The Art of the Follow Up Message: How to generate replies, book demos, and close deals by improving your follow up game

Following Up: The Problem 


If you are in sales, a business development role, a fundraiser, a company or organization President trying to close a deal, or an account coordinator trying to get approval on a social media post… you are likely spending much of your day sending follow up emails, texts, and phone calls. 

Or you are ignoring your follow up and not creating the results you need to grow. 

As cliche as it sounds, a salesperson’s biggest mistake is failing to follow up

However, following up is often more difficult than people in leadership roles consider. Here are a handful of the most common follow up pitfalls you may be facing. 

  • Juggling several follow up requests at once and failing to organize them.

  • Counting on your memory to determine what feels like a good time to check in.

  • Your follow up efforts are focused on solving YOUR problem (not getting an answer) rather than solving THEIR problems.

  • Failing to provide a clear call-to-action.

  • Failing to recognize the reasons why you are not receiving a response.

Before I give you the impression I am a follow up wizard and close every deal I ever propose… I don’t.

However, I do pride myself on my follow up game and have confidence I NEVER lose deals due to a lack of follow up. 

I’m also happy to have heard statements like this from our clients, “Do you know why Optimize Consulting gets more done? Because they ping the shit out of me and cut through the noise”. 

Here are some helpful tips on how you create more results by improving your follow up game.

Following Up: The Solutions


Let’s start with the basics… Why aren’t people responding to your follow up message? Typically, it’s for one of these three reasons.

  1. They don’t see the value in what you are proposing
  2. Your request is not a high priority item at the moment
  3. They are an incredibly busy person and difficult to nail down 

You must try to put yourself in their perspective. What would motivate this person to respond to my email, text, or phone call? 

Here are some useful tactics and concepts to generate responses:


  • Provide a clear call-to-action (CTA): Ideally, you are providing your prospect with a clear action on each follow up message. Ask them for an approval, to book a demo on your calendar, sign the contract… these CTAs must be easy to understand and not create any confusion.

  • Provide the prospect with value: Oftentimes, our follow up efforts are focused on solving OUR problem and not THEIR problem. We just want a response! You are more likely to receive a response when you continue to be of service to the prospect and keep the message focused on providing them with value. Lay out why their response will create value for them or solve their challenges.

  • Don’t end with “let me know”:  Don’t ever use the words, “let me know”. This is a weak call-to-action and you won’t get a response. Part of a strong CTA is creating a sense of obligation to respond. If you end your email with, “Let me know if you’d like to talk next week!” your prospect has zero obligation to reply to your email.

    Tip: We’re found ending most emails with a question generates far more replies

  • The frequency of your follow up: There are countless studies and experts who have come up with a specific number of how many times you should follow up with someone. I’m not going to pretend to know the exact number. Instead, I suggest a ballpark of 5-7 quality follow ups. Once you have followed up seven times, remove the prospect from your deal pipeline and add them into a lead nurturing campaign.

    The big lesson here is you cannot count on one message getting the job done. The person you’re following up with is likely very busy and needs to be reminded about your message. In the end, they will even state how much they appreciate you persistently following up on them.

  • Organize and create a system: At any given point during the week, I am following up with 2-3 potential deals, 1-2 budget approval requests, and 4-6 content approval requests. Put bluntly, I can’t possibly remember all of it. It is essential you create a system to remember your follow ups with either a CRM such as HubSpot or a task manager like Asana. Whenever possible, terminate the risk of human error.

  • Email & task automation: Whenever possible, find ways to automate follow up messages using email sequences and task reminders. As an example, many of our clients use HubSpot’s sales sequences to follow up with leads. These sequences email the prospect five times and contain small tasks for the user to complete (such as making a phone call, connecting on LinkedIn, interacting on social media, etc). The automation stops once the lead responds or is manually opted out.

    Automating your follow up also enables you to track open rates, reply rates, clicks, deliverability, test copy, reorder tasks, and remove human error from the equation.

  • Don’t rely on just email: Cutting through the noise of someone’s inbox is becoming a daunting task. You must employ other methods of communication such as texting, phone calls, and LinkedIn to get the job done.

    Please don’t send a message to your client or prospect on all platforms at once. Use your best judgement on how to reach these individuals.

  • Be remarkable or unconventional: We’ve all dealt with prospects who are difficult to reach. Instead of becoming frustrated, find a way to make your follow up remarkable or even unconventional. Fortunately, passing as remarkable isn’t all that difficult.

    Sending a handwritten note is considered unconventional in today’s day and age.

    Consider sending a personalized gift to your prospect.

    Do something your prospect will remember you for. It’s safe to assume they receive dozens if not hundreds of emails each day and you’re not the only one asking for their time. 


To make things simple: Providing Value + A Clear CTA + Consistency = A winning follow strategy. 

If you need help building an automated follow up strategy for your sales team, fundraising operation, or for internal company tasks, let us know! 

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