Stop Asking GPT to Produce. Start Asking It to Push Back.

If I am being honest, I am a lazy GPT user a lot of the time.

Read this and summarize it. Find this information for me. Explain this concept.

Using it like a better version of Google is not necessarily wrong. I am all for getting quick info. But when that is all you use it for, you are leaving the highest-leverage capabilities completely untouched. And for someone responsible for strategy, budget, people, and outcomes, that gap has a real cost.

Speed matters, but decision quality matters more. And the distance between a quick answer and a well-examined decision is where most of the value lives.

If you are a business owner, here are a few deeper ways to get more out of GPT.

Use GPT to pressure test your strategy before you commit to it

Think of GPT like a strategic co-founder sitting across the table from you. This co-founder understands your business, your constraints, your goals, and your challenges. Used well, it is a practical way to sharpen thinking before you commit to a direction.

Here, you are not asking GPT to produce. You are asking for pushback.

Bring the kinds of questions you would normally wrestle through with a strong C-suite leader:

• Should we narrow the customer we serve, or expand into adjacent segments?
• Is this a pricing problem, a positioning problem, or a trust problem?
• What has to be true for this bet to work?
• Is this AI initiative worth the investment, or are we chasing a trend?
• Where is our process creating confusion or friction for the people we serve?
• What is the smallest move that meaningfully reduces uncertainty?

I have found the more I explain context, invite critique, and argue back, the sharper the thinking becomes. For example, I will share a strategic direction I am leaning toward, ask GPT to identify the three weakest points in my reasoning, and then defend my position. That back-and-forth forces me to articulate things I had only been assuming, and it usually surfaces at least one blind spot I had not considered.

Use GPT to break your own plan before the market does

Another high-leverage use is evaluation.

Bring real plans, budgets, campaigns, or roadmaps and ask GPT to evaluate the logic. Ask it to surface assumptions, point out mismatches between goals and resources, and flag places where your plan conflicts with your stated priorities.

One of the most useful prompts is to ask where the plan is likely to break, and what the early warning signs would be. That is a pre-mortem, and it lets you pressure test the plan before you spend time and money executing it.

If you are stewarding donor funds or building a case for a board that speaks mission rather than tech, this kind of rigor is especially valuable. The cost of building the wrong thing is not just financial. It is organizational trust, team morale, and months you cannot get back.

Use GPT to hear what your customers actually hear

Ask GPT to assume the role of a customer and respond like a rational buyer.

Even if you know your audience well, you still carry the curse of knowledge. You know what you meant. They only know what they heard.

Feedback from real customers is gold. GPT simulations are not a replacement, but they are still useful, especially early in the process when you are still shaping the offer or the message.

Use it to pressure test incentives and friction:

• What would make this feel risky to me?
• What would I need to believe before I take the next step?
• What would make me ignore this even if it sounds interesting?
• What objections would I raise if I had to justify this purchase to someone else?

My friends Justin and Wade run Sermonary, a sermon writing platform for pastors. They coach users to get AI feedback from different listener types before preaching: new believers, single moms, skeptical men, long-time members. It is a practical example of using AI to anticipate how real people might hear what you are trying to say.

Turn GPT into an advisory board you can access on demand

One of the most powerful uses of GPT is turning it into a virtual advisory board.

Decisions rarely suffer because of a lack of intelligence. More often, they suffer from a lack of perspective. In a real board setting, you hear counter-arguments, you surface risks, and you work through the tension between ambition and capacity. A lot of founders do not have that room available on demand.

I created a custom GPT loaded with the writings, philosophy, and podcast transcripts of seven business leaders I admire. I call it O.R.A.C.L.E. (Objective Roundtable of Advisors, Counselors, and Leadership Experts). When I am weighing strategic options, I ask how this advisory group would approach the situation, what questions they would ask first, and where they would challenge my logic.

Sometimes I ask it to be the devil's advocate and write a red team report explaining why the plan will not work, and what would need to be true for it to succeed.

Instead of "Write this for me," try "Here is the situation. Help me think through it."

Where the deeper leverage lives

GPT can summarize articles and draft emails all day long. It saves time, and that is fine. But that is surface-level leverage.

The deeper leverage is this: bring it your real decisions.

Bring it the initiative you are unsure about. Bring it the hire you are rationalizing. Bring it the product expansion that feels exciting but unproven. Bring it the budget that looks clean but may not reflect reality.

This is the same principle I apply when working with clients on strategy. We do not start by building. We start by bringing the hardest questions to the table and examining them honestly before we write a single line of code. The best outcomes, whether you are prompting an AI or planning a product, come from the discipline to think rigorously before you move.

The founders who benefit most from GPT will not be the ones who generate the most content. They will be the ones who improve the quality of their judgment.

Here is a challenge for this week: bring GPT one decision you are currently stuck on. Not a task. A decision. Explain the context, the constraints, and what you are leaning toward. Then ask it where your thinking is weakest. You might be surprised what surfaces.

Want help thinking through your product strategy?

If you are wrestling with a product decision and want a structured thinking partner, our Clarity Day is designed for exactly that. We bring disciplined frameworks to your hardest questions so you can move forward with confidence.