Using AI for business decision-making works best when you stop asking it for answers, and you let it ask you questions first. At one of our virtual events, Gar Whaley and I walked through how we do this ourselves. This article covers the prompt I use and the habits that keep it working best.
Key Takeaways
- AI helps most with hard decisions when it interviews you before it advises you.
- A good prompt gives context, names your biggest constraints, and asks for one question at a time.
- AI tools lean toward agreeing with you, so you have to ask for disagreement.
- A person should fact-check every answer.
Table of Contents
Why You Should Use AI as a Thinking Partner
Most people use AI to search for information, write text, or summarize a transcript. This is a completely different job. Using AI as a thinking partner means introducing it to a real business decision you’re facing and letting it interview and challenge you, the way a board of directors would.
Think about all the business decisions that cost you sleep:
- Whether you should hire
- Which priority you should drop
- Why the same problem keeps coming back to haunt you
- How you should handle a hard conversation with an employee or a client
If you had a board to call upon, you probably wouldn’t settle for their thoughts alone. Gar is a team of one on sales, and he used to grab another Teal leader to pressure-test an idea. Now he starts with Claude, ChatGPT, or Microsoft Copilot before coming to us. I do the same.
But there is a catch. AI doesn’t know your business outright. So, a vague request will give you a generic answer. Telling it to “act as a genius that knows everything” doesn’t change that. During a recent virtual event where we talked about this, Gar explained it well.
He wouldn’t ask me whether a client should use Microsoft 365 or Google Workspace without explaining the client first. AI needs that same type of background, but many people leave it out of their prompts.
Habits You Should Build to Keep AI from Just Agreeing with You
Make sure you ask your AI tool of choice to disagree with you. They’re commercial products – so their goal is to keep you using them. That means that they tend to tell you that you’re right.
While that may feel good, it doesn’t help you weigh a serious business decision. These five habits will fix most of that issue for you:
- Give it context. Give it all the details surrounding your question, attach documents, or point the tool at relevant files.
- Iterate. Keep the conversation going; the first response is just the start.
- Ask to be interviewed. Anything you provide it up front is going to be too little info to provide informed advice.
- Ask for disagreement/challenges. What am I missing? What makes this a bad decision?
- Fact-check. Ask where the information came from, then verify it yourself.
How AI Handled a Hiring Decision in My Demo
In my recent live demo, I had Claude turn a vague hiring question into a two-week test. I made up a business where the office team said it needed another coordinator because clients were unhappy. This is the prompt I used:
Help me think through hiring another coordinator. I run a 25-person business. Our office team says we need another coordinator because we’re falling behind and clients aren’t happy. I’m unsure if it’s a workload problem, a responsibility problem, or how we handle the requests. Help me understand the problem and recommend a solution.
Then, I asked Claude to interview me one question at a time.
It followed up with questions like:
- What does “falling behind” mean?
- What is the actual request count over the last 90 days?
- Are the extra requests from new customers or existing ones?
I responded and Claude recommended tagging incoming requests for two weeks before hiring anyone. That way, I could tell whether the problem was workload-related, a responsibility issue, or how the company was handling requests.
A new hire costs you a lot, right? It’s a big investment. But two weeks of tagging requests costs you almost nothing. So, our theoretical executive walked away with a much cheaper first step to take.
Pro tip: I asked for short answers originally, but the replies got long once the conversation shifted into the advice territory. If you want short responses, keep asking the AI for it.
How to Use AI to Think Through a Business Decision
Like I mentioned earlier in the article, context is everything. So, when you want to use AI to think through a decision, you need a prompt that provides clear context.
This is the template I use all the time to work through tough decisions. I encourage you to give it a shot. Just copy it and fill in the brackets with your details.
AI Prompt for Decision-making Example
Help me think through [problem or decision]. Here’s what’s happening: [context].
What I’ve already tried is [attempts]. My biggest constraint is [constraint].
Before giving advice, ask me one question at a time, up to [number] questions.
Then help me compare options, challenge my preferred approach, and identify a practical next step.
Separate facts I provided from assumptions.
Pro tip:
- I highly recommend making sure it asks you one question at a time. If it asks you 10 questions all at once, but the first one was way off base, then you’re going to have to workshop the whole thing.
- Have AI ask you a lot of questions to get the best results – between five to ten.
- People tend to work through these types of questions faster by chatting because they can say a lot more when they talk. So, use the dictation tool or the microphone button built into Claude and ChatGPT.
Pick One Decision and Try Using AI to Solve it This Week
I really recommend choosing just one decision you’ve been circling around and run it through my prompt. Walk through it out loud, if you can. I use ChatGPT’s voice mode while driving or walking my dog, because I have the extra time. If you want help deciding which AI tools are best for your business, I’d be happy to help you walk through it. Check out our managed AI services page to learn more.
