How do you differentiate yourself without projecting your own biases upon your buyer? Stop and put yourself in your buyer’s shoes to avoid sales mistakes, that’s how.

In this episode of INSIDE Inside Sales, Darryl joins forces with Catherine Robles, Director of Sales at VanillaSoft, a sales expert and a champion of women in sales, to help you identify and avoid some of the most common rookie sales mistakes. The two of them will talk about bridging a generational gap between buyers and sellers, understanding your audience’s perspective and adapting to their preferences but not losing your voice in the process, and the importance of having fun. Listen to the show and learn how to zoom past all the obstacles and unlock your inner sales rockstar.

Sales mistakes to avoid

Avoid Sales Mistakes: 5 Traps That’ll Prevent You From Succeeding in Sales


  • There’s no shortage of advice and strategies available to sales newbies: how to find prospects, how to approach them, what to say… But learning what not to do might be even more useful for those beginning their career in sales.  
  • VanillaSoft’s Director of Sales, Catherine Robles, is an expert sales leader who shares valuable insights on how to avoid certain common pitfalls –– particularly the “traps” we can fall into even when we’re trying our best.
  • Catherine discusses why knowing yourself is crucial, the importance of tailoring your messaging to individual prospects, why shortcuts are a cop-out, and two more rookie mistakes to watch out for.

In sales, we spend a lot of time talking about how, why, when, and even where people buy.

Understanding a buyer’s psychology is, of course, one of the best ways to develop effective sales strategies. But it’s an imperfect science. What we do know for sure, 100% of the time, is, as the saying goes, people buy from people

“This is a human interaction at the end of the day,” says Catherine Robles, VanillaSoft’s own director of sales, who knows that real, meaningful relationships are what makes a business –– any business –– great, instead of merely good. 

But if you’re just starting a career in sales, building those relationships can seem daunting. So can a lot of other things, like sifting through the glut of sales guidance that sometimes conflicts with what we think we know.

That’s why Catherine’s input is invaluable for anyone who’s learning their sales craft. 

She’s an expert in the industry, a dedicated champion of women in sales, and my co-host on my other favorite podcast, The Drive. 

In an episode of INSIDE Inside Sales, Catherine talks about how to identify and avoid five of the most common traps that befall rookies in sales, including how to adapt to the buyers’ preferences without losing authenticity, why learning is earning, and the importance of having fun along the way.

Trap #1: Losing yourself instead of finding your voice

There are scads of sales advice, opinions, and methodologies out there –– heck, you’re looking at a phenomenal resource for it right here! Plus, chances are the leaders in your organization have refined the sales process, written scripts, and generally laid out everything they want you to do, from initial research to negotiating terms. 

But the truth is there’s no one way to deal with every buyer. There’s no magic words you can say. So don’t become so fixated on checking every box, so to speak, that you can’t find your own voice.

“Don’t lose yourself trying to follow all the best practices or adhering to a framework to the dot,” says Catherine.

So be yourself –– your best self. That starts with knowing who you are. 

You might ask: Um, what if I’m still figuring that out? 

The best way to start is by outlining your values –– and what makes you special, Catherine suggests.

Talk to the people around you. Seek feedback from your friends, co-workers and family –– but not your mom. (She’ll probably just tell you you’re perfect.) 

Keep those qualities in mind as you progress in your career, especially as you absorb other personalities, schools of thought, training, and coaching. That way, you’ll always keep it real –– and know what to play up to ensure you’re remembered.

Trap #2: Using a one-size-fits-all approach

Authenticity is crucial, and it will make your life much easier if you’re not putting on an act when you’re doing your job. So (as the advice above would suggest) do what comes naturally to you. 

If you were the class clown, don’t be afraid to use humor. If you’re a sports nut, engage prospects (providing they’re interested) on their home team’s playoff chances. 

It’s important, however, to be mindful of the recipient of your messages and adjust your communication style (and/or method) according to your audience. If you’re talking to a veteran CEO, you might be a little more formal than you would if you were talking to a peer. Remember, when you interact with potential clients, you’re the face of your company. 

Likewise, you shouldn’t project your biases onto a prospect. If you’re a Gen Zer who communicates with most of your colleagues on social media, don’t assume that the elder Millennial buyer you’re targeting will respond to Twitter DMs. 

It can take time to strike a balance between your gregarious, happy-hour persona and your cold-call-to-the-C-suite countenance. But the more confidence you build, the easier it will be to tailor your approach while still being 100% you.

Trap #3: Forgetting to have fun

Sales is a tough job. And it usually gets tougher as you climb the career ladder, because the stakes are higher. 

No matter where you are in your journey, though, “you will have days where you literally just want to sit down and cry for hours,” says Catherine. But (hopefully) that’s a rarity. 

Overall, “it’s a very fun profession,” she adds. “It’s a fun environment, and you should always look for a way to enjoy it.”

So look for things you can implement in your daily routines to keep your energy level up –– and bounce back from the inevitable challenges. You spend a third or more of your life at work, and it’s too short not to have fun as much as possible.

A serious bonus: When you’re having fun, you’re a pleasure to be around. Others will have fun, too. Which brings us back to people buy from people –– it’s arguable we can add to that. 

People buy from people they like.

Trap #4: Resting on your laurels

Once we get in the groove of selling, we feel more confident… and then we get comfortable.

We think we already understand everything. We assume there’s nothing left to refine.

But always keep learning is perennial advice for a reason.

“It’s always good to have your mind as open as possible for new and different ways of doing things,” says Catherine. “And when you change little things, you are challenging your brain as well.

So make it a point to invest in yourself. Don’t wait for (or expect) your company to do it for you. Expanding your knowledge will go with you no matter where you make your home or perform your role.

That being said, Catherine always counsels people to know: “You will hear a lot, but you are you.” 

It’s easy to be dazzled by someone’s success using a particular sales technique, but it doesn’t mean you’ll have the same experience. Plus, it takes time to achieve a high level of success. 

Or maybe what you learn isn’t as applicable to you as it is for others, but it’s still good to know. 

So be sure to share what you learn. If you can help someone, do it. Don’t hoard knowledge. It’s bad karma.

Trap #5: Searching for hacks

We get it: It’s tempting to put in the least amount of effort possible, to cut corners to reach a goal as quickly as you can. 

But… doing things well usually takes time. So don’t waste time looking for hacks. Avoid anything that suggests you might get where you want to go faster, without really learning anything along the way. 

Sure, there are cool productivity tips you can try, but there’s nothing that can replace the work it takes to grow and develop in your career. 

“When you’re young, because you want to prove yourself, you try to grab successful stories from others to try to replicate them immediately. Take your time to really understand what is happening,” says Catherine.

The biggest trap of all, she adds, is getting short-sighted, thinking, this is what they’ve given me. I’m just going to do my best, and that’s all that matters. 

Remember, “this is your journey,” she says. “Don’t forget where you want to be.”