There are only a few questions you should ask in 2025

There is often a feeling of uncertainty with technology and business transformation.

That is not the case for 2025.

There are only a few questions business leaders need to consider.

The path is obvious.

And it all revolves around AI.

This past year, I’ve sat next to some investment firm leaders and watched them fumble and self-destruct, reliving a late-‘90s investment strategy.

They didn’t get it. So, the purpose of this last essay from 2024 is to share my thoughts.

I may not be correct, but I’m not totally wrong.

Here are the questions I am asking in every business conversation.

Let’s see if you agree.

Does the CEO have a fundamental knowledge of AI and automation?

This should be the first question any board, investor, or candidate should ask when evaluating a new company.

The ability to revolutionize workplace efficiency will occur in 2025.

This will manifest in a matrix fashion within verticals as well as horizontally across functional teams.

Powerful CEOs are good at building teams and products that use disconnected elements to harmonize into a profitable enterprise.

That is the main required skill set of a CEO.

In 2025, it's imperative for C-suite executives, especially CEOs, to possess a solid understanding of AI and automation technologies because this will become an essential component.

Think of AI as a new employee. And AI automation as an entirely new division.

This knowledge is crucial for making informed decisions, setting realistic expectations, and driving AI initiatives forward.

CEOs should be able to:

• Articulate the potential impact of AI on their industry
• Understand the basics of machine learning and data analytics
• Recognize the ethical implications and potential risks associated with AI implementation
• Establish the basics of an AI strategy and encourage its use among employees
• And, I also like to see if a CEO can get their hands dirty and use AI tools in their daily routine. This helps to set the tone for the entire organization.

When looking for investor firms, are they investing in companies with an AI strategy or use case?

As AI becomes increasingly important in 2025, investors should prioritize companies with clear AI strategies or compelling use cases.

And honestly, in this advisor’s opinion, should run from VC and PE firms that lack a logical strategy on how to evaluate and implement AI.

Just this last year, a well-respected investor told me at a board meeting that this was a useless diversion.

In fact, investor firms that have this attitude should be shunned.

This is especially true in healthcare startups, the space where I spend much of my time.

Given the thousands of “ways to support healthcare” decision making and choice of point solutions, it is no wonder that any remaining big ideas are elusive.

This will change with incorporating AI solutions and automation. Now healthcare point solutions can gain greater efficiency at a much lower cost and can further speed up employers in their journey to move away from traditional insurance companies to technologically advanced third-party administrators.

All the back end processing - the proprietary software of a traditional insurance company - can now be replaced with teams of AI agents.

Investors firms that recognize this and can take advantage of the moment will thrive.

Those that don’t, well, they will die.

Does your company or target company have an opportunity to solve a current problem quickly with AI and automation?

In 2025, the ability to transform business operations rapidly through AI and automation is a critical factor for success.

This question helps identify companies with high potential for disruptive innovation and exponential growth.

When evaluating this opportunity, consider:

• Existing pain points: Are there significant inefficiencies or challenges in the current business model that AI could address?
• Data availability: Does the company have access to large, high-quality datasets that could fuel AI-driven insights and innovations?
• Industry readiness: Is the industry ripe for AI-driven disruption, or are there regulatory or cultural barriers to overcome?
• Scalability potential: Could AI solutions be quickly scaled across the organization or to new markets?
• Competitive advantage: Would AI implementation provide a significant edge over competitors?
• Time-to-market: How quickly could AI solutions be developed, tested, and deployed?
• Potential impact: What's the estimated magnitude of improvement in efficiency, customer experience, or revenue generation?

For example, a retail company might can revolutionize its operations by implementing AI-driven inventory management, personalized marketing, and automated customer service, potentially transforming its business model within months rather than years.

Healthcare solutions might leverage historic data to provide more personalized health recommendations in real-time, find fraud, waste, or abuse of medical spend, or coach patients in better decisions regarding their health.

The fact that AI agents work 24/7 means that expensive call centers may become a thing of the past.

I’m not suggesting that there won’t be a need for humans in the loop, but humans now have agent support, which will radically improve outcomes.

Can you do a quick evaluation of AI capabilities by using AI? Sure.

Here's how I do preliminary research on a company's AI skills:

Take this prompt and replace the name of the company with your investment or evaluation target. It is sometimes helpful to include their headquarter's location or even their website.

AI COMPANY ANALYSIS PROMPT 2025

You are an AI business analyst specializing in AI transformation and strategic implementation. Please analyze the following company [COMPANY_NAME] and provide a detailed report addressing these critical 2025 AI readiness factors:

1. Executive AI Leadership Assessment
- Evaluate the CEO's understanding and vision for AI implementation
- Analyze public statements, interviews, and strategic decisions regarding AI
- Review the company's current AI initiatives and their alignment with the CEO's vision
- Assess the executive team's technical competency in AI and automation

2. AI Investment Strategy Analysis
- Examine current AI-related investments and partnerships
- Evaluate the company's R&D spending on AI technologies
- Analyze their AI talent acquisition strategy
- Review any AI-focused subsidiaries or acquisitions
- Compare their AI investment approach to industry benchmarks

3. AI Transformation Potential
A. Current Infrastructure Assessment
- Evaluate existing technical infrastructure
- Assess data quality and availability
- Review current automation levels
- Analyze digital transformation progress

B. Opportunity Analysis
- Identify key areas for AI implementation
- Estimate potential efficiency gains
- Calculate possible ROI from AI integration
- Evaluate competitive advantages through AI adoption

C. Implementation Readiness
- Assess technical capability for rapid AI deployment
- Evaluate organizational change readiness
- Review regulatory compliance preparation
- Analyze workforce adaptation potential

4. Risk Assessment
- Identify potential implementation challenges
- Evaluate ethical considerations
- Assess cybersecurity preparedness
- Review data privacy compliance

5. Comparative Analysis
- Compare AI readiness with industry peers
- Benchmark against AI industry leaders
- Analyze competitive positioning

Output Format:
- Executive Summary (250 words)
- Detailed Analysis (by section)
- Risk Factors
- Recommendations
- Overall AI Readiness Score (1-10)

Note: Replace [COMPANY_NAME] with the target company you want to analyze

Every question should revolve around AI

I know there will be naysayers that suggest that fundamentals will still play a role in decision making.

I will give in to that.

But we are amid a revolution that some have compared to electricity.

AI is not a solution, but the business applications and knowledge of how to incorporate the technology into business systems will revolutionize how we approach building businesses from here on out.

Focus on these questions in 2025.