[AI SPRINT] Why Microsoft Is Paying Big to Land Copilot AI Customers

Did you know Microsoft is offering up to $32,500 to salespeople for landing each new Microsoft Copilot customer?

That tells us one of two things (or maybe both):

• Either Microsoft Copilot isn’t compelling enough to sell itself, so they need a hefty investment to reel customers in.

• Or, Microsoft believes every Copilot customer is a long-term goldmine, worth far more than $32,500 down the road.

Let’s unpack the second scenario, and why I think Microsoft is making such a bold bet.

The AI OS Battle Has Begun

When business leaders are dipping their toes into AI, one of the first questions they ask me is:

“Which AI platform should we use?”

The usual suspects always come up—ChatGPT, Microsoft Copilot, and increasingly strong challengers like Claude from Anthropic and Perplexity AI.

For most businesses, my advice is simple:
Start with ChatGPT Teams or Enterprise (on a monthly plan).

Why? Because your goal right now isn’t to lock yourself into a long-term AI platform but to start learning how AI can revolutionize your company.

Here’s why I think ChatGPT is the best launchpad today:

• Immediate setup: You can start using it today with little to no upfront cost.

• Familiarity: 20–30% of your employees are already using it informally.

• Best functionality: It’s leading the pack in capability and evolving quickly.

• Low switching cost: It’s a two-way door decision. You can easily pivot to another platform down the road.

That last point is crucial. What most leaders don’t realize is that a battle for the AI Operating System of your company is raging right now, and each provider is trying to land their customers for the next 20 years.

And trust me, Microsoft knows the stakes. They’re fighting tooth and nail to win the battle. That’s why they’re willing to spend big to acquire customers.

But the million-dollar-question is: which AI is best for your company?

To help you figure that out, I’m launching a new initiative:

I’m interviewing 20 companies (5 for each platform) to uncover how they’re getting the most value out of these tools. And I’ll share the results here.

So, what is an AI Operating System?

Fast forward five years: my bet is that your workday won’t revolve around email or creating documents. Instead, your company will rely on what I call an AI Operating System, seamlessly integrated into your workflows.

Imagine this:

• Instead of checking email first thing in the morning, you’ll ask your AI for a prioritized task list—and tackle it with the AI.

• Purpose-built AI agents will handle specialized tasks, from sales outreach to generating financial reports. You’ll interact with these agents much like you would with employees.

• Your AI will know the status of your projects and work across systems, making collaboration faster and smarter. Need to send an email? You’ll just ask the AI to compose and send it.

Choosing and building the right AI OS for your company might be the single biggest transformation your business will ever undertake.

That’s why I recommend starting with ChatGPT: it lets you explore how to best use AI in your company without locking yourself into a long-term commitment.

In the remainder of today’s issue, we’ll: 

• Explore the second step of the AI SPRINT Framework: POSITION Your Company to differentiate itself with AI.

• Review this Week’s AI Resources: including a great Harvard Business Review article about AI Adoption in 2024.

• Share this Week’s AI Prompt: Use AI to conduct Scenario Planning.

This Week’s Resource List

• 6 Ways AI Changed Business in 2024, According to Executives (5 minutes) Executives report that AI drove significant advances in automation, supply chain optimization, customer experience personalization, and new revenue models, while also raising concerns about workforce adaptation and ethical use.

• What Warren Buffett, Mark Cuban, Jamie Dimon and other business leaders said about AI in 2024: ‘the consequences will be extraordinary' (6 minutes) Business leaders like Buffett and Gates shared their views on AI’s transformative impact, comparing it to electricity or the atomic bomb, while warning about ethical risks.

• The State of AI Strategy in 2025: Key Survey Findings Revealed (4 minutes) A Cirrus Insight survey reveals businesses are still early in AI adoption, with challenges in data quality and talent, emphasizing the need for clear AI strategies.

POSITION Your Company: The Second Step in the AI SPRINT Framework

Last week I introduced the AI SPRINT AI Adoption framework, six-steps any company can follow to effectively implement AI, overcoming high consulting costs and complexity. AI has the potential to disrupt markets, create new opportunities, and fundamentally change how businesses operate, and evaluating that is the second step of the SPRINT Framework: POSITION your Company to Differentiate itself with AI. 

This step is about understanding where you stand today and identifying where AI can give you an edge tomorrow.

To effectively position your company with AI, answer these three critical questions:

1. What sets us apart today?
   Start with your core strengths. What do you do better than your competitors? Whether it’s exceptional customer service, superior products, or an innovative business model, identify what makes you stand out. Then ask: how could AI amplify or protect this advantage?

2. Where are our biggest competitive risks?
   AI isn’t just an opportunity—it’s a potential threat. Are there areas where competitors could use AI to outpace you? For example, could faster data analysis, more personalized marketing, or automation in operations put your market position at risk? Understanding these threats is key to staying ahead.

3. What unmet needs exist in our market?
   AI is a powerful tool for identifying and serving unmet customer needs. Look at your market and ask: where are customers underserved or dissatisfied? Could AI help you solve problems no one else is addressing? Finding these gaps is often where the biggest opportunities lie.

Answering these questions will help you define where AI can make the greatest impact, either by strengthening your current position or enabling you to leap ahead of the competition. This clarity is the foundation of a strong, differentiated AI strategy. In my workshops, I bring in the best methods of evaluating competitive strengths and identifying new opportunities, allowing a leadership team to create a new AI-enabled business strategy in a single day.  

This Week’s AI Prompt: Scenario Planning

Leaders are often faced be imagining different scenarios that may come true, and then creating plans to prepare for them. AI is a great partner to help do this effectively. Try this prompt: 

Generate three potential scenarios in the case of a [market downturn] using the TOWS Matrix, for our business [describe]

Example: Generate three potential scenarios in the case of high climate change risk using the TOWS Matrix, for my residential construction business.

This Week’s Takeaway

If you’re just starting out with AI, go with ChatGPT Teams or Enterprise—it’s simple, flexible, and gets your team learning right away without a long-term commitment. Focus instead on tools that can boost your team’s productivity now, while keeping an eye on how these decisions will shape your future AI Operating System.

Action Step: Reach out today to schedule a leadership workshop or discussion to unlock AI's potential for your organization. Use this as a chance to SPARK Action and get your team thinking about your next moves in the AI journey.

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