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Welcome to the “Savvy Seller”
Shadow Seller’s stories that  simplify…

Welcome to Shadow Seller's blog, where we're all about ditching outdated sales methods for cutting-edge excellence. Here, we offer insights and strategies to boost the savvy of sales leaders, pros and CEOs. Dive into innovative sales tactics, bust myths, and discover hidden gems to streamline your workflow and enhance productivity. Our posts are packed with practical tips and real-world examples to shake up your sales approach. Whether you're a sales vet looking for an edge, a sales leader trying to finally overcome some of those repetitive problems or a CEO aiming for growth, you've found your resource. Join us on this journey to sales success and stay tuned for content on making sales simpler and more effective. Welcome aboard Shadow Seller's world


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Artificial intelligence (AI) has sparked equal measures of enthusiasm and apprehension. Among the fears is a concern that over-reliance on AI will lead people to stop thinking for themselves, allowing machines to replace human judgment, leading to a "dumbing down" and a "vanilla-ization" of ideas. While this fear is not unfounded, it misses a crucial point: how one uses AI is a choice.

And let's be clear what we're talking about here - using GenAI in helping sellers is a little different to using AI in autonomous vehicles. Here one can flip the argument around - no matter how you slice it, most auto accidents are the result of human errors...enough said?


(Listen to the podcast instead)




With great power comes great responsibility

AI is a powerful tool, but like any tool, its impact depends entirely on how we wield it. There is indeed the risk of misusing AI as a substitute for human thought—leaning on it to provide not just answers and information but decisions, abdicating our responsibility. AI's most transformative potential, however, lies in its ability to enhance human thinking, not replace it.


AI can help you:

  • Research Faster: Scouring to provide insights that would take a human days or weeks to compile.

  • Summarize Effectively: Condensing vast information into digestible insights that make complex topics easier to understand.

  • Assemble Knowledge: Drawing connections across disparate pieces of information to present a more comprehensive view of an issue. Joining the dots, so to speak.

  • Enable you to: stop second guessing yourself. Wondering about stuff you haven't thought of.

A great example goes back to the sales preparation and meetings that are the scourge of the "sales week." Using AI in sales gives you the situational fluency you'll need to succeed in those meetings.


Give A.I. a job description

By leveraging AI to handle specific tasks (like those above), we can focus on interpretation, judgment, and decision-making - higher order thinking! Instead of spending hours gathering data, we can use AI to collect and organize the information, allowing us to make better, faster, more definite decisions.


This brings us back to the central point: using AI effectively is about making choices. Will we let AI do the thinking for us, or will we use it as an amplifier of our own capabilities? It’s a matter of mindset and intention.


I don't like Mondays


The start of the workweek exaggerates all this. The Sunday Scaries and Monday trepidation set in. For many sales teams, the pressure is compounded by the ritual of Monday morning sales meetings, where the "bosses" expect a clear picture of progress and plans. Here is where AI can help.


What "the management" people really want to know is "what have you done and what are you going to do?" It's a review - preview. Next week is the same script. In sales things don't necessarily change on a weekly basis, so if nothing much happened - tell them. If you intend to do "nothing" much on a particular deal this week, tell them that also, and tell them why! The importance of "nothing happening" is whether it's deliberate or not!


You can be using AI to help you present a set of considered statuses and actions for each situation. The beauty of this approach is that while the "bosses" may debate the strategy or plan you propose, they cannot argue that you lack one.


Finally, you can stop second guessing yourself. Your sales AI has presented you with some alternatives - you can decide on which one to go with - but you can be confident you've probably seen them all. This is not just due to your choice to use AI, but more importantly your choice in how to use AI.





 
 
 

Socrates - the greatest "questioner" of all time
Socrates - the greatest "questioner" of all time

The Power of the Right Prompt: Maximizing A.I.'s Potential in B2B Sales and Beyond

A.I. has swaggered into the business world, promising to revolutionize everything from sales to lunch breaks (maybe). And while A.I. is undeniably brilliant, its brilliance depends on details: the questions you ask and the conversations you have (i.e. prompts you feed it.) At the heart of this high-tech miracle is a skill as old as time (or at least as old as Socrates) —asking the right question. Yes, it’s that simple. And no, your vague, half-baked questions won’t cut it.


Tell me more…Why the Right Prompt Matters

A.I. systems are like that overachieving student in your high school class. They’re strangely smug and arrogant. They’ll give you the perfect answer to the question you’ve asked. Ask them something vague or ill-conceived and you’ll get a similar response. Prompts are like your gym membership: the effort you put in determines the results you’ll get.


The Timeless Art of Asking the Right Question

Let’s not pretend asking good questions is a 21st-century concept. Socrates built his whole career on it 2500 years ago.. The rules haven’t changed much:

  • Clarity: Would you ask a prospect, “What’s your problem?” (Well, not unless you’re actively trying to get kicked out.) Be specific.

  • Context: Tailoring questions to the client’s unique situation has always been Sales 101. A.I. isn’t psychic (yet), so feed it context.  

  • Purpose: Know what you want and ask for it.

  • Curiosity: I remember participating in a call a couple of years ago with a typically poor Salesforce seller. He’d bought into the “be curious” idea, and thought all he had to do was use the word “curious” as many times as possible. Well, here’s the news – prospects aren’t into your curiosity (they never were), so ask the questions that demonstrate some thought and expertise you have in their business.


