Follow-Up Sequences That Don't Annoy

9 min read

Most salespeople either don't follow up enough or follow up badly. The data is clear: 80% of deals require five or more touchpoints. But those touchpoints need to add value, not just check in.

The Problem with "Just Checking In"

"Just wanted to check in" tells the recipient nothing and gives them no reason to respond. It's the sales equivalent of small talk—polite but pointless. Every follow-up should have a purpose beyond reminding them you exist.

Even worse are the guilt-trip follow-ups: "I haven't heard from you..." or "Did you get my last email?" These create negative emotional associations with your name. Not helpful.

A Better Framework

Each follow-up should do one of these things: provide new information, offer additional value, share relevant social proof, change the angle of approach, or make responding easier. Here's what that looks like:

Subject: Question about [specific thing]
Personalized opening. Clear value proposition. Simple question. Easy call-to-action.
Subject: Resource on [their problem]
Share something useful—article, case study, data point—related to the problem you solve. Brief note: "Thought this might be relevant given [what you know about them]."
Subject: How [similar company] solved this
Brief story about a customer like them. Focus on the problem and result, not your features. "They were dealing with X, we helped them achieve Y."
Subject: Different thought on [topic]
Approach the problem from a new direction. Maybe they don't care about efficiency but care about risk. Maybe the original value prop didn't resonate but a related one will.
Subject: Quick question
Ask a yes/no question. "Is solving [problem] a priority this quarter?" Give them an easy way to respond even if it's a no. "If timing isn't right, just say so—happy to reconnect later."
Subject: Should I close your file?
The breakup email. "Haven't heard back, so I'll assume timing isn't right. I'll close out your file unless you want to chat. No hard feelings either way." Creates urgency without guilt.

Timing Considerations

Space follow-ups by 3-5 days initially, extending to 7+ days for later touches. Sending daily emails burns your list fast. But waiting two weeks between touches lets momentum die.

Best days: Tuesday through Thursday. Best times: 7-9 AM or 5-7 PM in their timezone. Avoid Monday mornings and Friday afternoons.

When to Stop

Six emails over four weeks is a reasonable sequence. If someone hasn't responded after six thoughtful touches, either the timing is wrong or they're not interested. Put them in a long-term nurture and move on.

One exception: if they opened or clicked but didn't respond, they're interested but busy. These prospects might warrant a few extra touches or a different channel (phone, LinkedIn).