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Complex Deals

What An MBA Didn’t Teach You About Sales

The sales profession is challenging. You need to work hard at it to succeed. You need to learn from the best. You need to improve your skills continuously. If you think you can sell since you are a hit at parties and have a lot of friends, you may soon find that you are a failure as a salesperson. Blunt truth:

because the sales profession is so hard, you have to focus on doing everything in sales very well, or you will be considered a failure.

I call this blog, Skinned Knees because I try to relate all of the learning that I have done over the past 4+ decades (while skinning my knees in the learning process).

I hope that you learn from my mistakes so that your business will grow!

AI Sales Automation: Why Your Chatbot Is Not a Sales Process

Imagine preparing for an important customer meeting. You open your favorite AI assistant, give it the prospect’s name, and ask for a summary of the company’s business challenges and the questions you should ask. Within seconds, you receive a beautifully written briefing. The assistant identifies potential operational problems, competitive pressures, and several opportunities to demonstrate the value of your solution.

There’s just one problem. One of those impressive insights concerns an acquisition the prospect supposedly completed last year.

Except the acquisition never happened.

The artificial intelligence fabricated a plausible business event and presented it as fact. Had you trusted the briefing, you might have opened your meeting with a question that immediately damaged your credibility.

This scenario illustrates a much larger problem with how B2B sales organizations use AI.

We’re asking artificial intelligence to perform too many different kinds of work without distinguishing which tasks require intelligence and which require reliable execution.

That distinction matters more than the sophistication of the AI model you choose.

The Problem Isn’t Just Hallucinations. It’s Process Design.

Salespeople increasingly rely on ChatGPT, Claude, Gemini, and other Generative AI applications to prepare for meetings, research prospects, write follow-up messages, and analyze opportunities. Those are legitimate applications of AI. In fact, I’d question why a salesperson with access to these capabilities wouldn’t use them. But consider what happens before the salesperson receives a useful answer.

They retrieve information from their CRM, gather previous meeting notes, identify stakeholders, check pricing, and reconstruct details from previous conversations. They paste everything into their AI assistant, ask a question, verify the response, and correct any mistakes.

Tomorrow, they repeat the process for another customer.

The AI may have improved the quality of their analysis, but the underlying sales process remains largely manual.

When twenty salespeople independently reconstruct the same process every day, you don’t have an AI adoption problem. You have a sales management problem.

You’re paying experienced professionals to repeatedly assemble information that your existing systems should already provide.

The solution isn’t necessarily better prompting. It’s better workflow design.

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Stop Asking AI to Write: How Salespeople Can Use AI to Think Better

Most salespeople are using artificial intelligence too late in the sales process. They gather the account information. They interpret what matters. They decide what argument to make. They formulate the questions. They determine what the buyer probably cares about. Then, after doing all of the difficult thinking themselves, they hand the last 10% of the job to AI and say, “Write me an email.”

When the result sounds generic, they conclude AI isn’t particularly useful for serious B2B selling. The problem is not necessarily the technology. The problem is where they inserted it into the process.

A salesperson can get significantly more leverage from AI by using it before the answer is obvious. That means treating the system less like a copywriter and more like a junior analyst, researcher, sales coach, and thinking partner.

The Skill Is Not Prompt Writing

An entire industry is built around prompt libraries. “50 Best Prompts for Salespeople” sounds useful because it promises a shortcut. It also teaches the wrong lesson.

A prompt that worked for someone else’s account, market, buyer, sales process, and objective may be almost useless for yours. The more strategic the sales problem becomes, the less likely a canned prompt is to fit it.

The more durable skill is learning to decompose commercial work into reasoning steps.

A useful sequence is:

  • Context.
  • Objective.
  • Constraints.
  • Reasoning steps.
  • Output.
  • Critique.
  • Revision.

Instead of asking AI to jump from context directly to output, make it work through the intermediate decisions with you.

Suppose you are preparing for a meeting with a CFO. A weak request is:

“Write an email to the CFO.”

A stronger conversation begins by asking AI to identify the financial issues most likely to matter to that executive based on the evidence you provide. Then ask which conclusions are facts, which are inferences, and what additional information would increase confidence. Challenge the assumptions. Compare several possible value arguments. Only then should you ask for the email.

The writing is now the consequence of better thinking.

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