Artificial intelligence (AI) excels at spotting patterns and automating workflows, but what about the messy, one-off challenges that arise in real sales conversations? This is where skepticism can creep in. However, with the right approach, AI can still serve as a valuable tool for managed service providers (MSPs). In this edition of Ask an MSP Expert, we explore how AI can assist with challenges such as repurposing a webinar or re-engaging a quiet lead by creating content that feels personal and relevant. Kendra Lee, founder of KLA Group and an expert in MSP marketing, discussed how MSPs can effectively leverage AI in these scenarios in a recent webinar.
Can AI really help with one-off customer challenges?
This is a common concern, especially when the issue is about a single prospect rather than a broad sales strategy. Many MSPs are not sure how AI could help convince just one hesitant customer to move forward with their services, and the learning curve felt like another barrier.
The truth is, AI can still offer real value in these situations. If you’ve had conversations with that prospect, you can upload a few transcripts and describe the problem. Tools like ChatGPT can then suggest different ways to respond, reposition your offer, or even draft a follow-up email. If the first suggestions don’t quite land, you can tell it what’s off and it will keep refining its approach.
One important note on privacy. If you’re using AI to analyze client interactions, make sure you’re using a paid version of the tool. Free versions may not guarantee confidentiality, but paid versions typically don’t use your data for training or share it elsewhere.
How do I make sure AI-generated emails or posts don’t sound like they were written by a robot?
Plenty of MSPs have the same reluctance, especially when using AI to create client-facing content. The key is making sure the output actually sounds like you. One way to do that is by uploading a transcript of a real conversation or email thread, then telling the AI to use that tone and language. You can be direct, ask it to use a professional advisory voice or to stick closely to the phrases you already use.
You can also guide the AI by telling it what not to say. Words like “transform” or “modern” tend to show up a lot in AI-generated content. If that doesn’t match your style, just tell it to rewrite the content without those words.
Can I use AI to help me repurpose past content, such as a webinar?
Yes, and it’s one of the most effective ways to get more mileage out of the content you’ve already created. Take a webinar, for example. Instead of just sending out the slide deck, you can use AI to generate personalized follow-up content for each attendee. Here’s how:
- Upload the webinar transcript into a tool such as ChatGPT.
- Prompt it to act as a sales strategist and ask for a customized follow-up plan based on the session. Include attendee details, such as:
- Name and company
- Questions they asked
- Topics they engaged with
- Ask the AI to generate:
- 2–3 tailored takeaways
- Suggested next steps (e.g., applying a strategy, booking a follow-up call)
This turns one webinar into multiple high-impact touchpoints without starting from scratch. It also creates a natural reason to stay in touch: “Did you get the action plan I sent over?” or “Has your team had a chance to look into the ideas we discussed?”
AI doesn’t have to be complicated to be effective. Start small by repurposing a webinar, refreshing a follow-up email, or reframing a sales message. Just be sure to review and refine anything AI generates before using it. Remember, your voice and judgment still matter.
Ready to learn more ways to effectively use AI to assist you? Watch the webinar replay now!
Photo: Vesna Art / Shutterstock
This post originally appeared on Smarter MSP.