Help Clients Discover Where AI Delivers Value (Plus A Free 6-Step Playbook To Run Next Week At Your MSP)!

👋 Welcome to the grind

Guess who’s back (back again)? After narrowly losing a battle with some rogue gremlins in the system, we’re coming to you with a special Monday morning edition of the newsletter. Sure, it’s fashionably late—but it’s still packed with everything you need to catch up, crack a smile, and kick off the week like a pro. If you're building an MSP, navigating change, or just want a voice that gets it, subscribe and come along for the ride.

Coffee Chats Recap: Helping Clients Discover Where AI Delivers Value.

Curious how to get your customers excited and educated about AI when they don’t even know where to start? Charles Henson of NCI has cracked the code for MSPs who want to step into that trusted advisor role. Read on for the playbook (below)

(Watch the episode)

🔍 What we learned:

Charles Henson emphasized that many customers don’t realize where AI fits in their workflows, making it the MSP’s job to spark ideas and lead conversations. By deploying AI internally, streamlining processes like invoice auditing, and building secure, compliant practices, Charles demonstrated how MSPs can educate clients, address security concerns, and drive practical adoption. “You can’t lead clients on AI if you haven’t rolled up your sleeves and used it yourself,” he shared.

💡Biggest Takeaways:

• Start Internal, Then Share: MSPs must first use AI tools themselves, turning a 20-minute ticket into a 2-minute process, before advising customers on real-world value.

• Lead with Security: Clients may already be using AI without oversight, so always start with security-focused conversations about how and where their data is flowing.

• Facilitate Curiosity & Collaboration: Hosting in-person or virtual demos and workshops with coffee and donuts drives engagement and cross-customer brainstorming. “If they drive to your office, they’re coming to learn.” (see the playbook below!)

• Empower All Levels: Your primary stakeholder may never use AI, but their team might, so bring end users into the conversation to discover hidden use cases.

✅ Recommendations:

• Kick off AI discussions by sharing your own practical success stories, especially low-hanging fruit like automated audits or email enhancements.

• Always review AI tool terms and security or configuration settings before adoption.

• Run regular AI educational sessions, record and share them on-demand, and tailor playbooks by industry for maximum impact.

• Create a transparent, learning-first culture around AI inside your own MSP and ask clients openly: “How are you already using AI today?”

Thanks to Charles for his refreshing honesty, practical tips, and security-first mindset on integrating AI into everyday MSP life. Want more actionable customer engagement strategies or cybersecurity nuggets? Follow for future recaps and stop by and say hi to me or Charles at GTIA Channelcon!

Selling AI to Clients By Hosting A Killer Meetup: A 6-Step Playbook

Inspired by a recent chat with Charles Henson, I started thinking about how MSPs can stop just talking about AI and actually start selling it. Not with cold emails or pitch decks, but by creating conversations, building trust, and showing clients how AI can solve real problems in their business.

So here’s a six-step tactical playbook you can actually use (like, this week) to get AI conversations started and land your first wins.

Step 1: Host an AI-Focused Client Meetup (and Let AI Plan It)

Pick your format: lunch, breakfast, coffee meetup, cocktail hour. it doesn’t matter as long as it’s in person. The key is to bring your clients and their teams together in a relaxed setting where you can open the door to real conversations about AI.

But here’s the twist: let AI help you plan it. Use ChatGPT or another tool to write the event description, generate catchy invitation emails, and even script phone call reminders. If your dialer system supports AI voice, go the extra mile and use that to invite attendees with a human-sounding message. The idea is to show rather than tell.

Important bonus tip: When you invite clients, don’t just stop at the decision-makers. Invite their team members too. Invite the people who are already testing AI in their workflows and can be your biggest allies in the room.

Step 2: Confirm Attendance with a Personal (AI-Powered) Touch

A day before the event, make sure you reach out personally. That could be an email, a text, or a call, whatever works for your audience. This touchpoint matters more than you think. It makes sure they show up.

One clever approach? If it’s a coffee meetup, take their coffee order when they RSVP, then text to confirm it the day before. It’s personal, thoughtful, and reinforces that they’re expected and welcome.

