How to Make Clients Listen, Trust, and Work With You

Communication is the backbone of every successful freelance project. Whether you're managing clients or collaborating with teams, the way you communicate can make or break a project.

In this episode of the Freelance Sucks podcast, we talked with Jeremy Coffey, a freelance program manager, and project and team leader, about how to talk to clients and teams in a way that they listen to you and work together towards a mutual goal.

From this episode, you'll learn:

✅ How to start conversations that set the right tone for collaboration
✅ The difference between talking to executives vs. team members
✅ The best way to handle disagreements with clients
✅ How to ensure alignment when clients shift directions
✅ A simple communication technique that makes client relationships easier

Watch now and take control of your freelance journey! 🚀

🎧  Or listen to it here on Spotify  

Why communication is key to freelance success

Freelancers don’t just sell skills—they sell trust and collaboration.

Every freelance project involves working with people—whether it's clients, internal teams, or stakeholders.

However, when communication is unclear or misaligned, projects quickly become stressful, inefficient, and frustrating.

Common freelance communication challenges include:
🔹 Clients who expect results without understanding the process.
🔹 Teams that resist change or feel left out of key decisions.
🔹 Constant shifting priorities that derail progress.
🔹 Miscommunication leading to extra revisions, wasted time, and lost revenue.

The good news? Mastering communication can prevent most of these problems.

1. How to start client conversations for better collaboration

Starting a project on the right foot isn’t about jumping straight into deadlines and deliverables—it’s about creating a human connection.

Treat the first conversation as an opportunity to learn about the client and their motivations.

Why this works:
✅ Every business is a people business—understanding personal concerns smooths collaboration.
✅ Stakeholder mapping helps identify who will be impacted by your work and how they might react.
✅ Some clients welcome change, while others are protective of past decisions—adjust your approach accordingly.

Pro tip: Don’t start with "Here’s what I’m doing." Instead, start with curiosity and build a relationship before discussing business.

2. The difference between talking to executives vs. teams

Not everyone in a company communicates the same way. You must adapt your style depending on whether you speak to an executive decision-maker or a team member responsible for execution.

Executive-level communication:
✅ Keep it brief and results-focused—executives don’t have time for small talk.
✅ Show KPIs, impact, and measurable outcomes.
✅ Avoid deep technical explanations unless specifically asked.

Team-level communication:
✅ Build trust by understanding how they work and prefer to communicate.
✅ Recognize that execution teams care more about workflow and process than just the final result.
✅ Learn their challenges and adjust your approach to fit their working style.

Pro tip: Never assume developers or technical teams only want facts. Everyone works better when they feel heard and understood.

3. What to do when a client disagrees with you

Disagreements are inevitable in freelancing. However, how you handle them determines whether the project stays on track or turns into a disaster.

Instead of defending your point, focus on diplomacy and solution-oriented discussions.

What works best:
✅ Offer multiple options instead of just one rigid solution.
✅ Ask, "What concerns you about this approach?" to open up a productive conversation.
✅ If all suggestions are rejected, revisit the original brief—misalignment often starts early.
✅ Avoid surprising clients in meetings—always prepare them in advance.

Pro tip: Clients don’t like to feel ambushed with unexpected solutions. Keep them involved throughout the process.

4. How to ensure alignment when clients change directions

One of the biggest challenges freelancers face is clients shifting priorities mid-project. Instead of getting frustrated, adjust your strategy.

Assume good intent and communicate proactively.

How to handle shifting goals:
✅ Keep detailed records of discussions to refer back to previous agreements.
✅ Regularly check in to reconfirm priorities before making big moves.
✅ If resistance arises, address it directly but with kindness.
✅ If someone blocks progress, have a private conversation instead of escalating conflicts.

Pro tip: The best freelancers stay adaptable while maintaining structure.

5. A simple habit that makes communication with clients easier

One of the easiest ways to improve client communication is to use the "Yes, and..." technique from improv.

How it works:

• Instead of saying "No, that’s out of scope," say "Yes, and let’s discuss how we can fit that into the plan."
• This keeps the conversation open while setting boundaries.
• Clients feel heard without you overcommitting.

Why it works:
✅ Keeps the dialogue positive and collaborative.
✅ Prevents the client from becoming defensive.
✅ Helps guide the conversation toward a productive outcome.

Pro tip: The pause after saying "Yes, and..." also gives you time to think before responding.

TL;DR

Freelancers don’t just sell skills—they sell trust and collaboration.

✅ Build strong client relationships by focusing on understanding their motivations.
✅ Adapt your communication style for executives vs. teams.
✅ Handle disagreements diplomatically and offer multiple solutions.
✅ Keep projects aligned even when clients change directions.
✅ Use "Yes, and..." to set boundaries while keeping clients engaged.

Quotes from this episode

1️⃣ "Every system is a people system—understanding that makes you a better freelancer."
2️⃣ "No one likes surprises in meetings—clear communication prevents conflicts before they start."
3️⃣ "Always assume the best in people. It helps you move past resistance and find solutions."
4️⃣ "Freelancers aren’t just hired for skills—they’re hired for how well they integrate into teams."
5️⃣ "The 'Yes, and…' approach makes client conversations easier while protecting your boundaries."