8 Business Strategies for Managing Difficult Clients Like a Pro - Part 1

Set the tone early:

• Expectations should be expressed clearly during the sales process and throughout the business relationship.
• Clarify what’s included—and what isn’t. If certain requests trigger extra charges or delays, be upfront about how you will handle those situations..
• Use email summaries after calls to confirm what was discussed and agreed upon.
• Use client-accessible tools (like a shared portal, if possible) to track progress and eliminate “I thought you were going to…” misunderstandings.

It’s also important that you have systems in place that cover these processes, and that you are willing to pivot when they need tweaks in order to improve the client experience.

Setting expectations early helps avoid confusion later—and gives you a documented record if you need to revisit the agreement. One of the best ways to document expectations is by having clear, through contracts in place.

Strategy 2: Create Contracts That Protect Your Business

If you’re still using templates from a free site—or worse, working without a contract at all—you’re leaving your business wide open to risk. A strong client agreement doesn’t just outline terms; it reflects your values and protects your business when things go sideways.

Here are key terms your contract should include:

• Scope of work and specific deliverables
• Payment terms, due dates, and late fee policies
• Refunds, cancellations, and what happens if the client ghosts you
• Dispute resolution procedures, including mediation and arbitration
• A jurisdiction clause (so any legal action happens in your preferred location)

But beyond legal language, your contract should set the tone for a respectful working relationship. Want to offer flexible payment plans? Prefer collaborative mediation over court? Spell it out.

When you work with me as your LIFTed Business Advisor and attorney, I’ll help you review and update your contracts as your business evolves—so you can stay protected and aligned with your goals. To learn more, book a call using my link below.

 
Despite setting clear expectations upfront and having solid client contracts in place, you’ll eventually need to deal with clients who miss payments. 

Strategy 3: Use a Professional, Consistent Collections Process
Even good clients miss payments sometimes. Cards get declined, invoices get lost, or personal issues get in the way. The key is having a process that protects your revenue without damaging the relationship.

Start with a gentle reminder. A friendly email may be all it takes. If that doesn’t work, follow up with another reminder and a phone call. Many times, a five-minute conversation resolves the issue and preserves goodwill.

It’s also important to get curious with the client. Don’t make assumptions about their willingness to pay, ability to pay, or whether they’re unhappy with your service or product. Ask them, from a warm, open place, what’s in the way of them making a payment. Be willing to listen and propose solutions. 

Still no response? Send a formal notice that references your contract—outlining next steps like suspending service or pursuing collections. Always keep communication professional, clear, and grounded in your written agreement.

When done right, your collection process won’t feel aggressive. It will feel organized, respectful, and consistent—and that benefits your reputation, even with non-paying clients.

Of course, not every difficult situation is about payment. Sometimes, the client paid, but now they’re unhappy with what they received, or they’re making demands that go beyond your original agreement. That’s where the next strategy comes in: building a process for resolving disputes quickly, calmly, and professionally.

Strategy 4: Build Dispute Resolution Into Your Business Model
Despite your best efforts, sometimes clients don’t like the work you delivered or claim it wasn’t what they expected. Others simply change their mind. Having a built-in dispute resolution system protects you from turning a simple complaint into a courtroom battle.

Here’s how:

• Make space for honest feedback. When clients feel heard, they're less likely to escalate a dispute.
• Stay calm and curious. Ask questions to get to the root of their concern.
• Include a mediation clause in your agreement. This ensures that disputes start with collaboration—not litigation.
• Consider an arbitration clause for situations where mediation fails. Arbitration is typically faster, less public, and more affordable than court.
• If you serve clients in multiple states, always include a jurisdiction clause. 

Dispute resolution should feel like an extension of your values—not just a legal backup plan. That’s how you build a resilient business. Please book a call with me using the link below so I can support you.

These first four strategies will help you prevent many problems before they start. But not all client challenges are about policy—they’re often about people. In Part 2 of this series, we’ll cover:

• De-escalate emotionally charged situations with empathy and authority
• Protect your online reputation when clients go public with complaints
• Build long-term client relationships that prevent future problems
• Know when it’s time to bring in professional legal support

Be sure to check back next week to get all the details.

Don’t Let Difficult Clients Break Your Business

No matter how amazing your service is or how great your communication, disputes happen. But with the right legal systems in place you can minimize your risk, protect your peace of mind, and stay focused on growing your business.

When you work with me, I start my process with a LIFT Business Breakthrough™ Session, where together, we’ll take a look at  your legal, insurance, financial, and tax systems. Then we’ll create a flat-fee advisory relationship that evolves with your business—supporting you not just when things go wrong, but every step of the way.

We’ll make sure your foundation is strong, your systems are up to date, and your business is prepared for every opportunity and every challenge.

Book a complimentary 15-minute discovery call to get started.

This article is a service of Sky Unlimited Legal Advisory PC, Personal Family Lawyer® .  We're not your traditional law firm, we stand apart from the rest by helping you make informed and empowered decisions on how to deal with your business throughout life and in the event of an emergency. We offer a complete spectrum of legal services, including a New Business Planning Session or an Existing Business Review Session, which includes a review of all the legal, insurance, financial, and tax systems you need for your business. You can begin by calling our office at (650) 761-0992 today or book online to schedule a Business Planning Session and mention this article to find out how to get this $950 session at no charge.