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Use AI to pressure-test business decisions by creating a virtual board that challenges assumptions instead of politely agreeing.
Most business owners do not need more encouragement. They need a smarter way to be challenged before the market, the bank account or a key employee does it for them.
That is where AI becomes genuinely useful. Not as a magic answer machine. Not as a business coach wearing a robot costume. The trick is to stop asking AI whether an idea is good and start asking it to identify what would have to be true for the idea to work.
That one question changes the whole conversation.
Instead of: "Should I open a second location?"
Ask: "What would have to be true for a second location to make sense, and which of those assumptions are weakest?"
Now you are not getting a cheer squad. You are getting an assumptions audit.
Most business owners do not need more encouragement. They need a smarter way to be challenged before the market, the bank account or a key employee does it for them.
That is where AI becomes genuinely useful. Not as a magic answer machine. Not as a business coach wearing a robot costume. The trick is to stop asking AI whether an idea is good and start asking it to identify what would have to be true for the idea to work.
That one question changes the whole conversation.
Instead of: "Should I open a second location?"
Ask: "What would have to be true for a second location to make sense, and which of those assumptions are weakest?"
Now you are not getting a cheer squad. You are getting an assumptions audit.
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Create the room before you ask the question
A useful AI board works best when it has context. Create a dedicated workspace or project for your business decision-making. Add your business summary, target customer, current numbers, service lines, known constraints, pricing model, team structure, pain points and any decision you are considering.
Then tell the AI how you want it to behave. The goal is not to make it sound clever. The goal is to make it useful.
A simple instruction might be:
"You are my commercial decision board. Do not simply agree with me. For every plan, identify the core assumption, the cash risk, the operational risk, the customer risk and the easiest test we can run before committing. If you do not have enough information, ask for it."
A useful AI board works best when it has context. Create a dedicated workspace or project for your business decision-making. Add your business summary, target customer, current numbers, service lines, known constraints, pricing model, team structure, pain points and any decision you are considering.
Then tell the AI how you want it to behave. The goal is not to make it sound clever. The goal is to make it useful.
A simple instruction might be:
"You are my commercial decision board. Do not simply agree with me. For every plan, identify the core assumption, the cash risk, the operational risk, the customer risk and the easiest test we can run before committing. If you do not have enough information, ask for it."
The four seats at the table
When reviewing a decision, ask AI to respond from four seats.
The customer asks: "Why would I care? Why would I buy now? What alternatives do I already have?"
The operator asks: "Can we actually deliver this without breaking the team or the service experience?"
The CFO asks: "What happens to cash, margin, working capital and fixed costs?"
The sceptic asks: "What are we pretending is certain when it is not?"
Most owners naturally sit in the founder seat. That is valuable, but it is only one angle. The founder sees the opportunity. The other seats help expose the cost of being wrong.
When reviewing a decision, ask AI to respond from four seats.
The customer asks: "Why would I care? Why would I buy now? What alternatives do I already have?"
The operator asks: "Can we actually deliver this without breaking the team or the service experience?"
The CFO asks: "What happens to cash, margin, working capital and fixed costs?"
The sceptic asks: "What are we pretending is certain when it is not?"
Most owners naturally sit in the founder seat. That is valuable, but it is only one angle. The founder sees the opportunity. The other seats help expose the cost of being wrong.
The prompt pack
Use this when you are considering a new hire, new product, new location, price change, system change or major customer contract.
Prompt 1 - The pre-mortem:
"Imagine this decision failed 12 months from now. Give me the five most likely reasons. For each reason, identify the early warning sign, the financial impact, and one action I can take now to reduce the risk."
Prompt 2 - The assumption audit:
"List every assumption this plan relies on. Rank them from most proven to least proven. Tell me which assumption should be tested first and design a low-cost test."
Prompt 3 - The cash version:
"Translate this plan into cash consequences. What costs happen before revenue? What revenue may be delayed? What tax, payroll, stock or debtor timing issues should I model?"
Prompt 4 - The customer resistance test:
"Argue against this offer from the customer's perspective. Why might they not buy, delay, negotiate, or choose a competitor?"
Prompt 5 - The decision memo:
"Turn this into a one-page decision memo with the recommendation, assumptions, expected upside, downside risk, cash impact, first test, and decision deadline."
Use this when you are considering a new hire, new product, new location, price change, system change or major customer contract.
Prompt 1 - The pre-mortem:
"Imagine this decision failed 12 months from now. Give me the five most likely reasons. For each reason, identify the early warning sign, the financial impact, and one action I can take now to reduce the risk."
Prompt 2 - The assumption audit:
"List every assumption this plan relies on. Rank them from most proven to least proven. Tell me which assumption should be tested first and design a low-cost test."
Prompt 3 - The cash version:
"Translate this plan into cash consequences. What costs happen before revenue? What revenue may be delayed? What tax, payroll, stock or debtor timing issues should I model?"
Prompt 4 - The customer resistance test:
"Argue against this offer from the customer's perspective. Why might they not buy, delay, negotiate, or choose a competitor?"
Prompt 5 - The decision memo:
"Turn this into a one-page decision memo with the recommendation, assumptions, expected upside, downside risk, cash impact, first test, and decision deadline."
What to do this week
What to do this week
Pick one decision you have been avoiding. Put it through the AI board. Do not ask for a final answer first. Ask for assumptions, risks and tests. The best decision may not be the most exciting one. It is the one where you know what needs to be true before you bet the business on it. Share the results with us, we’d love to hear how you go.
Website disclaimer note: This article provides general information only and does not take into account your circumstances. It is not a substitute for tax, legal, financial, employment, cyber security or other professional advice. Obtain tailored advice.
Pick one decision you have been avoiding. Put it through the AI board. Do not ask for a final answer first. Ask for assumptions, risks and tests. The best decision may not be the most exciting one. It is the one where you know what needs to be true before you bet the business on it. Share the results with us, we’d love to hear how you go.
Website disclaimer note: This article provides general information only and does not take into account your circumstances. It is not a substitute for tax, legal, financial, employment, cyber security or other professional advice. Obtain tailored advice.
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macchiato with Chris.
Got questions?Maybe it’s time for a macchiato with Chris.
Got questions?
Maybe it’s time for a
macchiato with Chris.
Ready to kick-start your
self-made journey?
© 2026 Denari Advisory. Liability limited by a Scheme approved under Professional Standards Legislation.
Strategy and Site by Touching Base
Ready to kick-start your self-made journey?
© 2026 Denari Advisory. Liability limited by a Scheme approved under Professional Standards Legislation.
Strategy and Site by Touching Base
Ready to kick-start your
self-made journey?
© 2026 Denari Advisory. Liability limited by a Scheme approved under Professional Standards Legislation.
Strategy and Site by Touching Base
