Benchmark Business Group

Pleasantly Persistent: The Art of the Follow-Up

September 16, 2025

The follow-up. It's one thing every agency and financial professional has in common. It’s also a big sticking point for many teams, often because they're afraid of coming across as pushy or aggressive. In a world with more ways than ever to connect, from texts and emails to calls and social media, it can feel harder than ever to actually reach a client. 

This is where the concept of being pleasantly persistent comes in. It's the perfect blend of being proactive and assertive without crossing the line into aggressive territory. It’s about showing your clients you care enough to keep trying, while also respecting their time and space.

Here’s how you can master the art of being pleasantly persistent:

1. Set Yourself Up for Success

You're busy. Your clients are busy. Without a solid system, follow-ups will inevitably fall through the cracks. The most successful professionals use a robust CRM (Customer Relationship Management) system or a simple calendar with reminders. The key is to schedule your next follow-up as soon as you finish the last one. A quick note in your calendar like "Call John about his renewal" or "Email Jane about her term conversion" can make all the difference.

2. Communicate Your Intention Clearly

When you follow up, don't leave your client guessing. Why are you calling? If it's a service matter, this is often the easiest part. You can say, "I'm calling because we need this information to renew your policy and avoid a lapse in coverage." The urgency is clear, and the client knows exactly why you’re reaching out. For sales-related follow-ups, the approach is similar, but it requires a different kind of motivation. Lean on your customer service promise. For example, if you’re calling to discuss a double-term conversion, try this: "As you know, our promise to clients is to keep them informed about opportunities that could positively impact their financial future. I’m calling because I've identified an opportunity that I think you'll want to hear about." This shows you're not just selling; you're fulfilling a commitment to their well-being.

3. Drop a Hint on Your Next Move

If you have to leave a voicemail or send an email, let them know you’ll be in touch again. A simple line like, "I'll reach out again in a few days if I don't hear back from you" or "Looking forward to hearing from you. I'll check in again next week" manages their expectations and keeps the ball in your court.

4. Use Thoughtful Language

Sometimes, a client goes dark, and you can't get ahold of them. If the topic is important, consider using language that shows concern. "I haven't heard back from you on this important topic, and I hope everything is okay" is a great way to re-engage without sounding demanding. It reframes the follow-up from a task to a gesture of genuine care. Another effective tactic is to be upfront about your reluctance to bother them. Try something like, "I really don't want to bother you, and if you'd prefer, I don't reach out about this, please let me know. But it's important because..." This shows respect for their boundaries while underscoring the importance of your message.

5. The Power of Multi-Channel Follow-Up

Your clients are on different platforms, so your follow-up strategy should be too. If you've left a voicemail and haven't heard back, don't just call again two days later. Diversify your approach:

  • Voicemail → Email: After a day or two, send a concise email referencing your call. Something like, "Hi [Client Name], I left you a quick message yesterday regarding [topic]. No need to call back, just wanted to make sure you saw this email as well." This covers your bases and gives them another way to respond.
  • Email → Text: If the client has opted in to text communication, a friendly follow-up text can be less formal and easier for them to answer. "Hi [Client Name], just sent you an email about your upcoming renewal. Could you take a look when you have a moment?"
  • LinkedIn/Social Media: For professional connections, a brief, professional message on LinkedIn can sometimes get a response when other methods fail. "Hi [Client Name], I hope you're having a great week. I've been trying to connect with you about [topic] and wanted to see if you had a moment to chat soon. Best, [Your Name]."

This multi-channel approach isn't about bombarding them; it's about making it as easy as possible for them to get back to you, on their preferred platform, when they have a spare moment. It's a key part of being pleasantly persistent.

Key Takeaways for Your Team

  • Implement a CRM or calendar system to ensure no one slips through the cracks.
  • Practice your opening lines so you can clearly and confidently state your intention.
  • Encourage a culture of empathy. Remember that clients are people with busy lives and may have a valid reason for not responding immediately.
  • Embrace the power of pleasant persistence. It’s not about badgering clients; it’s about serving them well and showing that their financial well-being is your top priority.
  • Have a multi-channel follow-up strategy to increase chances a client will respond.

By adopting these strategies, you can transform your team's follow-up process from a dreaded chore into a powerful tool for building trust and growing your business. What's one small change you can make today to be more pleasantly persistent?

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