Publication Date

September 5, 2025

Summary

Most clients don’t reply until the 5th or 6th follow-up. Not because you’re annoying — but because they’re drowning in work, waiting on budgets, or simply not ready yet.

The Truth About Follow-Ups

Here’s the truth about follow ups: Silence doesn’t mean “no.”

It just means they haven’t replied yet.

Fun fact: most (85%) of my clients in the past 8 years came from the 5th or 6th follow-up.

And they weren’t annoyed or put off — they were grateful I kept reaching out.

No, literally, they said things like:

“Thanks for being so persistent. We really need your help right now.” – Luke Lappala, Coding Dojo
“I'm so glad you reached out again. Can we meet this week?” – Gregg Blanchard, Sendview

Because on the other side of that “no reply” is someone:

→ juggling 3 people’s jobs thanks to layoffs

→ dealing with budget chaos and hiring freezes

→ genuinely interested but not ready to say yes yet

The timing isn’t personal. It’s just timing.

And when it does become the right time? You’ll be the one they think of — because you stayed on their radar.

How to Follow Up Without Being Weird

Following up isn’t annoying. But following up without context is annoying. Here’s how to do it the right way.

1. Introduce Yourself (anytime after they accept your connection request)

DO NOT send follow-ups without introducing yourself first. Be a human.

But also — don’t pitch in your intro message.

Just say: hi, this is who I am and here’s why I connected. Try this template:

“Hey [Name], thanks for connecting! I’m a [type of freelancer] for [types of companies you help]. I saw [something about them], [your remark about it].”

2. First Follow-Up (2 weeks after connecting)

Now we validate the lead. We’re still not pitching — we’re gauging fit. Try this message:

“Hey [Name], do you ever work with freelancers at [Company]?”

3. Second Follow-Up (2 weeks later)

Whether they responded or not, you can now offer help. This is still gentle — not a hard pitch.

“Hey [Name], I’m taking on new projects starting [Date]. Any need for [your service] at [Company]?”

You're just reminding them you exist and making the next step easy. Not convincing them. Or selling yourself. Just letting them know you’re here to help.

4. Quarterly Check-Ins (every 3 months)

Plans and budgets shift quarterly. This is when the biggest “yeses” happen.

Use the same message as follow-up #2 (above).

You can follow up 5 more times leaving 3 months between each one.

And, no, you’re not going to be perceived as desperate if you do this. It’s professional. THIS is how sales works.

Why Follow-Ups Are So Necessary for Freelancers

Most freelancers tell themselves a story when a prospect doesn’t reply:

“They don’t want to work with me.”
“I’m being annoying.”
“I should stop.”

But here’s the actual story behind the scenes:

→ People are overwhelmed.

→ They’re busy.

→ They’re drowning in notifications and platform chaos.

They are not sitting around analyzing your message.

When it finally is the right time?

They hire the person whose name is familiar — the person who kept showing up with warmth and consistency.

Your follow-ups become proof of:

reliability
professionalism
resilience
support, not pressure

That’s why follow-ups convert.

The Emotional Part No One Talks About

Following up requires emotional endurance.

Freelancing asks you to grow in ways no traditional job ever did. The work itself isn’t hard. But the instability is.

The “did I say the wrong thing?” spiral is so real. The impostor feelings are intense.

You have to decide — consciously and compassionately — that the discomfort, silence, and awkwardness are worth the payoff of landing clients and making money on your own terms.

This isn’t about “getting over it.” It’s about growing through it. And you can. You’re built for this. You wouldn’t have started if you weren’t.

FAQ: Follow-Up Strategy for Freelancers

How many times should I follow up with a potential client?

Up to 5–7 touchpoints total. Most conversions happen on follow-up #5 or #6 — not the early ones.

How long should I wait between follow-ups?

Two weeks between the intro and your first two follow-ups, then move to three months between check-ins.

What if I feel annoying?

Feeling annoying is emotional. Being annoying is sending 4 messages in a week. You’re not doing that — you’re following a professional cadence. And you’re not being annoying! This is where mindfulness comes in.

What if they still don’t respond after multiple follow-ups?

That’s okay. Some people never will. Keep them on quarterly check-ins and spend more time on new leads. It’s probability math, not a final verdict.

Do I change my message each time?

You should have 3 message types (templates above). But, for quarterly follow-ups, you can simply use the same message detailing your availability, a call to action, and your services. Simple, clear, repeated messages perform best. Don’t overcomplicate it.

Is following up on LinkedIn different from email?

Slightly — LinkedIn relies more on timing and visibility. Quarterly messages are extra powerful because budgets and priorities shift throughout the year.