Solutions to Your Biggest Sales Challenges

Solutions to Your Biggest Sales Challenges

No one ever told me that being a successful salesperson meant I needed to train as a locksmith. 

They probably didn’t tell you either—frustrating, right? 

But the truth is, on the hardest days, that’s exactly what the sales industry feels like. When I can’t make sales, it feels like I’m running around with an ever-changing set of keys that never seem to fit a world full of ever-changing locks. 

I might have all the right prospects lined up, but if I can’t figure out the perfect way to unlock their trust? It doesn’t matter. If I can’t get through to a prospect, they transform from an exciting potential opportunity to a crushing defeat. 

If you feel like you’re trapped out in the cold with a set of keys that just won’t fit…you’re far from alone. This past year, the average closing rate for most businesses and industries stayed below 30%. (1) That’s a lot of unopenable locks. 

Luckily, there are many ways to attack your sales challenges and crack the code on conversions. Let’s dig in.

What are the challenges of a sales team?

There are endless challenges when it comes to sales, but let’s take a closer look at the top 9 sales challenges facing frustrated salespeople in 2023.

Sales Challenge 1: Competing for prospects

Put yourself in your prospect’s shoes for a moment. You’re wandering around your office one day and you say to yourself, “Huh, I could really use a new filing cabinet.” Suddenly, the room goes dark as a swarm of salespeople surround your floor-to-ceiling windows armed with the latest filing cabinets. You try to escape through the door, but you can’t; they’re waiting on the other side. By the time you catch your breath, you don’t even want a filing cabinet anymore—you just want to be left alone.

That feeling of overwhelm is what you’re actually up against when you try to out-compete your competitors. You know you’re not the only one vying for your prospect’s attention, so take that into consideration. You don’t need to use hard selling tactics to get ahead—you just need to know your stuff. Be prepared to answer prospects’ questions by: 

  • Keeping up to date on the inner workings of your products 
  • Gathering and preparing sales enablement tools like demos or case studies
  • Staying informed on trends in your prospects’ industries 
  • Strategically timing your outreach to stay relevant, but not overwhelm your prospect

The best thing you can do to outshine your competitors isn’t yelling louder than them—it’s being the most informed, helpful, and communicative. 

Sales Challenge 2: Lack of time

If you feel that your key challenge is that you just don’t have the time to knock on doors? You’re probably right. It’s easy to dismiss someone saying “I don’t have the time!” as lazy or bad at time management. But that’s not always the case in sales, and it’s certainly not always your fault. 

The average salesperson in 2022 only spends about 33% of their day talking to prospects—and it’s not for lack of trying. (2) Here’s what the rest of your time is being eaten up with: 

  • Email writing (21%) 
  • Data entry (17-20%) 
  • Lead generation and qualification (17%)
  • Internal meetings (12%)
  • Scheduling (12%) 

Sure, some of these pesky activities are necessary. But good lord, do you really need to spend 17-20% of your day entering data? In 2022?! Assuming you work eight hours a day, that’s 416 hours a year. Entering data

We can do better than this. 

Budgets may vary from company to company, but so do the prices of sales automation software. If you want more time, automate tedious tasks and get your humans back to human interaction. 

Sales Challenge 3: Getting a prospect to respond

Obviously you can’t force anyone to get back to you, even after 100 calls and emails. However, you can try and improve your odds by reaching out through appropriate methods. If you’re running around with a skeleton key to every ancient castle in Europe, it doesn’t matter how experienced you are: you’re never going to open a smart door keypad. 

Millennials and Gen Z increase their buying power every day. Appealing to and communicating effectively with millennials is particularly crucial nowadays; this generation currently makes up the majority of purchase decision makers in major companies. (3) 

Another defining feature of these generations? They hate phone and email spam. Don’t misinterpret this preference—these generations are not anti-social. In fact, they’re some of the most social humans on the planet. However, spam calls and emails are now so prevalent and aggressive that cold calling is actually more likely to turn away these buyers than convert them. 

The key to getting a response? Social media. 

