669 - Why Personalities Still Decide the Biggest Deals
In this episode, Jens Heitland explains why AI has leveled the playing field in B2B strategy and negotiation, and why the ability to read personalities in the room has become the real competitive advantage in closing large deals.
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Why Personalities Still Decide the Biggest Deals
Business development has changed more over the last two years than in the decade before it, and most of that change is invisible until you look closely at how large B2B deals actually get built.
Real B2B deals still follow a familiar shape. Conversations stretch over months, sometimes half a year for the largest ones. Negotiations happen mostly online, but there is almost always a physical meeting somewhere in that process, often more than one. That part has not changed.
What has changed is everything that happens before people sit down together. Both sides now have access to the same AI models to shape their opening position, anticipate objections, and prepare counterarguments before a single word is exchanged in person. A tool that used to belong to a handful of well-resourced teams is now available to anyone with an internet connection.
This changes what actually creates advantage in a negotiation. When both sides can use AI to build a stronger strategy and counter the other side's likely moves, the strategic layer stops being a differentiator. Everyone arrives prepared. Everyone has already run the numbers, mapped the objections, and rehearsed the pushback.
What is left, and what ends up deciding the outcome, is what happens between the people in the room. Reading personalities, understanding what someone actually needs beyond what is written in the deal terms, and knowing how to work with that information rather than around it. This is a human skill, and it has not been replaced by anything AI can produce.
The organizations and individuals who understand this are building leverage in two layers at once. They use AI to strengthen their strategic position going in, and they use relationship skill to translate that position into an outcome that works for everyone at the table. A strong strategic position with no relationship skill behind it tends to stall once negotiations get personal, and relationship skill with no strategy behind it tends to produce goodwill that never quite turns into terms.
A lot of business development teams right now are overcorrecting toward the first layer. Everyone is focused on the AI tooling, on prompting better, on getting sharper counterarguments out of a model. Very few are still investing in the part that actually closes deals, which is understanding the person across the table well enough to find where a genuine win-win sits.
None of this means ignoring AI in business development. The tools are useful, and increasingly necessary just to keep pace with a counterpart who is also using them. Treating AI as the strategy itself, rather than as preparation for the relationship work that follows, misses where the real advantage now lives. The negotiation is still decided in the room, by people, even as everything leading up to it has changed.
Highlights:
00:00 BD Has Changed Fast
00:08 B2B Deals Still In Person
00:28 AI Shifts Negotiation Prep
00:57 Personalities Decide Outcomes
01:17 Relationships Over AI Hype
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Transcript :
The interesting part with business development as a whole is that it has changed dramatically over the last two years, I would say. If you look at B2B settings, quite often their large deals are still decided in person, or at least built in person and negotiated maybe online in between, but there's always a physical meeting, at least one or two, because most of the time, the timeframe of these conversations are half a year or something on real big deals. The interesting part of that is that it has completely changed because everyone has the possibility to go into ChatGPT or any of the other AI models, and then use that to look up what the other side might strategize against and/or for. So you're using a tool that is helping you to build a strategy, plus it helps you to counter-argument the strategy from the other side. So what was interesting with this is that in the end, the personalities in the room make the difference. And if you know how to work with personalities, and that's true human trait, it enables you to be super powerful in a way that you can drive win-win between everyone. If you understand that, and then you build the leverage for yourself using AI, that's fine, but really look into the relationship angle of that as the number one thing, because a lot of others are not doing that anymore. They just focus on the AI stuff.