Top 10 Sales Challenges

Selling has never been easy, and it seems like the sales challenges continue to grow. Here are the top 10 challenges you must overcome to succeed in sales:

1. The legacy approach
2. Uncertainty
3. Poor time management
4. Acquiring a first meeting
5. Creating value in a first meeting
6. Being ghosted
7. Accessing the necessary stakeholders
8. Controlling the process
9. Client-stalled opportunity
10. Competing client priorities

Sales Challenge 1: The Legacy Approach

There may be no greater challenge than the legacy approach to sales. This is what we mean when we say “sales is broken.” From the self-oriented "why us" introduction to the desperate questions designed to pitch a product or service as a panacea to a client’s “problems,” the old approaches no longer create value for clients.

People still cling to these approaches because they worked for a long time. But legacy methods are also being sustained by sales leaders who are more comfortable when their teams sell the way they used to.

Sales Challenge 2: Uncertainty

Our accelerating, constant, disruptive change (ACDC) has created an environment of uncertainty. The 21st century started with a recession that was quickly followed by 9/11, and it hasn't stopped providing challenges. In less than 25 years, we’ve also faced a once-a-century pandemic, runaway inflation, and a looming threat of a recession.

When people are uncertain, they often choose to wait out a storm. This is a needs-based selling problem. Clients who want to avoid making a mistake may engage with a salesperson but avoid moving forward until they believe it is safe. In times of uncertainty, this challenge rules many clients’ ability to make the changes they need.

Sales Challenge 3: Poor Time Management

The technologies and tools that were supposed to improve productivity, including some sales automations, seem to make us less productive. Our many screens demand our attention, whether it's the distractions of social media or the time spent on technologies unrelated to creating or winning opportunities. The more time a sales force spends on non-sales activities, the less time there is to sell. Time management is a real sales challenge.

The only two things sales leaders should prioritize are creating new opportunities and winning deals. You need guardrails, like call blocks, and strong priorities to ensure your time is spent on sales. Here are five rules to improve time management.

Sales Challenge 4: Acquiring a First Meeting

Whether it is email, a social media platform, video messaging, or text, every medium has been pitched as something the sales force must use to succeed. One reason salespeople have trouble getting a first meeting is because they use something other than the good, old, reliable telephone—the only synchronous medium available.

The second reason salespeople have trouble getting a first meeting is that their value proposition isn't compelling enough for a contact to give the salesperson their time. You can lay the blame on the legacy approach, in which salespeople asked to introduce themselves and their company. Unless you have a compelling value proposition, meetings will elude you.

Sales Challenge 5: Creating Value in a First Meeting

The first meeting is critical to a salesperson. It's a tryout. An audition. Fail here, and you are done. Your clients don’t need a legacy salesperson sitting across from them. Clients need someone who has the knowledge and experience they are missing. When we talk about creating value, we are talking about educating the client and helping them improve their results.

The reason we call people decision-makers is that they make decisions. Those who cannot prove they can help the client make a good decision will not acquire a second meeting, unless it’s because the contact needs to prove they looked at three companies. The salesperson who moves forward is the one who created the greatest value in the sales conversation.

Sales Challenge 6: Being Ghosted

Given a choice between being ghosted and having your contact tell you to go to Hell, I'd prefer the latter. At least I know where I stand. Having been ghosted, a salesperson doesn't know whether they should follow up or what they might have done to offend the client. (One thing they can be sure of is that they underperformed in their audition.)

More and more often, contacts cut off all communication. They don't return calls or emails, making it challenging for the salesperson to know what to do.

Sales Challenge 7: Accessing the Necessary Stakeholders

A contact who tells you they will be the only person making the decision is lying. They know they are lying. Maybe they want to maintain control of an initiative, or maybe they are vetting you so they can tell the people who will make the decision you weren't right for the change they are trying to make. Of all the sales challenges, this one is one of the most difficult to solve.

Companies seek consensus because, right or wrong, they believe it improves internal commitment to the change they need, while creating accountability to make sure it improves their results. If you cannot reach the stakeholders, you will have a terrible time winning a deal decided by a task force.

Sales Challenge 8: Controlling the Process

We sometimes give buyers too much grace, believing they know what they are doing. The truth is that many buyers would find the journey much easier and safer if they had someone to guide them. In The Lost Art of Closing, I called this controlling the process.

When clients skip conversations that would help them improve their results, they provide the salesperson with a difficult sales challenge. If the salesperson isn't aware of why these conversations are important to the buyer, or doesn’t believe the buyer needs someone to lead the way, they will lose deals they might otherwise have won.

Sales Challenge 9: Client-Stalled Opportunities

The client is full, hot, and moving fast. Each meeting results in another meeting. The salesperson is certain this deal will cross the line, only to have all communication halted. What happened? The senior leader changed their priorities. The company is now the target of an acquisition by its largest competitor. Your contact resigned.

The salesperson has done nothing wrong, yet their opportunity is stalled. There are few ways to recover from this challenge.

Sales Challenge 10: Competing Client Priorities

Even though the contacts loved what the salesperson shared, the related outcome isn't a priority for the client. There are all kinds of cool things a company might do to improve its business. There are also constraints of time, energy, and money.

Most salespeople are unaware they need to help make what they sell a priority for the client. In Eat Their Lunch, I wrote about displacing a competitor. Had I been given another 5,000 words, I would have added a chapter about displacing priorities. As a salesperson, you are responsible for making your initiative a priority for the client.