There seems to be a growing class of business development and sales coaches, consultants and wanna-be sales gurus right now who are very good at two things:
Reading books or attending seminars.Then trying to use AI to turn that information into content and act like they’ve really been there and done that. Then they bombard the social feeds with inaccurate nonsense regarding complex B2B selling. They hide behind all the AI generated business hipster language.
They use words like:
· Clarity
· Leaning into things
· Quiet
· Alignment
· Signal
· Noise
You can spot it instantly. The same recycled language. The same polished certainty. The same words showing up over and over again, as if complex, high-stakes B2B decisions ever unfold that way in real life.
They don’t.
In real life complex B2B software and services selling, you know when you get CLARITY? When the implementation is done, the customer is happy and your commission check clears in your bank account. That’s Clarity!
If you’ve actually been in the room—under pressure,multi-million dollar agreements,multiple egos in motion on both sides,careers on the line—
you already know this:
Most deals that close never feel clear while you’re in them. You are often navigating power plays, your competitors undiscovered board relationship, the IT teams preferred choice. These things are issues you have to dig into as best you can to find the truth.
They will almost never be 100% clear:
Not at discovery.Not after the demo.Not after legal.Not even after a verbal.
What gets you through those deals has nothing to do with clarity, alignment, leaning in, leaning back and falling off your chair… or whatever the hip new AI generated business lingo is…
What gets you through is…
Sales Gut Instinct.
Sales Gut Instinct is what you rely on when:
Emotions are running hot
The loudest executive isn’t the real decision-maker
The quiet IT lead hasn’t said much, but your main competitor is wining and dining him offsite
The CFO that seems agreeable while sharpening the knife
Everyone says they’re aligned—and you feel in your gut that they’re not
This is where theory, hacks, great followup lines, great closes and the rest collapses. What to do next has to become instinctual. It’s not the right AI prompt that gives you the answer here.
You can’t framework your way through this moment.You can’t checklist it into submission.And no AI-generated insight is going to tell you what actually matters now.
Here’s the part that never makes it into playbooks.
You can be working a deal that’s going exactly as you expect.
The use case is solid, you have solutions to Big Ugly Problems.The numbers work.The champion is engaged.The presentation went well.
Then the deal just… disappears.
No explosion.No dramatic loss.Just momentum that dies.
Months later—you find out why.
You hear your competitor hired a salesperson who already had a personal relationship with the CEOs best friend.
Not clarity.Not strategy.Not product.Not superior execution.
In real life shit happens. You couldn’t have predicted it and there’s nothing you could have done about it. You didn’t really understand what happened on that one until 6 or 8 months later. At that point you truly have clarity on that deal.
So if you’re building a career in sales, scaling a tech. software or services company and you want to pay your mortgage and other bills and meet and exceed quota consistently. Heed my warning here, be careful of the AI generated expert advice and strategy dressed up as a coach, a consultant, a new found guru way to sell . If they have’t lived in the room for years having successes, failures and some real scar tissue, they probably aren’t worth listening to or worse yet betting your career and reputation on their advice.
“Everyone has a plan until they get punched in the mouth.”— Mike Tyson
Timothy Barone
Field Memos — observations from real B2B software & services work.More field memos to come…