In business, entrepreneurs encounter a wide array of clients. While many client experiences will be positive, there will also be tough ones who challenge your typical ways of doing business and push you to grow for the better.
From scheduling check-ins to getting a better understanding of their previous experiences with business, there are many ways to approach a situation with a difficult client. Below, 18 Forbes Business Council members each share additional steps entrepreneurs can take to ensure tricky clients still have a positive experience and end up happy with the end result.
1. Put Yourself in Their Shoes
A tip that’s worked well for me is to put yourself in their shoes. Think about how you’d want to be treated if the roles were reversed. How would you want to be addressed? What kind of resolution would leave you feeling satisfied and positive? The key to creating a good experience is to acknowledge their concerns, apologize for any issues, and do your best to make it right. – Sharmylla Siew, Cobalt Funding Solutions
2. Ask Open-Ended Questions
I ask open-ended questions to understand their pain points, objectives and any past experiences that may influence their behavior. This helps uncover underlying concerns that might not be immediately apparent. Once expectations are clear, I establish structured communication. This includes sharing a detailed project plan, outlining milestones and providing regular updates to keep them informed. – Puneet Gaur, Next Quarter
3. Make Them Feel Heard And Important
Most prickly people feel as if they aren’t being heard. If you open the discussion and make them feel as if their voice matters and is important, they are more likely to participate and listen. Everyone wants to know that they matter, so give them the floor to express their concerns, ideas and complaints. Then, move forward. – Seth Lederman, Frannexus
4. Leverage A Performance-Driven Empathy Technique
I use a performance-driven empathy technique to rephrase their concerns, empathize with them, and validate their point. I then go even further by mentioning things they missed to provide even better results for them. This unconventional approach shows deep understanding and positions me as their partner. It also dilutes their negative feelings, builds trust, and focuses on future solutions instead of present issues. – Ines Nasri, WebPower USA LLC
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5. Uncover And Leverage Commonalities
Great salespeople know how to uncover and leverage commonalities with nearly anyone. Sometimes, this requires a lot of patience. When you do break through to a challenging client, however, they often become loyal followers. – Kevin Markarian, Roopler
6. Build A Relationship Beyond Emails
Take time to meet your clients in person, schedule video calls or even make a casual phone call to check in. Building personal connections helps diffuse tension, build trust and create a collaborative environment where the customer feels heard and valued, which is key for a positive experience and a successful outcome. – Natasha Cox, Avani Services
7. Lead With Curiosity Over Judgement
Approach them with curiosity, not judgment. Mirror their concerns to show deep understanding, then reframe challenges as collaborative problem-solving. Validate their emotions while subtly guiding the conversation toward solutions. Ask them to tell you more to disarm defensiveness and foster trust, making even the prickliest clients feel heard, respected and ultimately satisfied. – Kristina Aran, EVOLVE Integrative Psychotherapy
8. Focus On Understanding Their Previous Experiences
Prickly customers are sometimes hiding invaluable feedback for your products. Many times, this kind of behavior is caused by a former bad experience with another product, making them reluctant and closed. The key is to find the proper way to understand what the underlying problem is and build on that. This will help you gather information for your product and gain trust. – Massimiliano Melis, AITEM
9. Be Empathetic And Patient
With prickly clients, I’ve learned that empathy and a bit of patience go a long way. Start by really listening—sometimes they just need to vent. Then, focus on solutions that show you’re on their side. Clear communication and small wins along the way can turn skeptics into fans. It’s all about showing you care and that their success matters to you. – Braden Yuill, Virtual Coworker
10. Manage Client Expectations
Managing client expectations is critical. Whether you run a professional services organization or a consumer-facing, brick-and-mortar business, regularly confirming each client’s expectations for a positive outcome, asking for feedback and adjusting during the service is critical to having a happy client. Always ask if there is anything more you could have done so you also continually improve. – Jennifer C. Wolfe, Esq., APR, Whisper Creek Spa
11. Set Up A Transparent Progress System
When dealing with a challenging client, try setting up a transparent checkpoint system to observe progress. Instead of waiting until the project is finished to share results, schedule regular updates with visuals, insights and space for feedback. This keeps the client feeling informed, involved and valued while addressing their concerns in real time, reducing friction and building trust. – Michael Shribman, APS Global Partners Inc.
12. Keep Clients Engaged
For more particular clients, I make sure to keep them engaged by showing what I am working on and making sure they feel they have a voice and are being heard. If there is something they want that is not realistic, I will show them why. I then offer options to give them peace of mind and help them stay focused on their goals. Keeping them engaged in their project is essential. – Natalie Boehm, The Defeating Epilepsy Foundation
13. Lean On Relational Experts
At Prolific, we lean on our relational experts. We have identified those within our company who excel at building relationships. They are likable and kind, and people are naturally drawn to them. We try to strategically integrate these people into interactions, allowing them to leverage their relationship-building abilities. This approach has often turned around relationships that seemed hopeless. – Brad Benbow, Prolific
14. Document Everything
Documenting everything is a lifesaver with challenging clients. Keep clear records of all communications, decisions and progress. It ensures transparency and avoids misunderstandings. When conflicts arise, you can refer back to the facts. This shows professionalism and keeps things on track. Clients appreciate clarity and accountability, even if they’re tough to please. – Sabeer Nelliparamban, Tyler Petroleum Inc.
15. Deliver Tangible Progress Early On
Deliver an early milestone or small success to build confidence and reduce their skepticism. Prickly clients often soften when they see tangible progress. This proactive approach shifts the narrative from combative to collaborative. – Reggie Young, Exit Advisor – Business Broker
16. Schedule Additional Touchpoints
One simple but very effective tip is to schedule additional client touchpoints. If your typical meeting cadence with clients is every other week, schedule weekly calls with clients who need more education and support. You might also implement weekly email reports to ensure your efforts are in line with their needs. Good communication can solve many issues! – Emily Reynolds Bergh, R Public Relations Firm
17. Reframe Their Toughness As A Positive
When dealing with a prickly client, compliment their toughness by praising their high standards or attention to detail. This will reframe negativity as a strength, boost their ego and shift the tone of the interaction to something more constructive. – Hope Horner, Lemonlight
18. Be Humble And Respectful
Stay humble and respectful, as it helps build trust and diffuse tension. Take time to understand why they may feel frustrated and address their pain points with a human-centric approach. I’ve found that active listening is a game-changer. Often, difficult clients just want to feel heard—and when they see you genuinely care, collaboration becomes much easier. – Manoj Balraj, Experion Technologies
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