5 Rules for Sharpening Your Sales Game

I’ve been in sales most of my life, and one thing’s for sure. There’s no such thing as a sure thing. Tactics evolve. Relationships change. Products come and go. If you’re not constantly sharpening your tools, you’re falling behind. That’s just how it goes. It’s why sales, all these years later, still excites me. And it’s why I recently sat down with Jeffery Eisenberg on my podcast, Strange Currencies. To dig into some of the most effective ways to keep your sales game sharp. It’s not just about what works today, it’s about staying ahead tomorrow.

Look, there’s no magic formula for crushing it in sales. If there was, we’d all be using it. And I wouldn't be here writing this. So don’t think of these as some rigid playbook or quick-fix hacks. These are fresh ideas—new ways to think about your sales game.

Rule #1: Time Is the Biggest Barrier, Not Budget

We all like to blame the budget when a deal falls through. But the real culprit is time. You’ve got to put yourself in the buyer’s shoes. Before you reach out, ask yourself: “What’s this person’s day like? How much time are they losing in their role, and how can I help them get it back?”

Why It Works: Budget’s easy. You can always play with numbers. But when you show someone how you’ll save them time? Now, that’s sales magic.

Rule #2: Take Fewer, Better Swings

The internet made sales easier in some ways. But it also made the noise deafening. Everyone can email anyone, and that’s a problem. Sure, you could blast your message to a list of 10,000 prospects, but where’s the quality in that? Find your niche, get creative, and focus on fewer, better touches.

Example: I started a podcast to engage potential clients in a more unique, personal way. I also throw contests to keep clients involved. Handwritten notes? They go a long way. You’d be shocked at how effective snail mail is in this digital age. We even send customized gifts to clients every year.

Why It Works: In the Attention Economy, you can’t just ask for attention—you’ve got to earn it. And when you go the extra mile, people notice.

Rule #3: Know Thy Competition

Sales calls aren’t about you—they’re about the buyer. So why not start your next call by educating the buyer about their competitors? If you’re selling to a car company, for example, research the other car brands and weave that into your pitch. Help them look smarter in front of their bosses.

Why It Works: Everyone has a boss. Including your buyer. When you arm them with competitor insights, you’re helping them shine. And when they look good, they’ll be more likely to take your proposal seriously.

Rule #4: Allow Others to Watch You Work

You can’t see yourself in action—at least not from the right angle. So, why not invite someone you respect to watch you work? Whether it’s a mentor or a fellow sales pro, their feedback can be invaluable. Like a tennis pro watching your stroke, ask someone you admire to sit in on a sales call with you and offer you notes after.

Why It Works: You’ve got to get comfortable with being observed. When you do, you’ll unlock new levels in your sales game.

Rule #5: Master the Art of the Subject Line

Think of the subject line as your modern-day handshake. You’ve got a split second to make a memorable first impression. Tall order, but trust me, it’s worth the extra effort. Here’s my trick. Write the email first, then tackle the subject line last. Brainstorm as many options as your noggin can churn out, then narrow it down to the one that feels right. The goal? Strike a balance between grabbing attention and not being annoying.

As Luke Sullivan put it in his famed advertising book, Hey Whipple, Squeeze This, “To those who defend the campaign based on sales, I ask, would you also spit on the table to get my attention?” A bit dramatic, sure. But you get the point. Grab attention, but don’t cross the line into obnoxious click-bait territory.

Why It Works: If you can stand out in an inbox, you’ve already won. Period.

Tiger Woods said it best. “No matter how good you get you can always get better, and that's the exciting part.”

Keep sharpening those sales tools and stay ahead of the game.