Lessons I’ve Learned in Sales: My Takeaways So Far

Sales can be a wild ride, full of ups, downs, and everything in between. Coming from coaching basketball, where recruiting had its own kind of sales, diving into B2B sales was a big shift for me, but I quickly fell in love with it. I am no Sales Expert but over the years, I’ve picked up some key lessons that have made a big difference. Whether you’re new to sales or just looking to sharpen your approach, these insights might hit home for you.

Listen More Than You Speak

• Honestly, this one’s huge. It’s easy to get caught up in trying to pitch or sell, but the real magic happens when you stop talking and start listening. Clients will tell you exactly what they need if you give them the space.
• Tip: Make it a habit to ask open-ended questions and really listen to the answers. It’s amazing how much you can learn when you’re not the one doing all the talking.

Sell Value by Solving Pain Points

• In B2B sales, it’s not just about the product—it’s about how you solve a specific problem for your customer. Pinpointing the pain points for each prospect and customizing your pitch to show how you can address those needs is key. Every industry has its own unique challenges, so what works in one might not work in another.
• Tip: Dive deep into understanding your customer’s business. Tailor your approach to highlight how your solution specifically addresses their pain points, not just the features of your product. The more relevant you are, the better.

Relationships Over Transactions

• At the end of the day, sales is about people. Building genuine connections goes a long way, and often, it’s those relationships that lead to long-term success. A quick sale might feel great, but a loyal client is gold.
• Tip: Don’t just reach out when you need something. Stay in touch, share useful info, and be there for your clients even when it’s not about closing a deal.

Prospecting is Key

• One of the biggest mistakes in sales is blasting out emails to anyone and everyone. Effective prospecting means finding the right people—the ones who actually need what you’re selling. It’s about quality over quantity.
• Tip: Do your research and build a targeted list. Look for decision-makers or the right contact within the company, and tailor your outreach to them. It’s way more effective than a generic, mass approach.

Embrace Rejection and Keep Going

• Rejection is just part of the game. It’s easy to get discouraged, but the key is to keep pushing forward. Sometimes a “no” is just a “not right now.”
• Tip: Instead of taking it personally, use each rejection as a learning opportunity. What could you tweak for next time? It’s all part of the process.

Have a Follow-Up Strategy - ?This is VERY Important in my View?

• Following up is where deals are often won or lost. It’s not just about making the first contact and hoping for the best; it’s about persistence and perfect timing. In my experience, 98% of my initial outreach emails don’t get a response. But here’s the thing: most of my engagements happen because I keep following up and never give up.
• We have a client now that took me six months to land, but I stayed consistent with my follow-ups. You never really know what’s going on with that potential client—they could be on vacation, swamped with work, or maybe they just missed your email. The key is to stay on their radar. Persistence truly pays off because you never know when the right time will be.
• Tip: Set reminders and have a solid follow-up game plan. Whether it’s a quick check-in, sharing a relevant article, or just a friendly touch base, the goal is to stay on their radar without being overbearing. It’s all about being helpful, not pushy. One thing that’s worked well for me is sending an email and then following up with a LinkedIn connection request or message. It adds a personal touch and another way to connect, making it harder for you to slip through the cracks.

Data is Your Friend

• We’ve got so much data at our fingertips, and it’s an absolute game-changer. Whether it’s tracking your pipeline, diving into customer behavior, or just keeping tabs on your own performance, leveraging data helps you make smarter, more strategic decisions. Tools like Apollo.io and Crunchbase are my go-tos—they give me the insights I need to target the right prospects and stay ahead of the game.
• Tip: Regularly check in on your numbers. It’ll help you see what’s working, what’s not, and where you can improve.

Stay Adaptable

• Things change fast—new tools, new trends, new challenges. The best salespeople are the ones who can roll with the punches and adapt to whatever’s thrown their way. This is especially true in B2B, where each industry has its own dynamics.
• Tip: Keep learning. Whether it’s new tech, a fresh strategy, or just a different way of thinking, staying flexible keeps you ahead of the curve.

Personalization is Key

• Nobody likes a cookie-cutter, generic pitch—especially if your clientele includes other sales professionals. They can spot a copy-and-paste job from a mile away. The more you personalize your approach, the better your chances. It shows that you’ve done your homework and are genuinely interested in solving their specific problem. Trust me, I get a ton of those generic emails myself, and they usually end up unread. If you want to stand out, put in the extra effort to tailor your message. It makes all the difference and can be the key to getting that crucial first response.
• Tip: Take the time to customize your outreach. It doesn’t have to be a lot—sometimes just mentioning something specific about their business or needs can make all the difference.

At the End of the Day

Sales is all about learning and evolving, and honestly, I’m still learning every single day—1000%. I don’t think you ever really stop. These are just some of the lessons that have stuck with me, but everyone’s journey is unique, especially when you factor in the differences across industries.

I’m curious—what’s been your biggest lesson in sales?