Dealing with Difficult Customers: Understanding Them, Yourself, and What To Do About It

The moment I announced my forthcoming book, Sell to the Rich (April 2025), I received inquiries as to whether I would be addressing the issue of dealing with difficult clients because “wealthy people are often so difficult to work with.” It was not my intention to address this topic at all because I have a strong aversion to the judgments and assumptions underlying this belief that affluent buyers are difficult to deal with. My immediate response was, “Let’s start by not stereotyping that wealthy people are difficult because if that’s your perspective, you can’t be surprised that’s what you’re experiencing.”

But I did decide it’s a helpful topic to address and will do so in my typical fashion— what might be your role as a luxury service provider, how can you get the results you want, and because there will be some difficult customers, wealthy or not, some practical ideas to deal with the situation.

Wealth does not equate to difficulty. Instead, looking from a perspective of empathy and understanding you will see that their wealth and social standing often bring added layers of complexity to their personal and professional life. By recognizing this, luxury service providers have an opportunity to rise to a higher standard, delivering not only the expected service but also demonstrating a remarkable depth of understanding.

Understanding Them and Their Lives:

The Complex Lives of Luxury Clients

It’s easy to paint an image of the wealthy client as overly particular and demanding, even difficult. This impression, however, misses a deeper truth. Many affluent clients are juggling extraordinary demands on their time, emotional energy, and financial resources. Their lives might appear seamless from the outside, yet they are managing complexities that most of us will never encounter.

For some, their estates and households operate like small corporations. They employ staff, oversee events, manage multiple properties, and coordinate numerous professional and social responsibilities. This high level of organization is essential, not indulgent, to meet the demands of their lives. Just as with any individual balancing a demanding career and personal life, affluent clients often seek service providers who can help relieve some of this weight—professionals who understand, and accommodate, the sheer magnitude of what they’re carrying. Yes, the weight they are carrying can sometimes boil over to appearing “difficult” but if you understand this fundamental truth of their lives, you can receive the added pressure with greater understanding, consider it less of a personal attack, and if possible, alleviate some of the weight, for which they will be very grateful.

The Duality of the Luxury Client’s Life

While it’s true that luxury buyers enjoy the finer things in life, their lives also include struggles and sacrifices that are often overlooked. For many affluent individuals, the gap between appearances and their reality can create a greater than typical dissonance that can be very difficult for them to manage. They may work tirelessly to cultivate the perfect life, successful businesses, sustain philanthropic projects, and support family and friends through challenging times—all while managing the same human experiences of grief, loss, family dynamics, aging parents, and troubled teens, that the rest of us face. However, the gap between their reality and their appearances can be far greater. Emotionally, on a human level, this gap is very difficult to manage.?

This reality can leave luxury clients feeling as if they live in two extreme worlds, the one they present to the world and the one they experience internally. This duality brings added pressure, intensifying the already weighty responsibilities they bear. And sometimes they may not manage this dissonance very well. They are humans having a very human experience, just like everyone else. By approaching them with understanding, luxury service providers can become a grounding presence—someone who genuinely listens and sees beyond the surface with compassion to the real, struggling human just making it through this thing called life.

What You Can Do:

Set Aside Assumptions

Start by setting aside preconceptions about “difficult” or “demanding” behavior. When affluent clients ask for high standards, it doesn’t mean they are coming from a place of entitlement. Their expectation for quality and service often stems from a desire for consistent standards and trust, as they seek professionals who can reliably uphold the level of care they require. It takes a commitment to see beyond the stereotypes and approach clients with the curiosity and kindness needed to build true rapport. By setting aside assumptions and embracing an empathetic approach, luxury providers have the chance to create interactions that respect the lives of their clients while elevating their own professionalism. Remember, how you see the world is how the world sees you. Make it a practice to put into the world exactly what you want to receive in return.?

Consider It Your Call to Greatness

Ultimately, working with affluent clients is an invitation for service providers to step up to their own call to greatness. It’s an opportunity to listen attentively, speak candidly, and genuinely serve their unique needs. Providing exceptional service to this clientele is more than a transaction; it’s a partnership. It’s about understanding their lives and supporting them in ways that genuinely matter. Every interaction is an opportunity to connect with empathy, respect, and a clear-eyed view of their unique pressures and ambitions. By choosing to view affluent clients through this lens, service providers can rise to a higher level of service and find in themselves more than they ever could have imagined. The privilege of working with affluent clients comes with an invitation to grow, not only in skill but in character. It’s a reminder that wealth does not shield anyone from the trials and complexities of life. This compassionate approach isn’t just good business—it’s the true mark of greatness.

