Top 3 Elite Boutique Superday Questions

October 05, 2025

The most competitive banks to break into are the elite boutiques.

They’re more selective than every other firm & have the most intense technical interviews on the street.

Every kid wants a spot at an elite boutique because of their “lean” deal teams.

Deal teams are smaller, so analysts “wear more hats” & take on a wider range of responsibilities.

That means they end up doing more technical work requiring thinking instead of boring admin tasks.

Plus - the boutiques pay more & are known to have better culture than the bulge brackets.

I placed at an elite boutique from a Midwest non-target nobody in NYC had ever heard of.

There were three types of technical questions they emphasize that I got grilled on.

Here’s an overview of each type and how to prep accordingly.

TABLE OF CONTENTS

  • 1 - TELL ME ABOUT A RECENT DEAL

  • 2 - MARKET QUESTIONS

  • 3 - MERGER MODELS

1 - TELL ME ABOUT A RECENT DEAL

This question gets asked in many different forms.

  • “Tell me about a recent deal that interested you or that you’ve been following…”

  • “Can you run me through a recent M&A deal we advised on?”

  • “Talk about an M&A deal that interested you recently and whether or not you think it was a good one…”

You need to do your homework & research four recent deals for every interview.

Two “general” deals & two deals specific to that bank.

Then you need to memorize key metrics & plan the structure of your answer.

Here was my strategy for sourcing deals & structuring each answer.

STEP 1 - FIND GENERAL DEALS

Any deal older than two months isn’t recent enough.

There are two newsletters you can use to keep track of recent deals.

I skimmed each every morning for five minutes & wrote down a deal that naturally interested me in the notes sheet of my phone.

For Term Sheet - you can skip to the deal list at the bottom. They break them out into sections.

Focus on the deals in the the “PRIVATE EQUITY” & “EXITS” sections (Example Below).

Transacted is very similar to Term Sheet.

Most deals they list will be the exact same, but sometimes one will have some that the other won’t.

You can go straight to the section titled “DEALS, DEALS, DEALS” in Transacted (Example Below).

STEP 2 - FIND BANK-SPECIFIC DEALS

To find deals the company you’re interviewing at advised on - first go to their website.

Every bank has a “closed transactions” page full of “tombstones” like the one below.

Here are links to few of those closed transaction pages.

STEP 3 - RESEARCH KEY DETAILS

Every Sunday, I went to that notes sheet on my phone & picked two deals to add to my “log”.

The log was just a word doc that had the following details filled out for each deal.

  • Purchase Price: Dollar amount, Valuation multiple, Premium paid

  • Financing: Percent mix cash / stock / debt, Names of lenders

  • Advisors: Lead investment bank on buy side and sell side

  • Dates: Both announcement and closing

  • Rationale: Motivation for both buyer and seller

  • Background: Recent performance of each company

  • Deal Context: Anything unusual with the negotiations / agreement?

Every deal has a press release on the PR NEWSWIRE website.

The “Transaction Details” section of that press release is where you find the relevant info.

STEP 4 - STRUCTURE & REHEARSE YOUR ANSWER

I used the framework below to outline my answers.

Articulating in a clean & concise way is just as important as the content.

  • 1. Brief Snapshot / Overview

  • 2. Deal Rationale

  • 3. Financial Implications

  • 4. Process

  • 5. Market Reaction

  • 6. Personal Thoughts

After outlining on a piece of paper, I rehearsed to the mirror in by bedroom.

Once I felt like I had it down, I scheduled mocks with upperclassmen to get feedback.

If you’re interviewing with a specific bank, mock with the upperclassmen that interned there.

They’ll have the insider scoop on deals closed by that bank which could give you a huge advantage.

2 - MARKET QUESTIONS

The boutiques like to test whether or not you keep up with the markets.

You need to stay up-to-date on the current state of the economy & all major industry news.

There are two types of market questions they like to ask.

  • Current Events

  • Interest Rates & Stock Market

Here was my strategy to prep for these.

Nobody has time to read the WSJ cover-to-cover every morning.

You just have to know which resources to use & where to look within each.

CURRENT EVENTS

I took an IB class in college led by a former partner from a top bank in CHI.

He gave us WSJ quizzes every week to make sure we were up-to-date on current events in M&A.

Here are some example questions from those quizzes.

  • “Which car rental company has recently been taken public again, after its business had collapsed and delisted at the beginning of the pandemic last year?”

  • “What are two reasons that equity markets have seen indices setting all-time highs?”

  • “What conglomerate has recently split into three public companies? What three industries will these businesses be classified under?”

  • “What major food and snack corporation recently acquired both Dot’s Homestyle Pretzels and Pretzels Inc.? What was the total transaction value?

All of those are fair game for boutique interviews.

I skimmed the WSJ “Business & Finance” headlines every morning as part of my routine.

You should have free access to the WSJ through your university (check here)

Just make sure to pay extra close attention to major events during interview season.

INTEREST RATES & STOCK MARKET

The Morning Brew daily newsletter is the easiest way to follow high-level macro trends.

The “Markets” section is the one you’ll want to pay the most attention to.

They might straight up ask you for cold hard numbers. Examples below.

  • “Can you tell me where the 10-Year Treasury is trading right now?”

  • “Where did the S&P 500 (or Dow / Nasdaq) close at yesterday?”

  • “What is gold trading at right now? How about crude oil?”

Just make sure to keep a pulse on each of the benchmarks in Morning Brew for those.

However - it’s more likely you’ll get asked open-ended questions on broader trends & movements.

Here are a few examples.

  • “What’s your view on interest rates right now?"

  • "How do you think the recent movements will impact the markets and M&A?”

  • “What are your thoughts on the performance of the stock market over the past few months?”

To prep for those, I sat down & wrote an outline on a piece of paper before every interview.

For both (A) Interest Rates & (B) The Stock Market - I wrote down

  • (1) What the main drivers have been in recent months

  • (2) How they’ve impacted the M&A environment and

  • (3) Formed a well-educated opinion on where I think they’ll end up moving forward

3 - MERGER MODELS

The boutique I interned at only advised publicly traded companies.

That meant EPS & accretion / dilution calculations were a must-know for every potential candidate.

Even after interviews, merger math was a core part of our first few weeks of training.

I just used the BIWS guides to prep for these.

Here’s what the merger model guide looks like.

Merger model questions will start out conceptual before getting into the calculations.

Here are examples of merger model conceptual questions I got asked during superdays.

  • What are the most common reasons a company would acquire another?

  • What are the advantages & disadvantages of each purchase method in M&A deals?

  • Do buyers prefer to finance deals using debt or stock? How about sellers?

  • What’s the general rule of thumb for calculating accretion/dilution for all-stock deals?

  • What are the two main types of synergies?

  • Which type of synergies are most likely to be realized? Revenue synergies or cost synergies?

  • What’s the difference between vertical & horizontal integration?

  • How does forward integration differ from backward integration?

  • What is a 338(h)(10) Election?

If you pass those, they’ll start diving into the math.

Math questions have a “follow-up” format where they keep adding extra parts for complexity.

Here’s an example progression.

  • (1) A company with a P/E multiple of 25x buys another for a P/E multiple of 15x. Will the deal be accretive or dilutive?

  • (2) For that same deal, let’s say the buyer has 10 shares, a share price of $25 and a net income of $10. The purchase equity value is $150 and the seller’s net income is also $10. Calculate the percent accretion and walk me through the math.

  • (3) Now let’s say you used all debt instead to do the deal with an interest rate of 10%. Is the deal still accretive? If so, at what interest rate does it turn dilutive?

Cheers 🥂

- Jack