Follow-up is where most deals are quietly lost — and where most people get it wrong in one of two ways. Either they send one message, hear nothing, and give up (leaving money on the table), or they keep "checking in" in a way that reeks of desperation and slowly annoys the prospect into a permanent no. Both fail. There's a third path: persistent follow-up that adds value every time and never makes the prospect feel chased. Done right, follow-up builds the relationship instead of straining it.
Here's the difference between persistence and pestering, and how to stay on the right side of it.
Good follow-up is persistent without being desperate — each message adds value, so you stay top of mind without seeming to chase.
The distinction:
Don't "check in." Show up with something worth their attention.
The two default approaches to follow-up fail for opposite reasons. Quitting after one message fails because a single touch rarely lands at the right moment — the prospect was busy, distracted, not ready, or simply forgot. Most positive responses come after the first message, so giving up early forfeits the majority of deals that were still winnable. Silence isn't a no; it's usually just noise, and treating it as a no leaves money on the table.
Desperate follow-up fails for the opposite reason: it's persistent but empty. The endless "just checking in," "any update?," "circling back" messages add nothing — they're requests for the prospect's attention with nothing offered in return. Each one says "I want something from you" and gives no reason to respond, so they accumulate as irritation. This is what makes follow-up feel desperate: not the frequency, but the emptiness. A prospect getting their fifth content-free "checking in" feels chased, because every message has been about the sender's need with nothing for them. The desperation isn't in following up; it's in following up with nothing to say.
The insight that resolves both failures is that the problem was never frequency — it was emptiness. The fix isn't to follow up less (that's just quitting) or to follow up more carefully-worded (lipstick on an empty message). The fix is to make each follow-up add value:
| Desperate follow-up | Value-add follow-up |
|---|---|
| "Just checking in" | "Saw this — thought of you" |
| Asks for attention, gives nothing | Gives something useful, asks nothing |
| About the sender's need | About the prospect's interest |
| Feels like chasing | Feels like helping |
When every follow-up gives the prospect something genuinely useful — a relevant article, a helpful insight, an answer to a question they raised, a resource tied to their situation — it stops feeling like chasing and starts feeling like help. You're not asking "any update?"; you're saying "here's something I thought would be useful to you." That message is welcome no matter how many times it arrives, because each one gives rather than takes. The same persistence that feels desperate when empty feels generous when valuable. This is the same principle that separates good cold outreach from spam: relevance and usefulness are what earn attention, and their absence is what gets you ignored. Change the content, not the cadence.
The deepest reframe is that persistence itself isn't the problem — empty persistence is. Persistent follow-up is genuinely welcome when each touch is useful, because you're repeatedly demonstrating that you understand the prospect's situation and are willing to help before they've bought anything. That builds the relationship and trust, which is exactly what moves a deal forward. The prospect who receives a series of genuinely helpful, no-strings messages doesn't feel chased — they feel like they've found someone worth working with.
So the goal isn't to follow up less to avoid seeming desperate; it's to make every follow-up worth receiving, at which point persistence becomes an asset instead of a liability. Stay top of mind by being consistently useful, not by repeatedly asking for updates. This is also why follow-up is where deals are won — not because persistence alone closes, but because valuable persistence builds the trust that closes. The prospect's silence is your invitation to demonstrate value over time, not your cue to either vanish or pester. Show up repeatedly with something worth their attention, and persistence stops being a risk and becomes the relationship.
To make your follow-up persistent and welcome:
The throughline: most people lose deals by either quitting too early or pestering with empty messages — and the fix for both is value, not frequency. Make each follow-up genuinely useful and persistence stops feeling like desperation and starts feeling like help. The prospect's silence is an invitation to demonstrate value over time, not a cue to vanish or chase. Don't check in — show up with something worth their attention, and follow up as many times as you have something useful to say.
Q: How many times should I follow up before giving up? There's no fixed number, because the right answer is "as long as you have something useful to offer." Quitting after one message forfeits most winnable deals, since the majority of positive responses come after the first touch — silence is usually just noise, not a no. But persistence only works if each message adds value. So the limit isn't a count; it's whether you still have something genuinely helpful to say. When you do, keep going; the persistence is welcome because it's useful.
Q: What makes follow-up feel desperate? Emptiness, not frequency. The "just checking in," "any update?," "circling back" messages add nothing — they ask for the prospect's attention while offering nothing in return, so each one says "I want something from you" and accumulates as irritation. A prospect getting their fifth content-free check-in feels chased because every message has been about the sender's need. The desperation is in following up with nothing to say, not in following up itself.
Q: What should a good follow-up actually contain? Something genuinely useful to the prospect: a relevant article, a helpful insight, an answer to a question they raised, or a resource tied to their specific situation. The goal is to give rather than take — "here's something I thought would be useful to you" instead of "any update?" That message is welcome no matter how often it arrives, because it demonstrates you understand their situation and are willing to help before they've bought anything. Change the content, not the cadence.
The follow-up that doesn't feel desperate is the one that adds value every time. Most people fail at follow-up in one of two ways: quitting after one message, which forfeits the majority of deals that were still winnable, or pestering with empty "just checking in" messages that accumulate as irritation. Both lose.
The fix isn't frequency — it's value. When every follow-up gives the prospect something genuinely useful, persistence stops feeling like chasing and starts feeling like help, and a helpful message is welcome no matter how many times it arrives. Empty persistence feels desperate; valuable persistence builds the relationship that closes the deal. The prospect's silence is your invitation to demonstrate value over time. Don't check in — show up with something worth their attention.
No following, no network, no luck. Just an unglamorous system I ran for eighteen months. Here's exactly what I did.
I went from 200 to 11,000 subscribers without hiring anyone. AI didn't write my newsletter — it did everything around it.
I chased big, audacious goals for years and burned out every time. Then I built my whole life around wins so small they felt like cheating.
Comments
Sign in to join the conversation
No comments yet. Be the first to share your thoughts!