightly tough love, but still love.

So consider this a quick reset before your next interview.

I am hitting send on this and going straight back to sourcing, and if you have sent me a one to one email and have not heard back yet, please feel free to bump me. Gently :’)

Did someone forward this newsletter to you?

•Chief of Staff to VC Founder – ATX [Apply here]

•Operations Manager – Chicago Nonprofit [Apply here]

•EA to CFO - Dallas Healthcare Org [Apply here]

Good luck if you applied!!!!

Inaugural edition, unfortunately inspired by real conversations from this week.

There are a handful of moments in interviews where the entire tone of how you’re perceived can shift, and it’s usually something super small and seemingly insignficant. An answer that goes slightly sideways. A question that lands flat. A moment where you reveal more than you meant to.

So we are starting a new series!

There are patterns here, and once you see them, they are very fixable.

Let’s start with three.

This question seems straightforward enough, and yet it is where a surprising number of otherwise very strong candiates accidentally torpedo themselves by dramatically oversharing.

I have heard full retrospectives on being ghosted. Explanations of why other processes fell through that nobody asked for. Mild existential spirals about how long the search has been taking. And listen, I get it, job searching is genuinely demoralizing and it is a lot to hold. But the interview room is not the place to unpack any of that!!

None of that is useful in this moment. More importantly, none of that is what they are asking.

What they’re actually trying to figure out is simple:

A strong answer is calm and grounded in what is happening right now, not in what has happened over the last several months.

Something along the lines of:

If you are in other processes, be honest. If you are not, also be honest! You can still frame your search as deliberate.

And more broadly, this is the mindset you need to carry into every interview, every introductory call, every room you walk into during a search (and in general): you are someone WORTH COMPETING FOR. Humility matters in this profession, it is actually one of the things that makes a great EA or CoS, but there is a version of humility that becomes self-erasure, and it is costing people. You can be gracious and grounded and still know your worth. Those things are not in conflict. Walk in like someone who has options, because the best candidates always do, and interviewers feel the difference.

This is the question where people, very earnestly, talk themselves out of the job they are actively interviewing for.

Take it from someone who learned this the hard way. A few years ago I made it to the final round interviewing at Neuralink for a Technical Recruiter role, which was somewhere around the seventh or eighth round if I'm remembering correctly, I've tried to block some of it out. The final round was a presentation, and I got to choose between two prompts: find candidates for a role they were actively hiring for and present on why they'd be a good fit, or present a plan for how you'd improve their overall recruitment process.

I chose the second one. Obviously. It felt more ambitious, more strategic, higher business impact. I was very proud of myself for about 72 hours.

What I did not know, and what nobody told me, is that which prompt you chose was itself the entire test. And I chose wrong.

The right answer was the first one. Do the immediate, concrete, unglamorous work that actually helps us right now. Not the sweeping organizational vision. Not the big picture thinking. The work. I walked in trying to prove I was thinking at the next level and walked myself right out of the building.

So when you're asked about your aspirations and your instinct is to talk about where you're headed rather than how excellent you intend to be at the thing in front of you, remember that story. The people hiring for these roles are not always looking for someone who's already mentally somewhere else. They are looking for someone who wants to be deeply, genuinely good at this.

The strongest answers manage to do both, and they do it by going deeper into the work, not away from it.

There is a quiet but important shift in framing there, from “what’s next” to “how well”.

And that shift is what makes the answer land!!!

This is where interviews are either closed well or totally fumbled.

Despite what it may feel like, this is not a polite formality tacked onto the end of a conversation. It is your last real opportunity to demonstrate how you think, what you prioritize, and whether you actually understand the role you'd be walking into, which in an EA or CoS context matters more than almost anywhere else, because reading the room and asking the right question at the right moment is essentially the entire job description.

And honestly, don't even wait until the end. The questions you came with don't have to sit in your back pocket until you're given permission to use them. You can weave them in throughout the conversation, redirect, reframe, create natural openings. If you're doing it right, you're not just answering their questions, you're shaping the whole thing. That is what it looks like to already be in the seat, and the best candidates do exactly that.

Weak questions are broad, easily searchable, or focused on benefits before you've established any value. Asking what a typical day looks like, what the culture is like, or leading with remote work policies all fall into this category. This seems like a better question, but don’t even ask what the first 30, 60, 90 days look like. Come in with a self-onboarding plan already mapped out yourself. I know that sounds like a lot, but it is genuinely one of the most underleveraged moves a candidate can make and almost nobody does it, so if you read nothing else in this article, read that part again and actually do it.

Stronger questions are specific, operational, and oriented around impact.

The throughline in all of these is the same: you did the work before you walked in, you're connecting what you found to the actual scope of the role, and you're asking something that genuinely can't be answered by reading a job description. That is what separates a good question from a great one in this context.

The hard truth is that this profession selects for people who are almost pathologically prepared, who have already thought three steps ahead, who ask the right question before anyone knew there was a question to ask. That is who you are! SHOW IT! Show it in how you answer, in what you ask, in how you walk into the room. The interview is not the place to hope for the best. It is the first real test of whether you can actually do the job.

Stuck in your job search? Not sure how to handle a tricky interview question or navigate the hiring process? Submit your question anonymously, and I’ll answer it in an upcoming newsletter.

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