A Gentle Reminder: How to Follow Up on Sales Without Being Annoying

A Gentle Reminder: How to Follow Up on Sales Without Being Annoying

Ah, January—the holidays have come to an end, and professionals worldwide are slowly returning to their offices. 

Whether it’s unfinished business from last year or new opportunities that aren’t sparking a response, sales professionals eventually have to re-engage their prospects. 

The only problem is that these reminders can get really annoying real fast if you don’t approach them with care, risking them ending up in oversaturated email purgatory. 

In this article, we’ll explore this fine line between being kind and persistent, and outright annoying in your reminders, along with some proven templates, to help you ensure they are both effective and warmly received.  

What is a gentle reminder? 

The definition of a gentle reminder is quite straightforward— it’s a courteous and tactful message intended to kindly nudge a prospect or client without irritating. It’s a strategic sales communication technique to keep your prospects active, encourage action, and maintain the rapport you’ve worked so hard to build. 

Gentle reminders are technically considered follow-ups, as they follow the initial messages with shorter, supplementary information and/or instructions, but they differ from traditional sales/marketing follow-ups in one key way. 

Follow-ups are usually sent after the initial message gets ghosted in an attempt to grab prospects’ attention one more time, whereas reminders emphasize already established communication or agreements, which also make them more likely to be opened and replied to. 

Similar to simple follow-ups, gentle reminders have the main objective of prompting the recipient to take the next step in the sales process and are most commonly delivered through emails, social media messages, or voicemails.  

Why is a gentle reminder important? 

There are numerous sales scenarios where kind reminders are appropriate and even necessary (more on that shortly), so their specific importance will vary from case to case, but generally speaking—here’s why they work so well: 

  • They maintain momentum → there are various reasons why sales journeys may stall, be it holidays or simple oversight, and gentle reminders ensure that these opportunities follow through in a tactful and polite manner. 
  • They demonstrate professionalism → unlike with traditional follow-ups where you’re uncertain if your message is ghosted, gentle reminders are virtually always welcomed as they help prospects stay on top of their commitments, showing professionalism and attentiveness on your behalf. 
  • They improve conversion rates → persistent yet polite follow-up reminders help reignite previously shown interest or agreed commitments with sales prospects, which has the potential to significantly increase the likelihood of closing a deal. 
  • They build strong relationships → regular, thoughtful communication fosters trust over time and positions you as a reliable partner acting professionally to move the deal forward, rather than just another salesperson pushing for the sale.  

How to send a friendly reminder without being annoying  

As we all probably know, effective follow-ups are an entire art of their own, and friendly reminders are no different. They require thoughtfulness and finesse, even though they are quite short messages. After all, the last thing a salesperson would want is to undermine a potential deal by seeming too pushy or obtrusive. 

So, here are the key strategies to keep in mind when crafting those gentle reminders:  

  • Timing is everything: 

Much like with most things in life, timing is everything when it comes to reminder follow-ups. It’s always best to reach out while the interaction is still fresh in your prospect’s mind. Alternatively, if your reminder has to do with an important upcoming meeting—24 to 48 hours before is the sweet spot. At the same time, avoid bombarding your prospect with constant reminders. 

  • Personalization is key:

It goes without saying that you should personalize each and every message you send to your prospects, always addressing them by their name and adding any other relevant personal touches to build a stronger connection.

gentle reminder email with personalization

With gentle reminders, it’s also crucial to mention the specific key details regarding your previous conversations to avoid generalized messages. 

  • Provide value:

Salespeople have to offer some sort of value throughout every step of the sales journey, including kind reminders. Rather than simply saying “Hey, just a friendly reminder that …”, offer additional and relevant insights or resources that align with your upcoming communications and address any potential pain points or challenges your prospects may be facing. 

  • Keep it clear and concise: 

This one’s pretty straightforward—get straight to the point by being direct about the purpose of your friendly reminder. It shows professionalism and respect for their time. Just make sure to include some form of a CTA, whether it’s scheduling a meeting, signing a contract, and so on. 

  • Balance a friendly and professional tone:

Always maintain professionalism in your sales messaging, use polite language, and avoid any hint of impatience, even if your prospect isn’t being as responsive as you’d hope them to be. Instead, express understanding of their busy schedule and express empathy, which will only increase the chances of getting a response.

  • Leverage multiple channels:

Multichannel outreach has proven over and over that it’s often far more effective than simply sticking to one channel, such as email or LinkedIn. Instead, try to understand how your prospects prefer to communicate and experiment with different methods. 

For instance, your prior communication could have been via email, but your gentle reminder could be a quick phone call or a short LinkedIn message. 