When Empathy and Understanding Isn’t Enough:

Being in the public arena as a luxury service provider does mean on occasion that no matter what you do— a deep understanding of their lives, mustering up all the greatness in yourself you can, simply won’t be enough. Again, I believe this has more to do with the amount of exposure you may face than it has to do with any socio-economic group.?

But there will be customers that are simply difficult. Here are some ways to manage challenging clients while maintaining a professional and healthy relationship:

Set Clear Expectations from the Start Clearly define what clients can expect from you and your service from the onset. If needed, determine this in a contract to allow both parties to refer back to it if expectations shift over time. Transparency helps clients understand not only what they’ll receive but also what is outside of the standard scope, establishing a respectful foundation from the beginning.

De-escalate with Empathy

When clients are upset or acting unreasonably, validating their feelings can sometimes be enough to de-escalate the situation. Responding empathetically doesn’t mean conceding; it shows you’re listening and willing to address reasonable concerns. Understand also that often, “difficult” behavior comes from underlying stressors unrelated to you. A calm, empathetic approach may help you understand and address any actual concerns without taking reactions personally.

Set Boundaries

You can’t fault anyone for crossing a boundary if the boundary wasn’t clearly stated in the first place. Be sure to set clear communication boundaries. When and how they can expect to reach you. If a client request goes beyond the scope of work, say something like, “I’m committed to providing the best service possible, and to do that, I’ll need to keep our focus on [defined boundaries].” If a request falls outside your role, respond with a firm yet respectful “no,” followed by offering an alternative. For example, “That’s outside my scope, but I’d be happy to suggest a resource that could help.”?

The Client is Not Always Right

No provider should tolerate any form of abuse. When you have exercised as much empathy as you can and are still facing strong opposition, make it clear that any form of verbal or physical mistreatment will not be tolerated. If a client crosses into disrespect or aggression, calmly state that such behavior is unacceptable and terminate the working relationship. The customer is most definitely not always right and while some, such as a sales associate, may face consequences from an employer, your self-respect and emotional safety comes first.

Fire When Necessary

Yes, on a very rare occasion, we may have to fire a client. If a client repeatedly disregards boundaries, consider providing an exit option with diplomacy, such as, “It seems like my services may not be the right fit for what you’re looking for. I’d be happy to recommend someone else who might better suit your needs.” It’s always acceptable to part ways with clients who threaten your well-being or the quality of your work. Ending a relationship thoughtfully preserves both your reputation and your peace of mind.

In the end….

Letting go of assumptions, gaining empathy by understanding their lives, and considering the opportunity for personal growth will likely ward off almost all ill-fated situations. Yet, on occasion, a difficult client may present themselves. One other thing to consider— if there seems to be a pattern of difficult clients over time or a “cluster” of difficult clients during a particular time, consider the source. It could be a “type” of client you are attracting that is not aligned with your values. And the source could also be you. I know that when I have gone through some challenging personal times, perhaps my patience was limited, or my attitude was less than ideal, I tended to have more difficult customer interactions. Which of course only worsens one’s attitude and so on. So always look inward for what might need to be shifted to see a different result. What’s essential is cultivating a practice where your values and standards are non-negotiable, benefiting you and your clients alike.

Through this newsletter, I hope to inspire you and provide insights that will give you an edge in your luxury business. The diamond edge--sharp, precise, intentional, and cuts through. All necessary elements to be exceptional in business.

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Few people can speak about the emotions and behavior of the luxury market better than Jeffrey Shaw. Having been a preeminent portrait photographer in the U.S. for 40 years serving the most discerning clientele, as Jeffrey says, "I don't just know this market, I was in their closets."

A speaker who lights up an audience with innovative marketing and branding ideas, offering a whole new perspective on business, customer service, and the behavior of luxury buyers to motivate business owners and luxury brands to implement proven strategies, grow their businesses, and raise standards in the world.

The author of LINGO and The Self-Employed Life, a TEDx speaker featured on TED.com, host of the popular podcast, The Self-Employed Life, Founder of The Self-Employed Business Institute and The Exceptional Business Academy.

For more information about Keynotes, Coaching, Luxury Marketing, and the year-long High Achievers Mastermind- www.jeffreyshaw.com.