7 Ways to Follow Up with Past Clients and Silent Prospects Without Annoying Them [Email Templates]

My friend Justin sent me a text I found confusing. He asked, “Is there a site you suggest for me to find writing jobs?” I could certainly rattle off a list for him. But why didn’t my friend, whom I have hired in the past for freelance writing work, ask me if I needed help with anything?

Following up with past clients is the single easiest and best way to drum up new freelance projects. It’s easier to sell something to someone who has already cut you an invoice, someone who is already in the habit of paying you.

Chances are, you guided these clients down the know-like-trust path. By the end of the project, you had earned some or all of their trust. I will assume for a moment that you didn’t destroy the client’s website with advanced virus phage destroyers or accidentally burn down her office building. (Who knew the incendiary headlines you wrote would catch like that?)

You got the job done on time and on budget (mostly), and you weren’t a complete jerk. Why wouldn’t the client want to hire you again?

This post will help you avoid Justin’s mistake. I’ll cover the reasons why we don’t reconnect, as well as a sample email to reconnect with clients.

Table of Contents

• 4 Reasons We Don’t Reconnect with Past Clients
• 7 Ways to Follow Up with Past Clients and Silent Prospects
• Go ahead and steal my 12 email templates
• Best practices when sending re-engagement emails
• FAQs

4 Reasons We Don’t Reconnect with Past Clients

1. Mediocre Results

Let’s face it: Sometimes, we can’t, won’t, or don’t do our best work. Afterward, we’re pros at concocting reasons and excuses. (Note: I can go head to head with the best complainers out there!)

However, griping is a waste of creativity and emotional energy. Seth Godin hit the nail on the head in his post “The bad client/clueless boss trap“: “The winning sentence is, ‘Despite having a lousy client or uninformed boss, we were still able to do great work.'” And later, “You get better clients as soon as you act like the creator who deserves better clients.”

(Related: 3 Types of Freelance Clients You Don’t Want)

This is a bitter pill of truth to swallow if you’ve ever had a truly beastly client. (I know I have.) For all the other scenarios, where you know you probably don’t deserve repeat business, you can still learn and grow.

Send this reconnecting email to the former client who may have been right to part ways with you:

Hi Egbert,

I was thinking about you this morning, and after reflecting on our project, I concluded that, even though our project didn’t go the way I hoped, I can still use the experience to learn and grow. Are you willing to give me honest feedback and help me improve?

Sincerely,
Amanda

2. Your Prices

Your pricing can work for you or against you. Pricing is branding. If you want to increase the perceived value of your products and services, then raise your prices.

Being “affordable” or giving clients “a good deal” may seem attractive or even noble, but a value proposition built around low or competitive pricing actually weakens positioning. To value-conscious clients, low prices signal a lack of experience or confidence. By contrast, high prices signal your expertise and professionalism. Clients who appreciate a satisfying experience and predictable results will care less about price and more about value.

By raising your prices, you may price yourself out of reach of past clients. That’s okay. Not all of the clients who help us build our businesses will stick with us through the entire lifecycle. If you don’t get repeat business because you’re now “too expensive,” then your freelance or consulting business is on the right trajectory! (Just remember to keep tinkering with your value proposition and client experience to make your value abundantly clear.)

3. Their Forgetfulness

Even people who are 100% convinced that you’re the perfect fit for a writing project will forget to contact you. Other priorities and emergencies will chew into their brainspace.

They will keep pushing the next conversation back and back and back until they forget about the project entirely. In fact, prospects and clients may forget about you entirely.

Mr. Local CEO may meet other freelancers or consultants with your skills. He may want to help so-and-so’s nephew at church who just finished his degree in English and could use a writing project or two. You catch wind of this low-grade betrayal later, and think, “What the heck?! He said he liked my work. I could have done that for him, and done it better!”

Sure, you could have. You could have had that client’s repeat business, plus all of the referrals he would have sent your way.

Thankfully, you’re going to learn from that missed opportunity and follow up with old leads by email every six weeks.