  • Know when to step back:

Last but not least, it’s good to know when to call it a day, so to speak. Set your own limit on how many attempts will indicate that it’s time to pause your efforts, because continuous friendly reminders will stop being friendly at some point in time, and it’s best to avoid getting there. 

It’s best to cut your losses but leave the door open in your final reminder message, showcasing that you’re open to continuing the discussion when the prospect is ready.

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Best gentle reminder email templates for sales 

Time to put theory into action with these 9 diverse gentle reminder email templates spanning across various sales scenarios. While your reminders can be LinkedIn messages, short voice messages, etc., emails are undoubtedly the most common channel sales professionals use. 

These are just ideas for you to get the gist of how they work, so feel free to adjust them to your liking. Let’s get started. 

Scheduled demo reminder

The first gentle reminder email example is one of the more common ones in sales communications—a reminder of the upcoming product demo. 

Prospects have already shown interest in your product, so this message is purely about reminding them of the upcoming meeting while also kindly offering to answer any questions beforehand or reschedule, should they need to.

Reminder: Upcoming Demo on [Date]

Hi [Prospect’s Name],

I hope this message finds you well. This is a friendly reminder about our scheduled demo on [Date] at [Time]. I’m excited to showcase how [Your Product] can [solve specific problems or improve a process].

If you need to reschedule or have any questions beforehand, please feel free to let me know.

Looking forward to our meeting.

Best regards,

[Your Name] / Email signature

Scheduled demo reminder

Upcoming meeting reminder

Similar to the demo reminder, sales meetings often have a lot at stake, so a friendly nudge about the upcoming date, time, and agenda is very professional and good practice on your part. 

This template takes it a step further by offering the prospect to add anything from their end to the agenda.

Upcoming Meeting with [Your Company] on [Date]

Hey [Prospect’s Name],

Just a gentle reminder of our upcoming meeting on [Date] at [Time]. We’ll be discussing [agenda or topics], and your insights will be invaluable.

Please let me know if there’s anything specific you’d like to add to the agenda.

Best,

[Your Name] / Email signature

Upcoming meeting reminder

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Pending documents reminder

Once some agreements have been reached with your sales prospects, there will probably be some form of documentation involved. Engaging them with a friendly message that you’re still awaiting said documents will show your commitment to the deal while potentially reminding them to take action, given their busy schedule, so it’s a win-win.

Kind Reminder: Awaiting [Document Name]

Hi [Prospect’s Name],

I hope you’re doing well. I wanted to follow up regarding the [document name] we discussed. Once I receive it, we can proceed with [next steps].

If there’s any assistance you need or questions I can answer, please don’t hesitate to reach out.

Have a good one,

[Your Name] / Email signature

Pending documents reminder

Contract signature reminder

Pretty similar to the previous template, only rather than documents pending from your prospects you are instead waiting for their signature. Once again, all the hard work has already been done up to this point, so templates like these keep it extremely light and friendly while leaving the door open for any potential questions or concerns.

Action Required: [Your Company] Contract

Hey [Prospect’s Name],

I hope all is well. This is a friendly reminder to review and sign the contract for [project or service]. Once signed, we can kick off the [project or service] and start working towards [specific goal].

If you have any questions or need further clarification, I’m here to help.

Best regards,

[Your Name] / Email signature

Contract signature reminder

Trial period expiry reminder

Converting trial users into long-term paid customers is one of the biggest sales goals in B2B companies, and this template facilitates this process with a friendly reminder that their trial is about to run out.

Timing is of extra importance in this scenario, so make sure to send this message well in advance rather than a few days before their account gets closed and they have to take action.

[Product] Trial Ending Soon – Reminder

Hi [Prospect’s Name],

I hope you’re enjoying your trial of [Product] so far. I wanted to remind you that your trial period is set to expire on [Date]. To ensure you continue experiencing the benefits without interruption, consider upgrading to a full plan.

I’m here to assist with any questions or help you make the most of [Product]. Let me know how I can support you.

Best regards,

[Your Name] / Email signature

Trial period expiry reminder

Gentle reminder for payment

Discussing pending payments may sometimes feel like sticky business, but it doesn’t have to be if you remain friendly and professional while offering enough time and any assistance from your end that the prospect may need.

Friendly Reminder: Invoice Due Soon

Hi [Prospect’s Name],

I hope this note finds you well. I wanted to send a friendly reminder that Invoice #[Invoice Number] is due on [Date]. Please let me know if you need another copy of the invoice or any additional information to process the payment.

We greatly appreciate your prompt attention to this matter and are here to assist if you have any questions.

Thank you,

[Your Name] / Email signature

Gentle reminder for payment

Inbound lead qualification 

Once inbound leads have shown interest in your product, great salespeople know that it’s best to not waste time and engage them right away. 

