- Expertâ˘ish Freelancer
- Posts
- EF #14: đ The Five Pillars of Follow-Up Success
EF #14: đ The Five Pillars of Follow-Up Success
A Freelancer's Blueprint for Turning Prospects Into Clients

Welcome to the 14th edition of Expertâ˘ish Freelancer, a newsletter that helps you launch or elevate your freelance business. Every other Friday, get tips tools, and insights based on my 35+ years as a freelance writer.
New here? Welcome! đ Subscribe for free.

On a press trip to Panama, I visited Miraflores Locks to see massive ships transition
between the Pacific Ocean and the higher elevation of the Panama Canal.
Hi Friend!
I hope youâre all safe after Hurricane Helene decimated a large swath of the Southeastern U.S. Iâm in Central Florida, and we totally lucked out on this monster storm. Feeling very blessed. Hope you are, too.
I love some of the freelance writerâs groups Iâm in on Facebook. (I listed a few of my faves in the Resources section of Expertâ˘ish Freelancer website.) They help me keep the pulse on the freelance industryâwhatâs working, whatâs not, the trends, the challenges, and the success stories.
I happen to see one recent win a freelance writer posted aboutâhow she landed a client after nearly a dozen follow-ups. And this ties in perfectly with this weekâs Freelance Focus: the Art of the Follow-Up.
By the way, if you missed last Fridayâs Bonus #8: Letter of Introduction (LOI) Template that arrived in your inbox, I encourage you to download it ASAP. I make Bonus Items available to download for one to two weeks, and then they disappear.
Todayâs newsletter dives into the art of following up.
đ Key Takeaways:
Persistence pays off
Tailored approach is crucial
Strategic timing matters
Todayâs edition is brought to you by Authory. Sponsors help keep the newsletter free, so please click on their link to check out their offer! âŹď¸
Finally! A portfolio that's auto-updating andďťż backs up your work.
Authory saves you hours with a portfolio that's always up-to-date.
Protect your work from site shutdowns.
Be ready to impress potential clients and employers, anytime.
Friday Freelance Fuel
Hereâs your weekend To-Do list to inspire next weekâs success.
â Laugh: I loved this LinkedIn post from Jay Acunzo, highlighting the diverse roles/services offerings of todayâs freelancers. Took me a second to get the joke, and then I đ.
â Read: Are you guilty of using the worst opening line (âI hope you are wellâ) for an email? Me, tooâespecially when reconnecting with someone after a while. Redpoint offers a few alternatives.
â Do: ARS Technica explains how to opt out of AI training on LinkedIn in your Data Privacy section.
Freelance Focus: The Five Pillars of Follow-Up Success
In one of the Facebook writerâs groups Iâm in, I recently saw this post from a freelancer and it caught my attention.
Y'all, I just got a test assignment with a company I first sent a LOI to in August 2023. It took a total of TEN follow-up messages.
I reached out to Kaitlin for a bit of backstory and she shared this:
âMy niche is B2B tech, or at least it was primarily until tech started getting hit economically. A well-known cloud services company was long on my list of target prospects, but I nearly gave up keeping in touch with them. I actually decided to start trying to win them as a client back in 2021 when I wrote a story about them for an industry news and review site. Honestly, my last message to them was nothing special: âHi [firstname], circling back on this. Do you need freelance content? Warmly, Kaitlin.â But I also like to send new clips as a follow-up message.â
This ties in perfectly to todayâs focusâthe art of following up.
Why Freelancers Struggle with Following Up
Youâre staring at a draft email, wondering if sending that follow-up message will make or break a potential opportunity. âAm I being a pest?â you ask yourself.
Been there myself.
The follow-up process can fill freelancers with uncertainty, leaving you second-guessing your every move. đą From the nagging fear of appearing desperate to the challenge of figuring out what to say, freelancers often find themselves paralyzed by the prospect of reaching out again.
Add to this the anxiety about optimal timing (Is it too soon? đł) and the delicate balance between persistence and professionalism, and it's no wonder freelancers choose to let promising leads slip away rather than risk an awkward interaction.
Why Mastering the Follow-Up Is Your Secret Weapon
If you want to survive as a freelancer, youâve got to master the art of the follow-up. If not, youâre leaving money on the table
Rather than throw numbers at you to convince you that follow-ups work, feel free to check out this Hubspot article about key stats to help you sell smarter in 2024.
From my own personal experience, Iâve had success many times over the years by continuing to stay in touch with prospects. As usual, Iâve got no percentages to share. đ Iâm not a number-tracker. (Donât judge. đ)
But I know, anecdotally, that Iâve gotten work from as little as one follow-up to as many as a dozen or more follow-ups before Iâve snagged a project.
If you want to stay top-of-mind for potential clients, youâve got to embrace strategic follow-ups.
Why Traditional Follow-Up Methods Fall Flat
Many freelancers fall into the trap of using generic templates without customizing them, lessening their effectiveness.
Others bombard prospects with an aggressive follow-up cadence that quickly transforms interest into irritation. Yikes!
And, sadly, others adopt the wait-and-hope approach, delaying follow-ups so long that the opportunity has grown cold. đ§
The Five Pillars of Follow-Up Success
The secret to effectively following up involves a mix of elements. Hereâs what works for me.
#1 Personalize Every Follow-Up
Reference your previous interaction by following up on the initial email. Over time, this email thread creates a chronological conversation.
Donât assume your prospect remembers what you previously discussed weeks or months ago. Include project details or respond to any previous points the prospect mentioned (such as the freelance budget is frozen until Q3).
