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You can buy the best AI money can get.
But if your prompts are lazy, you’ll get lazy results.
That’s not a tech problem. That’s a structural problem.
Just like the foundation of a house…you can’t support significant weight or all the items you want if the foundation isn’t sound or won't support what you need.
The truth: AI can only amplify what you put in.
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Everyone wants better, faster, smarter outputs, but most are sabotaging themselves with vague, context-free instructions and shallow inputs.
If you want outputs that impress clients and win deals, you need to engineer clarity and discipline at the front end.
If you're in social selling, account management, or business development, weak prompting means weak personalization, weak proposals, and overall weak positioning. It signals carelessness to prospects and clients.
I’m going to provide you with 5 different prompt bad habits (or sins, penalties, infractions, flags) that you can avoid and how you can improve.
Let’s dance.
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Why it Matters
The quality of your AI output is directly determined by the quality of your input. This is the GIGO problem, Garbage In, Garbage Out. No AI model can fix lazy thinking.
78% of business leaders now use AI in their workflows, but output quality remains inconsistent.
The difference between an AI output that lands and one that misses is precision. Not model capability. Precision.
Senior executives who use AI effectively outpace competitors not because they have better tools, but because they know how to ask better questions. Specificity wins.
When your AI outputs are off, stop blaming the system. Start with your process. The best AI results don’t come from luck; they come from the discipline, depth, and clarity of your inputs.
I’ve written on AI prompting in the past; check out past articles here:
The 5 Bad Habits
Bad Habit #1: Vague Instructions
The Habit: You ask AI to "write a better pitch" without defining what "better" means.
Why It Fails: The AI has no guardrails. It guesses at tone, length, format, or audience. You get generic output that could apply to anyone.
The Fix: Be brutally specific
Instead of "Write a sales email," say:
"Write a 2-paragraph sales email to a CMO at a Fortune 500 construction company based in Tampa, Florida. The tone is professional but conversational. Reference their recent LinkedIn post about digital transformation. Highlight one specific result we delivered for a similar company. End with a request for a 15-minute call next Tuesday. Keep it under 200 words."
Specificity eliminates guesswork. The AI knows exactly what to build.
Bad Habit #2: Missing Context
The Habit: You feed the AI information without explaining why it matters.
Why It Fails: The AI doesn't know your industry, your client, your goals, or your voice. Output sounds generic because it is.
The Fix: Always set the persona, task, context, and format.
"I am a VP of Business Development with [insert company] at a SaaS company selling compliance software to healthcare firms with under 500 people in the Southwest Region (FL, GA, AL, MS, SC, LA). My goal is to reach out to a prospect who just posted about compliance challenges. The specific post from LinkedIn is here [insert LinkedIn Post]. Write a personalized outreach message that speaks to their specific concern and positions our unique approach."
Now the AI understands the weight of the moment.
Still, keep adding that value!
Bad Habit #3: No Desired Format or Outcome
The Habit: You don't tell the AI how you want the output structured.
Why It Fails: You get walls of text, or scattered ideas, or formats that don't fit your use case.
The Fix: Specify format and constraints upfront.
"Write a 5-point account management plan for Q1 for an account that focuses on the architecture market growth in our commercial real estate for healthcare in South Carolina. Use bullet points. Each bullet should be one sentence. Include specific metrics we'll track. Format for a Slack message, not a document."
Format control shapes usable output.
Bad Habit #4: No Iteration or Refinement
The Habit: You accept the first output as final.
Why It Fails: First drafts from AI are rarely perfect. They need refinement, adjustment, a second pass.
The Fix: Treat prompting as a creative, experimental process.
After the first output, ask: "Refine this for a more conversational tone" or "Make it 40% shorter" or "Add one question at the end that prompts engagement." or
Each iteration improves precision and quality. Small tweaks produce dramatically better results.
Highlight a specific section and ask for additional context to the overall section so you are able to elaborate on it.
Bad Habit #5: Not Defining Success
The Habit: You ask AI to do something without clarifying what success looks like.
Why It Fails: You get output you have to heavily rewrite, wasting the time you were trying to save.
The Fix: Define the win state before you prompt.
"Write a proposal summary that will make our CFO say yes. It should answer three questions: Why now? Why us? What's the ROI? Use data, not flowery language. If I'm reading this in 90 seconds, I should know exactly what decision I need to make."
Now the AI targets the outcome, not just the task.
How Improving Your Prompting Can Help You Win
When you master prompt precision, you compress time. What took an hour now takes 15 minutes. What took a day now takes an hour.
But more importantly, you improve trust.
Weak AI outputs look weak. They signal carelessness. They undermine your credibility with prospects and your team. Clean, precise AI outputs amplify your message and your professionalism.
Executives who prompt effectively use AI as a leverage tool, not a crutch. They shape output to match their voice, their market, their moment. They stay in control.
Your competition is probably still prompt-bombing, sending generic AI outputs that sound like everyone else. You can be different. You can be precise. You can turn AI into a competitive advantage, not a timesaver.
In social selling, the personal touch is what converts. Poor prompting turns personalization into broad, tone-deaf nonsense. Good prompting turns it into targeted, sharp, memorable outreach.
Action Item
This week, audit one AI output you've created recently. Does it follow the five bad habits? Pick one habit that's hurting your work the most.
Then rewrite that single prompt using the framework above: specific instructions, clear context, defined format, one round of iteration.
Compare the output. The difference will tell you everything you need to know about the power of precision.
Stop prompt-bombing. Start prompt-crafting
Pack Some Additional Punch
Here are a few tips to really hit it out of the park when reaching out
Send during the week, responses on Friday and Saturday get a lower response rate
Keep your messages less than 400 characters. The more characters significantly decrease the chance of having engagement. Shorter is sweeter!
Not connected yet? Leverage the “Add a note” when you connect, make it personal and not blind. Every little effort helps.
The human touch goes a long way in today's digital landscape.
Build towards it, don’t jump the gun.
What the Internet Taught Me This Week
From new tools, recent trends, and market updates, here is what has been on my mind.
If the US Has to Build Data Centers, Here’s Where They Should Go. Check it out here
Hegseth unveils ‘transformation’ of DoD acquisition system. Check it out here
Why a lot of people are getting hacked with government spyware. Check it out here
AI isn't the differentiator anymore. Everyone has access to it.
Prompt precision is.
The executives and business developers who win aren't the ones with the fanciest AI subscription. They're the ones who treat prompting like a craft, with very specific inputs, clear context, defined outcomes, and iterative refinement.
Your AI outputs reflect your thinking. If your prompts are lazy, your outputs are lazy. If your prompts are sharp, everything improves.
Stop accepting mediocre AI work. Start building better briefs. And you don’t have to pay crazy prices for an AI tool to solve this for you either.
The five bad habits are costing you time and credibility every single day. Fix them, and watch your productivity and your professional standing shift.
See you next week.
Whenever You're Ready, Here are 4 Ways I Can Help You:
Unlocking Hidden Potential - Reconnecting with Past Clients for Explosive Growth - Check out my free eBook on how you can find hidden gems in your past clients and help you crush your sales goals.
AI for Business Development - Download our free eBook on how you can effectively leverage AI prompts to your advantage. From properly setting up your preferred AI tool, to how to shape your prompts, save time, and get the outputs you are looking for.
Sales Resources at Your Fingertips - From tools, tips, demos, and how-tos, check out our Pages and content that can provide you with additional support, whether it be social selling, account management, or something else.
Cribworks Advisor Program - Want more than just resources? Reach out to me and see if our Advisor Program can help you scale your business.



