After nearly 20 years in sales, I've seen it all. I've closed deals with some of the biggest names in business, and I've also had my fair share of rejection. But through it all, I've learned 5 simple things which apply to nearly any sales role:

I've had prospects tell me no more times than I can count. But I've also had prospects tell me no 5, 10 times before saying yes. So if you're ever feeling discouraged, remember that persistence is key. Sounds simple, but it’s true.

People buy from people they like and trust. And one of the best ways to build rapport with a prospect is to tell them a good story. So next time you're on a sales call, be sure to have a few stories up your sleeve. Or better yet, be able to tell a story versus simply talk products and features. Prospects will remember a great story how product X saved a business unit from missing a critical deadline, versus how efficient it this feature makes your team.

It's not enough to just talk about your product or service. You also need to listen to what your prospect is saying. What are their pain points? What are their goals? Once you understand their needs, you can start to tailor your sales pitch accordingly. This starts with good discovery questions.

Sales is a grind, especially right now. So it's important to have a sense of humor to keep yourself sane. If you can make your prospect laugh, you're already halfway there. If you can integrate humor into you’re selling style, you’ll stand out. Prospects will have a positive memory of your last interaction if you leave them with a smile on their face.

There will be times when you feel like giving up. But if you want to be successful in sales, you can't give up. Just keep pushing forward, and eventually you'll reach your goals. This shouldn’t be confused with persistence.

Number four is most important. It keeps you balanced and sane. Not just at work with your peers or leaders, but also your prospects. Humor is human. People like dealing with people, especially those they like and trust.

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In a recent call, a prospect answered with a name other than what my CRM showed (let’s call him Bob). If I hit my quota the way Sales Ops “nails” their sales data, I’d be out of a job:

“Shoot, I’m sorry. I’ve got the wrong number man, sorry to bug ya.”

“Well, that’s my legal name, but I go by Bob.”

“Oh, well in that case I’m glad to connect with you. I was wondering if you can help me out with a note I have about your account?”

“That depends, is this a sales call?”

I paused for a second…I’ve always been 50/50 on this because even though my goal is to sell something, the point of the call might be to gather info or find a contact.

“Eh, to be blunt, I’m not sure. Mind if I take 60 seconds to tell you why I was calling you specifically, and then you can tell me if it makes sense to discuss or if there is someone else I should talk to?”

“Go on…”

I ended up uncovering a critical project this team was working on and it was set to go live by the end of the month. Anything not connected with this priority was immediately shoved to the back burner.

Did it result in a massive mega deal? No, but it might have. Having a sense of humor with such a blunt question helped to set a touch point for a meeting, which is half the battle with any prospecting call.

I hope you enjoyed these insights into the world of sales. If you want to learn more about how to be successful in sales, be sure to subscribe to my newsletter. I aim to share tips, tricks, and frameworks I’ve learned over my career, and most importantly where I learned them from, so you too can enjoy a fruitful career in sales.

Join me next week to look at ways to demonstrate sales skills to prospective hiring managers and make yourself stand out from the rest.

Thanks for reading!

Jason