Craft personalized, concise, and persuasive follow-up messages. I donât know if thereâs an ideal length to an effective follow-up, but keep it short. Iâve found just 3-5 sentences typically work for me.
#2 Timing is Everything
If I met someone in person, connected on LinkedIn, or we talked on the đ, Iâll follow-up within 2-3 days of first contact. If I connected via email, Iâll follow up in 1 week.
Depending on what the prospect says (or whether I get a reply at all), Iâll space out subsequent follow-ups so Iâm not a pest. 𪰠Follow-up #2 goes out 2 weeks later, #3 goes out 1 month after that, and #4 goes out 1 month after that. If Iâm really interested in working with this prospect, Iâll continue to follow up about every 3 monthsâsometimes via email and sometimes on LinkedIn.
Depending on the prospect/industry, respect busy periods (like holidays or monthly publishing deadlines).
Donât follow-up right after a major news/weather event. (I read a LinkedIn post from a Florida-based exec, saying âRead the room, peopleâ after he received multiple pitches and follow-up sales messages the day after Hurricane Helene caused extensive damage to his coastal community.) Donât be that freelancer. đ
#3 Provide Value in Every Interaction
Find different ways to add value to your follow-ups. Offer relevant industry insights, resources, articles, or solutions to demonstrate your expertise.
Offer quick tips related to their business.
Highlight new skills, awards, certifications, or services you've developed.
Share fresh clips.
#4 Create a Follow-Up System
Use whatever works for you to schedule and track follow-ups. I tried using Customer Relationship Management (CRM) tools (like the free option through HubSpot), but I found them too cumbersome for my basic needs. You might like them. I go old school by using a mix of Excel spreadsheets and my Outlook calendar. đ
Set reminders for different stages of follow-up. Iâll add âFU: Mary Smithâ (nope, not that FU đ) on my calendar on the exact day to follow up.
Develop templates as starting points, but always personalize them to each prospect.
#5 Focus on Building Relationships, Not Just Closing Deals
Ask about their current projects or challenges. For instance, if you discover in your research (ahemâŚyou are doing some research on key prospects, right?) that the company just launched a new project, you can offer your relevant services to help.
Focus on building rapport and trust with potential clients. If youâve got testimonials on your website or LinkedIn profile, link to them for social proof. If the prospect talked about a big conference or event, ask how it went.
Offer congratulations on recent achievements, like an award or a promotion you read about on social media.
Finally, plan a strategic sequence of at least 3-5 follow-ups, varying your approach each time. You might even conclude with a well-crafted âbreak-upâ email that can (sometimes) surprisingly re-engage silent prospects. Track which follow-ups generated the best responses and continuously refine your strategy based on whatâs working. (While I donât personally use email tracking tools, Iâve heard good things about free options like HubSpot Email Tracking, Streak, and Boomerang for Gmail.)
Action Step!
Ready to put your knowledge into practice? Now that youâve got a better understanding of the importance of following up, take action! Choose one prospect youâd really like to work with and draft a personalized follow-up email. Focus on providing value, building rapport, and addressing any specific concerns.
Spoiler Alert! Iâll be sending another Bonus Item next Friday, which includes a sample follow-up sequence you can tweak to your needs. Youâre welcome. đ
High/Low
âŹď¸ High: Expertâ˘ish Freelancer hit 1000 subscribers this week. #IThinkICanIThinkICan
âŹď¸ Low: When it rains, it poursâI got three pitch rejections this week. #ouch
Mindset Matters
In my yoga classes, the teachers encourage us to cultivate a positive and resilient mindset. Just as we persist through challenging poses, we can apply this perseverance to our follow-ups. By focusing on connecting with prospects and building trust with them, we can approach each follow-up with intention and confidence. Remember, like yoga, progress with follow-ups is often made through consistent practice and patience.
When Youâre Ready Hereâs How I Can Help:
Turn to Expertâ˘ish Freelancerâs Tools & Resources page highlighting valuable resources to help you successfully run your freelance business. Youâll find apps, tools, training, services, websites, blogs, podcasts, books, videos, and more! If youâve got a resource you love, let me know about it.
Ask Me Anything! Your questions and feedback help shape future newsletter content. (Iâve already answered a few subscribersâ questions in past issues.) You can reach me at [email protected].
Follow me on LinkedIn. I share more freelance tips/insights most weekdays.
Share Your Success Story. I would LOVE to hear how youâve implemented any of the ideas in Expertâ˘ish Freelancer and found success. I might even include your win in a future newsletter. You can reach me at [email protected].
How would you rate this issue of Expertâ˘ish Freelancer newsletter? |
Thanks for allowing me into your inbox!
I look forward to sharing my freelance journey with you, and I look forward to hearing about yours. Iâm just here as your guide. Take what works for you, and tweak it to your needs. Rinse. Repeat.
Iâll be back in two Fridays with another edition of Expertâ˘ish Freelancer.
In the meantimeâŚ.
Be kind. Do good. Give thanks. đ
With gratitude,
Lisa
Namaste, freelancers!
FYI: In yoga, the instructor often closes the session by saying ânamasteâ as a way of acknowledging and honoring the light, spirit, or goodness within each person in the class. đ§ââď¸ Itâs often used as a closing to convey unity (weâre all interconnected), gratitude (thank you for this shared experience), respect (I respect you and your journey), and peace (may you find peace within yourself). Essentially, it's a way to acknowledge the shared experience and to leave with a sense of peace and connection. đ