EP55D Following up consistently without seeming pushy

Following Up

Following up has always been a thorny area for me. I worry about appearing pushy, overbearing, or annoying when I send reminders or check in with potential clients or collaborators. Early in my business, this hesitation caused me to miss opportunities. I would send one email and then wait weeks, hoping the person would respond, only to realize that silence didn’t mean disinterest — it meant I hadn’t made follow-up easy.

Example 1: The Missed Opportunity

I had a promising lead for a website redesign. After our initial conversation, I sent a detailed proposal but didn’t follow up promptly. A week later, the client had already signed with another designer. My fear of “bothering” them had directly cost me the project.

Example 2: Overcompensating

Conversely, I once sent three follow-up messages in one week to another prospect. They felt harassed and politely declined. I realized that my overcompensation, driven by anxiety about missing a sale, can backfire just as easily as under-following.

Why Following Up Is Tricky

For solopreneurs, every touchpoint matters. Without a team to manage outreach, the responsibility for nurturing leads falls entirely on us. But striking the right balance is difficult: follow up too little, and leads fall through the cracks; follow up too much, and relationships are strained.

How I Manage Follow-Up Effectively

  • Set a cadence. I schedule follow-ups in advance, spacing them to be persistent without being intrusive.
  • Provide value. Each follow-up includes something useful — a resource, insight, or reminder — rather than just “checking in.”
  • Track interactions. I keep a simple log of emails, calls, and outcomes to avoid duplicating efforts or forgetting leads.
  • Personalize messages. Clients respond best when follow-ups reflect their context and needs, not generic templates.

Conclusion

Following up is a skill that separates thriving solopreneurs from those who lose momentum. When done thoughtfully, it strengthens relationships, builds credibility, and maximizes opportunity. By balancing persistence with respect, I ensure my clients feel supported rather than pressured, turning potential “nos” into meaningful connections.