AI Can’t Fix Bad Sales Reps

AI can make your reps sound smarter, but it can’t make them better at selling.

This week I sent an AI tip to a few clients, and I've included part of it below. It’s genuinely useful because it helps salespeople prep more consistently for meetings and stop scrambling five minutes before a call. But it got me thinking.

Because AI "hacks" also expose a bigger risk: They can create the illusion of skill.

Here’s the analogy:

If I’m a weak guitar player and you hand me a souped-up guitar and a ridiculous effects board, I’ll sound better… briefly.

Then anyone with ears will realise what’s really going on.

Behind the effects is still a pretty average guitar player (especially according to my son).

Sales works the same way.

If we give teams advanced AI tools without teaching and reinforcing the fundamentals, we’re not improving performance. We’re just increasing the cost of sounding mediocre.

This is happening in the market NOW. For example, I’m getting more targeted outbound messages lately. You probably are too. The research is sharper. The writing is cleaner and more targeted. You can almost feel the AI fingerprints all over it - like this newsletter's image above. Then, when I follow up with a sales rep, it's the same old frustrations - disorganized questions, weak qualification, a rush to set up a demo, etc.

So yes, AI helps salespeople mega-prep but can they run the meeting?

Can they control tone and pacing?

Can they ask a strong question in a way that earns an honest answer? Do they know where to take the conversation next?

AI is great at helping us know what to do.

Sales fundamentals are about how to do it.

Let's make this the year of HOW.

The big point

Don’t confuse better prep with better selling.

AI can help with research and structure. It can’t replace presence, listening, and control.

This idea runs through my upcoming book Sales Punks (out next month). The rebels aren’t the ones with the flashiest tech stack. They’re the ones who master the basics so well that buyers feel safe, understood, and ready to move.

Use AI. Absolutely.

Just don’t let it become the effects board hiding weak playing.

Here's the "AI Research Hack" email. Feel free to use it!

If you’ve worked with me, you know I’m obsessed with meeting structure, especially framing meetings. Not because it’s “salesy,” but because it prevents good conversations from drifting into chaos.

So, use the meeting leadership tools we've been working on and combine them with this repeatable AI research method.

The goal: generate a pre-call brief on any person or company by connecting Perplexity (or a similar AI tool) to your calendar. You’ll get context, news, and smart questions so you stop scrambling before calls.

If this feels too advanced, skip to Step 3 and just run the research manually using your AI LLM.

Step-by-step

1) Connect your tools Log in to Perplexity.ai (or LLM of choice) → Account → Connectors → enable Gmail + Calendar.

2) Create the calendar event In Google Calendar, create the meeting with:

• The person’s full name in the title
• Their work email added as a guest (If testing, choose “don’t send invite.”)

3) Use this prompt

“It’s [current date + time]. Look at my calendar and prepare a pre-call memo for my next meeting:

4) Make it reusable Click Spaces, create one called Call Prep, paste your instructions, and before meetings just type: “Prep for my next call.”

Pro tip: Ask the AI to improve the prompt by interviewing you. Tell it:

“I want a better call-prep prompt. Ask me five questions about my role, the meeting goal, what I already know, and what I need to leave with.”

Source: The Rundown.ai

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