I watched a sales rep torpedo a $2 million deal at a client dinner.

He stood up, three drinks deep, and launched into a rambling toast about “synergies” and “partnerships” that lasted so long people started checking their phones. The CEO he was trying to impress? Stone-faced. The deal? Dead two days later.

This is crucial to remember, especially this holiday season: How you handle holiday toasting etiquette in dinners, events, and parties impacts your credibility and close rate. And one of the simplest tests of your executive presence? How you handle a toast.

Most reps either freeze up and say nothing, or they wing it and make it awkward. Both are mistakes. A well-executed toast has all the tenets of great salesmanship: on-point, sincere, and focused on the other person.

Here’s how to nail it every time.

Follow These Rules for Raising Your Glass

The host goes first. If you’re hosting the dinner or event, it’s your job to kick things off. Make sure everyone’s glass is full before you start. If you’re the guest, wait for the host to lead. Jumping the gun makes you look eager and out of sync, and that’s never a good look in sales.

Short, simple, sincere. The best toasts are like the best pitches: They get to the point. No one wants to sit through a five-minute soliloquy about the honoree’s life story. Hit the highlight, make it personal, and sit down. Aim for 30 to 60 seconds max.

Skip the glass-clinking in large groups. In a big room, just raise your glass and take a sip. If it’s a small group and you want to clink, do it gently and make eye contact. It’s a small gesture, but it shows presence and respect. A light touch is all it takes. 

Sip, don’t guzzle. Especially if multiple toasts are coming. The last thing you need is to be the rep who can’t hold their liquor at a client event. Stay sharp. Stay in control.

Use a closing line. “Here’s to…” or “Cheers” signals you’re done. It gives people permission to drink and move on. Don’t just trail off awkwardly.

If you’re being toasted, don’t drink. It’s like applauding yourself. Instead, stay seated, smile, and let the moment happen. If you want to respond, stand after the toast and offer a brief thank you or return toast.

Alcohol isn’t required. Water, sparkling water, juice—it doesn’t matter. The toast is about the gesture, not the beverage.

Be Prepared. Keep It Brief.

If you know you’re attending an event where a toast might be expected—client dinners, partner events, award ceremonies—prepare in advance. Write it down. Practice it. Know exactly what you’re going to say.

Start with the honoree’s name and your relationship to them. Then deliver one memorable line—something sincere, maybe a little witty—and wrap it up. Simple. Clean. Professional.

The same rule applies to sales conversations, by the way. Get in, add value, and get out. That’s how you stay memorable for the right reasons.

It’s Your Move This Holiday Season

Master your holiday toasting etiquette, and you master a small but powerful piece of executive presence. It’s one more way to show clients, prospects, and partners that you’re polished, prepared, and worth doing business with.

Now get out there and raise your glass like a pro.

Holiday toasts are great, but they won’t build your pipeline. If you want to win Q4, you need a real plan. Get access to Jeb Blount’s on-demand Outselling the Holiday seminar and arm yourself with the strategies top performers use when everyone else is coasting.