What are the 3 most common freelancer complaints? (And how sales strategies can solve them)

woman with phone freelancer

Freelancing doesn’t have to be so hard.


When I started freelancing I was completely floored by how easy it seemed to be. Easy? Yeah, you don’t hear that often. Despite the sea of talk about turbulent clients, unpaid projects, and dearth of recurring work, I was able to leap right into having several great clients who were respectful, responsive, and paid a monthly retainer. Now, I had plenty of other problems (like how my writing lacked punch), but client-management wasn’t one of them. What gave? Why did I have such a different experience than most?


Quite simply, I had a background in sales. 


I spent the four years prior cold-calling crowds of people and getting rejected by untold thousands. I had built up some pretty thick skin and a bag full tricks that made this process a painless breeze, and I don’t even consider myself very good at it. I was early on in my sales career when I left it, which goes to show you that simply having basic sales knowledge make all of the different in helping you establish consistently profitable freelancing work. 


After all, you’re freelancing because you have something that you’re terrific at, be that coding, writing, planning, marketing, or branding, and you want to to focus on doing that as much of the time as possible. I can tell you from my humble experience that by applying sales tactics, you erase the common, avoidable headaches and spend more time doing what you love!


Even if you’re not a salesperson. Because none of us love sales. 


So, what are these secrets already?


Here are the top 3 freelancing complaints and how can sales strategies help:


#1: “Clients never do what they say they will.” 


The Sales Answer: Up-front contracts. This is a technique popularized by David Sandler in which you discuss everything that “might” happen right up front with the client so that you can hold them accountable. Every human feels a deep-seeded need to appear consistent to their word, for nobody likes to be a liar. And in a world where you don’t have any (easily) legally enforceable contracts or leverage, your best friend is simply reminding them that they told you so, respectfully. Here’s what it should look like: 


Freelancer: Just so that I’m clear, you’re awarding the project to me?

Client: Absolutely, we just have to discuss as a team first. 

Freelancer: That’s fine. And in case I don’t hear back by Thursday?

Client: Feel free to follow up with me. 

Freelancer: Great. If don’t hear back by end of day Thursday by noon, I’m going to give you a phone call.

Client: That’s fine.


Now you have up-front permission to call several times on Thursday. It works the same when you talk about meetings, late fees, or any sort of deliverable. Get them to agree up front and you’ve put yourself in a position where if they don’t follow up, they’ve contradicted themselves. This principle is the reason that in sales you’ll see prospects' CEOs apologizing to very junior salespeople for missing a meeting: we all feel that urge, and nobody likes a liar. 


#2: “It’s hard to consistently be getting jobs.” 


The Answer: Manage your pipeline. Lot’s of freelancers out there hunt through hundreds of jobs to find one that appeals to them, apply, and then sit back, get comfortable, and wait. In sales this is practically sacrilege. You have to visualize how many things would have to go right for you to actually make money from that application.


If the client simply never responds, what are you supposed to do? It’s over. If they do respond, but you have a call and their expectations are unrealistic, what are you to do? It’s over. If you do the work for them and they change course and drop the project without paying you, what are you to do? Again, it’s over. It’s like shooting an arrow that needs to blow through five targets in a row. I’ve had hundreds of applications that I thought were an absolute shoo-in that never materialized as revenue. Don’t get left hanging.


Where there are many points of failure, you have no choice but to start managing it like a numbers game. For every job you want, apply to five. For every job you must get paid on, have two backups. The best way to organize your process is to think of it as a sales pipeline, where you figure out how many clients you want and then work backwards to figure out how many phone calls turn into clients, and how many applications turn into phone calls, and that’s how many jobs you actually have to apply for. Do this, and you’ll solve the problem of having consistent jobs!


#3: “It’s hard to get more work from existing clients.” 


The Answer: Always under-promise and over-deliver. A lot of freelancers go about setting realistic expectations, which is both admirable and completely wrongheaded. If clients are satisfied but not impressed by you, they’ll only outsource projects when absolutely necessary. If, on the other hand, you give clients a reason to be so delighted with your work that they brag to their friends about how they "have a gal” (or guy) who handles all of their web dev/ writing/ marketing, etc.


You can do this by simply setting lower expectations and then delivering exceptional results. If a client asks you how long it will take you, add on a day and then submit it early. If a client asks how many articles they can get for a fixed cost, price it higher and throw in one for “free.” When they see you as a surprisingly valuable resource, they’ll start to think of you as an extension of their team and start handing off projects to you at a much higher rate. 


So, are you feeling like a real sales guy yet?


Don’t worry, I don’t, and you should’t either. Sales professionals simply exist in a world where coming up with systems for getting clients to comply is an absolute necessity, and we can dabble in their dark arts. And if you ever find yourself complaining about one of these aspects of freelancing life, you know it’s time to pull some sales strategies out of your bag. 


At the end of the day, you’re freelancing because you have something that you’re terribly good at, be that coding, writing, planning, marketing, or branding, and you want to to focus on doing that as much of the time as possible. By using up-front contracts, managing your pipeline, and under-promising and over-delivering, you guarantee that you’ll waste less time being disappointed and focus on that part that you’re most passionate about!

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