Step 3: Start with the “AI Planned This” Mic Drop

At the start of the event, share the story of how you used AI to pull the whole thing off. Show them the emails you generated, the call scripts you used, and the scheduling tools you automated, all powered by AI.

This sets the tone: you’re not just talking about AI, you’re using it in real life. That’s credibility. That’s a conversation starter. That’s a mic-drop opener.

Step 4: Share Real Use Cases from Inside Your MSP

Now it’s time to dig into the meat of the conversation. Don’t hold back… get specific.

Talk about how you’re using AI to:

• Automatically triage and route service tickets.

• Draft sales proposals and marketing content.

• Summarize client meeting notes and follow-up tasks.

• Generate knowledge base articles from ticket history.

• Monitor client systems for unusual activity or trends.

Be transparent about what’s working and what’s still experimental. If you’ve saved your team hours of manual work, share the numbers. If you’ve made mistakes along the way, share those too. Authenticity wins trust. Use visuals or live demos if possible to make it real.

And here’s the kicker: record the demo. Whether it’s a screen recording, an audio capture, or even video, make sure you document the discussion. You can repurpose it for future webinars, internal training, or follow-up conversations with attendees.

Step 5: Run an Interactive AI Workshop (and Record It)

Now that you’ve planted the seed, get your clients actively thinking.

Split them into groups by department or industry and guide them through an interactive workshop. Give them prompts like:

• “What’s the most repetitive task you do every week?”

• “Where do you wish you had more time or better data?”

• “What do you think AI could improve, if anything?”

Use sticky notes, whiteboards, or collaborative docs. You want them ideating together and surfacing their own business problems, because those are your future sales opportunities.

Step 6: Build a Living Repository of AI Use Cases

As you host more events and conversations, start capturing everything: the use cases clients bring up, the problems they want to solve, and the workflows they dream of automating.

Organize these insights in a shared repository—this could be a Google Sheet, Notion board, CRM notes, whatever works for your team. Tag them by industry, business function, and complexity level.

This living database becomes a goldmine for:

• Future demos and presentations.

• Building starter AI playbooks tailored to specific roles.

• Productizing services based on recurring client needs.
  

Over time, you’ll have a client-informed roadmap for where AI is headed in the SMB space and you’ll be perfectly positioned to lead the way.

🎙️ I’m Live Next Week

Enterprise Down to MSP: How to Translate Compliance Matters with Cody Rivers! (Thursday July 17, 9am ET)

Tune in for a compelling look at translating compliance from enterprise to MSP with Cody Rivers of Reveal Risk

Are you ready to decode the labyrinth of enterprise compliance and make it actionable for MSPs? Join me, John Harden, and Cody Rivers, Managing Director at Reveal Risk, as we unravel the complexities of compliance in our unscripted Coffee Chats episode. Whether you're navigating towering regulations or just tackling small-scale requirements, Cody's expertise will help you understand how to adapt and thrive.

What we’ll cover:

• Initiate your compliance journey: What compliance requirements does Cody see commonly misunderstood in enterprise environments?

• Lessons learned: Which compliance strategies from enterprise should MSPs adopt, and which should they avoid?

• Real talk on real impact: What single compliance concept does Cody view as essential for every MSP professional to understand in order to achieve success?

Share your thoughts or questions in the comments, invite your colleagues to join, or let us know how you approach AI conversations with clients.

🎧 Register here 

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• Channel Futures: 5 Takeaways Addressing MSP Challenges (as written by some smart guy named John Harden)

📬 Hit Me Back

This week’s chats raised some big questions—so let’s keep the conversation going.

👥 What communities have actually helped you grow, not just network?
🤝 What does “pairing” look like outside of engineering in your world?
💡 How are you balancing AI’s power with the human need for trust, belonging, and growth?

Whether you're building a team, shaping culture, or just trying to fix fewer blinking lights and more people problems, we want to hear your take. Drop a reply, share a story, or tag someone who’s doing it right.

Let’s build the future—together.