How to Avoid the "Just Checking in" Circle of Death

Hey there, I’m just checking in on our last conversation…

Hey there, I’m just checking in on whether you saw our proposal…

Hey there, I’m just checking to see if you had a chance to review our…

Okay. We get it. You’re just checking in. But here’s the thing:

So are hundreds of other sales people trying to get your prospect's attention. There’s no question: following up is one of the most important pieces of the sales process, but you can kill a follow-up by “just checking in.”  

But if “checking in” with your prospects and leads is all you’re doing, week after week, you’re killing your chances for success. The best alternative? Personalize your follow-ups and provide real value to your audience.

Here’s everything you need to know about it, plus 16 better ways to check in with your leads and prospects.

So, What’s Wrong With Just Checking In?

It’s a simple enough way to grab your lead’s attention. It’s easy to do. It’s short. What’s the issue with it, then?

Here’s what:

• You can annoy your prospect: Office workers receive over 70 emails, chat messages, text messages, and phone calls every day. Remote workers receive six times more emails than their hybrid counterparts. And the more buying power someone has, this likely increases. Your leads are overwhelmed—they don’t need yet another meaningless check-in.
• You blend in with (literally) everyone else: Like we said, “just checking in” is easy and straightforward. It requires very little effort, which is why most sales folks will resort to it. If you’re one of them, nothing about it is compelling enough to spark a response over all the other check-ins in your lead’s inbox.
• It’s inactionable: Your generic check-in doesn’t give your prospect the next step they actually want to take. It doesn’t fulfill their need—it adds more work to their plate to come up with a response instead.
• It’s repetitive: How many times can you say “just checking in” before it stops making sense? How many alternative, blanket phrases are there? The magic of sales is in following up, but if you only send broad check-ins, you’ll give up by your second or third attempt.

A meaningful follow-up strategy can literally transform your sales results. Here are 16 ways to do it without ever writing “just checking in.”

5 Alternatives to “Just Checking In” With Cold Leads

You’ve sent your cold email. The result so far? Crickets. But the opportunity isn’t lost yet—that’s where the power of mindful follow-up comes in.

Close’s follow-up philosophy is to go for a maximum of six follow-ups after your initial cold email. You don’t yet have a relationship with that person that gives you permission to do more than that. But six follow-ups means six opportunities—here’s how to make the most of them without the dreaded “just checking in” snooze-fest.

1. Ask For The Right Person

One of the reasons your cold email didn’t land a response is that it didn’t go to the right person. And that ‘wrong’ person is probably busy. Make their job easy by asking for the right person without adding more questions or pitches to their plate.

Example:

Hey [first name],

[Your name] from [company name] here. I’ve been trying to touch base with the person in charge of [responsibility], but I’m having trouble finding them. Basically, I wanted to show them how [solution] can [improve relevant metric/solve relevant pain point] for your team.

Could you point me in the right direction here?

Thanks,

[Your name]

Why this works: With this approach, you’re making it easy for the person on the receiving end to toss the ball to someone else—and give you a better chance of moving the conversation forward.

2. Send a Gentle Reminder

How many times have you opened an email, told yourself you’ll get to it later, and then… Never did? Your cold leads do the exact same. With this approach, you’re floating your first email to the top of their inbox and recapping a simple action they can take to move things forward.

Example:

Hey [first name],

If your inbox is anything like mine, it gets chaotic way too easily. Did this email slip through the cracks? If so, let me know if you have any questions at all.

[Recap your call-to-action from the first email in one sentence.]

Thanks,

[Your name]

Why this works: A gentle reminder does exactly what it says on the tin. It doesn’t include a different pitch, links to resources, or walls of text, so it won’t overwhelm your lead—it simply recaps what you proposed in your initial email, giving it a fresh chance to turn into a sales conversation.

3. Answer a Question They Asked Online

The trickiest part about cold emails is that they can feel quite, well, cold. Generic. If your lead receives a dozen cold emails every day, yours might blend right in—even if you researched and personalized it to perfection.

The antidote? Answering a burning question your lead recently asked on social media like LinkedIn or X (Twitter), or an industry forum. It doesn’t get more personalized and relevant than that.

Example:

Hey [first name],

Just saw your question about [topic] on [platform]. We’ve recently discussed this issue internally, so here are some tips that might help you:

[Add a few bullet points with direct advice or answers to that question/issue.]

