A principal who arrives alone is telling you he can decide. A principal with four advisers is telling you he can't, or won't.
Neither is wrong, but the second one means every answer you get will come back changed, and you should price your time accordingly.
People lead with what they actually care about. If the first question is about price, the deal is about price. If it's about timing, someone has a deadline they haven't mentioned.
If it's about who else is looking, they're worried about being the only one at the table, which tells you something about their own conviction.
This is the one that matters. Ask something slightly awkward — not aggressive, just awkward — and watch.
Some people answer it. Some deflect and come back to it later, unprompted, which is a good sign. Some pretend they didn't hear. The third group will do the same thing when something goes wrong in the deal, and something always goes wrong.
A counterparty who asks nothing about your side is either not serious or has already decided.
Genuine interest in how you make money, what you need from the structure, where your limits are — that's a sign of someone planning to do business, not just to test a number.
Everyone has a story about a transaction that went badly. Whether every one of those stories casts them as the victim is worth noting.
By the time a deal reaches documentation, the outcome is usually already decided. Not by the terms, which will move around for weeks yet, but by whether the two sides can actually work together. You can read most of that in the first hour.
None of this is a substitute for diligence. You still check everything. But diligence tells you what an asset is; the first meeting tells you what the next six months will be like, and that's the part you can't get from a data room.
The corollary is uncomfortable: they're reading you the same way. Who you brought, what you asked first, how you handled the question you'd rather not have been asked. Worth remembering the next time you walk into one.
Voxen Energy
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