4. Your Silence

When past clients or prospects go quiet, we mistakenly assume that they must not want or need more help.

We don’t want to annoy them, so we match their silence with our own. This is a costly mistake. Never assume that people will get in touch with you when they need something.

It’s your job to stay in touch, and staying in touch is as easy as sending a simple email to catch up with the client.

Let’s dive in to 7 tasteful ways to remind clients and prospects you exist.

7 Ways to Follow Up with Past Clients and Silent Prospects

When any of your clients needs help, you want to be the creative who comes to mind. In order to stay top of mind, you must be the boomerang.

Most of Balernum‘s steady growth has come from opportunities I’ve had to sell to past clients. I don’t have to go from cold to sold because they already trust me. I know their brands, cultures, and communication styles. The devil you know is better than the devil you don’t.

So how do you get more business from past clients?

You can use these 7 sample emails to approach old clients. And remember, you don’t really need an excuse to reconnect. Following up with former or “inactive” clients is one way to show them you care. Most of us don’t need a lot of clients. We just need happy clients.

1) Offer to solve a problem.

One of the most important things that I did for my creative consultancy was transition away from being a writer (that is, a specialist) to being a problem-solver (that is, an expert-generalist). Now, when someone asks what I do, I don’t say, “I’m a writer.” I say, “I am a brand strategist and marketing consultant. I help gutsy founders build brands people care about.”

Because I’m a strategist and consultant, I am bigger than my individual skills. I’m bigger than copy and content. I have more things to sell than web pages and blog posts.

What about you? Do you normally identify yourself as a copywriter? I recommend that you position yourself as a problem-solver, not a vendor:

• Sell the benefits of your work, not your skills.
• Sell the disappearance of problems.
• Sell the arrival of desirable outcomes.
• Sell the value of goals achieved.
• Sell smiles and rainbows.

Instead of talking about “high-quality blog posts,” a blogger can say this: “We help companies look good, get found online, and use the internet to generate new leads.”

Being a problem-solver will set you up well later, when you follow up:

Hi Cassandra,
‍
I was just going back through my portfolio, and I smiled when I saw the work we did together. How is business? What challenges are you facing? I’d be happy to make an introduction, share a blog post, or send you a book if there’s a specific problem you’re trying to solve.

Just let me know!

Regards,
Timmy “The Terrible” Trogdor

2) Rep your new skills.

Let’s say you do land a big project. The client is pleased with the outcome. She now has a fabulous website with a high conversion rate. As far as she is concerned, you’re the Willy Wonka of the World Wide Web.

Several months pass. You do more work. You learn. You grow. You add some new offerings to your menu. By the power of Grayskull and Google Juice, you can make the money flow like money.

Perfect. You now need to send a follow up email to former clients about a new service. You can offer to help Cindy Lauper steward her newfound passion for all things content marketing without being annoying or spamming her inbox.

Here’s a reconnect email sample to help you drum up business:

Hi Cindy,
‍
First off, well done on launching the new blog! Your post about homelessness in D.C. was inspiring. I ended up making a donation to the charity you recommend.

And speaking of blogging, I would love to pitch in and help. Since you and I last spoke, I have helped several bloggers grow their email lists and grow their reach.

What do you think about a 20-minute call on Friday at 1:30pm EST?

I’d like to hear about your experience so far, and I can also walk you through the details of my content marketing packages.

Cheers,
Steven Tyler

3) Cite a recent life event.

This one is self-explanatory. Any number of life events and professional accomplishments offer a compelling reason to say hi or congratulations or even to express condolences. Here’s an email template you can use:

Hi Megatron,
I was thinking about you the other day, and then I saw on Instagram that your husband just opened a new bakery. Congratulations!

You all may have your hands full. Do you need help with anything? I’ve got some availability in July and would welcome another opportunity to work with you. If you’d like to discuss, we can use this thread, or you can try my mobile: (202) 456-1111.

My schedule on Friday is pretty clear.

Thanks,
Optimus Prime

4) Find gaps.

