The Art of Showing Up

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Picture this: You meet a potential client at a conference. The conversation clicks. They seem interested. You promise to follow up next week.

But then the week gets busy. Your inbox fills up. You have other priorities that now populate your day and week. You have new priorities that you are focusing on. That follow-up email? It slips your mind. Days turn into weeks. The opportunity fades.

In the rush of daily business, even the best connections can fall through the cracks.

This issue isn’t about missing leads, it’s about missing moments. The difference between a lost deal and a loyal client often comes down to one thing: the follow-up.

Today, we’ll show you how to combine AI’s precision with your own authenticity, so no opportunity ever slips away again.

Was this newsletter forwarded to you?

Sometimes that “hot” lead is all about timing. The timing could be 1 week, 1 month, 6 months, or 1 year, the next time you see them at a conference.

You still need to develop the relationship to drive trust, lower risk, and develop an understanding of each other’s needs.

Most businesses drop the ball, then blame the game. It’s not about working harder. It’s about working smarter.

Let AI handle the reminders. You handle the relationship.

Let’s dance.

First Touch - Share Something Useful

Let’s first break down a few statistics on this:

• 48% of salespeople never even make a single follow-up attempt after a cold call, yet 80% of sales require five follow-ups or more to close.]

• Only 3% of salespeople make six or more follow-up attempts, but your chances of reaching a lead increase to 90% when you try six times compared to just 10% on the first attempt.

• 50% of companies are failing in their lead follow-up process and losing sales opportunities, with 24% of companies not even offering a way for prospects to submit sales inquiries on their websites

I’ve also talked about the follow-ups here:

3 Strategies to Turn Tradeshow Conversations into Conversions 

Don't Let Them Slip Away: Mastering the Art of Sales Lead Follow-Up 

Evaluating and Enhancing Your Sales Funnel 

Most businesses are losing deals, not because their solution is bad or their pitch is weak, but because they simply don’t follow up.

Think about the last time you reached out to someone—maybe a prospect, maybe a partner, maybe a customer. You sent the first message. You waited. Maybe you got busy, maybe you forgot, maybe you told yourself, “I’ll get to it tomorrow.” And just like that, the opportunity faded into the background noise of your inbox.

In a world where everyone is busy, the people who win are the ones who show up, again and again. Not with spam. Not with generic templates. But with real, timely, authentic follow-ups.

So…Where Does AI Come Into Play?

Every day distractions, our day-to-day priorities, and even life get in the way. However, you want a support system that can help you with all the leads and follow-ups that you have had over the months to make sure you stay on top of them.

It’s about making sure you never drop the ball. It’s about making your consistency automatic, so your relationships become intentional.

How to Leverage AI with the Follow-Up

Here is a simple breakdown on how you combine AI with your own authenticity to build a follow-up system that actually works.

When you input a new contact into your CRM, details matter. The more content and context you add, the better data you will have.

First and Foremost - A Little Preparation

• Don’t rely on your memory for all of your leads. Use your CRM’s Tasks/Notes/Reminders tools for the Company and Contacts to customize each specific follow-up that you need to do

• If you don’t want to use your CRM’s internal AI tool, use your favorite AI tool

• Time Management is key - Set aside time in your calendar to focus on responding to leads. Do not shoot from the hip. Whether you do it Monday at 1pm or Thursday at 11am, schedule time in your calendar

A. Automate the Reminders - Not the Relationship

Set up AI-driven reminders for every important touchpoint. Use your CRM, your email tool, or even a simple app. The goal? Never let a follow-up slip through the cracks again.

But here’s the kicker: Don’t let the AI do all the talking. Use it to nudge you, not to replace you. When it’s time to follow up, take 60 seconds to add a personal note, a relevant question, or a comment that shows you listened.

Here’s a practical example of how to automate reminders without losing the human touch:

Let’s say you just had a discovery call with a potential client, Sarah, on Monday. During the call, she mentioned she’s launching a new product next month and is worried about her current marketing strategy.

• Step 1: Set Up the Reminder
  Right after the call, you log the meeting in your CRM (like HubSpot or Salesforce) and set an AI-driven follow-up reminder for Thursday. The CRM will ping you when it’s time.

• Step 2: Draft the Follow-Up
  When the reminder hits, your CRM suggests a basic follow-up template:
  “Hi Sarah, just checking in after our call. Let me know if you have any questions.”