Love it or hate it, social media sales work. That’s why social media advertising sales have already jumped 4 billion dollars since last year. (4)  If you want responses from prospects, you need to reach out to them where they’re most likely to respond. 

Sales Challenge 4: Prospect reluctance

I wish I had something more reassuring to say here. But in all honesty, prospect reluctance is extremely smart on their end. There are so many different companies vying for our money and our loyalty these days that caution is often the smartest buyer decision. It’s no wonder that 60% of customers say no four times before saying yes. (5) They have to be sure they’re making the right decision. 

Of course, the logic of a challenge doesn’t make it go away, so how do you move hesitant buyers through the pipeline? The obvious answer is persistence, but I’d argue there’s a little more to it than that. You have to continue outreach, certainly, but you also have to accomplish something with each piece of that outreach.

Think about the following during your outreach messages: 

  • Am I presenting any new information? 
  • Am I addressing any of my prospect’s previous concerns? 
  • Why am I sending this message? Is it just because of time? If so, can I find a better reason? 

By the way, when crafting messaging, my personal favorite strategy is The Change Curve. It’s a game changer. 

Sales Challenge 5: Inability to handle rejection

Metaphor is almost unnecessary for this one. Rejection feels like someone slamming a door in your face. It hurts. Unfortunately, rejection is part of the sales package. The trick to this sales challenge isn’t eliminating rejections—it’s learning how to navigate them so that one slammed door doesn’t keep you from knocking on the next one. 

Part of that process is experience and building a thick skin, but the more important part is separating your work from that rejection. Sure, there are soul-crushing times when losing a sale is a direct result of something you did. But more often than not, rejections simply happen. It doesn’t matter how much prep you did, or how kind you were, or how snazzy your product was—you can’t make someone buy something they don’t want. 

The best thing you can do, especially if you’re a sales manager, is create a team understanding that rejection happens. When rejection becomes normalized in the workplace, nobody feels like they’re the only one failing. And that makes it so much easier to pull yourself back up, brush yourself off, and keep plugging away.

Sales Challenge 6: Training and coaching

This one’s primarily for the sales leaders, so if you’re managing a team, listen up. It is partially the responsibility of each salesperson to reach out and take classes or ask questions, but individual reps cannot provide their own training. 

If you are demanding more open doors from your sales team, then you need to provide new keys. It’s that simple. Every sales person is only as good as their knowledge. If you launch a new product, but don’t train your sales staff on it, it’s not on them when they fail. 

Many sales leaders or companies shy away from training because of the cost, but I can tell you from experience that the money you spend on training or coaching is nowhere near the money you will lose without those services.

Sales Challenge 7: Losing track of deals

Let’s say you have 50 identical sales opportunity doors in front of you. You knock on each door once and eliminate 10 doors. You then have 20 doors that want second knocks immediately and 20 that want more time. How do you remember which is which? 

It’s a trick question, because you don’t—at least not in your head. 

No one could possibly be expected to keep track of hundreds of prospects without help. Not only is it not possible, it’s not a great use of your time. 

That said, most salespeople don’t have the tools they need to accurately track their deals through the sales pipeline. The best way to tackle this challenge is by instituting a user-friendly CRM. Much like a last-minute grocery list, it’s best if you just write it all down. 

If you don’t have access to a CRM and it’s truly not in the budget, start with a simple spreadsheet. Any amount of tracking is always going to be more beneficial than not tracking at all and banging on random doors throughout eternity. 

Sales Challenge 8: Lack of prospects and leads

What if your challenge isn’t getting through doors, but finding doors to begin with? This is actually a very common sales challenge. The problem with getting through one door is that it doesn’t guarantee another door behind it. It’s unsurprising that many salespeople get to the end of the pipeline, pop the champagne, and then realize that they forgot to line up their next batch of leads. They then have to spend hours scouring and qualifying before getting back on track. 

How to avoid it? 

There are a few different schools of thought for this one. The easiest by far is automated lead generation, but if you don’t have access to that technology, start with delegation. Not all salespeople are equally strong in every single aspect of the sales process. If you have people who excel at closing, put them on the front lines! If you have people who are great at introductions, but not necessarily great at sealing the deal, have them prospect. 

