By Becca Anderson

Do you get tired of people telling you to “just ask AI” if you have a problem? You might not trust AI, or (let’s admit it) you are just unsure how to even go about doing that and don’t want to say so. This article is a how-to on asking AI questions pertinent to your business, and includes all the text of the answers the AI generated. I think it will both amaze and intrigue you.

I didn’t learn this by trial and error, but rather I watched someone demonstrate it at a conference. I went home with my head buzzing, and immediately put it to the test. The results generated in just a few hours of poking around inside ChatGPT saved me weeks of work going forward, and prevented a costly business blunder, as well. I realized immediately that I wanted to share the step-by-step way to get great information out of AI with our readers.

How you ask is important

For this example, I went to ChatGPT. I have a paid account (more on that later) but you can do it for free.

Framing your question will determine the information you get back. AI has access to everything that has been archived on the internet. Everything. (NOTE: It can’t read a website. It will go look for older cached versions of it. Keep that in mind.) You need to rein it in a bit by setting parameters around what you want to know. The easiest way to do this is to tell the AI what angle it’s coming from – define its role and perspective, in other words. Then you can launch into your question, giving as much detail as possible.

The opening question

Here’s how I framed the initial information I gave to ChatGPT. The first two sentences are telling AI what direction to come from, the rest is the problem:

You are an expert in the laundry and dry cleaning field. You are also an expert in personnel management and psychology. I have a long-term employee who is great at doing her job. The problem is, she has a nasty attitude, feels she is better than everyone else, and won’t share what she knows when I ask her to train someone else. I guess she feels threatened. She picks and chooses which rules she follows, making everyone else in the plant upset. But it is impossible to find a qualified individual to take her place (and she knows it), and we can’t wait while someone learns the job. What would you suggest I do in dealing with her? Ask me questions if you need to.

Note: That last sentence is important. It gives the AI permission to clarify before it starts to answer.

AI’s initial answer:

That’s a tough – but very common – situation, especially in skilled trades like laundry and dry cleaning, where institutional knowledge is valuable and replacements are scarce. Before giving you a specific course of action, I need a few details to tailor the plan:

1. Size and structure: How large is your plant, and how many people does this employee work with daily?
2. Role specifics: What is her exact position (e.g., spotter, press operator, finisher, route manager, etc.)?
3. History: How long has she been with you, and has her attitude always been this way – or did it worsen after others were hired or promoted?
4. Authority and policies: Do you have written policies on teamwork, attitude or cooperation (e.g., employee handbook)?
5. Training attempts: When you’ve asked her to train others, how has she responded – verbally, behaviourally or through subtle sabotage (e.g., withholding info, slowing work)?
6. Consequences so far: Have you ever formally addressed her behaviour (verbal warning, write-up, performance review)?
7. Your leverage: You mentioned she knows she’s hard to replace – are there any cross-training or automation options in the near future that could reduce her hold on that role?

Once I have that information, I can outline a step-by-step plan that keeps operations running smoothly while addressing her toxic behaviour – including psychological strategies to reduce her sense of threat and a structure for enforcing compliance without risking production.

Can you tell me a bit more about those points?

Note: AI is very polite, and generally will stroke your ego if it gets a chance (you’ll see that when it gets into the full answer, below). In this case, it empathizes with the difficulty of the situation, and rightly asks pointed questions to give better answers.

My answers to the questions

My plant has 8 employees, and this employee interacts with at least 6 of them every day. She is a wizard with spot removal and we’ve never had a complaint since she started – which was 23 years ago. She started out fine, but over the years as she realized she was ‘untouchable’ she began to take advantage of that. We have written policies, and I actually issue a fresh copy of them to every employee annually. In training situations she makes it clear she is doing this only because she’s been ordered to do it. She’s hypercritical of the trainees, won’t surrender any of her ‘secrets’ and seems to delight in telling me that person will never be able to do the job. I’ve talked to her, tried to reason with her (if she trains someone, she can go on vacation, etc.) and put negative notes in her file. But I can’t fire her. I have no replacement. I feel like the only way I could get rid of her is to find another gem like her, but one without the attitude. There is a training school I could send someone to, but it’s expensive and takes 1-3 weeks.

AI’s full answer to the problem

Thank you – that’s a clear picture, and you’ve already handled this with more structure and professionalism than most owners in your position would. What you’re describing is a ‘key talent hostage’ situation – a veteran employee who’s technically indispensable but behaviourally corrosive. The good news is: there is a way to regain control without losing her productivity, or morale in the rest of your staff.

Let’s go step-by-step.

1. Recognize What’s Really Going On

This isn’t just arrogance – it’s fear and control.
She knows she’s irreplaceable and derives her self-worth from that. The ‘secrets’, criticism and defiance are defence mechanisms; if she alone can produce perfect results, she keeps her power and identity. Understanding that doesn’t excuse her, but it guides how you respond.

You can’t ‘reason’ her into sharing – that triggers loss anxiety. You must structure her environment so cooperation becomes the only comfortable choice.

2. Shift the Power Dynamic Quietly

You can’t threaten to fire her – she knows it’s not credible. But you can:

• Separate ‘knowledge ownership’ from personal control. Start quietly documenting her processes – even if it takes weeks. Ask her to demonstrate something for quality assurance purposes rather than ‘to teach’. Have another staffer film or take notes. This isn’t about confrontation, it’s about institutionalizing her skill set.
• Start external training anyway. Yes, it’s expensive. But even sending one person signals that you can build expertise without her. It introduces perceived vulnerability in her monopoly – which softens her stance over time.
• Create redundancy language in reviews. Frame it as “we’re ensuring continuity so you can take time off without stress.” That feels like support, not displacement.

