Derivatives Foundation interview preparation

Questions

100

Traced to a firm

29

Firms

19

Updated

September 2026

Asked at

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

Topic

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

Level

AnyCoreIntermediateHard

Type

AnyTechnicalCaseMarket viewBrainteaserFit

1. 044A client holds a large concentrated equity position and wants protection but hates paying premium. What do you show them?Option strategiesIntermediatetechnicalWealth managementEquity derivatives

   Say this

   A zero-cost collar: buy a put, fund it by selling a call, struck so the premiums net to zero. It gives them a floor without a cash outlay, and the price is giving up the upside above the call strike. If they will not accept an upside cap, the honest answer is that protection costs money and there is no way around it.

   Then walk it

   1. Structure it concretely: stock at 100, buy the 90 put, sell the 112 call, and the two premiums roughly offset. They are now locked into a band between 90 and 112 with no premium paid.
   2. The asymmetry in the strikes is the skew at work. Puts are more expensive than equidistant calls, so to fund a 10 percent-out put you have to sell a call closer than 10 percent out. Explaining that asymmetry to the client is part of the job.
   3. Alternatives worth showing: a put spread, which is cheaper than an outright put and still leaves upside open but only protects a band; or a longer-dated put, which costs more in absolute terms but far less per month of protection because vega scales with root time.
   4. For a genuinely concentrated founder position, there are also prepaid variable forwards and exchange funds, which address the concentration rather than just the price risk. Those have tax and lock-up consequences that usually dominate the pricing question.
   5. Constraints to raise before the structure: is the client an insider, does the position have a lock-up or pledge, and what does the collar do to their tax position. In several jurisdictions a tight collar can be treated as a constructive sale, which triggers the tax event they were trying to defer. That is the reason the call strike is often set wider than the pricing alone would suggest.
   6. And the behavioural risk: a collar that caps upside at 112 will feel like a mistake if the stock goes to 160, and the client will remember whose idea it was. So I would document the trade-off in their own words, and size the collar over part of the position rather than all of it.

   Where candidates lose it

   Presenting the zero-cost collar as free. It is not free, it is paid for with the upside, and the skew means the upside you give up is closer than the downside you protect. Also raise the tax and constructive-sale issue — that is the difference between a textbook answer and advice.

   Expect next

   • Why is the call strike closer than the put strike?
   • What are the tax consequences of a tight collar?
   • What would you do instead if the client refuses any upside cap?
2. 045Straddle or strangle — how do you choose?Option strategiesIntermediatetechnicalProp trading firmsVolatility trading

   Say this

   Both are pure volatility positions with no directional view. A straddle buys the at-the-money call and put, so you pay more and get maximum gamma right where spot is. A strangle buys out-of-the-money strikes, so it costs less and needs a bigger move, but it gives you more exposure to the tails per rupee spent.

   Then walk it

   1. Straddle: highest gamma and vega concentrated at the strike, highest premium, highest theta bleed. You want it when you expect a move and you expect it soon, and when you will delta hedge to harvest the path.
   2. Strangle: cheaper, wider break-evens, lower theta per day. You want it when you expect a large move but are unsure of timing, or when you specifically believe the wings are underpriced relative to the body.
   3. The wings-versus-body choice is a skew and kurtosis view, not just a cost decision. Long strangle, short straddle is a butterfly — that is a pure bet that the distribution is fatter-tailed than the smile implies.
   4. Break-even arithmetic: a 4.5 percent straddle needs a 4.5 percent move by expiry. A strangle costing 2 percent with strikes 5 percent out needs a 7 percent move. So the strangle wins only in the big-move scenarios and loses in the moderate ones.
   5. In practice the choice is often dictated by liquidity and margin. In Indian index options the out-of-the-money weekly strikes are extremely liquid and cheap in absolute rupee terms, which is why retail gravitates to strangles — and why the margin framework treats short strangles more punitively after the 2020 peak-margin reforms.
   6. The limitation for both: if you are not delta hedging, you are betting on the terminal price, not on volatility, and a stock that swings wildly and closes flat pays you nothing. State which trade you are actually putting on.

   Where candidates lose it

   Framing it purely as 'strangle is cheaper'. The real distinction is where you want your gamma and whether your view is about the body or the tails of the distribution. And name the unhedged-versus-hedged difference, because otherwise you are describing a direction bet.