• Step 3: Personalize the Message
  Instead of sending the canned message, you take 60 seconds to add a personal touch:
  “Hi Sarah, I’ve been thinking about your upcoming product launch and the challenges you mentioned around marketing. I came across a case study this week that might spark some ideas for you—happy to share if you’re interested. Let me know how things are shaping up!”

B. Draft with AI, Edit with Heart

AI can draft a follow-up in seconds. That’s great for speed. But speed without soul is spam. Take the draft, scan it, and add something only you could say. Reference a detail from your last conversation. Mention a recent win of theirs. Ask a question that matters to them.

Here’s an example:

“Congrats on the Innovation Award, Alex. I saw the news and wanted to reach out. I remember you mentioning that industry event coming up, and I can only imagine how much prep you’re putting in. If you want a fresh set of eyes on your presentation or need to bounce around ideas, I’m in your corner. Hope your week’s rolling in the right direction.”

C. Sequence Your Touchpoints, But Make Them Human

AI can help you map out a sequence: Day 1, Day 3, Day 7, Week 5 (however you sequence it). But don’t send “bumping this up” emails. Mix it up. Congratulate them on LinkedIn. Share a relevant article. Offer a quick tip. Ask for feedback.

Ask your favorite AI tool to break down this specific ask for you, so you have a template ready to go.

Every touchpoint should feel like a step forward in a relationship, not a step closer to a transaction.

When you combine automation with authenticity, you stop being “just another salesperson.” You become the person they look forward to hearing from.

Third Touch - Show Your Skills

Let’s talk outcomes.

When you master the art of the follow-up with AI and authenticity, everything changes.

Stand Out

Most people follow up once, maybe twice, and then disappear. When you show up consistently, you stand out. You become the person who keeps their word, who respects their time, and who actually cares.

You Build Trust

Trust isn’t built in the first conversation. It’s built in the second, the third, the fifth. It’s built when you remember the details, when you check in just because, when you add value without asking for anything in return.

You Turn Connections Into Compounding Growth

Every relationship you nurture becomes a potential referral, a repeat customer, a brand advocate. The more you invest in follow-up, the more your network works for you. It’s not just about closing a deal—it’s about opening doors that stay open.

Effort Pays Off

Most businesses ride the feast-or-famine rollercoaster because they don’t have a system. When you automate the basics and show up with authenticity, you create a pipeline that’s always moving.

Use AI to make it effortless.

Action Item This Week

Don’t overthink this. Start simple to enhance all those leads that are sitting in your CRM, collecting dust. They probably would love to hear from you.

• Pick one person you should have followed up with, but haven’t.

• Set an AI reminder for 1 week from now.

• When it pings, send a message that’s honest, specific, and real. No fluff. No, “just checking in.” Tell them why you’re reaching out, reference something personal, and ask a question that matters.

• Repeat tomorrow with someone else.

Do this for a week. Watch what happens.

Because in a world where everyone is automating, the real winners are the ones who automate the system and humanize the message.

What the Internet Taught Me This Week

From new tools, recent trends, and market updates, here is what has been on my mind.

1. DeepSeek aids China's military and evaded export controls, US official says. Check it out here

2. U.S. House Bans WhatsApp on Official Devices Over Security and Data Protection Issues. Check it out here

3. US critical infrastructure could become casualty of Iran-Israel conflict. Check it out here

Let’s call it what it is: the difference between a lost deal and a loyal client is rarely about price, product, or pitch; it’s about who shows up when it matters. You’ve seen how AI can keep you organized, but it’s your authenticity that turns reminders into relationships and touchpoints into trust.

Don’t let your follow-up be an afterthought. Use automation to stay sharp, but let your humanity do the heavy lifting.

The brands that win aren’t the ones who shout the loudest; they’re the ones who keep showing up, every time, with something real to say.

Now, it’s your move. Pick one relationship that matters. Set the reminder. Send the message that only you can write. Because in a world full of noise, consistency and care are what cut through.

Ready to make your next follow-up count? Start today.

See you next week.

Whenever you're ready, here are 4 ways I can help you:

1. 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.

2. Build your Sales CRM - Download our free Sales eBook on How Your Sales Team Can Maximize Your CRM Tool. Whether it’s Hubspot, Salesforce, or another CRM tool, make sure you leverage it to your advantage.

3. Awesome Sales Resources - Transform your sales engagement and capabilities across Social Selling, CRM, Lead Generation, Enablement, and more.

4. Cribworks Advisor Program - Want more than just resources? Reach out to me and see if our Advisor Program can help you grow your business.