Coaching and The Truth About AI in Sales: Great at “Or,” Terrible at “And”

My Real-World Experience + 11 Ways It’s Already Saving Me Hours

Are you intrigued by AI and what it can help you do to sell more efficiently? Me too.

Over the past 18 months I’ve worked extensively with AI and can tell you that while there is huge potential for what it can become, and there are many things it can do well today, there are some serious limitations when it comes to sales.

I’ll share my experience. Since most of it is good, I’ll start with the bad where I will describe AI more as a mathematical operator.

For example, for the past year, I have wanted to create an age-progression video of my son, from when he was in Little League through to his senior year in college. The first problem was that until very recently, it was nearly impossible for AI to create proper baseball swings. Hands were backwards, stance was facing the wrong direction, field wasn’t properly designed, swing looked more like golf or hockey than baseball, etc.

Eventually it could create a video of my son taking an actual baseball swing at any one age but I already had those videos! I could get it to do an age progression, but even with reference images of each age, it created an entirely different person. It could do an age progression of an imaginary person, but not playing baseball. It could do any one of the many elements required to create my age-progression video but not all of them together. Fantasy yes. Reality no.

Let’s take sales prospecting.

AI can extract some intelligence for personalization. AI can write an outbound message. AI can automate your workflow. AI does a terrible job of combining all three. You know this because you receive the cringy personalizations with horrible messages, and stalking-like workflows that you can’t stop. They never have logos or email signatures and are easy-to-spot must-delete spam intrusions into your email and LinkedIn messages.

Here’s a recent example that landed in my inbox—classic AI trying to personalize but failing spectacularly at relevance:

Dave,

Noticed you were engaging with AI and outbound tools on LinkedIn. Since you’re already interested in A.I. agents, I thought this one could really help for Top sales magazine | top-rated speaker | sales transformations | sales performance improvement expert.

We’ve just rolled out an AI voice agent that holds real conversations and can make hundreds of outreach calls for Top sales magazine | top-rated speaker | sales transformations | sales performance improvement expert weekly.

The best part? it runs 24/7, handles the workload of an entire team, and costs about the same as a part-timer.

See what I mean? Great at pulling data points (the ‘or’), terrible at weaving them into anything useful or human (the ‘and’).

Or this one where layered my comments on the screen shot.

No wonder these get deleted instantly. My conclusion is that AI can do the “or” operation but not the “and” operation:

• AI can extract (your LinkedIn activity/bio bits) — check.
• AI can write a draft pitch — check.
• AI can automate sending — check.
• But combine them intelligently? Nope → results in this Frankenstein mess that’s impersonal, irrelevant, and off-putting.

On the other hand, AI is already transforming how I work every day in the following key areas. Let’s talk about 12 things that AI does well for me, each capable of saving hours at a time, not to mention the cost savings:

1. Research and Fact-Checking – I routinely have Grok (xAI) do some research and some fact-checking for my articles.
2. Editing your writing (think articles, letters, proposals) I share all of my article drafts and proposal drafts with Grok for feedback and get terrific suggestions for added context, flow, accuracy, typos and grammar.
3. Complex Price Estimates – I have recommended to multiple clients to teach AI how they create their estimates. Then they can upload images, measurements, notes if appropriate, provide the specific variables for any job, to create estimates in minutes instead of hours.
4. Brainstorming – I have brainstormed concepts, tools, strategies, articles and books with Grok.
5. Automating tasks – This is an obvious one.
6. Cleaning spreadsheets – Think scrub, merge, purge and revise with updated information
7. Coding – I have saved thousands of dollars by asking Grok how to fix problems that routinely pop up with WordPress (which hosts the Kurlan website and this Blog) each week. Grok produces instant code.
8. Step-by-step instructions – There is a lot I don’t know how to do but AI always provides me with step-by-step instructions, like the WordPress fixes I mentioned above.
9. Assistant – Dictation, check for, arrange, explain, find out, optimize, summarize, etc. Zoom has a great built-in AI agent that does a great job summarizing my Zoom meetings. Along with the transcript, it nearly eliminates the need to take notes. Not a Zoom user? Going on face-to-face meetings? The Pocket app goes with you and does the same thing.
10. Knowledge Base – Teach AI everything there is to know about your business by uploading documents, slides, spreadsheets, URLs, etc. and have it be your team’s goto source for info.
11. Call Analyses – Companies like Gong have progressed to the point where it can produce terrific analyses of phone calls made through its platform. These analyses are used for sales coaching.
12. Slide Decks – Fast, beautiful, relevant slide decks created in seconds. I used Gamma.app, uploaded the article you are currently reading, and it produced this slide deck in seconds. I uploaded the deck to Grok which recommended 5 quick, easy edits.

Those 12 things summarize how I’m using AI to reduce team size, save time, and get more things done more quickly.

That said, I’m excited about the current AI project I’m working on.

The Future of Sales Coaching: Why Only 7% of Managers Do It Well + AI Dave as the Solution

There are existing AI sales coaching tools. They’re OK. You can role-play the sales part with an AI agent and get feedback. That’s useful. But it’s not the same as getting live coaching from me.

Live coaching with me is worth every penny of the $1,000 an hour I charge. Ask anyone who has received that coaching. Why? The advice is always real world, timely, relevant and actionable, but more importantly, the role plays are life changing. I provide three types of coaching:

• I debrief salespeople to learn what they did wrong and then role-play the part of the salesperson to demonstrate how the conversation should have sounded.
• I pre-call strategize with salespeople and let them play the sales part and I provide real-time coaching, as they proceed through the conversation, to improve their effectiveness.
• I’ll have two salespeople role-play with each other and provide real-time coaching to redirect, improve questioning, or alter strategy of their conversation. Here’s an 25-minute example of that:

I’m developing an AI coach – let’s call it AI Dave – You’re On Demand Sales Coach at a Fraction of the Normal Rates – that can do all of that as me. I’m on my fourth platform, but very close to getting there. It will be unique in its ability to do all three types of coaching, with role-plays playing either the salesperson or prospect, with real-time mid-conversation coaching, useful debriefs, and lessons learned. It’s very exciting. It won’t be released until it’s near-perfect and when it’s ready it will be available on demand by subscription. AI Dave whenever you need me for a fraction of the price. I’m thinking along the lines of unlimited use for $299/month instead of $1,000/hour. How does that sound?

One good reason for outsourcing your coaching or subscribing to AI Dave is that only 7% of sales managers do this consistently and effectively. 7%. Salespeople don’t get the coaching they deserve.

In addition to deal specific coaching, the four areas where salespeople need the most coaching are:

1. Converting calls to meetings – The average salesperson scores only 36 in the Hunting Competency
2. Reaching actual decision makers and stakeholders – The average salesperson scores only 42 in the Reaches Decision Makers Competency
3. Consultative Selling (listening and asking questions) – The average salesperson scores only 42 in the Consultative Seller Competency
4. Fully Qualifying – The average salesperson scores only 49 in the Qualifying Competency

See the scoring data for salespeople in all 21 Sales Core Competencies, filter by industry, see how you and your company compare at this free site.

In the mean time, if you or your team need impactful, high ROI coaching, and/or training for sales, sales management and/or sales leadership, you can reach out to us by clicking here.