Review your clients’ website. Scan their socials. Audit their marketing mix. Ponder their design, photography, copywriting, and strategy. Do you see any weaknesses? What do they really need? Write out and send several recommendations.

You can customize this reconnecting with old clients email template:

Hi First Name,
It had been awhile since I checked out your website, so I paid a visit on Monday. I’ve outlined some recommendations at the bottom of this email.

If you implement them in the next month or so, I think you’ll see [insert desired outcome here].

I’m happy to take the lead on that project—that is, unless you’ve got higher priorities that you want me to take care of.

Check out my recommendations, and let’s hop on a Skype chat tomorrow. Does 2:30pm work for you?

Thanks/Regards/Cheers,
Your Name

‍+++
‍
‍Recommendation #1
Recommendation #2
Recommendation #3
Recommendation #4

5) Fill gaps.

If you’ve got some time on your hands, why not surprise and delight an old client by solving a problem?

• Images – Do the hero images on a client’s Home page suck? Go to your free, license-free, royalty-free, commercial usage stock photography site of your choice, and pick out some new ones. I use Unsplash quite a bit. Search.creativecommons.org is another good place to start.
• Web Pages – Maybe you were responsible for writing ten pages of new web content, but your client later added more content that isn’t very good. Edit a few pages.
• Design – Did you find a solid case study on the client’s blog? Hire a designer to create a beautiful infographic for her.

Give the gift of a problem solved. Then, ask your client if she wants more help. Here’s an email template for reconnecting with old clients:

Richard,
‍
I hope you’re doing well! I noticed that the hero image on your website is low-res. Your pink and leopard print unitard just doesn’t pop the way it could. Here’s a link to a high-res version that will work better: [link].

Speaking of, do you want me to do a comprehensive audit and tell you about other things you could improve? That’s something I do quite a bit for clients, and the results tend to be eye-opening.

Google tends to penalize websites that have problems, such as loading too slowly, and I can normally find some quick fixes to improve a site’s overall health and performance.

What do you say?

Billy
P.S. This video of you is AWESOME: [link]. Please, please, please let me put it on your homepage. 🙂

6) Make introductions.

Whom might your client benefit from knowing? Send an email requesting permission to make the introduction:

Hi First Name,
‍
I was thinking about you the other day. I think you’d benefit from knowing [Somebody Else]. He is a [profession/business focus/specialization here], and he really cares about [result/outcome/passion/hobby here].

I’d like to introduce the two of you over email. Is that okay with you?

Sincerely,
Your Uber-Thoughtful Writer

7) Send resources.

Is your client a third-party logistics company interested in content marketing? Do various Google searches until you find an industry-specific blog post, video, or app that can help them.

Share it in an email:

Hi First Name,
‍
I found this the other day and thought of you. I know you all are interested in [insert interest here], so this post might help you [insert desired outcome here].

How are things going? I’d love to catch up.

How about 15 minutes tomorrow? I’m free at 1:30pm and 4:45pm. Let me know if either time words for you.

Thanks/Regards/Cheers,
Your Name

Generosity is the single most attractive thing in business.

If you want to close more sales quickly, give more.

8) Buy coffee or lunch.

Treat your clients to lunch. Read more here: There’s Nothing Wrong with a Free Lunch

Hi Bluto,
‍
It’s been awhile since we connected. Can I buy you coffee next Friday morning? I’d enjoy hearing the latest from you, and I want to give you a book I just finished reading.

Your sworn enemy,
Popeye

9) Ask open-ended questions.

After you finish projects, offer to check in a couple of months to see how everything is going. Here’s the important part: put a reminder in your calendar. Feel free to steal these Million Dollar Beauties:

• How’s business?
• Do you need anything?
• Do you have any bottlenecks?
• What are your goals for this year?
• What are you excited about?
• What would you like to see happen?

Here is what open-ended questions look like in action:

Prince Harry,
‍
I had a reminder in my calendar to follow up with you, and I saw on LinkedIn that you’re stepping away from most of your duties with the royal family. Good for you! I’m curious… What are you excited about? And what are your goals for this year?