Remember, unless you really are a solo salesperson, you can always attack a single door with a multi-key strategy.

Sales Challenge 9: Answering prospect questions

Alright, let’s look at our last sales challenge: answering prospect questions. What if you’re making progress with a door, but all of a sudden, it requires you to answer a riddle to pass? Despite your previous efforts, I have to tell you, the wrong riddle answer will lock the door forever. 

Consumers are highly informed these days. Most of them do research before ever approaching companies about large purchases and many will even do their research on small day-to-day buys. When they ask you a question, you need to be at least as informed as they are—if not more. 

You can’t anticipate which questions your prospects might ask, but you can have as many answers ready to go as possible with a dynamite sales playbook.

How do you handle sales challenges?

We’ve covered a few different ways to handle different types of sales challenges, but what about key themes to remember when approaching all challenges? Let’s take a second to hear from a few other folks on the subject. Everyone in sales—from the freshest salespeople to the most respected CEO—experiences sales challenges. Aside from hiring a certain type of consultant, Here’s what a few of the experts have to say about the sales struggle:

Industrial experts’ views on sales challenges

“Before LinkedIn and other social networks, in the sales world, ABC stood for “always be closing”. Now it means “always be connecting.”” — Jill Rowley, Sales investor and advisor for over 22 years (6)

I love this quote from Rowley because it simplifies the core of many sales challenge solutions—just connect. We’re seeing the rise of social sales for a reason. If people didn’t crave connection in their capitalism, we wouldn’t be having this conversation. In 2022, a connected and communicative sales person is worth their weight in gold, no matter the product or the price. 

“Don’t wish it was easier, wish you were better. Don’t wish for fewer problems, wish for more skills. Don’t wish for fewer challenges, wish for more wisdom. For things to change, you have to change.” — Jim Rohn, Business expert and analyst (7) 

Sure, Jim Rohn can be a little intense, but he’s not wrong. One of the biggest pitfalls I see salespeople fall into is wishing a challenge would disappear rather than looking for an actionable solution. I understand that desire, don’t get me wrong. Unfortunately, customers don’t work like that. The only way to open a door without unlocking it is to break it down—and that’s a crime. Instead, put that desire and energy into finding a new key.

“No amount of pre-call planning is going to help close business if you aren’t able to ask for what you need in order to conduct business. It’s a classic case of working on the wrong end of the problem.” — Colleen Stanley, President of SalesLeadership (8)  

Our last piece of expert advice packs a solid punch—especially for sales leaders. Despite visions of the solo traveling salesman, today’s sales industry is very much a team sport. And ultimately, the teams with more organized resources will always come out on top. It doesn’t really matter if you yell at your sales team to close more sales if you don’t give them the tools to do so. Similarly, if your sales team is struggling, but doesn’t tell you what they need, you can’t help them improve. Communication and sales enablement go a long way towards addressing all types of sales challenges.

Overcoming a sales challenge example

Alright, it’s time for my favorite part: tackling a sales challenge head-on. First, we’ll dive into my favorite strategy for building a sales challenge key and then we’ll look at a real-life example of engaging and influencing a consumer. 

First up, let me introduce you to the best sales challenge strategy on the market—the change curve. 

What is the change curve? 

OK, let’s start with the basics. According to Mind Tools (9), the Change Curve is a model designed to help you understand the stages of personal transition and organizational change. Here are the four stages and how people react at each one:

  • Status Quo: People react with shock or denial. Essentially, they want everything to remain how it is.
  • Disruption: Unfortunately, the next stage isn’t any easier. Here, they are angry and fearful. People worry how any change will affect them.
  • Exploration: Next, people become accepting. They know change is inevitable.
  • Rebuilding: Finally, people become engaged. They are excited to rebuild and see how this new change can improve their professional lives.

Now, you need to understand there is no level of employee immune from this. Resistance to change can come from entry-level employees to the C-Suite.

How to address the stages? 

