I once killed a $125M deal by being “too honest”

I'm not understanding your instinct here. My first thought would be "this guy I trust enough to spend 100m is super confident about another team too, even better to keep him around for further insights"

But that was the Yahoo era. He then repeat the same mistake with Steve? And Apple has a history of not paying much for M&A. It was really well known even in 2008. And $300M for P.A Semi was considered a very big deal back then.

They're notable stories and helpful to others who might make the same mistakes.

I'm more concerned that you are bothered by his honesty about past mistakes.

Steve had said "yes" and said Eddy Cue would take it from there, and was preparing to leave the meeting. Then Ali decided it would be good to start negotiating price right then and there.

Steve might have really been offended by Ali bluffing the sale price he could command. Or he could have been offended that this guy was such an obvious amateur.

Negotiation can happen later.

From the thread the difference was when he followed up his "I think we're worth $150M" with a corrected "I know we're worth $150M".

Jobs probably balked at the "I know" part because he knew Apple was one of less than 5 companies that had tons of extra cash in a financial crisis (2008) and had the strategic alignment to make the acquisition.

Plus Jobs undoubtedly already had internal estimates for cloning the company.

I don't think Jobs was being a dick, I think Jobs was just defining a strong negotiating point by telling this young entrepreneur that he sets the market price for acquisitions, not the startup. Sometimes aggression is a good negotiating tactic.

They apparently continued to negotiate after that, so it wasn't like it killed the deal.

Thinking you're worth 3x what your investors and your target acquirer thinks you're worth is what kills the deal.

Practically every significant real-world interaction involves judgment calls, heuristics, and personal feelings. They feed in to you taking your best guess based on your limited information.

So adding more time to the process doesn't always make it better. You may learn, for example, that the person seems untrustworthy. "Selling past the close" implies that the person doesn't understand the situation, and is pursuing more contact for some reason other than your own best interest. The disconnect suggests that you may not understand what's going on, and it may be in your best interest to break off a deal that may not be what you think it is.

Humans do practically everything on the basis of very incomplete information. They use timing and word choice, among many other things, to try to close that gap.

This is a very important lesson. This isn't a case of humans failing to be logical. It's a case of incomplete information, and if you treat it as if it were a complete-information game, you're going to lose. That's illogical.

If it were a job that we could send computers to, we would. We can't, because we can't define the job well enough for the computers to do it. And this is a lesson for all programmers as well: most of our job is not talking to the computers, but talking to the humans to figure out what they actually want. If they could have said it in complete and logical terms, they'd have written the programs themselves.

We all choose paths forward with uncertainty both about what is desirable and about how each path might get us there. The perceived trustworthiness of the people pitching each path factors into that decision, precisely because of the uncertainty involved.

Calling people "rational" or "irrational" doesn't make sense if there isn't an end goal to measure us against.

If you're buying an appliance, and you already agreed, and then the salesperson gives you additional info, you might change your mind ("oh, I thought the failure rate was 0.1%, you said it's 1%") even if in reality this may be a perfectly good enough appliance for you and a good sale for the seller. Optimal would probably be getting the sale done - even if that depends on untrue assumptions in your head not being challenged. Not getting the sale done means your back at square one, depending on what else you want to be doing with your time, that's not good.

When interacting with another party you have a mental model you build to try to figure out what they're thinking, but it's very incomplete. Adding information can change your mind, and even not necessarily in a "true" way - imagine you're on a date, it's going well, both parties want to hook up... and then they say something that makes you think maybe their political views are offensive to you. You might be making a wrong assumption based on what they said. Or they might just disagree with you that much. But you're probably not going to have as much fun tonight anymore! You may have a more "true" outcome but is that what you wanted?

But it is in itself an irrational thought, focusing on some ideal platonic "what should be" which is eminently not observable anywhere in the real world. NONE of us are hyper-rational creatures of pure logic. Myself too, holding that thought of "shouldn't we converge on strictly logical optimal resolution", were in fact influenced by emotion, timing, personalities, circumstance, and other carp going on in my life. As was everybody else.

Now, though I'm not in sales, I'm in people management role, and I've learned quickly that timing and choice matters. It matters in sales, but it also matters in architecture, requirements gathering, solution design, project planning, everything. No matter how technical or sales your role, you eventually HAVE to deal with people, they need to agree/approve/confirm, and people ARE people. If you have a goal in mind, it is only rational for you to take into account the personalities involved and realities of the process, and be aware of timing and emotions and words.

Note - This is what I say now; I'm still struggling to implement it fully myself - the decades of sciencey-techy are still strong in me :D

We're not evaluating an arbitrary collection of facts, we're evaluating a flow (ie time varient) of information from a source of unknown trusthworthyness and as such we are looking for more information than just taking everything stated at face value.

The goal is rarely (almost never?) to find an optimal solution (if that's even possible).

Also why would you assume outcomes would converge? That is not a given in most situations.

You’ve never gotten tired of a conversation with someone that didn’t know when to stop? If so then you are exceptional in you're curiosity. I am a very curious person, but I have plenty of topics that are like nails on a chalk board to me.

Plus, every conversation burns energy, and at some point, people will get tired or bored or both, so continuing indefinitely does not rationally lead to better outcomes. Continuing past that point will lead to worse and worse conclusions.

In most B2B sales that I have been involved in, you can summarize it down to a certain amount of budget, and a set of needs. If you can fill the needs within the budget, it's an easy sale and there is no buyers remorse. This is an oversimplification, but I think in many cases buyers remorse is rooted in the buyers realization that making a particular purchasing decision is going to reduce their overall cash reserves, and thus eliminate other potential decisions. The way most corporate budgets works is more of a "use it or lose it" scenario, where the buyers have more incentive to make actual purchases.

In regards to your last sentence, yes, nothing wrong with reinforcing the decisions that led to the purchase decision. But that is much different than introducing new factors (eg: we should buy this other company too) or altering your buyers perception (this other company or product is even better than what you agreed to purchase).

In fact the latter can lead to exactly the opposite of integrity.

> run out the door once it’s in your hand

Resisting the urge to add something at the door is crucial, more than one good meeting was ruined there (at least for me).

(This is how I stopped using YouTube)

It may not be that the other company really is that good, but if the CEO is so comfortable underselling their own team, that suggests the company is not as attractive as initially thought. Especially in a space where hype is the norm.