Sincerely,
The Duke of Weselton

Bingo. When your clients begin to associate you with their goals and you begin serving as a trusted advisor, rather than a vendor with a certain skillset, you’ll find that it’s really easy to sell them more work.

Go ahead and steal my 12 email templates.

Okay, that was 9 ways, not 7 ways, to follow up with past clients and silent prospects. But who’s keeping track?

What you do need to keep track of is all of the email templates I shared. I have created a handy swipe file with the 10 templates I shared above, plus 2 other templates that are really, really effective at WAKING UP silent prospects.

Put in your name and email address below, and I’ll send you the download link.

Best practices when sending re-engagement emails

1. Personalize your messages. This shows that you value the relationship and understand the client’s unique needs and preferences. For example, if you know they prefer short emails, be brief.
2. Follow up until you get a clear no. The answer is always a yes until you get a clear no. My past clients have thanked me for being persistent. I estimate that I’ve won 50% or more of my freelance and consulting engagements after the fifth follow up.
3. Share new insights, resources, and exclusive offers that are tailored to their specific and current needs. I mean, duh.
4. Write a captivating subject line. The subject line is the first thing your old clients see in their inbox, so it’s critical that yours grabs their attention. It doesn’t matter how good your email is if they don’t open it.
5. Include a clear call to action. Clearly state what you want them to do next and make it easy for them to take that step.
6. Schedule your follow-ups. You want to strike a balance between not being too pushy and not waiting too long. Note: I take this on a case by case basis.
7. Track and analyze the results of your re-engagement campaign to refine your approach. Use a tracking app like Yesware or email marketing platform like HubSpot or ConvertKit to keep an eye on metrics such as open rates, click-through rates, and conversion rates.
8. Conduct A/B testing and experiment with different subject lines, email lengths, and calls to action to identify what resonates best with your old clients.
9. Adapt and refine your email strategy based on the feedback and data you receive.

FAQs

Which of my past clients should I reconnect with?

You want to reconnect only with past clients you enjoyed. Reflect back on the project and relationship:

• Did the client pay on time? 
• Was the work itself enjoyable? 
• Was the client responsive, respectful, and reasonable? 
• Would you credit any mistakes, misunderstandings, and miscommunication to the client’s personality or unhealthy culture, or were circumstances to blame for?

A mentor once told me, “People show you who they are. They keep showing who they are. You should let them.”

You can forgive a client for mistreating you—in fact, forgiveness is better for your health—but chances are, the client hasn’t changed. You’re more likely to see history repeat than to have a dramatically different and more satisfying experience the next time around.  

Believe what the client has already shown you, and only reach out if you’d be eager to work with them again.

Why should I reconnect with my past clients?

Try not to take this personally, but you are easy to forget. When I say “you,” I really mean all of us.

Even if you knock the project out of the park and a client is effusive with his praise, he may simply forget about you by the time the next project comes along. He may give the website relaunch to the designer he just met at the gym. Or, she may farm out the big market research and industry insights report to the sharp consultant who married her college roommate.

We reconnect with past clients because they’re always meeting new people. To stay top of mind we must stay in touch. Don’t take it personally, and do build a follow-up habit.

Why do old clients disengage?

Old clients disengage for specific reasons, and once you identify them, you can tailor your re-engagement emails or DMs to address their concerns and bring them back into the fold:

• Changes in the client’s needs or circumstances. As time goes by, clients' needs and circumstances may change. Your “old” offerings become less relevant to them, but as your capabilities grow, you may find a new fit elsewhere.
• Perceived lack of value or relevance. If a past client feels that your services no longer provide value or aren’t relevant to the current situation, they may disengage. For example, an e-commerce company might tell my friend Liam, “We enjoyed working with you, but we’re not focused on SEO at the moment.”
• Competition. A competitor’s offers, expertise, or results may tempt your client to disengage with you and try someone new.
• Lack of communication or follow-up. If you fail to communicate or follow up, your clients may assume you’re too busy for them or feel neglected.