In this template, let’s say an inbound lead came across your website and scheduled a meeting with a sales professional through an AI Chatbot, which gives you the green light to ask strategic questions to better qualify that lead and prepare for that meeting.

A Few Questions Before Our Meeting

Hi [Prospect’s Name].

We’re thrilled you’ve shown interest in [Product]! May I just clarify your time zone, is it {{City}}?

Meanwhile, to better prepare for our meeting, could you please answer a few questions:

  1. [Question 1]?
  2. [Question 2]?
  3. [Question 3]?

Looking forward to your email and enjoy the rest of your day!

[Your Name] / Email signature

Inbound lead qualification

No-response kind reminder 

No response follow-ups can be dreadful, but they are critical nonetheless. This is somewhat of a last resort to kindly get your prospect back on track in their sales journey without crossing the line of being too naggy or annoying, so tread carefully and always keep it light and friendly. 

[Prospect Company] [Your Company]

Hi [Prospect’s Name],

I’m [Your Name] with [Your Company]. We previously discussed [Prospect Company] potentially using our product for [use-case].

I wanted to double- check if you’re interested in exploring this further?

Looking forward to helping [Company] reach its [Department] goals this year.

[Your Name] / Email signature

No-response kind reminder

Bear in mind that kind reminders can be used in numerous scenarios, not only in sales communications. For instance, marketing professionals may use them to follow up on link-building collaborations or to remind prospects of an upcoming webinar they registered for.  

With this in mind, we invite you to check out our comprehensive email template library that covers virtually all areas of business communication, from sales and marketing to business development, networking, and beyond. 

gentle reminder email example from our email template library

Common mistakes to avoid in reminder emails 

Now that we’ve covered the key strategies for crafting effective reminders and taken a look at some template examples, the last step is to take a look at the common mistakes one should avoid. 

Even with the best intentions, some friendly sales reminders may backfire, here’s what to avoid:

  1. Being too frequent with your friendly reminders and bombarding your prospect’s inbox can quickly turn them into pushy, non-friendly messages, significantly harming a potential deal in the future. 
  2. Using generic and impersonal messages in your kind reminders may very well demotivate your sales prospects to take action in their sales journey, even if there was some sort of interest or preliminary agreement in the past. 
  3. While professionalism is crucial in all sales correspondence, overly formal language may fail to reignite prospects’ interest and motivate them to take action. Instead, striking a balance with a friendly and conversational tone will often produce better results.
  4. Ambiguity is another destructive element of friendly reminders as they have to be clear and straightforward, stating or reminding the next steps or expectations for the prospect, rather than causing any form of confusion.  
  5. Finally, being overly apologetic can also hinder your sales efforts as they undermine your confidence and the value that you and your company bring. While it’s definitely polite to acknowledge the recipient’s busy schedule, excessive apologies are not the way to go. 

Automate your friendly reminders with Reply.io 

Friendly reminders should be personalized and relevant, so you might think that automating them will make them sound more robotic and generalized. 

Not with AI-powered tools like Reply.io that generate hyper-personalized kind reminders and other follow-ups based on relevant prospect data and their stage in the sales cycle. 

just a friendly reminder automated by Reply.io

With Reply.io, you can fully automate your friendly reminders and choose to send your kind reminders via email, LinkedIn, SMS, WhatsApp, or even calls, depending on your audience preferences. 

Whether it’s ‘x’ days after initial communication or ‘y’ days before an upcoming event like a product demo, Reply will take care of your friendly reminders on autopilot.

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Reply.io’s AI makes your multichannel outreach irresistible—whether it’s email, LinkedIn, or calls. Be unforgettable!

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Mastering the art of gentle reminders

Crafting effective sales reminders is an art that balances persistence with politeness, and even though they are short and straightforward messages, they ought to be treated with care. 

A well-crafted gentle reminder email could be the difference between an interested sales prospect showing up to a product demo meeting or not, resulting in a lost opportunity, or between a client making their payment on time and missing the deadline, causing issues for both parties, and the list goes on and on. 

By timing your reminders, personalizing them, making sure to provide value and a clear next step, and steering clear of the common mistakes mentioned in this article empowers you to maintain positive relationships and move your sales process forward without being annoying. 

Remember, it’s not just about closing a deal—it’s about building lasting partnerships through thoughtful and strategic communication.

If you’re looking to automate your sales reminders, along with all other sales communication, with the powers of multichannel outreach and AI—we kindly invite you to take Reply.io for a free spin. Who knows, perhaps we’ll be the perfect partnership for 2025 moving forward 😉!

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