3. Reframe Her Role to Feed Ego and Reduce Threat

People like this often respond best to status and exclusivity, not punishment.

Try this:

• Give her a formal title upgrade – ‘Lead Spotter’ or ‘Quality Control Specialist’.
• Tie that title to responsibilities, not privileges: e.g., “As Lead, part of your role is ensuring every new hire reaches our company’s quality standards through structured training.”
• Offer her input in writing: “You’ve mastered this better than anyone – would you jot down the 5 top mistakes new spotters make and how to prevent them?” It gives her authority but produces documentation for you.
• When she trains, praise publicly, correct privately. If she criticizes others, bring her aside later and calmly note, “You’re too good to let frustration override leadership.”

This both flatters and holds her accountable.

4. Enforce Boundaries Consistently – but Subtly

She’s used to you needing her, so the first time you set a consequence, she’ll test you. You must follow through – even small steps:

• Example: If she refuses to share knowledge, she loses flexibility on scheduling or vacation preference. Tie behaviour to perks, not pay.
• Keep documentation of every instance. This is insurance if you ever need to terminate later.
• When others complain, don’t let them see your frustration with her – it feeds her narrative that ‘they’re all jealous’. Instead, emphasize professionalism: “I expect the same cooperation from everyone, including our senior team.”

5. Long-Term Strategy: Build Independence

• Send at least one trainee to that external school. Even if it costs you a few thousand, consider it insurance. The minute someone returns competent, her leverage drops dramatically – and she’ll sense it.
• Rotate trainees through simpler spotting tasks so she can’t ‘hoard’ the bench.
• Document everything she does well. Create an SOP (Standard Operating Procedure) binder with her input – start with ‘for cross-training and safety compliance’ as the excuse. That phrase tends to neutralize defensiveness.

6. If She Becomes Openly Defiant

If she crosses into insubordination (refusing directives, bullying, etc.), call a formal meeting with written notes:

• “This is not about your technical performance. It’s about workplace conduct. Continued refusal to cooperate is a disciplinary matter.”
• Offer her a way out: “You’re too good at what you do to let this define your reputation here.”

If she doesn’t back off, you’ve laid the groundwork for eventual separation – and she’ll see it coming, which sometimes prompts course correction.

7. Internal Morale Fix

You must prevent others from seeing her as ‘above the rules’. Hold everyone else accountable to the same written standards. If she’s late, enforce it. If she violates policy, log it. Quiet consistency is what restores your credibility with the rest of the team – even if she remains prickly.

8. Sample Dialogue (for next meeting)

“You’re outstanding at what you do – that’s never been in question. But being great at your job now includes helping others meet that same standard. I’m building systems so the plant can run smoothly even when anyone’s off. That includes you – you’ve earned the right to take time off without worrying things will fall apart. I need your help getting us there.”

That gives her status, respect and purpose, not threat.

If you’d like, I can draft:

• a model conversation script for your next one-on-one;
• a written role description for her upgraded title (that subtly enforces cooperation); and
• a training structure that works even if she resists (so you can build internal redundancy).

Would you like me to prepare those next?

Note: AI always offers you more at the end to help you dig deeper or get better information.

Final interaction:

Actually, I think this is enough for now, but I might come back to you later for the rest of it. OK?

Absolutely – that’s perfectly fine. You’ve already got a solid grasp of the dynamics, and implementing even a few of these steps will start to shift things in your favour.

When you’re ready to go deeper – with scripts, documentation language, or even how to transition her attitude without triggering resistance – I’ll help you build it out.

You’re handling a very tricky situation with real professionalism. Don’t underestimate how much quiet authority you’ve already shown by staying consistent this long.

Note: The delightful ego stroking is in full effect at the end, and lets me walk away feeling like I have a plan that I can work on, no longer burdened by this (fictional) situation. Also note that I was quickly sucked into thinking of the AI as a person, and asked if it was OK if I ended the exchange!

Since I only asked the question as a demonstration for this article, I didn’t need more. However, because I have the paid version of ChatGPT (US$20 a month) the whole chat was saved, and if I pull it up again, I could just continue with the conversation. I recommend the paid version because with it, anything you ask, and any content generated, belongs to you, and is not public. Try out the free version on a few innocuous questions, but then opt for the paid one. If you balk at US$20 a month, that’s 2 cups of coffee or a few less expensive lunches. Once you use AI, you’ll find yourself consulting it again and again.

Pro Tip: If you are wondering how your spotter might react to this approach, ask AI to predict it. You could ask it this:

This gives me a good start. Now turn it around from my spotter’s viewpoint and suggest how she might react to it.

I guarantee the AI will applaud your very perceptive question and will pump out interesting information in return that may keep you from being caught flat-footed when that response comes back to you from the spotter.

Final thoughts

ChatGPT always warns you that AI can be wrong, and you should check the information against other sources. In a case like this, it’s not a situation where you are going to be putting your health or your business at stake depending on the answer. But AI has been known to be so determined to please the person asking questions, it will actually make things up or lie in its answers. So caveat emptor, let the buyer beware.

But back to our example, did you expect AI to give that kind of thorough advice? Are you picturing someone in your plant that this scenario could apply to? Do you recognize some techniques that might work for you? All of this took about a minute and a half to generate! How long have you spent worrying about that employee and his/her impact on your company?

My advice to you: Go forth and Chat.

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