Dearest Reader,

There’s a phrase that should come with a warning label in sales:

“It’s complicated.”

It sounds responsible, sophisticated even. It sounds like we're protecting everyone from making a dumb decision.

It is also how smart teams quietly stall their revenue.

I was on a client call recently with a group of deeply competent, technical experts. The kind of people who can hold 17 variables in their head without breaking a sweat.

And every time we got close to a clean next step, someone would toss another branch into the conversation.

“Well, it depends…”
“There’s a governance angle…”
“We should explore a different route…”
“There might be a compliance issue…”
“It’s a little bit complicated…”

None of it was malicious.
All of it was “helpful.”
And OMG it was slowly strangling the sale.

What’s actually happening

Complexity doesn’t enter the sales process as disorder, it enters as caution.

It’s the expert brain trying to be accurate.
Trying to anticipate objections.
Trying to cover edge cases.
Trying to prevent a future problem.

So the conversation expands.

One path becomes three.
One clean decision becomes a series of “let’s also consider…”
A proposal becomes an encyclopedia because we’re trying to compensate for earlier ambiguity with…more information.

And that’s when momentum dies.

Why this happens (especially with smart, technical people)

First: complex brains like complexity.

If we've built a career being the person who handles hard problems, complexity isn’t a threat.
It’s where we feel useful.
It’s where we feel safe.
It’s where we feel like we're doing our job well.

Second: expertise creates a weird blind spot.

When we know a lot, it’s hard to remember what it feels like not to know what we know.
So we add context that feels “necessary” to us…but reads as friction to the buyer.

Third: complexity is a socially acceptable way to avoid a decision.

If we choose a path and we're wrong, we take a hit.
If we keep exploring options, we look diligent.
We look thorough and careful.

But we are not moving.

And sales punishes “careful” when careful becomes endless.

What it costs us

1. It multiplies decisions.
   Every added pathway creates more internal alignment the buyer needs to do, more stakeholders to pull in, more reasons to delay.
2. It dilutes the message.
   We stop sounding like we have a point of view.
   We start sounding like we're trying to accommodate everyone.
3. It inflates assets.
   Long proposals are usually not a sign of seriousness.
   They’re a sign you didn’t force clarity upstream.
4. It reduces confidence.
   Not because we aren’t competent.
   Because we aren’t choosing.

Complexity doesn’t scale and it sure as hell doesn’t sell.

So, what do we do? Without becoming a caveman about nuance...

We don’t need to kill complexity...that will never happen.

But we do need to contain it.

Here are three simple rules I use with technical teams:

Rule 1: Decide the Base Case first.​
Before edge cases, before alternate routes, before “what if”…
Lock the simplest true version:
What are we selling?
Who is it for?
What problem does it solve?
What is the next step?

Sales becomes very tricky if we can't answer those questions cleanly.

Rule 2: Create a Complexity Budget.​
We get:
One primary path (the thing we're actually selling)
One secondary path (only if it supports the primary)
Everything else goes in a Parking Lot.

Not never.
Just not in this deal, not in this moment.

Rule 3: Separate thinking from selling.​
The team can keep a technical depth document.
But the buyer narrative stays clean:
Context → stakes → decision → next step.

If you're concerned complexity is creeping into how you sell, hit reply and let me know. I'll send you my complexity audit :)

Until next week,

Happy Selling!

Talica