Synchronicity in B2B Sales - Why the Best Deals Feel Like Luck
If you’ve been following along, you might reasonably conclude that I’ve recently fallen into some kind of mystical trend.
First I told you pipeline acceleration is Sales theater.
Then I argued happiness in Sales is agency.
Now I’m about to use the word synchronicity.
I promise you - this is not an invitation to light candles or start “manifesting” enterprise deals.
But I came across a video titled That TRULY Explains Synchronicities - Alan Watts, and it hit a nerve. Not because it turned me spiritual. Because it described, with surprising accuracy, something I’ve been writing about for years - without using the same vocabulary.
Synchronicity, in Watts’ framing, isn’t magic. It’s what becomes visible when the illusion of separation cracks.
And if you’ve ever worked on a complex B2B deal, you already know what that feels like.
Why the Best Deals Feel Like Luck
You’ve probably experienced this:
You’ve been chasing a deal for months. You’ve done the calls. The demos. The follow-ups. The “alignment meetings”. The gentle pressure. The escalations. The forecast updates. The internal debates.
And then, suddenly, it moves.
Budget appears.
Legal stops blocking.
Your champion gets traction.
Procurement becomes cooperative.
The decision happens.
From the outside, it looks like luck.
From the inside, it feels like one of those moments where everything aligns in a way that is almost too clean to explain.
And that is exactly what makes synchronicity a useful concept for Sales.
Because in B2B, alignment often feels miraculous only when you still believe you’re separate from the system.
The Illusion of Separation (Sales Edition)
Watts describes what he calls the hallucination of the isolated self - the idea that you are a little person inside your head, looking out at a world that exists independently from you.
Sales has its own version of that hallucination.
It’s the belief that there is:
your Sales process (inside)
and the customer’s buying process (outside)
And that your job is to push your process onto theirs.
This is the mental model behind most Sales training.
It’s also the mental model behind most pipeline meetings.
In reality, you are not outside the customer’s system trying to control it. You are inside it. You are one thread in their web of priorities, constraints, politics, budgets, reputations, and internal timelines.
When you forget that, you start performing.
And that’s what I called out in What if Everything You Know About Pipeline is Wrong.
Pipeline acceleration is Sales theater.
Not because Reps are lazy.
But because the idea itself is built on a false separation.
The 17% Problem (And the Synchronicity Effect)
In that pipeline piece, I used one data point that should permanently change how you see your job:
B2B buyers spend only 17% of their time meeting potential suppliers.
Which means, for every hour they spend with you, they spend multiple hours without you - debating internally, aligning stakeholders, navigating risk, and protecting careers.
Now ask yourself this:
If you only have 17% access to their reality, how much do you really think you can accelerate their decision?
By one day?
One week?
One month?
A quarter?
Yes, you can sometimes help. You can reduce friction. You can create clarity. You can provide momentum.
But the larger and more political the deal becomes, the more your “urgency creation” becomes a performance.
And the moment the deal moves, it feels like synchronicity - not because the universe smiled at you, but because the system finally aligned.
The Sales Version of Wu-Wei
Watts borrows a concept from Lao Tzu: wu-wei. Often mistranslated as passivity, it describes action that moves with the natural current of a system rather than against it.
It’s often translated as non-action or effortless action. But the point is not passivity.
It’s the difference between forcing and flowing.
If you want a Sales translation, it’s this:
There is a way to run discovery like an interrogation.
And there is a way to run discovery like a conversation.
The first one is what happens when you show up with your framework clenched in your fist.
MEDDIC.
SPICED.
Challenger.
Whatever your organization worships this quarter.
You ask questions because the model requires them.
You steer the conversation because you need the boxes filled.
You jump too quickly to qualification because you need to “control the process”.
The customer feels it immediately.
The tone becomes tense.
They become guarded.
They give you safe answers.
You get data - but not truth.
And you leave the meeting with a CRM that looks great… and a deal that’s still dead.
The second version feels completely different.
You are still learning.
You are still qualifying.
You are still driving.
But you are not forcing.
You are listening with genuine interest, not performing competence.
You are not trying to prove you’re right. You are trying to see what’s actually happening.
This is where the most important information emerges.
Not as a checklist.
