3 File Sharing Mistakes That Cost Me Clients (And How to Avoid Them)
I learned these lessons the hard way. Don't make the same mistakes I did when sharing files with clients.
Three years ago, I lost a potential client because of a file sharing mistake. The project was mine to lose, and I lost it.
What happened? I sent them a Google Drive link with the wrong permissions. They couldn't access it. By the time I fixed it, they'd moved on to another freelancer.
That mistake cost me about $3,000. Here are the three biggest file sharing mistakes I've made, and how to avoid them.
Mistake #1: Not checking permissions before sending
What happened
I uploaded a proposal to Google Drive and sent the link to a potential client. Got a reply 20 minutes later: "Link doesn't work."
I'd set the file to "Only people with access can view" instead of "Anyone with the link." Classic mistake.
By the time I fixed it and sent a new link, their impression of my professionalism was already damaged. They ended up choosing someone else.
How to avoid it
Before sending any file link, click it yourself in an incognito browser window. If you can access it without logging in, the recipient can too.
Better yet, use services that don't have permission settings to mess up. Temporary file sharing services just work - upload, get link, share. No permission headaches.
Mistake #2: Sending files that are too large
What happened
I sent a client a 4GB video file through Google Drive. Their internet was slow. The download kept failing. They gave up and asked for a smaller version.
I should have compressed it first. The 4GB file could have been 800MB with no noticeable quality loss. Would have saved everyone time.
The real cost
Large files don't just waste time. They make you look like you don't know what you're doing. Clients wonder: "If they can't figure out file compression, can they handle my project?"
How to avoid it
Rule of thumb: If a file is over 500MB, ask yourself if it needs to be that big.
- Videos: Compress to 1080p unless they specifically need 4K
- Images: Export at web quality (1920px wide is usually fine)
- Documents: PDF format is usually smaller than Word docs
I use Handbrake for videos. Free, easy to use, and can reduce file sizes by 60-80% with minimal quality loss.
Mistake #3: Not including download instructions
What happened
I sent a Dropbox link to an older client. They didn't have a Dropbox account and the website was confusing them. They kept trying to create an account instead of just clicking download.
Spent 20 minutes on a phone call walking them through it. Could have avoided all that with better communication upfront.
How to avoid it
When sending file links, include simple instructions:
"Here's the file link: [URL]
Click the link and press the download button. No account needed.
The link expires in 24 hours, so download it today if you can."
Those two extra sentences prevent 90% of client confusion.
Bonus mistake: Keeping files shared forever
This one didn't lose me a client, but it was still a problem.
I used to share Google Drive links and forget about them. A year later, I'd realize old project files were still accessible to former clients. Not great for security.
Now I use temporary file sharing for anything that doesn't need to be permanent. Files automatically delete after 24-48 hours. No manual cleanup needed.
What I do now
My current file sharing process is simple and hasn't failed me yet:
1. Choose the right tool
One-time transfer? Temporary file sharing.
Ongoing collaboration? Google Drive.
Professional deliverable? WeTransfer.
2. Compress large files
Anything over 500MB gets compressed first. No exceptions.
3. Include instructions
Always explain how to download, even if it seems obvious.
4. Test the link
Open it in incognito mode before sending. Make sure it works.
The checklist I use
Before sending any file to a client, I check:
- ✓ Is the file compressed to a reasonable size?
- ✓ Did I test the link in incognito mode?
- ✓ Did I include download instructions?
- ✓ Is this the final version? (No "final_v2_really_final")
- ✓ Does the filename make sense? (Not "IMG_1234.jpg")
Takes 30 seconds. Prevents hours of headaches.
Learn from my mistakes
I wish someone had told me these things three years ago. Would have saved me a $3,000 lesson and a bunch of embarrassing client calls.
File sharing seems simple, but small mistakes add up. Check your permissions. Compress your files. Include instructions.
Your clients will appreciate it. Your future self will thank you.