You've been told to "always be curious" and express it. Likewise, be confident when selling. Radiate confidence. Be confident when reaching out to new and existing customers from cold. Full stop. Both ideas are dangerous. 

Yes, confidence makes sellers attractive. Just like the dating scene, confident sellers tend to earn more attention and close more deals. Yet there is nuance.

Punch line: Confidence is not a personality trait. It’s a decision catalyst.

Thus, confidence is a framework for assessing risk, not a feeling. 

Confused? I was at first too. Think about it: Your job isn’t to project confidence; rather to create it—in others. This way they have what's needed to buy.

When they are confident, customers are not fearful of taking action. They aren't hesitating about the commitment to change which follows.

Consider this. Sales is a con game. No, not like con artist, Joe Mantegna plays in the classic movie, House of Games. (And if you haven’t seen it, fix that!) I’m talking about the good kind—where you transfer confidence (beliefs) to others with good intention.

Example: You might say I conned my wife into marrying me. She’d probably say the same. See that? We both bought in to each other’s confidence.

Buyers do the same thing. They buy into the belief—they can trust themselves to make a decision that won’t blow up in their face.

Anxiety kills decisions. Confidence makes them.

That’s where the best sellers stand out. They don’t provoke confidence—they instill it. They transfer it.

Indecision is the default state

“The biggest competitor you face isn't a competitor at all—it's your customer’s own struggle to make a decision,” says Brent Adamson, a Challenger Sale enthusiast and co-author of The Framemaking Sale.

Adamson introduced the idea of sensemaking in sales—shifting from being a “provider of answers” to a “facilitator of clarity.”

This ties closely to confidence. The idea is revolutionary: buyers don’t need more content or more options—they need help making sense of what they already have.

Sellers can build trust by guiding buyers through conflicting information. This boosts a buyer’s confidence in their ability to decide.

It does not attempt to influence the decision.

“The best sellers are not confidence generators—they’re confidence restorers.”

Thus, buyers don’t hesitate because your value proposition isn’t strong enough. They get stuck because they don’t feel safe. Think one-page decision guides, risk-mitigation checklists, peer examples that validate specific choices.

Tools which help the buyer explain and justify the decision to others, increasing internal confidence.

Within buyer's organizations, there’s a minefield of unknowns:

• Political resistance
• Cross-functional friction
• Skeptic stakeholders
• Internal capability gaps

These are the real reasons deals stall. And too many sellers respond by trying to raise excitement or create urgency. It backfires.

Remember: Your job is to reduce anxiety—not raise excitement, and not manufacture urgency.

Anxiety kills decisions. Confidence makes them.

Confidence isn’t a feeling

This is the AH-HA! of my post today. Confidence is a framework for assessing risk, not a feeling. 

Here's the rub: Buyers don’t evaluate solutions. They see everything through the lens of risk—especially risks they can’t control: internal execution, political approval, reputation fallout.

“A buying decision is a risk management problem before it’s a solution choice issue," says Sharon Drew Morgen, who concurs. 

No one wants a new vendor. They want fewer problems. Confidence comes when they believe change won’t cost more than it solves.

It seems obvious. But how dialed in to this truth are you? Hmmm?

Confidence starts with curiosity

Confidence-building doesn’t start with persuasion. It starts with provocation. Specifically, provoking curiosity.

You earn the right to influence when you help people start asking themselves the right questions—the uncomfortable, high-leverage ones.

Meditate on this. Then do it. Reframe persuasion as facilitated realization.

Realization happens when prospects reach their own conclusions. When they begin to say, “This isn’t sustainable,” without you needing to push.

You can help them get there.

5 moves that build confidence

1. Be aware of low-confidence signals
   "Just following up" and "Looking forward to your thoughts" sound polite—but project insecurity. They lower your perceived status.
2. Mirror status. Provoke, don’t pander.
   Ask provocative questions that signal you’re not afraid of the truth. For example:
   
   

   “Who benefits from allowing this (bad) situation to exist?”

3. Be confident or walk away.
   If you can’t stand behind the product or offer, find one you can. Transfer of belief requires you to believe first.
4. Challenge the status quo.
   Ask questions the buyer should be asking but isn’t. Facilitative, not leading. You don’t need the answer—they do.
5. Be disinterested—not disengaged.
   Express want, not need.
   
   

   “Radiate confidence that you don’t NEED the business.” — Tony Hughes, The Law of Principled Disinterest

Fear of (post-sale) fallout

It's true! “The last thing buyers want is to buy. Literally: the last thing. People don’t want to make a purchase. They merely want to resolve a problem with the least disruption/cost," says Sharon Drew Morgen.

Buyers don’t fear you. They fear what happens after they say yes.

• Internal blowback
• Failed implementation
• Finger-pointing

That’s the hidden tax on every B2B deal. If your sales process doesn’t eliminate it, your proposal is just a liability with nice formatting.

Confidence is about predictability. If the buyer can’t visualize surviving the fallout, they’ll freeze—even if the ROI is huge.

For sales leaders

Stop training your reps to be agreeable. Start helping them:

• Reduce buyer anxiety
• Transfer beliefs, without persuasion
• Ask better questions—ones that help buyers lead themselves

“They don’t need help buying what you sell. They need guidance from the perspective of a decision to change—and the ripple effects driven by the change," says Vincent Messina, a leader of global sales teams for companies like Blackline.