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About six months ago, I was working with a client, and we came back from a conference here in DC with a list of warm contacts and a familiar problem.
Not a leads problem. A HOW problem.
Six to eight genuinely strong engagements over a few days. Prospective clients. Existing customers we wanted to deepen. Contacts we had been trying to get in front of for months. Real conversations, real energy, real potential on both sides.
And then we went back to work. Other priorities popped up on both of our calendars.
And slowly, without anyone making a conscious decision to let it happen, those conversations started slipping.
And slipping. And…slipping.
I would ask about them in our weekly meetings. Someone would say they sent an email. Someone else would mention they had not heard back. And then the conversation would move on to whatever proposal was being submitted that week, which conferences we were attending next, what pricing needed to get done.
Was this newsletter forwarded to you?
This should sound like a story that is all so true to many companies.
Not the part where the leads went quiet. The part where nobody in that room asked a single question about HOW the follow-through was actually happening. Who was reaching out. Through which channel. With what kind of message. Based on what they actually knew about that specific person.
That question, not whether we were following up but how, changed everything.
So, what are you going to do about it to improve the follow-through? We dive into that today.
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Coverage
Many organizations treat follow-up as a binary. Either someone did it, or they did not. Either the lead is active, or it is not. Either we sent something, or we did not.
And that is what they record. They tell their boss. And they move on.
That framing misses the most important variable entirely.
When I looked at how my client’s team was following up on those conference leads, the pattern was immediate and uncomfortable. The follow-through was one-dimensional.
The default was email. Generic email. The kind that goes to a BCC list of everyone you met at the event, dressed up with a first name in the greeting and a vague reference to having a great conversation.
That is not a high-quality follow-through. That is the appearance of follow-through. And the people receiving it know the difference the moment it lands in their inbox.
The lazy version, BCC everyone and hit send, takes roughly the same amount of time as the personalized version. The barrier is not effort. It is the absence of a defined standard that makes personalization the expectation rather than the exception.
With AI at our fingertips with almost limitless capabilities, the ability to stand out and differentiate ourselves amongst all of the other competitors in the market, personalization is absolutely paramount. Capitalize on it.
When nobody has ever defined what a quality follow-up looks like, the default is always volume over quality. Send more emails. Touch more names. Rinse and repeat.
Wonder why the conversion rate never moves?
The villain in every company that is quietly bleeding warm opportunities is not a person who forgot to follow up. It is a leader who sat in the weekly meeting, heard that the conference leads were going quiet, nodded, and let the conversation move to next quarter’s events without ever asking what HOW looked like for a single name on that list.
Past Issues
Want to check out past issues of Hustle in the Darkness? Check them out here:
The Dollar Signs Were Louder Than the Warning.
You Do Not Have One AI Problem, You Have Two
If Your Team Wouldn’t Buy It, Why Should Your Customers
Measure
Every day we work in the world of “priorities.” Priorities dominate both our personal and professional lives. In the world of leads after an event, this action usually takes a backseat to other priorities we have in our professional day-to-day lives.
Most follow-through sequences collapse after two or three attempts. Someone sends an email and gets no response. They send a follow-up and get silence. They move on to something more immediately promising and the lead gets quietly buried under newer priorities.
Here is the number worth sitting with.
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It takes eight or more meaningful touchpoints before many prospects will engage substantively.
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Not eight emails. Eight meaningful contacts, across channels, over time, each one demonstrating genuine attention to what that specific person cares about.
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Most teams are stopping at three and calling it a dead lead. They are not even halfway there.
Do the math on your own company pipeline right now.
How many:
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Warm conversations from the last six months collapsed at attempt two or three?
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How many of those contacts are still the right person at the right organization for what you do?
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How many of them would have converted at touchpoint seven or eight if someone had stayed in the room long enough?
That is not a leads problem. That is a persistence and personalization problem. And both of those are leadership decisions, not sales execution failures.
Practice
When my client’s team pivoted their approach, the results changed with it. Not immediately. Not from everyone. But consistently, over time, in a way that the BCC approach had never produced.
Did everyone do it? No. Some people are stuck in their same old methods.
So, what are a few of the things did they change?
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Personal LinkedIn messages that referenced something specific from the original conversation.
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Comments on recent posts that demonstrated genuine attention to what that person was actually thinking about professionally.
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Emails written to one person, not a list, with a reason for reaching out that had nothing to do with closing a deal and everything to do with demonstrating that the relationship was worth investing in.
On LinkedIn, it means showing up in someone’s world before you ask them for anything. Building visibility and presence that makes you part of their professional landscape so that when timing aligns, you are already there.
On email, it means writing to one specific human being with a reason for reaching out that proves you have been paying attention to their world and not just waiting for them to be ready.
On the phone, it means calling at the right moment with genuine purpose. A real reason to have a real conversation that moves the relationship forward in a way that no written channel can fully replicate.
None of this is complicated. All of it requires a standard that most organizations have never formally set. And that standard is a leadership decision, not a sales training problem.
This applies everywhere. Tradeshow leads. Cold outreach. Dormant client relationships. New business conversations. The channel and the context change. The principle does not. Make it personal. Build for the long term. Do not stop before the eighth touch.
Table
Not every lead is going to convert. That is not a process failure. It is a reality of how decisions get made at the senior level. Budget cycles shift. Internal priorities change. A conversation that felt close eight months ago can become an active opportunity today if the relationship stayed genuinely warm throughout.
The most expensive leads in your pipeline are not the ones you never generated. They are the ones you generated, had real conversations with, and then lost because the follow-through defaulted to whatever was easiest rather than whatever was most effective.
The difference between those two outcomes is rarely about the quality of the initial conversation. It is almost always about what happened, or did not happen, in the months that followed. And that gap lives entirely inside the HOW.
Don’t think about trying to boil the ocean all at once. Let’s start with one person.
Think about the single most valuable unconverted conversation from the last six to twelve months. The one that had the most genuine potential. The one where the energy was right and the timing just never aligned.
Answer these five questions about that one person right now.
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Who is specifically responsible for that relationship?
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What channel are they using to stay connected?
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When was the last touchpoint personal enough that the recipient knew it was written for them and nobody else?
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Where might I see them next?
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Do I have a mutual connection that can introduce me?
If you cannot answer all five cleanly, you have found your follow-through gap. Not in your pipeline numbers. In the HOW sitting behind them.
The only question is whether your follow-through was good enough to catch it before someone else did.
See you next week.
Whenever You’re Ready, Here are 4 Ways I Can Help You:
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Unlocking Hidden Potential – Reconnecting with Past Clients for Explosive Growth – Check out my free eBook on how you can find hidden gems in your past clients and help you crush your sales goals.
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AI for Business Development – Download our free eBook on how you can effectively leverage AI prompts to your advantage. From properly setting up your preferred AI tool, to how to shape your prompts, save time, and get the outputs you are looking for.
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Sales Resources at Your Fingertips – From tools, tips, demos, and how-tos, check out our Pages and content that can provide you with additional support, whether it be social selling, account management, or something else.
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Cribworks Advisor Program – Want more than just resources? Reach out to me and see if our Advisor Program can help you scale your business.
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