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Welcome to the 14th edition of Expert•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.

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Hi Friend!

I hope you’re all safe after Hurricane Helene decimated a large swath of the Southeastern U.S. I’m 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 writer’s groups I’m in on Facebook. (I listed a few of my faves in the Resources section of Expert•ish Freelancer website.) They help me keep the pulse on the freelance industry—what’s working, what’s not, the trends, the challenges, and the success stories.

I happen to see one recent win a freelance writer posted about—how she landed a client after nearly a dozen follow-ups. And this ties in perfectly with this week’s Freelance Focus: the Art of the Follow-Up.

By the way, if you missed last Friday’s 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. 

Today’s newsletter dives into the art of following up.

🔍 Key Takeaways: 

1. Persistence pays off

2. Tailored approach is crucial

3. Strategic timing matters

Today’s edition is brought to you by Authory. Sponsors help keep the newsletter free, so please click on their link to check out their offer! ⬇️ 

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Freelance Focus: The Five Pillars of Follow-Up Success

In one of the Facebook writer’s groups I’m in, I recently saw this post from a freelancer and it caught my attention.

I reached out to Kaitlin for a bit of backstory and she shared this: 

 “My 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: ‘Hi [firstname], circling back on this. Do you need freelance content? Warmly, Kaitlin.’ But I also like to send new clips as a follow-up message.”

This ties in perfectly to today’s focus—the art of following up. 

Why Freelancers Struggle with Following Up

You’re staring at a draft email, wondering if sending that follow-up message will make or break a potential opportunity. “Am I being a pest?” you ask yourself.

Been there myself.

The follow-up process can fill freelancers with uncertainty, leaving you second-guessing your every move. 😱 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? 😳) 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, you’ve got to master the art of the follow-up. If not, you’re 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, I’ve had success many times over the years by continuing to stay in touch with prospects. As usual, I’ve got no percentages to share. 📊 I’m not a number-tracker. (Don’t judge. 😉)

But I know, anecdotally, that I’ve gotten work from as little as one follow-up to as many as a dozen or more follow-ups before I’ve snagged a project.

If you want to stay top-of-mind for potential clients, you’ve 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. 🧊 

The Five Pillars of Follow-Up Success

The secret to effectively following up involves a mix of elements. Here’s 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.

• Don’t 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 don’t know if there’s an ideal length to an effective follow-up, but keep it short. I’ve 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 📞, I’ll follow-up within 2-3 days of first contact. If I connected via email, I’ll follow up in 1 week.

• Depending on what the prospect says (or whether I get a reply at all), I’ll space out subsequent follow-ups so I’m not a pest. 🪰  Follow-up #2 goes out 2 weeks later, #3 goes out 1 month after that, and #4 goes out 1 month after that. If I’m really interested in working with this prospect, I’ll continue to follow up about every 3 months—sometimes via email and sometimes on LinkedIn.

• Depending on the prospect/industry, respect busy periods (like holidays or monthly publishing deadlines).

• Don’t follow-up right after a major news/weather event. (I read a LinkedIn post from a Florida-based exec, saying “Read the room, people” after he received multiple pitches and follow-up sales messages the day after Hurricane Helene caused extensive damage to his coastal community.) Don’t be that freelancer. 🙄

#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. 📆

• Set reminders for different stages of follow-up. I’ll add “FU: Mary Smith” (nope, not that FU 😂) 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 (ahem…you 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 you’ve 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 “break-up” email that can (sometimes) surprisingly re-engage silent prospects. Track which follow-ups generated the best responses and continuously refine your strategy based on what’s working. (While I don’t personally use email tracking tools, I’ve heard good things about free options like HubSpot Email Tracking, Streak, and Boomerang for Gmail.)

High/Low

⬆️ High: Expert•ish Freelancer hit 1000 subscribers this week. #IThinkICanIThinkICan

⬇️ Low: When it rains, it pours—I got three pitch rejections this week. #ouch

When You’re Ready Here’s How I Can Help:

• Turn to Expert•ish Freelancer’s Tools & Resources page highlighting valuable resources to help you successfully run your freelance business. You’ll find apps, tools, training, services, websites, blogs, podcasts, books, videos, and more! If you’ve got a resource you love, let me know about it.

• Ask Me Anything! Your questions and feedback help shape future newsletter content. (I’ve already answered a few subscribers’ 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 you’ve implemented any of the ideas in Expert•ish Freelancer and found success. I might even include your win in a future newsletter. You can reach me at [email protected]. 

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. I’m just here as your guide. Take what works for you, and tweak it to your needs. Rinse. Repeat.

I’ll be back in two Fridays with another edition of Expert•ish Freelancer.

In the meantime….

Be kind. Do good. Give thanks. 😊

With gratitude,
Lisa

FYI: In yoga, the instructor often closes the session by saying “namaste” as a way of acknowledging and honoring the light, spirit, or goodness within each person in the class. 🧘‍♀️ It’s often used as a closing to convey unity (we’re 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. 😊