Most BD professionals are good at asking questions in meetings.
They ask about budget. They ask about timeline. They ask about pain points and previous attempts and what success looks like. These are the right questions and most experienced professionals ask them well.
But there is a different category of question — one that most BD professionals rarely ask, not because they don’t know how, but because they don’t know to ask it at all. These questions don’t surface what the client wants. They surface how the decision actually gets made.
There are three of them. They work best early in a relationship, before the deal has momentum and before your contact has become protective of the internal process. Once you’ve asked them — and listened carefully to the answers — you will know more about whether this deal is going to close than almost anything else you could have learned.
Why most deals die before you know they’re dying
Complex deals don’t fail in the final negotiation. They fail weeks or months earlier, in a room you were never in, in a conversation you didn’t know was happening.
The person you’ve been working with — the one who is genuinely interested, genuinely aligned, genuinely trying to make this happen — runs into someone they didn’t fully anticipate. A senior leader who hasn’t been briefed. A finance function with concerns that were never surfaced in your conversations. A committee that meets once a month and sees the world differently from your contact.
By the time you find out about any of this, the invisible decision-maker has already formed a view. And they formed it without you.
The three questions below are designed to surface this structure before it becomes a problem. They are not interrogation. They are not due diligence. Used well, they feel like genuine curiosity about how the organization works — because that is exactly what they are.
Question One: “Walk me through what happens internally once we have an agreement in principle.”
This is the most important question in complex deal-making and almost nobody asks it directly.
Most professionals assume they understand how decisions get made inside a client organization. They don’t. They understand how their contact describes the process when asked about it indirectly — which is a different thing entirely.
When you ask this question directly, something interesting happens. Your contact has to actually think about it. And when they do, they will often tell you — sometimes in more detail than they intended — exactly how the internal process works, who is involved, where things tend to slow down, and what has caused deals to stall in the past.
The answer is your map. Write it down. Every person, every function, every step they mention is a stakeholder you now know about. Every hesitation in the answer — the moment they say “well, it depends” or “usually it goes through…” — is a signal worth following.
What to listen for: Any mention of a person, a committee, a function, or a process that hasn’t come up in your previous conversations. These are the invisible stakeholders. You now have names or shapes for them.
What to do with it: For each stakeholder your contact mentions, ask yourself: do I know what their concern will be? If not, you have just identified a gap in your preparation.
Question Two: “Who else needs to be comfortable with this before you can move forward?”
The word “comfortable” is doing a lot of work in this question and it is not accidental.
“Who needs to sign off?” produces a procedural answer — a title, a name, a formal step in the approval process. That information is useful but incomplete. It tells you who is in the official chain. It does not tell you who has informal influence, who your contact is managing internally, or who could quietly kill the deal without ever appearing in the formal process.
“Who needs to be comfortable?” invites a different kind of answer. It asks your contact to think not just about the org chart but about the people they are actively navigating. The colleague who always raises objections. The senior leader whose instinct matters even when their sign-off isn’t formally required. The peer whose opinion the decision-maker trusts even though they have no official role in this decision.
These are the people who most often end a deal without ever being in the room with you. And your contact knows who they are.
What to listen for: Anyone described in relational terms rather than hierarchical ones. “My CFO needs to see the numbers” is a formal stakeholder. “My CEO tends to want to understand the strategic rationale before anything like this goes forward” is an informal one — and often more important.
What to do with it: For every person your contact mentions, ask a gentle follow-up: “What does that person typically want to understand before they get comfortable?” You are building the concern map that will guide everything you prepare from this point forward.
Question Three: “Is there anyone in this process who tends to ask hard questions — and what usually concerns them?”
This is the question that gives you the gatekeeper.
The first two questions surface the structure. This one surfaces the friction. Every complex organization has at least one person whose role — formal or informal — is to push back, to identify risk, to ask the question nobody else is asking. Sometimes this is a CFO. Sometimes it is a general counsel. Sometimes it is a board member who has seen a similar initiative fail before. Sometimes it is simply the person your contact is most nervous about.
When your contact answers this question honestly, you learn two things at once: who the hardest audience is, and what they care about. That combination is more valuable than almost any other intelligence you can gather about a deal in progress.
Not every contact will answer this fully. Some don’t know. Some are protective of the internal dynamics. Some will give you a partial answer and stop. That’s fine. A partial answer is still more than you had.
And sometimes — often, in fact, if you have built genuine trust with your contact — they will tell you exactly who is going to push back and exactly why. When that happens, you have just been handed the key to protecting the deal.
What to listen for: Specific concerns, not just specific people. “Our legal team always has questions” is less useful than “our legal team always wants to understand the data handling and liability exposure.” The concern is what you prepare for. The person is just the messenger.
What to do with it: Every concern your contact names is a question you now need to be able to answer — not in the meeting with your contact, but in the materials they carry into the rooms you’ll never enter. Your proposal, your summary document, your one-page rationale — all of it can be built to address these concerns directly, even if you never meet the person who holds them.
When to ask these questions
Timing matters.
These questions work best in the early stages of a relationship — after you have established genuine rapport and before the deal has developed enough momentum that your contact feels protective of the internal process. Once a deal is in active negotiation, these questions can feel like due diligence or pressure. Before that point, they feel like genuine curiosity.
The ideal moment is the second or third substantive conversation — early enough that your contact is still thinking openly about the process, late enough that they trust you enough to answer honestly.
If you are already deeper into a deal and haven’t asked these questions, it is not too late. You just need to frame them differently. “As we move closer to something concrete, I want to make sure I’m thinking about the right things on your end” is a natural entry point at any stage.
What changes when you have the answers
When you know the full decision structure — the stakeholders in every layer, the concerns each one holds, the gatekeeper who will ask the hardest questions — your preparation changes completely.
You are no longer preparing for the conversation with your contact. You are preparing for every conversation that happens after it. The internal briefing your contact gives to their CFO. The summary document that lands on the senior leader’s desk. The moment in the committee meeting when someone asks whether this has been thought through.
You are not in those conversations. But your preparation is. And preparation built specifically for the actual decision-makers — not for your contact, not for a generic audience, but for the specific people with the specific concerns you now know about — is the closest thing to being in the room that you have.
That is what these three questions give you. Not just information. Presence, in the rooms you’ll never enter.
A2A was built to help you do this work — before every deal, before every critical conversation. See how it works →
Ipalibo Da-Wariboko is the founder of Aligned to Act — a preparation platform for professionals who win business through relationships.
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