So, how can you prepare yourself as a salesperson for these varying emotions? You need to empathize and re-evaluate the four stages from your prospect’s perspective:

  • How will your service affect my job? Will I be good at it? Will it make me succeed or fail?
  • Who is this person to come in here and tell us what we’re doing is wrong?
  • OK, so maybe we can do things better, but I don’t have the time to learn this brand new way of doing things.
  • Actually, this will make my job so much easier. But how much will it cost?

If you can prepare your objection-handling for all these stages, emotions, and thoughts, you’re ready to use the Change Curve in your sales technique. But…how does this relate to Chick-fil-A?

Establish a baseline

First, you need to identify what your prospect’s current process/method is. After you’ve established the baseline of what they use, have tried, and what they know, you can then use this information to expand their worldview.

Recently, I was treating my daughter to lunch at Chick-fil-A. We sat at our table, when a woman walked by and said, “Isn’t this the best chicken you’ve ever had?” Now, here’s where the Change Curve becomes effective. I asked, “What makes it so great?” She talked to me about the texture, taste, mouth feel—I guess she was a foodie who loved fast food!—and the seasoning. (She’s in the status quo phase.)

Introduce a point of reference

Next, you need to introduce a point of reference. Ultimately, in sales it’s your product. In this case, I asked, “Have you ever had Daisy Mae’s in New Orleans?” If they say yes, your life just got a whole lot easier. If they say no, you explain how it’s the best fried chicken they’ll ever experience. You use your silver tongue to paint an idyllic picture of everything about this chicken, from the ambiance to the taste to even the napkins. Then, you question, “Is this something you’d be interested in trying?” Expect to hear a lot of excuses. (This is the disruption phase.) “I can’t afford to go to New Orleans.” “We never travel outside of the state.”

But, your goal is to get them the best fried chicken ever. So, handle objections politely and point out how they can have the best fried chicken ever if they really want to.

A bigger world 

You’ve now established there is a bigger world out there besides Chick-fil-A. (Personally, I love Chick-fil-A, so no disrespect to them.) For sales, you’re showing your prospect that a solution exists to their problem, and they can get it if they want. (This is the exploration stage.) With the woman, I made her contemplate what it was about Chick-fil-A she loved so much. Was it the taste? Is it the convenience? Or, is it the fear of having a bad experience somewhere else?

Then, it’s a matter of giving your prospect clear paths on how they can reach this solution. For her, I gave her directions to the poultry paradise in case she ever was in New Orleans. The key is, you want to make it user-friendly for them to get what they need. So, keep the lift as light as possible.

Use your worldview

Again, your unique experiences as a person will help you become a master salesperson. Who would have thought being a jazz musician would prepare me for a career in sales? But, it did, and your life has too. Do your research and find ways you can enlighten your prospect. Use analogies and metaphors—like I’ve been doing this whole time—to get people to understand. If you become a trusted resource to your prospect, you can create desire with or without scarcity.

I went into Chick-fil-A a week after I took my daughter there, and I saw the same woman. I told her about this other place I tried nearby. I explained how it’s good, but it doesn’t compare to Daisy Mae’s. She said she tried it as well, and thought it was good. And, she was intrigued how if she held the new place in high regards, then how good must Daisy Mae’s be?

A month later, I was back in Chick-fil-A and my friend was there. She loves Daisy Mae’s.

Build a sales challenge solution with a savvy sales consultant 

You can always get better at outsmarting the world’s sales challenges through trial and error, but wouldn’t you rather avoid the error part? The fastest way to hone your sales team’s skills is to work with experienced sales consulting

Contact my team today and unlock the skills you need to pick the toughest of locks.  


  1. Hubspot research, 2022,
  2. Zippia research, 2022,%2C%20and%2012%25%20scheduling%20calls.
  3. Gen Z’s Buying Power, Forbes
  4. Hootsuite research, 2022,big%20on%20social%20media%20ads.
  5. Invespcro research, 2022
  6. Jill Rowley, Sales investor and advisor
  7. Jim Rohn, Business expert and analyst
  8. Colleen Stanley, President of SalesLeadership
  9. Mind Tools, The Change Curve