   Expect next

   • Long strangle against short straddle — what have you built and what is the view?
   • Which would you rather own into an earnings print?
   • What does margin treatment do to the choice in India?
3. 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.

4. 048Explain a butterfly and an iron condor, and tell me what view each expresses.Option strategiesIntermediatetechnicalProp trading firmsVolatility trading

   Say this

   Both are short-volatility, range-bound structures with capped losses. A butterfly is short the body and long the wings — sell two at-the-money options, buy one either side. An iron condor is the same idea with a gap in the middle: sell an out-of-the-money put and call, buy further-out ones as protection. The view is that the underlying stays in a range and that implied volatility is too high.

   Then walk it

   1. Butterfly payoff: maximum profit if the underlying pins the middle strike at expiry, losses limited to the width less the credit. It has the highest payoff concentration of any standard structure, which is why it is the expiry-day trade of choice.
   2. Iron condor: a wider profit plateau between the two short strikes, smaller maximum profit, higher probability of ending inside the range. It is the same trade with less precision required about where the underlying lands.
   3. Read a long butterfly as short kurtosis. You are selling the body and buying the wings, which is a statement that the distribution is thinner-tailed than the smile implies. That is why butterfly prices are how FX desks quote the curvature of the smile.
   4. Both are short gamma and short vega in the middle, so they make money from time passing and from implied volatility falling. Both have their worst outcome on a large move in either direction, which is bounded by the long wings.
   5. Where they actually get used in India: Nifty and Bank Nifty weekly expiries, because the short-dated theta is large and the structures are margin-efficient once the wings are in place. That is also where they are most frequently oversized by retail traders.
   6. The real risk is the one the payoff diagram hides: the position is fine at expiry and can be badly underwater before it. A move to the edge of the range mid-life produces a mark-to-market loss and a margin call, and traders get closed out of positions that would have been profitable if held. Capped loss is not the same as capped margin.

   Where candidates lose it

   Drawing the payoff diagram and stopping. Two things earn the answer: naming the butterfly as a curvature or kurtosis trade, and pointing out that a capped-loss structure can still force you out early through margin. That second point is where retail traders in weekly options actually lose.

   Expect next

   • Why do FX desks quote the smile using butterflies?
   • Which is safer for a retail trader, and does the margin agree with you?
   • What happens to your iron condor two weeks in with spot at the short put strike?
5. 049What is a calendar spread and what are you really trading?Option strategiesIntermediatetechnicalVolatility tradingMarket making

   Say this

   Same strike, two expiries. Long the back month and short the front is a long calendar: you are long vega, short gamma, and long the term structure. What you are really trading is the slope of the volatility curve plus the difference between short-dated and long-dated realised volatility.

   Then walk it

   1. Positioning: the front month has most of the gamma and theta, the back month most of the vega. So long the back and short the front collects theta from the front and stays long vega on the back.
   2. The classic use is after a volatility spike. The front month is at 60, the back at 30, so you sell the front and buy the back, betting on mean reversion in the near term rather than on the level of volatility.
   3. It is also an event trade in reverse. If an earnings date sits in the front expiry, the front implied is inflated by the event. Selling the front and buying the back captures the event premium if the print is quiet.
   4. Risks are asymmetric and this is the part to get right. Short front-month gamma means a large move immediately is very painful, because the front option's gamma dwarfs the back's. The position is long volatility in vega terms and short it in gamma terms, and those two can lose at the same time.
   5. Roll and pin risk at the front expiry are real operational issues. You have to manage the front leg through settlement, and if it finishes at the strike you have a pin problem on one leg of a position you intended to hold.
   6. The honest limitation: a calendar spread is a term-structure view, so you can be exactly right about the volatility level and lose because the curve moved in parallel rather than flattening. Calendars are best sized small and judged on the spread between the two implieds, not on either leg alone.

   Where candidates lose it

   Describing a calendar as 'selling time decay'. It is a term-structure trade with opposite signs on gamma and vega, and the danger is an immediate large move against short front-month gamma. Naming the post-spike mean-reversion use case shows you know why anyone puts it on.

   Expect next

   • Which leg holds your gamma and which your vega?
   • What happens if the market gaps the day after you put it on?
   • How would you use a calendar around an earnings date?

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.