Derivatives Foundation interview preparation

Questions

100

Traced to a firm

29

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19

Updated

September 2026

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All firmsMSMorgan Stanley4Nomura4Akuna Capital2Amundi2HSBC2PIMCO2Bank of America1Barclays1Citadel1DRW1Goldman Sachs1Jane Street1Millennium Management1Mizuho1Old Mission Capital1RCRBC Capital Markets1Scotiabank1UBS1Wells Fargo Securities1

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All topicsForwards and futures10Options basics8Option pricing7The Greeks10Volatility7Option strategies9Swaps and rates7Credit derivatives4Market structure and clearing6Indian derivatives8Trading and markets9Brainteasers6Fit9

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1. 046If you think the market is overestimating volatility, what options strategy can you use?Option strategiesIntermediatetechnicalOld Mission CapitalProp Trading · Chicago · 2025

   Say this

   Sell a delta-hedged straddle, or sell a variance swap if one is available. The view is that implied volatility is above what will be realised, so you want to be short implied and long nothing directional — which means selling options and hedging the delta as you go, not just selling a strangle and hoping.

   Then walk it

   1. Cleanest expression: short at-the-money straddle, delta hedged continuously. You collect the premium and pay away the realised variance, so if realised comes in below the implied you sold, the difference is your profit.
   2. Even cleaner if the market exists: short a variance swap. The payoff is exactly the strike variance minus realised, with no re-striking and no path dependence in the exposure.
   3. If the view is specifically that implied volatility itself will fall rather than that realised will be low, sell longer-dated options where vega dominates, or sell VIX futures or calls. Those are different trades — one is a realised-volatility view, the other a mark-to-market view on the surface.
   4. Then the risk management, which is really what the question is testing. Naked short volatility has unbounded loss and negative convexity, so the professional version is an iron condor or a short straddle with wings bought — you cap the tail, give up some premium, and survive the event that proves you wrong.
   5. Sizing rule I would say out loud: size to the loss in a plausible tail, not to the premium collected. If a 5 standard deviation move ends the account, the position is too big whatever the expected value says.
   6. And the honest caveat: implied above realised is the normal state, so being short volatility is a bet that the premium is bigger than usual, not that it exists. You need a reason — a specific event that has passed, a supply imbalance, a spike that has already resolved — rather than a general sense that options are expensive.

   Where candidates lose it

   Answering 'sell a straddle' and stopping. A prop shop is testing whether you delta hedge, whether you cap the tail, and whether you can distinguish a realised-volatility view from a view on implied. Volunteer the sizing rule before they ask what happens in a crash.

   Expect next

   • How do you cap the tail, and what does it cost you?
   • Is your view about realised volatility or about implied volatility falling?
   • How would you size it?

   Reported by candidates at Old Mission Capital (Prop Trading, Chicago, 2025). Source: Wall Street Oasis.

Firm tags come from public, anonymous candidate reports on Wall Street Oasis: strong signal, not sworn testimony. Firms are named as the places a question was reported, not as partners of Fin Maverick. Answers are written for this page to show how to think out loud; they are not scripts to recite.