Questions to Ask a Managing Director in Investment Banking

The questions

Open any question to see why it works.

1. 1

   How did you end up covering this sector?

   A safe opener that is also genuinely informative, since most senior bankers arrived in their coverage group by accident and enjoy explaining the accident. The answer tells you how mobile people are between groups at this firm.

2. 2

   What are you spending most of your time on this month?

   Asking about this month rather than in general gets you a live answer instead of a description of the role. If the honest answer is pitching rather than executing, you have just learned what the group's pipeline looks like.

3. 3

   What does the pipeline look like for the group right now?

   You are asking about deal flow without asking about deal flow. A group with several live mandates staffs analysts differently from one that is mostly pitching, and it determines whether your first year is transaction experience or slide production.

4. 4

   What does an analyst actually own on a live deal here?

   Ownership varies enormously between banks: some analysts run the model and the data room, others format materials while an associate does everything else. Ask what the last analyst on a closed deal was responsible for by name of task.

5. 5

   How does staffing work, and who decides?

   A staffer with real authority produces a more even workload than a system where individual seniors grab whoever answered fastest. Ask what happens when two managing directors want the same analyst, since the answer describes your weekends.

6. 6

   What separates an analyst you would fight to keep from one you would not?

   Rarely about modelling skill. Expect answers about accuracy under pressure, flagging problems early, and needing no second check. Ask for a specific example, which turns a platitude into something you can actually practise.

7. 7

   How much of your week is analysis, and how much is managing a process?

   The honest answer at the senior level is very little analysis, and hearing that reframes what the career is. Follow up on when the shift happened for them, because that is the point at which people either adapt or leave.

8. 8

   What breaks people at the associate to vice president transition?

   This is the least discussed and most consequential step: the move from producing work to being accountable for other people's. Managing directors have watched many attempts and will describe the failure pattern precisely if asked directly.

9. 9

   How has this sector changed in the last two years?

   Asking about the industry rather than the bank lets them talk expansively, and their answer is a free market briefing. It also shows you are interested in the coverage rather than in the brand on the business card.

10. 10

    How do you win a mandate?

    Origination is the whole senior job and juniors rarely see any of it. Expect an answer about years of relationship, timing, and one idea that landed. It is the most interesting question you can ask a managing director about their own work.

11. 11

    When do you decide not to pitch?

    Saying no is where judgment shows. The answer reveals whether the group chases everything, which produces enormous junior workload for no fees, or is disciplined about where it can genuinely win.

12. 12

    What is the mix of work in this group across advisory, financing, and other mandates?

    The mix determines what you learn. A group weighted toward one product gives you depth and a narrow exit set. Ask what the last five completed transactions were, which is a concrete way to get the same information.

13. 13

    What does a managing director do that juniors never see?

    Client dinners, internal committee approvals, fee negotiations, and defending a deal to a risk committee are invisible from the bullpen. Hearing the list makes the hierarchy legible and gives you something specific to ask about later.

14. 14

    What is the hardest conversation you have with a client?

    Usually telling them their business is worth less than they believe, or that a deal should not proceed. The answer tells you whether this banker is an adviser or an order taker, which is the real difference between senior people.

15. 15

    Where do people from this group go afterwards, and do you stay in touch?

    Exit destinations are the currency of the job and everyone knows it. The second half of the question matters more: seniors who stay in touch with former analysts are the ones who make calls on their behalf.

16. 16

    What is your read on hiring this year?

    Headcount decisions are made well above the recruiting team's messaging. A managing director will usually tell you plainly whether the group is growing, flat, or backfilling, and that changes how you allocate your own time.

17. 17

    What should I be tracking each week to follow this sector properly?

    You are asking for a habit, not a reading list. Naming the filings, indices, or trade publications they check gives you something to reference in a follow-up conversation, which is the entire point of the coffee chat.

18. 18

    What is an answer you hear in interviews that immediately loses you?

    Direct, easy to answer, and unusually useful. Common answers involve rehearsed reasons for wanting banking, an inability to explain a number on your own resume, or claiming interest in a sector you cannot discuss for sixty seconds.

19. 19

    What did you get wrong early on?

    Framing it as their mistake rather than your instruction produces a real story instead of advice. It also signals that you are asking to learn rather than to be flattered, which is the tone that gets a second conversation.

20. 20

    If I end up with an offer, what should I be asking that I have not?

    A strong close because it invites them to advocate for you. It often surfaces the specific thing the group is sensitive about, whether that is hours, a recent departure, or how generalist the first year really is.