The Art of Being Annoying

A Founder’s Guide to Customer Connection.

By Stuart Allan

24 January 2025

As a start-up founder, I’ve come to realise that there’s an art to being annoying—yes, you read that right. While it may sound counterintuitive, the fine line between persistence and annoyance can be a powerful tool in building connections with customers. In the hustle and bustle of launching a business, finding that balance is crucial. Here’s how I’ve navigated this tricky terrain while maintaining professionalism and respect.

Connecting with Customers: The First Step

Every successful start-up begins with understanding its customers. But how do you connect with them in a meaningful way?

1. Listen Actively: Before reaching out, take the time to listen to your audience. Social media, forums, and feedback forms are gold mines for insights. Pay attention to their pain points and preferences; this will shape your messaging and offerings.

2. Personalise Your Approach: When you do reach out, make it personal. A generic email or message is easy to ignore. Instead, reference something specific about their needs or previous interactions. This shows that you value their time and opinion.

3. Be Present: Establish your brand presence across multiple channels—social media, email newsletters, or even community networking events. The more visible you are, the more likely customers will engage with you.

Polite but Persistent: The Fine Balance

One of the most challenging aspects of customer engagement is knowing when to follow up without crossing into the realm of annoyance. Here are some strategies that have worked for me:

1. Set Clear Expectations: When you first reach out, let customers know when they can expect to hear from you next. This sets a framework for communication and reduces the likelihood of them feeling overwhelmed by your messages.

2. Timing is Everything: If you haven’t heard back after your initial outreach, wait a reasonable amount of time—typically a week or two—before sending a follow-up message. This shows respect for their schedule while keeping your brand top-of-mind.

3. Use Humour Wisely: A light-hearted approach can go a long way in easing the tension of follow-ups. A playful reminder about your last email can make your message feel less like a chore and more like a friendly nudge.

The Annoyance of Being Read but Not Replied To

There’s nothing quite as frustrating as seeing that someone has read your message but hasn’t replied. It can feel like a personal slight, but it’s essential to remember that people are busy—especially in today’s fast-paced world.

1. Don’t Take It Personally: A lack of response often has nothing to do with you or your offering. People juggle numerous priorities daily; sometimes, they simply forget to reply.

2. Follow Up Respectfully: If you notice a read receipt without a response, it’s perfectly acceptable to send a gentle reminder. Something like, “Hey [Name], just checking in on my last message! I’d love to hear your thoughts,” can be effective without feeling intrusive.

3. Offer Value in Your Follow-Up: Instead of just asking for a response, provide additional value in your follow-up messages—be it new insights, relevant articles, or updates about your product that might interest them.

Chasing Up: It’s Okay!

In the start-up world, chasing up isn’t just acceptable; it’s often necessary for growth and connection. However, doing so respectfully is key:

1. Be Mindful of Frequency: Avoid bombarding your contacts with messages. A good rule of thumb is to limit follow-ups to once every couple of weeks unless there’s significant news or updates.

2. Respect Boundaries: If someone expresses disinterest or asks not to be contacted again, respect their wishes immediately. Building relationships is about mutual respect; pushing further can damage potential future connections.

3. Celebrate Small Wins: If someone does respond positively after multiple attempts, celebrate that interaction! Thank them for their time and insights; this reinforces positive engagement moving forward.

In Conclusion

Being annoying isn’t about being pushy or disrespectful; it’s about navigating the delicate balance of persistence and politeness in customer engagement as a start-up founder. By connecting authentically with customers, being polite yet persistent in follow-ups, and respecting boundaries while chasing up, we can turn annoyance into opportunity. So next time you find yourself hesitating before hitting “send” on that follow-up email, remember: it’s all part of the art—and sometimes the annoyance—of building lasting connections in business!