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The Alternative Board Blog

Difficult Customers Are a Blessing in Disguise

Jan. 29, 2025 | Posted by The Alternative Board

As business owners, we have all at some point experienced customers who are challenging to deal with. Any number of dynamics might factor into this strained dynamic. It might be that the customer possesses unrealistic expectations. Or perhaps they are combative by nature or passive-aggressive or so many other characteristics that just make them a little more unpleasant to accommodate. But we can learn a lot from difficult customers -- lessons that will not only help you close those deals, but also improve the customer experience for your entire book of business.

What to Learn from Challenging Customer Behaviors

Difficult customers come in many forms, but there are some common profiles we have all likely interacted with at some point. Keep in mind, these are not necessarily bad people; they are simply customers who exhibit less-than ideal behaviors that usually require extra effort and patience when closing a deal.

The following are some common challenging customer behaviors and how business owners can leverage these interactions for strategic improvement in their organization's overall customer experience.

Indecisive. These are the customers who tend to change their mind on what they ultimately want to purchase. They might request changes to terms and conditions, then when you accommodate those wishes, they flip-flop on the goods or services they want.

An effective approach to dealing with an indecisive customer is providing clarity, quantitative data, and perhaps even incentives to help them make purchasing decisions.

An indecisive customer might be a telltale of a complicated or overwhelming sales process. Consider a simpler and more transparent customer experience.

Demanding. A demanding customer often expects your top offerings at your lowest prices, even if they lack a standing relationship with the business. They may also request unreasonable turnaround times at no extra cost to them. Essentially the want more for less.

Consider offering tiered service levels to better navigate requests for upsells. If you can accommodate these requests without negative consequence to your team, operations, or bottom line, you might consider doing do. But also stand your ground when necessary.

Demanding customers can teach us the importance of creating clear timelines, scopes of work, and other dynamics that may currently be ambiguous in your sales process.

Complaining. Some customers seem to default to cranky and cantankerous. They never seem satisfied with your goods or services. They make the sales process mostly unpleasant and negative for you and your team.

Complainers can also be morale-killers, but it is important that you listen to and acknowledge their grievances. There may be a glimmer of truth in the gripes of even the naggiest customers. 

Complainers remind us of the importance of collecting regular customer feedback, then leveraging that input to adjust operations or approaches when appropriate. Feedback can also let us know whether these kvetchers are more the exception or the norm.

Read "3 Steps to Winning Back Lost Customers."

Ghosting. Radio silence is extremely disappointing, particularly when there is an expectation that a closed deal is imminent. Ghosters often first appear as  enthusiastic and on the verge of closing, but are then seemingly impossible to connect with.

These disappearing acts are reminders of the importance of structured and perhaps automated follow-ups.

Be as transparent and forthcoming with your customers as possible. Routinely provide all your customers with updates, next steps, and supporting information. Even if a ghoster never responds to your communications, you are still demonstrating value and professionalism by maintaining a connection.

Slow Paying. Slow paying customers can wreak havoc on AP/AR, particularly for businesses that lack a healthy cash flow. They may make promises or commit to certain payment terms, only to let the unpaid invoice linger for months on end.

Slow payers may have cash flow issues or various short-term financial challenges beyond their immediate control. Regularly connect with the individual (if you are a B2C) or the accounting department in a non-judgmental way to maintain the relationship and facilitate payment.

If you find that you have a number of slow payers or outstanding receivables, consider providing the most efficient billing and payment processes possible. From the start, offer you customers a variety of payment options that might best suit their needs. This approach can help build loyalty and decrease negative interactions with your customer base.

Read "7 Simple Ways to Wow Your Customers."

As business owners, we can learn a tremendous amount from even our most challenging customers. By noting their actions and listening to their perceptions, we can leverage that insight to refine our processes, improve communication, and enhance our overall customer experience. 

Read our 19 Reasons You Need a Business Owner Advisory Board

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Written by The Alternative Board

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