By Robert Thompson, Barefoot Consultants®
Let’s be honest—Upwork isn’t just about having a great profile or submitting excellent proposals. If you want to build a sustainable freelance business, one of the most important skills to master is communication.
That’s why we created a short, practical video on how to use Upwork Messaging like a pro—because even the most talented freelancers can lose jobs or damage client relationships by being vague, slow to respond, or unprofessional in how they interact.
Patty & I have coached freelancers from all over the world, and there’s a pattern among those who succeed: they communicate clearly, professionally, and promptly. That’s where the magic happens. Whether you’re chatting with a new lead or updating a long-term client, how you show up in messages matters.
So, what’s in the video?
I will walk you through all the essential features of Upwork Messaging—whether you’re using the desktop app, browser, or mobile. It’s a great refresher if you’ve been freelancing for a while, and it’s a must-watch if you’re just starting out. Here’s a sneak peek at what you’ll learn:
- Messaging tools across platforms – Know where and how to use Upwork’s built-in messaging tools, so you’re always connected, no matter the device.
- Using voice and video – Not every conversation needs to be typed out. Sometimes, a quick voice or video message can save time, build rapport, and clarify project details instantly.
- The importance of documentation – This one’s big. We’ll explain why keeping your communication on Upwork (instead of email or WhatsApp) protects both you and the client.
- Scheduling tips – Coordinating calls across time zones can be tricky. We’ll show you how to make it easier and avoid missed connections.
- Tone and etiquette – Learn how to come across as professional, approachable, and confident in every message. (Hint: It’s not about being stiff—it’s about being clear and courteous.)
- Common pitfalls to avoid – We’ve seen it all: unclear updates, overly casual messages, or going silent mid-project. The video covers how to steer clear of these traps.
Why this matters
It’s easy to underestimate how much your messaging style influences whether a client hires you—or hires you again. Think of every message as a small reflection of your brand. Are you someone who shows up on time, communicates clearly, and takes initiative? If so, clients will notice—and they’ll want to continue working with you.
On the other hand, poor communication is a leading cause of freelancers receiving negative feedback or losing repeat clients. That’s something you can avoid. And the good news? It’s a skill you can develop with just a little focus and practice.
Ready to level up your communication?
I’ve designed this video to be a practical, no-fluff guide to messaging on Upwork. Whether you’re new to freelancing or want to polish up your client communication, this is a great place to start.
Click here to watch the video
And if you want some hands-on help applying these strategies to your own freelance business, Patty & I would love to chat with. We offer one-on-one coaching tailored to your current stage in the journey—whether you’re just getting started or ready to scale up smartly.
Let’s make sure your communication works for you—not against you.