Claude for Business
09
Complex Level
90 minutes to complete

Use Claude as Your On-Demand Strategic Advisor

A great business strategist charges $500 an hour. Claude charges nothing. Here's how to get $500-an-hour thinking from it.

By Kyle Roelofs  ·  AI Architect

What You Get From This Lesson

A complete framework for using Claude as a strategic business advisor — for quarterly planning, pricing decisions, market expansion, crisis response, and any major business decision you face.

The most valuable thing a great advisor does isn't give you answers. It's ask you the right questions. Questions that force you to think clearly, challenge your assumptions, and see your business from the outside. Claude can do this. But only if you set it up correctly — and most people don't.

The Problem With Asking Claude for Business Advice

Most people ask Claude for business advice the same way they Google something: a vague question that gets a vague answer. 'How do I grow my business?' gets you a generic list of 10 things everyone already knows.

The secret to getting real strategic value from Claude is to give it a role, give it context, and give it constraints. A Claude that knows it's playing the role of a skeptical investor who's heard every pitch will give you very different feedback than a Claude that's just answering a question.

This lesson is about setting up Claude for high-stakes strategic thinking — the kind that actually changes how you run your business.

The quality of your output is determined by the quality of your input. Vague questions get vague answers. Sharp questions get sharp answers.

The Strategic Advisor Setup

Before any strategic conversation with Claude, you need to do a Business Context Dump. This is a 500-1000 word description of your business — what you do, who you serve, your current revenue, your biggest challenges, your goals for the next 12 months, and what you've already tried.

Once Claude has this context, it can give you advice that's actually relevant to your situation — not generic best practices that apply to every business and therefore apply to none.

Then you assign it a role. Not just 'business advisor' — something specific. 'You are a skeptical investor who has seen 500 pitches and funded 12. You ask hard questions and you don't accept vague answers.' That role changes everything about how Claude engages with your problems.

The Strategic Advisor Setup Prompt
For this conversation, you are my strategic business advisor. You have 20 years of experience building and scaling service businesses. You are direct, honest, and you ask hard questions. You don't tell me what I want to hear — you tell me what I need to hear. Here's my business context: [BUSINESS TYPE]: [what you do] [REVENUE]: [current annual revenue] [TEAM SIZE]: [number of people] [CUSTOMERS]: [who you serve] [BIGGEST CHALLENGE]: [what's holding you back] [12-MONTH GOAL]: [where you want to be] [WHAT I'VE TRIED]: [what hasn't worked] With this context in mind, I want to discuss [specific decision or challenge]. Start by asking me 3 clarifying questions before you give any advice. I want to make sure we're solving the right problem.

The Quarterly Planning Session

Once a quarter, I run a 90-minute strategic planning session with Claude. This is not a casual conversation — it's a structured session with a specific agenda. By the end, I have a clear 90-day plan with priorities, metrics, and the three things I'm NOT going to do.

The session covers: reviewing last quarter's results against goals, identifying the one constraint that limited growth most, setting the single most important goal for next quarter, identifying the three highest-leverage activities to achieve that goal, and deciding what to stop doing.

Claude facilitates this session. It asks the questions. It challenges my answers. It helps me see where I'm rationalizing versus where I'm thinking clearly. It's the closest thing to having a great business partner without the equity split.

Strategy is deciding what NOT to do as much as what to do. The businesses that win are the ones that say no to good ideas so they can say yes to great ones.

The Pricing Decision Framework

Pricing is the highest-leverage decision in your business. A 10% price increase with no change in volume is a 10% revenue increase with near-zero cost. Most business owners underprice because they're afraid — not because their prices are actually wrong.

Claude can help you think through a pricing decision systematically. Give it your current pricing, your costs, your customer value, your competitive landscape, and your revenue goals. Ask it to model three pricing scenarios and the implications of each.

Then ask it to steelman the case for raising your prices by 25%. Not to agree with you — to make the strongest possible argument for the move. Then ask it to steelman the case against. Now you have a real decision framework, not just a gut feeling.

The Pre-Mortem

Here's the most valuable strategic exercise I know: the pre-mortem. Before you launch anything — a new service, a new hire, a new marketing campaign — you run a pre-mortem with Claude.

The setup: 'It's 12 months from now. This [project/decision] failed completely. Walk me through the most likely reasons it failed.' Claude will generate a list of failure modes you probably haven't considered. Some will be irrelevant. Some will stop you cold.

The pre-mortem doesn't tell you not to do something. It tells you what to watch for, what to build safeguards against, and what assumptions you're making that might be wrong. It's the difference between walking into a decision with your eyes open and walking in blind.

Swipe File — Copy These Prompts

Ready-to-use prompts. Fill in the brackets. Send to Claude. Done.

Quarterly Planning Session Opener
I want to run a quarterly business planning session. My business: [description]. Last quarter's goal: [goal]. Last quarter's result: [result]. Play the role of a direct, experienced business coach. Start by asking me 5 questions to help me understand what actually drove last quarter's results — good and bad. Then we'll set next quarter's priorities together.
The Pre-Mortem
I'm planning to [describe decision/project]. Assume it's 18 months from now and this decision turned out to be a serious mistake. Walk me through the 5 most likely reasons it failed. Be specific to my situation, not generic. After the pre-mortem, tell me: which of these failure modes is most likely, and what's the one thing I should do before moving forward to reduce that risk?
Pricing Stress Test
I currently charge [price] for [service/product]. My cost to deliver is [cost]. My customers are [description]. Help me stress-test my pricing. First, make the strongest case for raising my price by 30%. Then make the strongest case for keeping it the same. Then give me your honest recommendation and the one metric I should track to know if the change was right.