Most investment bankers know how to build a pitch book. They know how to present credentials, show relevant transactions, explain market conditions, outline process, talk valuation, and position their firm’s capabilities. That gets you into the room, but it does not always win the mandate.

That was the central lesson from my recent conversation with Oren Klaff, author of Pitch Anything and Flip the Script, and one of the most recognised voices on high-stakes persuasion, capital raising, and deal psychology. Oren’s work is highly relevant to investment banking because our industry is full of capable people with similar materials, similar credentials, and similar claims. In many competitive situations, the difference is not whether one bank is technically competent and another is not. The difference is psychology.

How does the client see you? Are you another advisor trying to win the work, or are you a peer-level expert helping them think clearly? Are you pitching from a position of need, or leading from a position of conviction? Are you asking basic discovery questions, or showing that you already understand the situation?

Here are five lessons I took from the conversation.

Oren made one point early in the conversation that every banker should sit with. In high-stakes decisions, clients are not only evaluating features, benefits, credentials, or case studies. In his words, decisions often come down to relationship or FOMO: the trusted relationship that is hard to beat, or the sense that one advisor has more momentum, confidence, proof, and likelihood of winning than the alternatives.

That is uncomfortable because bankers like to believe the best deck wins. It rarely does. The deck matters. Technical quality matters. Transaction experience matters. But if the client already has a trusted relationship elsewhere, you are not just competing on content. You are competing against familiarity, comfort, and perceived safety.

The lesson is not to ignore credentials. It is to stop believing they are enough. Future MDs need to build relationship equity before the formal pitch. They need to create momentum around their ideas. They need clients to feel that working with them increases the probability of a better outcome. Credentials confirm the decision. They do not always create it.

Oren’s view on pitch dynamics was direct. When a company runs a bake-off, the client often sees itself as holding the money, the decision, and the power. The advisors are there to perform. In Oren’s language, the client is effectively saying: show us your tricks.

That creates a problem. If you enter the meeting as another advisor desperate to be chosen, you are already in a weaker position. Oren’s point was that it is very hard to win from that low-status position until the client sees you as a peer, or at least as someone with equal authority in the conversation.

This does not mean being arrogant. It means creating mutual evaluation. One of the strongest ideas from the episode was the need to make clear that the meeting is not only about the client choosing you. It is also about you understanding whether they are the right client, whether the situation is real, whether the timeline is credible, and whether the opportunity is worth your team’s focus.

That subtle shift changes the energy in the room. You are no longer asking to be picked. You are assessing whether there is a serious situation you can help solve. For VPs and Directors, this is especially important. You may not be the most senior person in the room, but you can still carry yourself like someone who has prepared deeply, understands the issues, and is there to contribute judgment rather than simply provide support.

Oren was particularly sharp on discovery. Many professionals ask discovery questions in a way that makes them sound junior. They collect basic information the client expects them to already know. They ask obvious questions. They wait for the client to give them all the facts before offering any insight.

Oren’s challenge was to do more work before the meeting and come in with a view. Instead of asking the equivalent of, “What problem are you having?”, an expert should be able to say: here is what we think is happening based on the information available, here is what typically happens in situations like this, here is where the pressure may be building, and here is what you may be trying to decide. Then ask: is that about right?

That takes risk. You may be wrong. The client may correct you. But even that can work in your favour if your analysis is thoughtful. Being directionally right, and prepared enough to take a view, puts you in a different category from the banker who needs every answer before saying anything useful.

Oren described the most valuable person in any company as the person who can “see around corners”, someone who can ingest incomplete information, make an analysis, and project a likely outcome. That is exactly what clients want from senior bankers. Not just information, but judgment.

Oren’s critique of the traditional pitch book was highly relevant. Too many pitches begin with information the client already knows: who we are, our team, our credentials, our capabilities, our transaction history, our sector coverage, our customer service, and our relevant experience.

His point was not that these things are irrelevant. It was that they are often confirmatory. They explain why you got the meeting. They do not necessarily help you win it. The valuable time is usually spent too late. By the time the banker gets to the client’s real situation, the market shift, the supply-demand imbalance, the strategic tension, or the reason to act, much of the meeting has already been used.

Oren’s advice was to move the insight up front. Lead with what is changing. He explained that the human mind pays attention to movement and change. In a pitch, that means starting with the shifts in the market, the pressure building around the client, the imbalance forming, and the decision that now needs to be made.

For bankers, this is a powerful lesson. Do not spend the first 15 minutes proving you are credible if the client already knows enough to let you in the room. Use the opening to prove you understand what matters.

One of the most practical parts of the conversation was Oren’s view on clients who delay. Every banker has experienced this. The client is interested but not ready. They want more analysis. They keep the advisor warm. They postpone decisions. They ask for more time while expecting the bank to keep capacity available.

Oren’s view was clear: unless you are willing to do something, you end up stuck in “just checking in” mode. The better approach is to create a reasonable timeframe, work backwards, and define the waypoints that need to be hit. If a decision is expected in 60 days, what must happen by day 15, day 30, and day 45? Does the board need to align? Does the budget need to be approved? Do other advisors need to be reviewed? Does the internal decision group need to meet?

Oren compared it to landing a plane. You do not simply point at the airport and hope. You hit the waypoints. If you miss the key waypoints, you cannot pretend you are still on track.

That is a useful way for bankers to think about client control. Control is not manipulation. It is professional process management. Clients may be smart, successful, and experienced, but they do not sell companies, raise capital, or run strategic processes every day. Bankers do. Part of the job is helping the client avoid self-inflicted damage, false starts, drifting timelines, and poorly managed decisions.

The key is to combine control with integrity. Strong bankers guide the process because they know what it takes to get to an outcome.

My biggest takeaway from Oren Klaff was simple: technical excellence is not enough if you cannot influence the room.

The best bankers understand the numbers, the market, and the process. But they also understand status, timing, psychology, confidence, client control, and how decisions are really made. They do not walk into meetings hoping to be chosen. They walk in prepared to lead a serious conversation.

They do not waste time proving what the client already believes. They lead with insight. They do not ask basic questions to discover what they should already know. They take a view. They do not let every opportunity drift indefinitely. They define the process and manage the waypoints.

For VPs and Directors trying to move from execution to origination, this is the real lesson. The next level is not simply about better materials. It is about better presence, better judgment, and better control of the conversation.

Because in investment banking, expertise gets you invited into the room. Influence helps you win it.