5 Common Sales Challenges and Overcoming them

Bryan and Kevin Ruef at Orange County Celebrates Entrepreneurs

When it comes to sales, there are many common challenges (regardless of industry). Although some of these challenges are easier than others to overcome – just remember that time will always make things easier. Here are some common sales challenges and how to overcome them. 

Challenge #1: Lack of Confidence

You can prepare all day long to sell your product, but if you don’t have confidence in your sales ability or what you are selling, you probably aren’t going to get far. Even if you aren’t 100% confident, there are some things that you can do before and during a sales call/meeting that can help you feel ready to take on any objection. 

Make sure that you are prepared before your call. Do your research on the company, on what you are selling. The more prepared you are for potential objections, the more confident you will be when they actually come up in a meeting. Think about what questions might come up and how you could tackle those questions. 

Most sales people have heard the saying “smile and dial,” and it’s true that smiling while talking can make you sound more appealing to customers. Consider getting a small mirror and speaking into the mirror when you make calls. Another option is printing out a picture of your favorite comedian. Whenever you see the picture you’ll smile – so just keep the picture around when on your calls. 

Challenge #2: Making a Good First Impression

A sale often begins with a firm handshake, good eye contact, an intriguing phone pitch, or even an eye-catching subject line. In person, it only takes a few seconds to make a lasting impression. One study even shows that it might be as quick as “a tenth of a second to form an impression of a stranger from their face, and that longer exposures don’t significantly alter those impressions” (Source).

So, how do you make a good impression and get your point across in a matter of seconds? Before meeting, calling or emailing your prospect, make sure that you have done your research. Look on their company website for updates, articles and blog posts. Search the internet for news articles about their company and what other companies in their industry are doing to grow and innovate. Make sure that you understand your audience. What is important to a Customer Service Representative is going to be different from what is important to the CEO. Focus on how your service can help your prospect, and why you reached out to them. Did you see recent growth in their company and understand the need to scale with that growth? Are they spending too much time using outdated manual processes and could they benefit from your software? Your pitch will determine if your customer is going to keep talking, stay on the line, or respond to your email. Show that you care about their time, and provide real value.

Challenge #3: Not Hearing Back

You’ve got a lead, now what? Before having a conversation with your potential customer, think about what you want the outcome of the meeting to be. Make sure to ask open ended questions.

If you can’t get a hold of your sales leads – KEEP TRYING. It’s critical to stay consistent with your potential customers. A recent study found it takes six calls to win a sale (source). Although it can be disheartening to struggle on the phones, another study found that 50% of leads never get a second cold call from salespeople (source). Use your CRM or spreadsheet to keep track of your interactions (and attempts) with leads to keep things organized. 

Challenge #4: Keeping the Deal on Track

The worst thing is when you have a deal in your pipeline, and it keeps getting pushed back because new issues arise. To avoid push back later on, make sure that you are fully transparent with the customer. Don’t be afraid to get the answers you need up front.

Is the person you are speaking with the main contact or decision maker? 

Are there other people in the company who you will need to coordinate with to make a final decision? 

Will those people need to see a demo, a presentation, or look over the contract? 

The sooner you figure this out, the better off you will be when it comes to closing the deal.

What is your customer’s timeline? Do they have a timeline at all? Once you get a timeline down, you will know how serious your customer is about buying and you won’t waste time trying to close a deal if the prospect has no intention of making a purchase in the near future. If they don’t have a timeline, consider re-evaluating their need for what you are selling or the features that you are pitching.

Does your customer have a budget? If possible, get an idea of this dollar amount. In doing so, you will know if your product is something the customer can realistically purchase, or if it’s just something nice to consider.

Challenge #5: In sales, does “no” always mean no?

When it comes to sales – “no” doesn’t always mean no. For most people, we’ve been programmed over the years to shut down when we hear “no.” When it comes to sales, a simple “no” can mean multiple things. To a seasoned salesperson, a “no” just means “not now.” Don’t be afraid to probe further to understand how you can provide value to your customer. 

Consider questions like:

  • Why not?
  • Is there someone else you think this would help?
  • What would make something like this interesting for you?

It’s important to pick up on the vibes being given from your customer, but try not to accept a simple “no” without some follow up questions. Perhaps you just haven’t found the right way to provide value (or maybe it’s just not the right time). Just remember, “you miss 100% of the shots you don’t take.”

Contributed by Kevin Ruef. As an OC local and UCSB alum, Kevin co-founded 10-8 Systems after exceeding multiple companies’ sales records (both domestically and internationally). With more than a decade in sales, his experience ranges from B2B, B2G, and B2C. Since the company’s start in 2019, Kevin is responsible for business development, strategic partnerships, and business operations. 

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