Here’s an [article/video/resource] with more on this. Let me know if this worked for you.

[Optional: Let’s connect on a call next week if that suits you—here’s the link to my calendar.]

Best,

[Your name]

Why this works: You’re fully focusing on serving the lead, rather than fulfilling your own needs. The call-to-action to book a call is optional, but if you’ve given them in-depth advice they couldn’t easily get elsewhere, they might realize you and your company could do a lot more for them and gladly jump on that call.

4. Send Them a Customer Success Story

Let’s say your lead saw and read your cold email. Not just once, but multiple times, because they do, in fact, need exactly what you’re offering.

But they don’t trust you yet. They’ve considered other, similar solutions, but they seemed hard to implement, tough on their budget, or just too good to be true. In this “just checking in” alternative, you get to show them how you’ve created success for someone just like them.

Example:

Hey [first name],

[Your successful customer] had a near-identical challenge like you. They didn’t just solve it—they got [results] using [your product] in a matter of [X days/weeks/months].

Read their success story and how they did it [here]. I’d love to make this happen for you, too. Do you have [amount of time] to discuss how we can help?

Thanks,

[Your name]

Why this works: You’re giving your cold lead a chance to put themselves in your successful customer’s shoes. You get them to nod their head as they read through and realize their challenges are solvable—and they have an open line of communication with that solution.

5. Send a Breakup Email

Your final email to unresponsive leads should be a breakup email. It’s your last attempt to reach them after your previous emails have gone ignored—there’s no point in spending any more time on them.

But the real goal beyond closing out this loop? To increase desirability and get a response. Get specific about the benefits your product can bring to this lead.

Example:

Hey [first name],

I was really looking forward to talking with you about [your product] that can get you [X benefit]—our approach has assisted [similar businesses/industry leaders] in overcoming [particular issues] and achieving [outstanding results].

I’m sure you’re busy, so since I haven’t received any response, this will be my last email to you.

If you change your mind and would like to explore what [your product] can help you achieve, please let me know. Always happy to chat.

Best,

[Your name]

Why this works: This email sparks FOMO. The clock is ticking, and the opportunity to see real results is slipping away. If you’ve done your research right and there’s a real product fit for this lead, this email might just do the job.

8 Ways to Avoid “Just Checking In” With a Prospect that’s Stuck in the Sales Process

We’re switching gears here—these “just checking in” alternatives are about those prospects that were super responsive and progressed through your sales funnel, but have either stopped responding or got stuck in your sales process.

They might be busy, overwhelmed with options, or waiting for another stakeholder to give them the all-clear to move forward, so here are some ways to nudge them.

The key difference from cold leads? When it comes to prospects you’ve already had interactions with and haven’t received a clear, definite ‘no’, you should keep following up as long as it takes to get a response. Here’s our simple follow-up schedule for these prospects:

• Day 1: First contact
• + 2 days: Follow up
• + 7 days: Follow up
• + 7 days: Follow up
• + 14 days: Follow up
• + 30 days: Follow up
• Still no response? Going forward, follow up once a month

6. Ask For a Status Update

This is a phrasing alternative to the vague “just checking in.” It’s an excellent way to be more direct and assertive in your follow-up while keeping it friendly and polite.

Example:

Hey [first name],

I’d love to hear how things are going at [their company name]. When we spoke about [your product] on [date], you mentioned you wanted to [speak with another stakeholder/review use cases/some other action]. Could you give me a quick status update in the next day or two?

Thanks,

[Your name]

Why this works: This email specifically addresses the most recent interaction between you and the prospect, including what they said they’d do after it. It gives them just one small thing to focus on in their response—you’re not asking them for a grand decision, just a note on where things stand.

7. Reach Out When Your Prospect Asked You To

When you last spoke with the prospect, they weren’t able to make the next move for one reason or another—having to speak with another decision maker, being too busy, or needing more time to think.

But they didn’t say ‘no’, and they gave you an exact time to reach back out. They’re interested, so never miss this chance to reconnect.

Example:

Hey [first name],

We spoke about [topic] back in [month]. You weren’t ready to make a decision at the time because of [reason], but you asked me to reach back out after [X weeks/months].

So here we are! Did you [talk to the key stakeholder/have enough time to think/etc.]? Let’s jump on a call if so. How does [date and time] work for you?

