Friday, November 24, 2023

[VIDEO] The 5 Key Skills for Good Decision Making

Posted By: George Deeb - 11/24/2023

I was recently interviewed by  ASBN , an online "television network" serving the small business community, about the five key skil...

I was recently interviewed by ASBN, an online "television network" serving the small business community, about the five key skills in good decision making.  As you will learn, being knowledgeable, intuitive, receptive, nimble and flexible are your keys to success here.  I thought this video turned out great, and I wanted to share it with all of you, to help you make better decisions in your business.  I hope you like it!!

The embedded video player didn't give me the option to change the size of this video.  But, if you want to see a bigger version, simply click the expand size button in the player above.

Thanks again to Jim Fitzpatrick and the ASBN team for having me on the show.  I look forward to our next interview together.

For future posts, please follow me on Twitter at: @georgedeeb.

Wednesday, November 8, 2023

Lesson #356: Artificial Intellegence is Revolutionalizing Sales Coaching

Posted By: George Deeb - 11/08/2023

I was recently introduced to James Critelli , a startup sales and marketing expert that is advising a company called Sybill , who is using a...

I was recently introduced to James Critelli, a startup sales and marketing expert that is advising a company called Sybill, who is using artificial intelligence (AI) and automation to streamline the workflows of B2B sales reps. One of the applications of that technology is helping to revolutionize how sales coaching is done.  They had some great ideas and solutions on this topic, and agreed to collaborate with me on this Red Rocket lesson, to help jump start your sales coaching to next generational thinking.

The world of sales coaching is changing rapidly, and as a sales leader, you need to be on top of the game. That's where generative AI, like ChatGPT, comes in. While generative AI has found a ton of use cases already in marketing and software development, its potential in sales, sales coaching, and training, and revenue operations is still in its infancy to be explored. In this post, we'll discuss how generative AI can elevate your sales coaching game, drive your team to hit quotas and propel your business forward.

The Role of AI in Modern Sales Coaching

AI has permeated almost every aspect of our lives, and sales coaching is no exception. Traditional sales coaching methods are increasingly being replaced by AI-driven tools and techniques that can help sales leaders and coaches analyze data, identify areas of improvement, and provide personalized training to their sales reps.

Why Generative AI Matters for Sales Leaders

Generative AI, such as ChatGPT, can generate human-like text based on a given input, making it an invaluable resource for sales leaders. All you need to do is figure out what to give ChatGPT as the context and the prompt, and it can play a variety of roles for you. In this post, we will discuss how you can use ChatGPT (or similar generative AI text systems) to roleplay a customer call, serve as a learning management tool for the product marketing material and other company-specific context for new reps, and help you identify weaknesses in reps’ handling of customers by analyzing call transcripts and emails and pointing out the issues.  

With the power of generative AI, sales leaders can automate various aspects of sales coaching, freeing up time for more strategic tasks and enabling them to focus on what matters most: driving revenue and leading their teams to success.

Identifying Coaching Opportunities With Generative AI

Analyzing Sales Rep Performance

Generative AI can analyze vast amounts of data, including sales rep performance metrics, to pinpoint areas that require attention. By identifying trends and patterns in how the rep has handled customer conversations on the phone, video calls, and emails, AI-driven tools can help you develop targeted coaching initiatives to address specific weaknesses.

For example, we fed the transcript of an old call to ChatGPT, and asked it to pinpoint the salesperson Nishit's areas of improvement from this call. 

These are helpful starting points, and should already get your wheels turning. What did we do next?

We asked it to give us specific examples from the conversation where the salesperson did poorly in “asking open-ended questions”, and a few sample ways in which the salesperson could have done better. 

Targeting Key Areas For Improvement

Once you've identified the areas where your sales reps need improvement, generative AI can provide insights into the best ways to tackle these issues. By generating personalized coaching plans, AI can empower you to provide tailored guidance that truly resonates with each member of your team.

AI-Powered Training and Development

Leveraging LLM-Generated LMS Systems

Generative AI can also play a crucial role in creating and maintaining Learning Management Systems (LMS). By generating customized LMS content tailored to your sales reps' specific needs, you can ensure they receive relevant training that helps them develop the skills they need to excel in their roles.

