As a freelancer, closing one $2000 deal is more profitable than ten $200 deals. The income is the same, but the effort varies hugely in each case.
The right approach should be to crack lesser but high-paying deals, especially those that lead to long-term collaborations.
But high-paying deals don’t always have to start as such. You can upsell your services to the same client. I did the same. According to Hubspot, 72% of salespersons who upsell increase their revenue by 30%.
When I started working for the client in May 2023, I earned $250 for the first month. Since then, I expanded my work with the client to receive a monthly pay of $1200 before I dropped them in May 2024.
That’s almost 5x the income for a little more work than earlier. A win-win situation for the client and me.
So how to retain freelance clients, how to upsell, when do you upsell, and when do you not upsell?
I’ve answered them all in this article.
How To Retain Freelance Clients Through Upselling
Choose The Client Wisely
Even before you start thinking about upselling, take some time to analyze what kind of clients you’d work with.
Remember that this process is going to be long-term. My longest collaboration with a client was 12 months. You surely need a green-flag client to continue the collaboration.
Be honest with yourself and note every red flag in a potential client according to you. You don’t want to onboard every lead and work your tail off. Be selective about your non-negotiables.
For instance, my deal-breakers are:
- When I don’t vibe with the prospect
- When their values don’t align with mine
- When they’re not certain about their goals
- When they downplay my services or compare prices
Set your non-negotiables right when you finalize your services and stay true to them. Usually, you can easily point out the red flag behaviors in prospects when you’re on the first discovery call. The more calls you attend, the faster you get at analyzing your clients. I’ve talked about the common red flags in clients in the last section of this article.
| Suggested Reading: Create Content for Every Stage of the Buyer’s Journey
For now, let’s continue with the ways you can retain existing clients:
The Beginning Of Upselling Starts During The Onboarding
As you analyze the prospect before signing the contract, so does the prospect analyze you.
Whether they approached you or the other way around, they’re not completely sold on you from the get-go. The way you present yourself says more than your previous results.
- Do you take time to hear them out and understand their problem?
- Do you make them feel you’re the right choice?
- Do you clarify every objection?
If yes, you stand a high chance of establishing trust right away.
“I’m so glad I decided to contact you.”
This is what the client said after our first call. If you can gain their confidence right away, it’ll lead to a long-term relationship.
But that’s not always the case. The first meeting is just the beginning. The real work starts afterward.
Deliver More Than You Promised
Rule #1: Never promise a specific result. (It’s business. I can’t guarantee you 6 bookings in 1 month.)
Rule #2: Promise delivery and overdeliver.
Promise what you can guarantee—the delivery. And then surprise them by giving more than you promised.
For example: If I offer ghostwriting service to my clients, I go a step ahead and suggest changes in their LinkedIn profile, the best way to do engagement strategy, and DM strategy for generating leads. I don’t promise them the number of leads but still deliver more than I promised for.
Gaining trust doesn’t seal the deal. In fact, the client can break the deal if you fail to maintain the trust. Don’t let the client regret their decision to choose you.
I focus on genuinely helping my clients achieve their desired results. Honesty comes first, even if it means saying ‘No’ at times. I like to believe I’m a partner in their journey, not just a service provider. That is reflected in our conversations and my work.
That strengthens the trust you built. The clients then know you have their best interest at heart.
Which brings me to the next point.
Don’t deliver services. Deliver experience.
Clients do come to you for your service. But they stay because of the experience you gave them. Make the experience more premium than the service.
That’s what happened with this client.
“I can’t imagine anyone else doing this. You’re never supposed to leave me.”
Listening to a client say this is the best feeling. That’s the sign that you can upsell without sounding sales-y or desperate.
Create A Feedback Loop
You can’t improve what you don’t measure. Schedule a fixed time for feedback every month. It ensures your client that you’re willing to bring your best and lets you understand where you need to improve.
It also works the other way around. Sometimes, the client isn’t on the same page as you. They can’t envision your plans, or there’s simply some miscommunication. A feedback loop at such times puts everything at ease and aligns your client’s thoughts with yours.
Always add these points to your feedback meeting’s agenda:
- Review of monthly goals
- Plans ahead
- Area of improvement from your side
- Area of improvement from the client’s side
Implement Changes And Resolve Issues
The immediate logical step after collecting feedback is implementing the changes. Be prompt in making those changes and examine the results those changes bring.
Communicate the changes you made and their implications with your clients.
I’d say, don’t wait for the feedback to resolve issues. If you find something’s off, be the first one to bring it to notice, offer a solution, and implement it.
Always ensure you’re keeping the client in the loop. Such proactiveness is always appreciated and rewarded. The reason’s clear—clients hire freelancers to lessen their load. If they have to be the first one to point out any problems, they feel that the purpose of hiring someone is defeated.
