How do you know when it’s time to give up on a prospect and stop hounding them, especially when you’re tasked with drumming up new business?
Sometimes it’s hard to give up on prospects who you’ve called, and called, and called. You’ve left voicemails, sent emails, and researched them on LinkedIn. Even though you’ve never spoken, over time, these prospects feel like people you know. Suddenly you’re comfortable calling repeatedly. If you could just get in the door, you know they’d want to meet with you.
But that’s probably not the case.
These prospects aren’t returning your calls or emails. Clearly, they don’t see the need to talk with you. Spending more time with them isn’t going to change their mind.
Yet onward many sales reps push. So how many times do you try to reach a prospect?
How do you know when it’s time to give up on a prospect and stop hounding them, especially when you’re tasked with drumming up new business? Some salespeople proclaim, “Never give up!”
But consider this.
There are plenty of prospects out there who could benefit from your help. Not only that, there are plenty of prospects who recognize they need help. It’s simply a matter of finding them.
If it feels like you aren’t making any headway, you probably aren’t.
Here are five questions to ask yourself if you’ve fallen into the prospecting rabbit hole:
- Are your opening statement and voicemail focused on them and their business issues – not you and your solutions?
- Have you tried to reach the prospect at least 9 times AND use multiple methods to reach them?
- Are you disciplined, attempting to reach them consistently, every few days?
- Have you spoken with anyone else in the organization to confirm you’re calling the right contact?
- Have you tried to reach another contact to determine if there is a need?
Yesterday a business owner was sharing the results from lead generation campaign follow-up calls. (We hold our clients accountable for call follow up!) He shared how were sending the campaign to two contacts within one company. One executive contact replied, “take me off your list!” The other executive contact replied, “Yes, let’s definitely meet! This is a priority.”
Before you give up on a prospect, you have to be able to answer “yes” to all five questions. That’s when you know you’re in the rabbit hole, and it’s time to make a change.
Now, before you jump for joy and throw away all your prospects, let me share that many sales people I talk with only make three attempts to reach a prospect. Often all three of those attempts are emails. Maybe one is a call.
Three attempts aren’t that many and don’t constitute a rabbit hole.
Prospects know sales people give up easily. So, in today’s prospecting world, you have to keep calling. (Yes, you can intersperse emails.) My rule of thumb is to call at least 9 times.
If a prospect is able to ignore you after 9 calls, he or she really doesn’t have a need right now. They’re telling you that without ever responding to you. Now you’re headed for the rabbit hole, and it’s time to find some new prospects to pursue, people who may really want your help. Sometime in the future this prospect may need you but not right now. Stop chasing them and move on to another group of prospects. Plan to revisit them in 6 months. Maybe they’ll be ready to talk then.
Chasing one prospect constantly doesn’t work out so well. There are many prospects out there who can use your help. Recognize when you’re headed for a rabbit hole and make a strategic course correction to go find those prospects who will want to meet with you now.


![6 High-Probability Moments to Send LinkedIn Connection Requests Prior to an Event Events create natural relevance. Conferences, trade shows, user groups, and local meetups give you a reason to connect that does not feel forced. The mistake sellers make is waiting until the event starts or turning the request into a pitch. A better move is connecting days or weeks ahead with a simple acknowledgment of the shared event. Example: Hi Sarah, saw you’re attending the Midwest Manufacturing Summit next month. I’ll also be there and am super excited! I’d love to catch up in person at the event. In the meantime, let’s connect here on LinkedIn. You are aligning with something already on their calendar. When you see them at the event or reach out afterward, your name is no longer unfamiliar. Following an Event After an event, connection requests work best when they reference a real interaction, even a small one. A short conversation, a question during a session, or a brief introduction creates enough context. The request should reflect that moment, not attempt to convert it into a follow-up. Example: Tim, I enjoyed meeting you at the conference last week. Your take on [subject/trend/idea] was intriguing. I look forward to staying connected and to our next conversation. This reinforces continuity and professionalism without pushing the relationship forward prematurely. After a Sales Call Sending a connection request after a sales call is one of the most underused opportunities in prospecting. If the call was answered and productive, the request reinforces credibility and continuity. Example: Thanks again for the conversation today. I appreciated your perspective on how your team is thinking about next quarter. I look forward to our next meeting and sharing some ideas I have with you and your team. If the prospect did not answer, a connection request can still make sense as a light reinforcement, especially early in the relationship. It keeps your name present without escalating pressure. Either way, the request works because the call establishes legitimacy first. After a Meaningful Interaction Not all interactions happen in formal selling environments. Thoughtful exchanges in comment threads, group discussions, or brief conversations in passing all create natural moments to connect. That might mean running into each other at a non-work event, crossing paths at an airport, or chatting briefly in a line somewhere unexpected. Example: Haley, it was a pleasure meeting you on our flight to Atlanta. Thank you for your restaurant recommendations! I look forward to staying connected, What makes this work is that the interaction was real. The request simply continues it. Mutual Connections Shared connections reduce perceived risk when handled with restraint. They signal that you operate in similar professional circles, not that you have permission to pitch. The mistake is overexplaining or implying endorsement. Example: Hi Mark, I noticed that you are connected to my good friend, James, and since you are also [interested in, working in, located in] I thought it might make sense for us to be connected also. A simple acknowledgment is enough. Familiarity does the work. Profile Views Profile views signal awareness, not intent. When someone views your profile after a call, email, or content interaction, a connection request can make sense as a low-pressure acknowledgment. Example: Wendy, thank you for visiting my profile. I had a chance to look at yours, and based on your interests, I thought it might make sense for us to connect. The discipline is resisting the urge to read more into it than is there. Want the exact framework for integrating LinkedIn into a disciplined outreach sequence without pitching, spamming, or wasting time? Buy The LinkedIn Edge by Jeb Blount and Brynne Tillman today. Sales Gravy is the number one sales training organization](https://salesgravy.com/wp-content/uploads/2025/12/6-Moments-LinkedIn-Connection-Requests-Actually-Work-in-Prospecting-Sales-Gravy-Blog-Featured-Image-768x401.jpg)