Customizing Quizzes and Assessments for Each Sales Rep

AI-driven tools can also create personalized quizzes and assessments that test your sales reps' understanding of the training material. This allows you to gauge the effectiveness of your training programs and make any necessary adjustments to help your team reach its full potential.

Roleplaying Sales Scenarios With Generative AI

Preparing for Important Calls

Roleplaying is a tried-and-true sales coaching technique, and generative AI can take it to the next level. By simulating various sales scenarios, AI-driven tools can help your sales reps practice their pitch, objection handling, and closing techniques before they ever step foot in a real sales call.

Enhancing Communication Skills Through AI-Driven Feedback

Generative AI can also provide real-time feedback on your sales reps' communication skills during roleplay sessions. This can help them fine-tune their approach, resulting in more effective sales calls and, ultimately, higher close rates.

AI-Assisted Call Scripts for Discovery and Demo Calls

Crafting Personalized Call Scripts

Generative AI can generate personalized call scripts for discovery and demo calls based on a sales rep's unique selling style and the prospect's specific needs. This can ensure that your sales reps are always equipped with the right talking points to guide their conversations with potential customers.

Gaining Insights from AI-Generated Script Analyses

By analyzing the AI-generated call scripts, sales leaders can gain valuable insights into what works and what doesn't in their team's sales conversations. This information can then be used to provide targeted coaching and feedback, helping your sales reps refine their approach and improve their overall performance.

Measuring the Impact of AI-Driven Sales Coaching

Tracking Progress and Growth

By incorporating generative AI into your sales coaching efforts, you can easily track the progress and growth of your sales reps over time. AI-driven tools can help you monitor key performance indicators (KPIs) and other metrics to measure the effectiveness of your coaching initiatives, allowing you to make data-driven decisions and continuously optimize your coaching strategies.

Celebrating Success and Motivating Your Team

As your sales reps begin to see the results of your AI-powered coaching efforts, their motivation and engagement will likely increase. Be sure to celebrate their successes and use their achievements as an opportunity to reinforce the value of AI-driven sales coaching, fostering a culture of continuous learning and improvement within your team.


Generative AI has the potential to revolutionize sales coaching, transforming the way sales leaders support their teams and drive performance. By embracing the power of AI-driven tools like ChatGPT, you can elevate your sales coaching game, boost your team's productivity, and ultimately grow your business to the next level.


Thanks again to James and the Sybill team for helping me with this post.  If you have any further questions on this topic, feel free to reach out to Sybill at 650-289-8160 and follow them on LinkedIn for future learnings here, as I am sure there will be many new advancements with AI in the coming years.

For future posts, please follow me on Twitter at: @georgedeeb.

Thursday, November 2, 2023

Lesson #355: Artificial Intelligence is Taking Over Marketing

Posted By: George Deeb - 11/02/2023

  Artificial intelligence (AI) has been around for decades.  I won’t bore you with its long history, summarized well in this article .  It h...


Artificial intelligence (AI) has been around for decades.  I won’t bore you with its long history, summarized well in this article.  It has even had a significant role in the marketing industry for many years (e.g., predictive analytics used in many advertising platforms).  But, what has recently caught storm is the use of generative AI in the creation of many marketing creatives.   Largely because the technologies are more accessible and easier to use than ever before.  I feel the industry is at the cusp of a major inflection point, and you better learn what is going on in this space, or you may be left behind.

Industry Research

There was a very good industry research study completed in March 2023 by, a generative AI cloud chat communications company. They surveyed 1,000 marketing professionals across over 16 different industries and company sizes from 1 to 5000+ employees. The results were fascinating—they learned that a whopping 73% of the respondents are already using generative AI to help create text, images, videos or other content.  That was the weighted average of B2B companies at a 78% usage rate and B2C companies at a 65% usage rate (I would have guessed the reverse of that).  With me being in the 17% that were not materially using AI today, I figured I needed to learn more here, and fast, to stay competitive with our industry peers.

