Why Most Salespeople Struggle With Complex Deals

Most companies are forecasting hope.

Selling has changed more in the last five years than it did in the previous twenty and yet most sales teams are still using methods designed for a different world.

Markets shift. More voices are at the table. Technology disrupts. Decisions slow down.

The only constant today is change, and if you don’t have a system that gives you clarity inside that chaos, you’re relying on luck.

And luck is not a sales strategy.

Complex Sales Are Not About Price or Product, They’re About Structure

One of the biggest ideas I learned early in my career (and still see hold true today) is this:

A sale becomes complex the moment more than one “yes” is required.

That’s when:

Multiple people have a say

Conflicting priorities collide

Decision-making becomes political

Approval must travel through layers

It’s why selling to one person is easy, and selling to a team, committee, or department can feel like walking through fog.

Yet most sales reps still approach these opportunities as if one great conversation will close the deal.

It won’t.

The Best Salespeople Don’t Rely on Charisma, They Rely on Systems

We’ve all heard the old clichés:

Good salespeople are born.”

Selling is 90% personality.”

You either have the gift of the gab… or you don’t.”

Nonsense.

The top performers, the ones who account for 80% of results, win because they:

Treat selling as a professional discipline

Follow clear, repeatable steps

Understand the political map inside an account.

Know who influences, who approves, and who blocks.

Allocate time deliberately.

Never confuse activity with progress.

In other words, they don’t rely on magic tricks or scripts.

They rely on a methodology/framework.

That’s the difference between the reps who “wing it” and hope for the best…

and the pros who consistently close large, complex opportunities.

Change Isn’t the Problem, Uncertainty Is

Every industry is experiencing massive shifts:

New competitors. Technology changes. Customer churn. Economic pressure. Restructuring.

Change itself isn’t what derails sales.

It’s the uncertainty around the change.

When you don’t know:

Who influences the decision

How approval works internally

What matters most to each stakeholder

Where the real risks are

Or what’s driving urgency

…then even a good conversation can turn into a languishing opportunity.

Clarity is the antidote to uncertainty.

And clarity comes from a professional selling system.

Here’s What the Pros Do Differently

The salespeople who perform at the top of their industry consistently:

1. Map the influencers and decision-makers early.

Not just titles, true power.

2. Understand buyer attitudes.

Which ones drive a deal forward and which ones stop it dead.

3. Avoid “phantom approvals.

Never rely on someone who isn’t a real decision-maker.

4. Watch for early danger signals.

Not when a deal collapses, but when it starts to wobble.

5. Protect the deal from anti-sponsors.

A massively overlooked component in complex sales.

6. Allocate their time across four essential tasks.

So they never hit dry periods or drought months.

7. Create repeatable processes.

Because consistency beats charisma every time.

Here’s the question for you and your team:

Are you selling professionally, or are you “getting by” on hope, talent, and territory?

In today’s world of constant change, only one of those survives.

Only one scales.

Only one closes deals predictably.

And it’s not the one built on luck.

Over to You

If you want to strengthen your team’s ability to navigate complex sales, build a consistent pipeline, and close with confidence. Let’s have a chat

If you’re a business owner, founder, or CEO and you feel the business is stuck or you know your sales could be stronger and you’d like to find out how I can help,

Check out this link

Joe Dalton

#Leadership #Management #Culture #ChangeManagement #ExecutiveLeadership #BusinessGrowth

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