7 Questions Every Company Must Ask Before Writing their AI Strategy
Across industries, companies are rushing to announce their “AI-first” strategies. The pressure is real: investors, boards, and even employees want to see a plan.
But many leaders are approaching this with shiny object syndrome, leading to AI First mandates and initiatives that produce little to no positive effect. Leaders are slapping “AI-first” on top of their current operations, without a clear view of the problems they’re solving or the value they want to create.
Instead of the transformation they hoped for, they get inefficiency: wasted time, rework, frustrated employees, and no real innovation.
If you want AI to become a competitive advantage, not just another expense line, it’s time to pause and ask sharper questions.
Here are seven questions every leadership team should answer before committing to their AI plans:
1. What problems are we actually solving for customers and employees?
Don’t start with the shiny object. Start with the pain.
Too many companies chase a demo or a feature without mapping it back to the actual customer or frontline frustrations. AI should never be the starting point, the problem should.
2. Where is the pain worth paying to remove today?
Not every friction point deserves your budget.
Identify the top three pain points that carry a tangible cost of delay: lost revenue, churn, compliance risk, wasted labor. If you wouldn’t pay to solve it today, it’s not a priority.
3. How will AI create new value, not just automate tasks?
Efficiency is the baseline. Transformation comes from reimagining the value you can deliver.
Cutting clicks is helpful, but game-changing AI strategies unlock new products, new services, or new experiences that competitors can’t easily replicate.
4. Do our people know how to think with AI, not let AI think for them?
This is the leadership blind spot.
AI is not a magic box. Teams must be trained to question, edit, and co-create with AI — thinking like product owners and innovators, not passive users. Otherwise, you’re simply multiplying mediocrity at scale.
5. Where will AI amplify human strengths instead of replacing them?
Your competitive edge is not in replacing people… it’s in making them sharper.
List the moments that demand context, creativity, judgment, empathy, or innovation. Then design AI to augment those moments, not eliminate them. That’s how you get adoption and long-term advantage.
6. What could we do now that was impossible a year ago?
AI is evolving at breakneck speed. The companies who win aren’t just automating, they’re spotting new possibilities.
Ask your team: What new capabilities exist today that fundamentally change what’s possible in our industry? That’s where you’ll find transformation.
7. How will we measure outcomes to know AI is working?
Treat your AI strategy like a product, not a project.
That means assigning product owners, setting clear goals, tracking adoption, and defining success metrics upfront. If you can’t measure the outcomes, you’re not ready to scale.
Final Word: The Future of Work is Entrepreneurial
The organizations that succeed won’t be the ones who jump on AI the fastest. They’ll be the ones who think like entrepreneurs: starting with customer pain, designing for value, and building adaptability into their teams.
At ThinkFree, we help companies identify and execute the major shifts that AI makes possible, while teaching teams the entrepreneurial skills to thrive in the future of work.
👉 If your AI strategy is due or not living up to it’s hype, let’s talk.