Thanks,

[Your name]

Why this works: This email picks the conversation back up right where you left if off, and acknowledges the details of the pause. If the prospect wanted to decline there and then, they would have, so turn into an active listener to figure out what they need to move the deal forward.

8. Recap Your Most Recent Interaction

One of the best ways to remedy the potential vagueness of a “just checking in” email? Getting as specific as you can be in as few words as possible.

In this strategy, you’re recapping your last interaction—a call, an email thread—with the prospect and prompting them to take the next step based on that.

Example:

Hey [first name],

Here’s a quick recap of what we discussed [on our call/over email] on [date]:

[Write up to five short bullet points with challenges, presented options etc.].

Are you free for a call on [suggested day] to move things forward?

Thanks,

[Your name]

Why this works: You’re not relying on your prospect’s memory to keep the conversation going. If they want to keep talking with you, they’ll have all the information they need to form their next questions, secure the budget, talk to other decision makers, and more.

9. Namedrop—And Be Smart About It

If you have a mutual connection with the prospect, don’t hesitate to tap into it. Ideally, this will be someone that recently interacted with your prospect so you can ask genuine questions about their needs.

Don’t be intrusive or try to deceive your prospect with this—reference a real conversation and show true interest in your prospect’s success.

Example:

Hey [first name],

I had [coffee/lunch] with [name] on [day] and your name came up—good things only! [He/she] mentioned you’re still on the hunt for [type of solution]. I was wondering if [your product] is still one of the options you’re considering.

If so, I can set you up with [a demo/free trial], and we can jump on a call so you can see what you and your team could do with [your product]. Can we make this happen in the next week?

Best,

[Your name]

Why this works: You’re borrowing the credibility of your mutual contact and referencing specific pain points and goals you’ve already learned about the prospect. This way, you’re giving them a straightforward next step that will give them enough information to make a decision.

10. React to Their Achievement or Promotion

Are you and your prospect LinkedIn connections? If not, it’s time to make it happen. When you notice a positive change in their career, like getting a promotion or hitting a company milestone, you get a chance to reach out with a purpose.

If you interacted with this prospect in the past but struggled to set up the next meeting, this email is the perfect candidate to get the job done.

Example:

Hey [first name],

Just saw your [promotion/success] on LinkedIn! That’s amazing and so deserved—sincere congratulations. I’m excited to see your next achievements and where this takes [their company] next.

If you’re still up for it, I’d love to chat for [X minutes] next week. Would [date and time] work? Let’s set something up.

Best,

[Your name]

Why this works: Because sincere flattery works, as does genuine interest in one’s career and success. Simple as that.

11. Send Them Exceptional Value

Personalization is the way to go to avoid the “just checking in” circle of death. You’ll likely need some support from your marketing team for this one because you need a resource that fits your prospect’s needs just right, but the result—creating mountains of value for your prospect—is worth it.

You can send a relevant blog post, a new white paper, a sample report, a timely ebook, or even a personalized video that covers the exact issue or situation you discussed when you spoke.

Example:

Hey [first name],

The last time we spoke, you mentioned you were [struggling with X, looking for Y, etc.].

[Your company] just published [a blog post/report/ebook etc.] on this exact topic and I instantly thought of you. Here’s the [link] if you want to check it out and implement our suggestions from it.

[Optional: add one or two brief sentences about the resource itself, highlighting the outcomes they’ll get from it.]

Let me know if it helps! I’m always happy to jump on a 10-minute call.

Thanks,

[Your name]

Why this works: This email focuses exclusively on the challenges your prospect told you about and is going through. You aren’t asking for anything in return—just genuinely serving them and earning trust points, with a gentle nudge towards a call as an option to pick your conversation back up.

12. Show Them How You Helped Similar Customers

You know your ideal customer like the palm of your hand. You know what keeps them up at night and how your product or service solves their challenges.

You’ve seen it happen time and time again—but your prospect probably hasn’t. Summarize the results your customers have seen using your solution to strategically show them exactly what’s possible for them. Aim for success stories of customers most similar to them, their industry, and pain points.

Example:

Hey [first name],

I understand that dealing with [pain points] is [tough/overwhelming/add a relevant descriptor]. The best news is that [your company] has helped companies with those exact challenges:

• [Proof/testimonial]
• [Proof/testimonial]
• [Proof/testimonial]
• [Proof/testimonial]

Thanks to [your company], these companies thrive. Are you up for a [X minute] call next week to go through how we can make this happen for you?