But if you always solve the problems before the client even notices them, they know they made the right investment.
Offer More Than What’s Written In The Contract
I’m not a designer but when my client was updating their services, I went ahead and created a new LinkedIn banner for them. They didn’t ask me to design one. It was something extra I offered them, for free.
I know it’s important to stick to the contract—and sometimes, it’s crucial, as some clients can exploit you. But there’s a lot of space between doing what the contract says and straight-up exploitation.
You can offer a little something here and there, like a free design or an extra post or copy for a landing form. Clients remember this extra effort, and as little as it may seem, such gestures contribute greatly when clients decide to sign a retainer.
Note: Never let these small gestures become regular enough that the client can easily exploit you. Remember, you deserve to get paid for the value you offer.
Respect The Client
Show you respect the client’s knowledge, their position, and time through your actions. Listen actively to their ideas, concerns, and feedback. It may happen that sometimes you don’t agree with their thoughts. Mention it politely without sounding condescending.
While you’re the expert in your field, remember that the client is the expert in their business. Value their insights about their industry and target audience.
Keep personal issues separate from work. Maintain a professional demeanor in all interactions, even if you develop a friendly relationship.
Even being honest about your mistakes and owning them shows your respect for the client.
Effective Communication
No long-term collaboration works without clearly communicating your expectations. From your working terms to your expectations of results, be honest and clear about what you can offer.
If conflicts arise, address them promptly and professionally. Focus on solutions rather than blame, and always maintain a respectful tone. Adapt your communication style to match the client’s preferences. Some may prefer formal emails, while others might like casual check-ins.
Grab Opportunities When They Show Up
Many times, your clients will expand or need more services than you initially signed the contract for. That’s understandable, given that businesses can change their needs.
Even if the client doesn’t feel the need, you can find some areas where they can use your help.
If you signed them as a ghostwriter, they might also need newsletter ghostwriting. Or website copy can go along with blog writing.
For me, it went from ghostwriting LinkedIn posts to:
- Newsletter copywriting
- Website copy
- Content creation and management for a new product
You get the gist. The client’s business started growing, and so did her trust in my services.
Whenever she asked me if I had the capacity and will to take up new work, I agreed. (The fact that I had the capacity was equally important. It’s because I never work with more than 2 clients a month.)
That brings me to the point—when you see a long-term collaboration budding that can result in a future partnership, don’t hesitate to offer more services than you thought. One good client means less stress, more referrals, and a familiar environment.
And if need be and you need to learn a few new skills, go for it. As the content manager, I had to understand Kajabi basics, which weren’t a part of my skill set earlier. But it was manageable, and you can rework the contract to include more pay for the extra work you’ll be doing.
Explore and add new skills to your portfolio as long as they’re not entirely tangent to your niche. You can always:
- Distribute and delegate work
- Hire interns and create SOPs
- Automate processes
The goal is to increase the MRR without burning yourself out.
Not to forget: Be open with the client about your working flexibility and availability as the workload increases. Though you’re happily accepting more work, it doesn’t mean you don’t convey any discrepancy with the client. At that point, the client is happily willing to make some adjustments. You’ve earned that privilege.
Common Challenges And Solutions In Retaining Freelance Clients
- Clients gradually adding more work without adjusting compensation: Clearly define project scope in contracts. When extra work is requested, discuss and renegotiate terms politely but firmly.
- Late payments or disputes over invoices: Set clear payment terms upfront. If there’s a delay, send a gentle reminder. Understand the client’s genuine problems. Work a clause for advance payments in your contract.
- Balancing quality as you take on more work from a client: Gradually scale up, outsource services if necessary, and be transparent about your capacity limits.
- Client’s business changes, requiring new skills or services: Stay adaptable, invest in ongoing learning, and be open to expanding your skill set when it aligns with your long-term goals.
- Becoming overly reliant on a single client for income: Diversify your client base, even when comfortable with a main client. Continuously network and market your services.
- Keeping your skills and services relevant as industry trends change: Stay updated with industry developments, attend workshops, and continuously upskill.
- Dealing with negative feedback or criticism from long-term clients: Approach criticism professionally, use it as a learning opportunity, and implement changes where necessary.
Red Flags In Clients To Avoid To Earn Consistently As a Freelancer
Here are some red flag clients you should always avoid if you want to make a consistent income through freelancing:
- Constant haggling over prices
- Unclear and constantly changing project scope
- Not having clarity about their requirements
- Poor communication
- Taking your work for granted or not acknowledging your efforts
- Unrealistic expectations
- Micromanagement
Final Thoughts On Retaining Freelance Clients
A business always has something more you can work on. Upselling is a matter of delivering quality service, understanding the client’s pain points, resolving them, and earning trust. When you see an opportunity, you’ll get it, or the client will offer it themselves. The real upselling starts way before you upsell.
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