Summary: In sales, relaxed assertive confidence is the calm, settled belief that when you ask, the answer will be yes. It is one of the most reliable traits separating top-performing salespeople from those who stall out. It is not arrogance, but the internal certainty you bring into every interaction, expressed through composure, directness, and a prospect-first mindset. Salespeople who develop relaxed assertive confidence ask more, expand more, and close more, not because they are louder, but because people say yes to certainty.

Vera Stewart Showed Up and Did Not Leave Without the Yes

I recently sat down with Vera Stewart on the Sales Gravy Podcast. Vera is the Augusta, Georgia-based celebrity chef, TV personality, and founder of a food brand that grew from a local cafe and mail-order business into a nationally syndicated television show. She is not a salesperson by title. In every way that counts, she is one of the best I have ever had on this show.

What makes her exceptional is relaxed assertive confidence.

Most salespeople have heard the phrase. Far fewer understand what it actually looks like in practice, because most confuse assertiveness with arrogance.

Arrogance is loud, off-putting, and self-centered. Assertiveness is the quiet internal certainty that when you ask, the answer is going to be yes. You have already decided you are going to win before the conversation begins. People lean into calm, settled energy. When you flinch or pre-apologize before you ask, you exude doubt, and doubt is contagious.

You Get What You Ask For When You Ask Like You Expect It

Vera was prepping for a large catering job during the Masters Tournament in Augusta when logistics got tight. They needed a refrigerated truck on-site, but it couldn’t be delivered until Friday because they didn’t technically lease the lot until that day. Someone on her team accepted that at face value. Vera did not.

She called and asked if the truck could go on the lot on Wednesday. Direct, no setup, no apology. The answer was yes.

Salespeople miss referrals, upsells, and expansion opportunities every day, not because the customer was closed to it, but because the rep never asked like they expected yes. As Vera put it, “All they can do is say no. And no is not a good word for me.”

So many reps open their asks with “You probably don’t need this, but…” or “I know this might be a stretch…” They are framing the conversation around a no before they even finish the sentence. Relaxed assertive confidence flips that. The ask itself assumes yes.

Rainmakers Decide to Win Before the Game Starts

When Vera found herself face-to-face with Bobby Flay on a nationally televised cooking competition, her first thought was not panic. It was: I am going to beat him. She spotted his mistake early. He added ginger to his batter, and she knew it would overpower everything else. In her mind, the competition was already over.

She told me she has been wired this way since the third grade, as the smallest kid in her class playing Red Rover. She was going to find the weakest link and break through every time.

During challenging times, I see this play out across hundreds of sales teams. Some salespeople hit all-time company records. Others could barely stay afloat. Same products, same market, same conditions. The difference was one internal question: is this a crisis or an opportunity?

The rainmakers chose opportunity. They recognized that virtual selling meant more conversations per day, not fewer, and they filled their pipelines faster than ever. The rain barrels waited for things to return to normal.

Vera has always been a rainmaker. She plants the seed of success first, then builds toward it.

Relaxed Assertive Confidence Is Prospect-Focused, Not Self-Focused

Relaxed assertive confidence is not about being full of yourself. Vera proved that when she pitched her show to a Savannah TV station. She did not walk in talking about how talented she was. She led with what the station would gain: eight commercial slots at premium rates. The confidence was there, but it was pointed at the other person.

When your certainty is focused outward, prospects feel pulled toward yes rather than pushed. I tell salespeople this all the time: you could say “purple cow, how about Thursday at two?” and get a yes, because people respond to the energy behind the ask before they even process the words.

Action Builds Confidence. Waiting Destroys It.

When Vera got the call about a “Cooking Channel carrot cake expert” opportunity that turned out to be a surprise throwdown with Bobby Flay, she said yes without hesitation. Her reasoning: by the time I need to be the expert, I will be the expert.

Nervousness is a signal that something matters, not a reason to hold back. The rep who picks up the phone a little nervous and makes the call will always outperform the rep who waits until they feel completely ready. Messy success beats perfect mediocrity every time.

Vera also mentioned that across her entire syndication network, she has never lost a station. One hundred percent retention. She stays committed to her partners and treats every relationship as something that needs to be earned continuously. That level of dedication communicates confidence on its own.

Every Ask Is a Chance to Level Up

Rainmakers are not born. They are built, one ask at a time.

Vera Stewart grew a nationally syndicated show from a single carrot cake by saying yes before she was ready, asking directly, and always keeping the other person’s gain at the center of every pitch. Zero lost stations. A brand built on confidence and follow-through.

Your pipeline, your accounts, your referrals — they are all waiting on the other side of an ask you have been putting off. Pick one. Make it today. And when you feel the nerves, remember: all they can do is say no.

Decide you are going to win. Then go prove it.

Relaxed assertive confidence is a skill, and like every skill, it gets sharper with the right training. 90 Days to Level Up Your Sales Skills is a hands-on, no-BS roadmap built for salespeople who are serious about getting better fast. Whether you are new to sales, stepping into a leadership role, or a seasoned rep looking to sharpen your edge, my book gives you practical tasks and actionable steps every week so you can see real progress in a single quarter.

Frequently Asked Questions

What is relaxed assertive confidence in sales? Relaxed assertive confidence is the calm, settled belief that when you make an ask, the answer will be yes. It is the internal certainty you have already decided to win, expressed through composure and directness. Salespeople with relaxed assertive confidence ask more, expand more, and close more because people respond to certainty before they respond to content.

How is assertiveness different from arrogance in sales? Arrogance centers on the salesperson and pushes people away. Assertiveness draws people in because it communicates conviction without ego. An assertive salesperson asks directly because they believe in the value they bring. The energy is collaborative, not combative, and prospects feel the difference immediately.

Why do salespeople struggle to ask with confidence? Most hesitation comes from fear of rejection. Salespeople hedge their asks to soften the blow of a potential no. Hedging signals doubt, and doubt makes prospects uncomfortable. When you frame your ask as if rejection is expected, you are asking the prospect to confirm your insecurity rather than respond to your value.

How do I build relaxed assertive confidence when nerves are real? Take action before you feel ready. Nervousness means the opportunity matters. Every direct ask you make, even when uncomfortable, builds the reflex over time. Confidence is the product of repeated action. Messy success compounds faster than perfect preparation ever will.

What does customer-focused confidence look like in a pitch? Walk into the conversation already certain of the value you create for the other person. Lead with their outcomes, speak to their gains, and ask directly for what you want. That combination of composure and preparation makes a pitch feel like a partnership rather than a push, and that is when prospects say yes.