After You’re Hired on Upwork: Increase Your Odds of Repeat Clients
Getting hired on Upwork can be tough. Even if you do everything right, it’s definitely a buyer’s market.
But if you stick with it you’ll get hired. Hardest part over, right?
Well, once that happens, which sounds better: A one-off job for the client and then back to grinding out more proposals? Or an ongoing relationship with the client, where you get offered work again and again, without having to scrounge the job feed?
The second option sure sounds better to me!
This post is about the things you can do to make working with you more pleasant for clients, so when they need more work done, they look forward to hiring you again.
By the way, I’m not talking about your quality of work or how much money you ask for. Of course that matters. You don’t need to read this to know that good-quality work at a reasonable cost is going to please the average client more than bad, expensive work.
Instead, I want to talk about things that will make you stand out over your competition and that are independent of work quality and money. They are behaviors that have a lot of impact but most people don’t bother doing.
These tips come from two sources: My own experience reviewing hundreds of Upwork proposals while hiring and working with 60+ freelancers, and views expressed by someone I know who himself has hired hundreds of freelancers on Upwork.
Does this mean it’s best to go as fast as possible under all circumstances? No.
If you’ve been hired to write a 5,000 word article in two weeks, turning in your work after a day would probably raise eyebrows, rather than impress. It would be like, “Was this just written with AI? How good can the quality be? I need it in two weeks, not today.”
Insane rushing is not needed to impress here. However, it would definitely look good to turn in your work a day or two earlier than the deadline.
Where speed really makes a difference is for small tasks, particularly ones that involve a lot of back and forth with the client. For example, I’ve worked with about ten different graphic designers to create YouTube thumbnails. The edits for these jobs are often very small. They’ll be things like moving text over a little on the image, or making an element larger.
For these very small tasks, if I have to wait 24-36 hours for each iteration, the days it takes to complete a thumbnail really adds up. But if the graphic designer makes these small changes the same day, it can greatly speed up the whole process.
If you’re in a field where clients ask for many small changes, and they’re the type of things you can do quickly on your end without lowering quality, cutting down the iteration time on those changes makes you stand out.
Having actions match words seems pretty basic, but I’ve seen people fail at this so many times, it’s worth mentioning. A freelancer will say, “I’ll get this to you on Tuesday” and then deliver it on Friday.
Even though speed is a premium resource, it’s MUCH better to say something will take a longer amount of time and be on time for that, than to give a faster time and then be late. In the first case, you’re reliable, whatever your pace. Being reliable will make you stand out, because so many people are not.
Anyone who has hired or managed other people has heard a lot of excuses already:
- “The traffic was bad.”
- “I was sick.”
- “My dog was sick.”
- “I’m moving, and things are crazy right now.”
- “My grandmother recently passed.”
- “There was flooding in my village.”
From the client’s perspective, maybe you’re telling the truth, and maybe you’re lying. In either case, how do your words help anything? The client is still waiting for the work to be delivered.
For minor mistakes or delays, it’s better to just apologize and not offer an excuse unless directly asked what happened.
For more major delays or problems, an honest explanation can be helpful, as it would be odd not to fully acknowledge the situation. But you’re probably better off saying things like “personal obligations” or “medical issues” rather than going into detail.
I’ve worked with a lot of people who go silent unless I follow up. Then they say, “I was just about to start working on it today” or “My grandmother just passed” or “I’ll get it done by tomorrow” (and then not get it done).
If you’re a freelancer, making the client be the one to reach out forces your client to do extra work, and to deal with the mental load of sending you a message. Many people don’t want to sound like nags, which puts them in an uncomfortable position when they have to check in asking for work progress, not sure how polite or direct they need to be to get their message across.
On top of this, many people who hire are managing more than one project at a time, which means you may be the fifth person they had to check in on today.
You can stand out by taking away this burden from your client. If it’s been a while since your last message and everything is going well, it’s good to say that. If there are issues, better to just say that now, instead of waiting to be asked about them. Even a very short message can accomplish a lot.
Another good option is to agree with your client up front about what reporting frequency will work for a given project, and then stick to that schedule.
5. Don’t Max Out Your Billable Hours Every Week

Sometimes the work clearly justifies using all your billable hours, and that’s fine. But if the amount of work you’re given varies from week to week, and you consistently bill your maximum hours, this gets noticed. You might not get called out for it, but when people need to be cut, your name is more likely to come up.
I’d go so far as to say it’s worth purposefully working less sometimes, or billing less even if you do the same amount of work, to make sure you don’t develop a reputation as a money sponge.
Following these tips will help you stand out from your competition, and you can start doing them today.
If you want to know how your Upwork profile, proposals, or portfolio look from a client’s perspective—and what might be holding you back—I can give you personalized feedback. Contact me to have a chat about your situation.