Best,

[Your name]

Why this works: It’s hard to argue with so many tangible results presented all in one place. If you share just one, it can feel like a fluke, but when you show your prospect there’s a pattern of success with your product, you make it harder to resist moving forward.

13. Ask Them About Their Goal

The last time you spoke, your prospect couldn’t stop talking about the thing their company wanted to achieve. They’ve gone MIA since. Is it possible their goal just magically disappeared?

It’s unlikely, so it’s worth gently asking them about it to pick your conversation right back up.

Example:

Hey [first name],

I remember you mentioned your company wanted to achieve [goal]. Is this still something you’re pursuing? If so, I’d love to jump on a call [next week/on a specific day] to see how we might help you get there.

Best,

[Your name]

Why this works: It’s short, simple, and focused on what they really wanted just weeks ago. If they’re still pursuing that goal and respond to your email, you’ll get a chance to ask about solutions they’ve considered and tailor your next step and pitch accordingly.

3 Follow-Up Strategies to Skip “Checking In” After a Deal Goes Cold

Some deals just don’t work out the first time around. The prospect tells you they’ve gone with a competitor, your solution doesn’t meet all their needs, or that they simply can’t commit at this time.

The good news? There’s still a way to reconnect with them—here’s how.

14. Reach Out After They’ve Implemented a Competitor

The fact a prospect chose your competitor doesn’t mean it’s a forever decision—nor that they’re 100% happy with what they got.

Set a reminder a couple of months after they told you they’ve gone with another solution to see how it’s going. This is a no-pressure, exploratory email, so avoid any hard sells and call-to-actions. Use open-ended questions.

Example:

Hey [first name],

It’s now been [number of months] since you started using [competitor’s product]. I was curious—how is it going with that? Any obstacles since then?

Best,

[Your name]

Why this works: This email reopens a communication path with a prospect that was a strong fit for your product. If there’s even the slightest chance they’re not satisfied with what they got from your competitor, it also reopens a sales conversation down the line.

15. Check In With Them Near Their Contract Expiration

Do you know the contract length your competitors offer? Your prospect may have told you back when they let you know they’ve gone with a different solution. If not, it’s worth doing some market research to find out.

Contracts and billing cycles often last a quarter or a year, so use that period as your trigger to reach back out to your lost prospect. You don’t need to mention your competitor or their contract—just ask questions to get a feel for where they’re at compared to your last conversation.

Example:

Hey [first name],

It’s been [number of months] since we last spoke. How’s everything going with [the problem they discussed with you]? Any gaps you’re looking to fill?

If so, I’d be happy to jump on a short call with you over the next week.

Best,

[Your name]

Why this works: Just like in the previous example, any dissatisfaction with their current solution might spark a reply to this email. If they think there’s a chance to invest their budget into a better option, they’ll take it.

16. Send Them an Update About a Product or Feature They Wanted

“We can’t use your solution because it doesn’t give us [feature]—we can’t function without that.”

It’s one of those sales objections we can’t quite do something about… Until we can. If you spend a few minutes every time you lose a deal to take note of the reason for losing it, you’ll have a list of prospects to reach out to every time you launch a new product or feature.

Example:

Hey [first name],

The last time we spoke, you told me that not having [product capability] is a deal-breaker for you. I have some great news: [explain the latest product or feature that matches what they needed to choose your solution].

How does that sound? Let’s catch up over the next week. Would [date/time] work for you for a 15-minute call?

Best,

[Your name]

Why this works: You’re giving your prospect exactly what they wanted, but you couldn’t offer the last time around. Prospects whose needs haven’t drastically changed will want to jump back into this conversation.

The Best Way to Avoid “Just Checking In”? Have a Real Reason to Contact Them

Here’s the thing: “just checking in” is meaningless. It puts your priorities first because it’s about starting or continuing a sales conversation—but it does nothing to meet the needs and priorities of your leads and prospects.

The better way? Having a genuine reason to reach out and making that the center of your email. Think about what they need and what you can add to the conversation to make it happen—a reminder, a hyper-valuable resource, a customized discount, or a success story from a customer just like them.

Following up the right way is the most underrated secret to sales success. Will it throw you outside of your comfort zone? No doubt. But it will get you the results you want because you’ll do what no one else does.

Grab The Follow-Up Formula, our free book with a strong, effective follow-up strategy you’ll want in your toolkit.