Questions to Ask a Managing Director in Investment Banking
Questions for a coffee chat, a networking call, or the last five minutes of a superday with a managing director, covering the group's pipeline, how analysts are staffed and judged, what changes as you move up, and what the senior job is actually made of.
The questions
Open any question for the note
How did you end up covering this sector?
Why ask it
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.
What are you spending most of your time on this month?
Why ask it
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.
What does the pipeline look like for the group right now?
Why ask it
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.
What does an analyst actually own on a live deal here?
Why ask it
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.
How does staffing work, and who decides?
Why ask it
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.
What separates an analyst you would fight to keep from one you would not?
Why ask it
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.
How much of your week is analysis, and how much is managing a process?
Why ask it
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.
What breaks people at the associate to vice president transition?
Why ask it
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.
How has this sector changed in the last two years?
Why ask it
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.
How do you win a mandate?
Why ask it
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.
When do you decide not to pitch?
Why ask it
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.
What is the mix of work in this group across advisory, financing, and other mandates?
Why ask it
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.
What does a managing director do that juniors never see?
Why ask it
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.
What is the hardest conversation you have with a client?
Why ask it
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.
Where do people from this group go afterwards, and do you stay in touch?
Why ask it
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.
What is your read on hiring this year?
Why ask it
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.
What should I be tracking each week to follow this sector properly?
Why ask it
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.
What is an answer you hear in interviews that immediately loses you?
Why ask it
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.
What did you get wrong early on?
Why ask it
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.
If I end up with an offer, what should I be asking that I have not?
Why ask it
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.
Coffee chats and superdays
Practical guidance for the conversation itself
Running the conversation
Fifteen minutes means four questions
A networking call is short and often interrupted. Pick four questions, lead with the pipeline and staffing ones, and let the rest go. Trying to work through a list makes the call feel like an interview in reverse.
Do not ask what you can find in a filing
Deal announcements, league table position, and recent transactions are public. Asking about them wastes the only asset in the conversation, which is access to a judgment you cannot look up.
End by asking who else you should speak to
Managing directors delegate this happily, and an introduction from them carries more weight than any application. Ask for one name rather than a general offer to help.
Afterwards
- Send a short note the same day referencing one specific thing they said, not the conversation in general.
- If they named something to track, follow it, then send one observation about it four to six weeks later. That second note is what makes people remember you.
- Keep a record of who said what. Groups are small and repeating a question a colleague already answered is noticeable.
- Do not ask for a referral in the first message. Ask after you have given them a reason to give one.
- If they connect you to an analyst or associate, treat that conversation as the more informative one. Juniors describe the job accurately.
What their answers tell you
- Talking about the last closed deal in detail suggests an execution-heavy group. Talking only about relationships suggests a coverage role with the work done elsewhere.
- Vagueness about staffing usually means there is no system, which means workload depends on who likes you.
- Warmth about former analysts is the strongest available proxy for how juniors are treated.
- If the pipeline question gets deflected twice, the group is probably quiet, whatever the recruiting materials say.
- A managing director who asks you a real question back is interested. One who only answers is being polite.