Let’s be honest—following up can feel like walking a tightrope. You want to stay on their radar but don’t want to be that salesperson they avoid. Over time, I’ve learned the power of a proactive approach to scheduling follow-ups. This kind of strategy not only eases the anxiety of “Am I being too pushy?” but also keeps you feeling purposeful and prepared. So, if follow-ups are something you dread or avoid, let’s dive into some strategies that have worked wonders for me and might just help you master this balancing act too.
Why Proactive Planning Works (and “Just Checking In” Doesn’t)
I used to rely on the classic “Just checking in” email, hoping to remind prospects of my existence. But you know what? It rarely worked. If anything, it left me feeling like I was chasing people who didn’t want to be caught. That’s when I realized: follow-ups need context. A simple “Hey, just following up” doesn’t give them a reason to re-engage—it feels like I’m making my needs their problem.
Once, I worked with a prospect who had shown interest but then went radio silent. Instead of doing the usual, “Hey, still interested?” email, I decided to approach it differently. I remembered she had mentioned a specific pain point in our last conversation, so I sent over an article on that exact issue. A week later, I followed up with a quick tip I thought she’d find useful. Each email was intentional and relevant. It was surprising, even to me, how much smoother the conversation became just by being proactive and putting myself in her shoes.
When you plan follow-ups that offer value, each message becomes part of a bigger picture, and you’re no longer “just checking in”—you’re adding something meaningful to their day.
Making Follow-Ups Feel Natural: Mapping Out the Journey
The key to follow-ups is thinking ahead. Early on, I used to reach out without much structure, letting each follow-up be a stand-alone message. But planning a follow-up journey creates a natural flow to the conversation. Here’s how I’ve come to approach it:
- Anticipate the Next Step: This means thinking through what the person might be considering at each point. After an initial call, they might be evaluating budget, discussing internally, or just reflecting. Knowing where they are helps me tailor what I say and prevents me from repeating myself.
- Time Your Follow-Ups on Your Calendar: Here’s something that transformed my approach: I started marking specific dates on my calendar for follow-ups, with details on why I’d be reaching out each time. If they said they’d be reviewing the proposal in two weeks, I’d set a follow-up for two days after that. Having a plan gave me confidence, and it meant I was reaching out at moments when it made sense.
- Offer Fresh Value Each Time: This approach means I’m constantly adding something new—a case study, a client success story, or even a tool or article they might find helpful. I remember following up with a potential client every few weeks, sharing different relevant insights each time. One time, it was a testimonial from a similar business; another, it was a quick tip for a problem they’d mentioned. Instead of feeling like I was pestering them, each message added value, keeping me on their radar in a way that felt authentic.
Building Trust and Showing Up with Genuine Value
It’s amazing how quickly a proactive, planned approach to follow-ups can build rapport and trust. With each new message, you’re proving that you’re there to help, not just sell.
A couple of years ago, I was working with a prospect who’d expressed interest but was hesitant about moving forward. Rather than pressuring them with “Any update?” messages, I started sharing mini-case studies from clients who’d faced similar challenges. Every message reinforced that we understood their pain points and had solutions. After a few weeks, they finally replied, thanking me for keeping them in the loop—and, to my surprise, they were ready to move forward. By creating follow-ups that served their interests instead of mine, we turned a quiet lead into a new client.
Wrap-Up: Make Every Follow-Up Count
When it comes down to it, follow-ups should be about creating meaningful touchpoints. If you’re dreading follow-ups or worrying you’re “just checking in” too much, try shifting the focus from your goal to theirs. By planning with intention, every message becomes an opportunity to show your genuine interest in helping them succeed—and that’s a follow-up they’re more likely to respond to.
So here’s my challenge: before your next follow-up, ask yourself, “What can I share that’ll add value to their day?” When you approach it this way, your follow-ups become a natural part of the sales process, and you become someone they’re glad to hear from rather than someone they feel they’re dodging. Give it a try—you might just find that scheduling follow-ups goes from awkward to automatic.
