Stop Asking These Questions If You Want a Buy-Side Offer

After years helping candidates break into the buy-side, I’ve noticed a pattern: the biggest career detours don’t come from bad interviews — they come from bad questions.

• Questions that show you haven’t done your research (for the role a RESEARCH analyst)
• Questions that show you don’t understand what the interviewer is testing.
• Questions that show you’re trying to “hack” the process instead of mastering the craft.

These questions don’t just hurt your chances; they also lead you down months or years of investing in low return-on-invested-time activities.

Here are the most common ones — and why they send the wrong message.

“Thoughts on…”

I don’t know if this is a Gen Z thing, but I’m not joining your vibe-seeking experiment.

Everywhere I look online — and especially in my DMs — people start with “Thoughts on [broad topic]?” I never answer those. Not once.

Here’s why: you don’t really know what you want to ask, but you expect someone else to unpack the entire subject while you sit back eating popcorn. That’s lazy. If you don’t know, there’s no way the other person can give it to you.

And don’t try to rephrase it. “What do you think of [broad topic]?” “Your opinion on [broad topic]?” Same thing. I’m skipping those too.

But if you come prepared, someone might engage. Ask something like “Thoughts on why XYZ Capital’s TMT sector head left for a competitor fund?” That’s specific, it’s informed, and it shows you’ve done the work and know what you are looking for (though I just dislike the “thoughts on …” opening at this point as a pet peeve.)

If you want thoughtful responses, start by asking thoughtful questions.

“How to sound smart in a buy-side interview?”

Trying to sound smart will get you nowhere in this profession.

If you actually read a lot, it shows naturally in conversation. If you fake it, it gets exposed instantly in front of the well-read investors.

You don’t sound smart to get the job. You need to be smart, and that’s what gets you the job—and more importantly, keeps you performing once you’re in. There’s no coasting on the buy side.

People often get it backwards: they cram for interviews instead of building knowledge every day. But if you put in the work, your intellect shows effortlessly during the candidate vetting process.

And remember—the industry is full of smart people who still can’t make money. So if you’re not even smart? You’ve got no shot.

“What are my chances?" "How will it take?"

I can’t answer that — I’m not a fortune teller.

I’m also not a shrink, though that’s really what you’re looking for: reassurance. You want someone to tell you it’s possible. Well, it is possible — but it depends entirely on how hard you’re willing to work for it.

It’s going to be hard and unfair. You’ll be competing against insiders with experience (current buy-siders) and adjacent experience (IB, PE, ER).

But it’s doable. I’ve done it. Many others have done it. And every single one of them will tell you the same thing: it was really hard.

If what you’re really asking is, “Can I break into a hedge fund without suffering?” — the answer is no. You can’t. You must suffer.

Everyone’s timeline is different. Maybe it takes 6 months if you live and breathe this stuff and are laser focused. Maybe you’ll never make it because you want the glory and the money more than the grind.

“Will AI destroy HF jobs?”