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October 31, 2024
At times, running a business can feel like you’re moving through thick fog — blindly plowing forward and completely unsure if you’re doing the right thing. At times like this, it pays off to pause and ask yourself the hard questions “Am I even going in the right direction?” or “Is our strategy the optimal one for this product?” That’s the type of question you usually ask your mentor.
But if you don’t have one — not to worry, you can easily turn an AI chatbot into a business mentor. With that in mind, here are 5 questions that can transform an AI question answerer into an expert business consultant, and help you restore a sense of direction when you’re at a crossroads. Let’s dive in.
Use this prompt when you’re evaluating multiple choices, and all of them seem viable, but you’re unsure how to choose between them. Delete the placeholder text in [square brackets] and replace it with the details of your situation.
"I'm unsure how to grow my [food box subscription] business: should I, A: [pour everything into expanding into our existing market] or B: [enter a new market]. How should I approach this, and what considerations should I take into account? Give me a detailed breakdown and ask clarifying questions if you need to."
What makes this question secretly very powerful is that while it may seem like you’re going through a unique challenge, it’s very likely that thousands of entrepreneurs have been where you’re at before. Consequently, their experiences made their way into business literature and online articles, which, in turn, made their way into datasets that the AI is trained on. Chances are, the AI’s answer will lead you to that “Aha moment.”
Many businesses struggle to truly understand their ideal customers, leading to ineffective marketing and product development. This question cuts to the heart of customer understanding:
"Our [conversion rates are lower than industry average despite positive initial feedback]. How can I identify if we're targeting the wrong customer segments, and what questions should I be asking to develop more accurate customer personas that actually reflect our best potential buyers?"
This question works because it presents a real problem (low conversion rates) and asks for both diagnostic help and a methodology for improvement. In our testing, Overchat's responses typically include surprising insights about customer motivation factors you might have overlooked, helping you refine your approach without costly market research.
Sometimes entrepreneurs get so caught up in their vision that they miss fundamental flaws in their business model. This question helps expose those blind spots:
"I've been running my [SaaS business] for [18 months], and [while we're growing, our customer acquisition costs remain stubbornly high and churn is increasing]. What elements of my business model might I be missing, and how would an experienced founder restructure this to build a more sustainable operation?"
What's powerful about this question is that it asks the AI to take on the perspective of an experienced founder and perform a critical analysis. It prompts the AI to think beyond surface-level symptoms to identify underlying structural issues in your business model, essentially giving you access to the pattern-recognition abilities of a seasoned entrepreneur.
In crowded markets, differentiation is crucial but often elusive. This question helps you uncover your unique positioning:
"Our market research shows [we're competing in a space with three established players who have similar offerings and greater resources than we do]. How can we identify our unique advantage, and what questions should I be asking our early customers to discover where we're truly different in ways that matter to them?"
Instead of asking for generic differentiation advice, this question focuses on discovery methodology. Overchat excels at this kind of strategic thinking prompt because it helps you develop a process for uncovering your advantages rather than just suggesting tactical moves. The question frames the AI as both mentor and methodologist.
Every business hits plateaus, and knowing how to diagnose and overcome these stalling points is invaluable. This question helps identify your next move:
"We've been stuck at roughly the same monthly revenue for [three quarters]. How can I systematically identify what's really blocking our growth, and what are the questions I should be asking my team, customers, and myself to uncover blindspots that might not be obvious from our metrics alone?"
This question works on multiple levels—it asks for a diagnostic framework while also probing for the right questions to ask of different stakeholders. It essentially treats the AI as a meta-mentor who can guide you through the process of gathering insights rather than jumping straight to solutions based on limited information.
In 2025, having an AI business mentor at your fingertips is no longer a luxury—it's becoming a competitive necessity. The right questions transform generic AI responses into customised business insights that previously would have required expensive consultants or extensive research. Whether you're using Overchat or another advanced AI platform, these five questions can help you tap into the strategic thinking power that these tools offer. Remember, though, that AI is a partner in your thinking process, not a replacement for your business judgment. The most powerful results come from combining AI-generated insights with your own knowledge of your business and industry.