Content Being Produced by Generative AI

The content getting created by generative AI is broad in scope.  The survey respondents said they were using it as follows:  email copy (44%), social media copy (42%), social media images (39%), chatbots for customers (37%), website images (36%), SEO content (35%), blog post copy (33%) and marketing/sales collateral (33%).  The rationale for using generative AI being: (i) you can improve your marketing performance (58%); (ii) you can improve your creative variations (50%); (iii) it is more cost effective than traditional ways of building creatives (50%); and (iv) it is materially faster creative cycles (47%).  I would add the additional benefits of better personalizing the content to the exact user, instead of applying a one-size-fits-all approach to your marketing creatives.  

And, to be clear, the content being produced by AI is across all forms of creatives:  text, images, videos, coding, etc.  It is revolutionizing pretty much everything a graphic designer or copywriter or website developer used to do for you.  As an example, check out this corporate video produced for my Restaurant Furniture Plus business by Synthesia’s AI technology.  It was produced in a couple minutes from a simple copy and paste of our About Us copy on our website, without any human involvement or professional actors involved.  That is pretty amazing (and scary if this life-like technology is not used in positive ways).

The Generative AI Tools Most Used

According to the survey respondents, these were the technologies most used by the marketers.  ChatGPT (55%) for human-like text. (42%) for natural language processing. (35%) for copywriting. (29%) for full article copy.  Lensa (28%) for image editing.  DALL-E (25%) for text-to-image generation.  MidJourney (24%) for text-to-image generation.  I am sure there are many others to experiment with, but these are the ones that the early adopters are using today.  I personally played with a few of these.  I would summarize my experience as the text based solutions were a lot more impressive in terms of producing high quality output than the image based solutions, understanding we are still early in the learning curve and technology advancements here.

How to Prepare… and What Happens if You Don't

First, it's time to embrace the simple fact that you need generative AI and that you can't ignore it. It isn't going away. So, slowly but steadily, immerse yourself in some (or all) of the tools above — how they work and what they can potentially offer. And, if you are working with a marketing agency, make sure that it, too, is well-versed in all the advancements (if yours is not currently using AI to improve campaigns, it may be time to look for a new one).

The ramifications for non-action will be swift: You either jump on board or prepare to eat the dust of the other AI first-movers — will essentially be going into a marketing battle with one arm tied behind your back. Performance will suffer (including lower engagement rates compared to competitors), as will profits.

What Does This All Mean?

Hopefully, you have a better understanding of all the advancements that are taking place in the marketing world today. Will generative AI end up replacing your human teams? Not entirely. I think it will make the humans materially more efficient, and you may need less humans than before, but humans will still be needed for strategic direction and quality control, to protect their brands. For example, if AI generated copy will upset Google and hurt your search rankings, someone will need to review that content and make sure it follows all of Google's rules. So, think of AI as an augmentation tool built for speed and efficiency, not as a full human replacement. You will still need to engage your marketing agencies or marketing teams, but they will be doing their work in material different, and presumably better, ways.

Every decade or so, the marketing industry appears to go through a rapid period of innovation and innovation. It feels like we are in the "early innings" of this most recent revolution, and I am excited to see how these AI technologies improve from here, and what additional AI advancements we will see in the coming years. It is time to pull up your boot straps and buckle in, as it is gonna be a helluva ride! Good luck as you experiment with these technologies on your own.

For future posts, please follow me on Twitter at: @georgedeeb.

Wednesday, November 1, 2023

When Investing, Chasing Growth May Cost You Millions

Posted By: George Deeb - 11/01/2023

I was recently speaking with an entrepreneur who'd passed on an investment because it would not need yield the company at least a 10x gr...

I was recently speaking with an entrepreneur who'd passed on an investment because it would not need yield the company at least a 10x growth opportunity. I told him those returns might be reasonable when investing in small businesses (under $5 million) but that he should consider lowering his ROI threshold when investing in larger ones. My logic was twofold: first, bigger companies are harder to grow as quickly as small ones, so the growth percentages will be lower; and second, there's the potential to make substantially more money on a bigger company investment, even if the ROI was only 3x to 5x. Here's how to know when it's better to focus on percentage returns vs. dollar returns when assessing your investment opportunities.

Read the rest of this post in Entrepreneur which I guest authored this week.

For future posts, please follow me on Twitter at: @georgedeeb.

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