As a flow.
Why Experienced Reps Look Like They’re “Lucky”
This is one of the hardest things to teach in Sales.
But it’s easy to observe.
The difference between a new Rep and an experienced Rep is often not knowledge.
It’s confidence.
The experienced Rep is relaxed enough to let the conversation breathe.
The new Rep is tense enough to turn it into a process.
The experienced Rep doesn’t panic when silence appears.
The new Rep fills it with pitching.
The experienced Rep doesn’t need to prove expertise.
The new Rep tries to win the meeting.
And here is a strange truth you’ve probably noticed:
It is easier to sign deals when you already signed one.
It is easier to sell when you’re already on target.
Not because you are suddenly blessed by luck.
But because you are less stressed.
More relaxed.
More open.
Less needy.
Less attached to being right.
More available to what is actually happening.
Yes, this sounds weird.
And no, it doesn’t fit in a CRM.
But it’s real.
And in Watts’ language, this is when you start noticing synchronicity.
Not because you are special.
Because you are present.
A Deal That Looked Like Luck
I remember a deal that still makes me smile.
My manager spent two hours in a meeting with a partner and the end customer. I wasn’t part of it, since it was part of an ongoing opportunity.
Later, I had a separate conversation with the customer. Nothing formal. No pitch. No agenda. I wasn’t trying to sell anything.
It was just a real discussion - about their setup, their challenges, how things actually worked.
Genuine interest.
And during that conversation, the customer casually mentioned an issue they were facing with their current provider.
Not a complaint.
Not a crisis.
Just a friction point they had accepted as normal.
One week later, we signed a contract to replace that provider.
Call it luck.
Or call it synchronicity.
Someone once said luck is when opportunity meets readiness.
The opportunity was there.
The dissatisfaction existed.
The timing was right.
But what made the deal happen wasn’t a magical alignment.
It was readiness.
And then something else - agency.
Because it was an unusual deal. We had to move lines internally. Adapt contract terms. Adjust our business model. Reframe how we positioned value.
Frictionless? No.
But in the end, my internal stakeholders were happy.
And my customer was happy.
Which is a pretty good definition of Sales.
Timing Is a Systems Problem
This is the part most Sales organizations struggle to accept.
Yes, you will be pushed to move the deal forward.
Yes, you will be pressured to “create urgency”.
And yes, sometimes you should.
But the bigger the deal, the more stakeholders are involved, the more political it becomes - the more limited your ability to shift timing.
I’ve been working on a deal that was supposed to close 18 months ago.
It will close.
Observers might call that blind faith.
It isn’t.
It’s simply awareness of what actually needed to change inside the customer organization.
Across departments.
Across priorities.
Across internal power.
At one point, a reorganization stole the project for months.
Then my champion ended up in a better position.
His internal narrative became stronger.
His political play became possible.
The deal didn’t move because I “accelerated” it.
It moved because the system changed.
And because I was paying attention.
Synchronicity Isn’t Magic. It’s Participation.
There’s one line from Watts that I genuinely like.
He says synchronicity does not mean you’re special.
It means you’re participating.
That’s a useful warning for Salespeople too.
Because when a deal aligns, it’s tempting to think:
“I cracked the code.”
“I mastered the process.”
“I know how this works now.”
And then you show up to the next meeting with that ego in your pocket.
You think you can replicate the sequence.
You start saying “I know” too early.
You stop listening.
And you lose the one thing that created alignment in the first place.
Presence.
There’s a line I heard recently that I can’t unsee:
Existence is not a problem requiring a solution, but an improvisation requiring participation.
If you replace “existence” with “complex B2B deals”, the sentence still holds.
The mistake most Sales organizations make is treating deals like problems to be solved by process.
But in enterprise Sales, deals are rarely solved.
They unfold.
Your job is not to force them into your timeline.
Your job is to participate so well that when the system aligns, you are ready.
And when it does, it will look like luck.
Not because you are special.
Because you were paying attention.
This piece is part of an ongoing exploration of what happens when you stop treating Sales as force and start treating it as flow.
See also: Be Like Water.
If you've experienced this - where a deal suddenly moved when you stopped forcing it, or where presence mattered more than process - I'd genuinely like to hear it.
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