The Fallacy of "No Dumb Questions"

Which brings us to the "There’s no such thing as a dumb question." Really? We’ve all been in those meetings where someone asks, “So, what exactly do we do here?” Dumb questions exist (although given the right timing and context that could be a devastatingly great question.) Poor questions are born of laziness, poor preparation, or obliviousness. Great questions are the opposite and also require the courage to ask them.

When it comes to A.I., the “no dumb questions” myth can lead to some truly mind-boggling prompts. The truth is, dumb questions waste time, annoy coworkers, and—in the A.I. world—yield useless results. So, let’s agree: there are such things as dumb questions.


How to Write Effective Prompts

Crafting effective prompts is creating meaningful conversations – and that’s what you need to have to get the most value from A.I. Even when, sometimes, things seem to deteriorate into an argument. All relationships have their “ups and downs.”

  1. Start with the end in mind: Know your goal. Don’t just meander into the conversational void – whether you’re talking to your A.I. or your garden variety human!

  2. Provide context: A.I. thrives on details (just like people). It’s all about context, subtleties and nuance. Be generous. For example, my wife ALWAYS accuses me of “not” getting the details! Maybe it’s a guy thing?

  3. Be specific and actionable: Lawyers love ambiguity, A.I. doesn’t.

  4. Argue and be demanding: Don’t be afraid to “argue” with A.I. Even A.I. loves a second chance, and rephrasing a question or providing more context will have surprising results!


The Role of Prompts in Sales and Marketing Success

Mastering prompt composition will help you get more things achieved in less time. When you use the insights A.I. provides you’ll simply become more creative, able to “personalize” at scale. Simply put, you’ll just be better, and feel better.


Bringing It All Together

In conclusion, the ability to ask the right question has always been important (ask Socrates.) Some people can just seem to do it, and the rest of us have to try a little harder. I sometimes refer to these conversations with our Sales Readiness A.I., Shadow, as interrogating them (they’re not people, yet so we don’t have to worry about their feelings…yet!) Technology has changed, but the basics haven’t. Clarity, context, and purpose still rule the day, as Socrates taught us! Oh yea, and maybe a little levity?

 
 
 

R.M.S. Titanic April 14, 1912
R.M.S. Titanic April 14, 1912

We went to the Titanic VR exhibition over the Xmas break. It’s fabulous and well worth $40. It tells the story of Titanic from conception through construction and launch, the people, the circumstances and the incidents all leading up to the eventual sinking. Titanic struck the iceberg at 11:40 PM (ship’s time) on April 14, 1912. The ship sent its first SOS distress signal approximately 45 minutes later. The S.O.S. signal in Morse code (... --- ...) was officially adopted by the International Radiotelegraph Conference in 1906, taking effect on July 1, 1908 (in case you wanted to know.)


Sales Jobs! Come on Down!

Skimming through LinkedIn job posts reveals an abundance of postings for sales jobs. HubSpot reports an average sales rep turnover rate of 35%. The old Sirius Decisions data concluded that nearly half of B2B companies suffered at this rate. Then there’s the challenge of getting new sellers up to speed. According to the Brooks Grp, on average, new sales professionals are ready to engage with customers after approximately 9 months of onboarding. They also maintain it takes 12 months for new sales reps to become competent and capable of carrying a full quota.  


Where’s all this going?

Good question…rather than continuing this course, can you “save” some of those sellers, and save yourselves a bunch of time, money and new hire heartache at the same time? While this might not be as S.O.S. worthy as the Titanic story (no one’s going to lose their lives) it’s alarming at least.


The A, B & C Players

Sales teams can generally be divided into 3 groups: A, B and C players. Leadership always loves to claim, "We’ve only got A players!" Sure—and everyone’s a rockstar, gets a trophy, and can bench press a bus. The truth is, A players are rare, and if you did manage to hire them all, you’d spend more time managing egos than sales.  It’s the “B" and "C" players where the turnover (and the opportunity) lies. These generally ignored individuals represent the most significant opportunity for growth through targeted coaching and support. The problem is that our old ideas of “coaching & support” never worked that well, and it seems easier to ship the blame for missed numbers to them. So, let’s just replace them. This gives leadership an excuse and keeps the recruitment team occupied!


Get on With It – Where’s the A.I?

OK, fair enough. According to Ethan Mollick in his book: “Co-intelligence: Living & Working with AI” - “In study after study, the people who get the biggest boost from AI are those with the lowest initial ability—it turns poor performers into good performers, and good performers into great. In a study of early use of generative AI at a call center, the lowest-performing workers became 35 percent more productive…In our study in BCG, we found similar effects. Those who had the weakest (or weaker) skills benefited the most from AI, but even the highest performers gained.”

This is why we call it the “equalizer” and explains why a good proportion of the millennials & Gen Zer’s are, at best, indifferent to AI as it breeches the walls of their subject matter domains.

 

Joining the Dots

We often use that phrase when talking about our A.I. Sales Readiness tool – Shadow. Shadow helps you (or your team) “join the dots.” Shadow does most of the research and most (but not all) of the thinking for you.

Having said that I’ll leave you to join your own dots on where this (not so) Titanic of an article is going. It’s simply this – don’t jump into replacing sellers too readily. Maybe it’s time for a different approach – an A.I. Sales Readiness Tool that can Save our Sellers, and help you avoid that sinking feeling!

 
 
 
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