How to Enhance Deep Thinking and Strategic Decision Making
"Shut down your computer", he yelled across the conference room. "Get a notepad. Thinking is a skill and you need to know how to do it right."
It was my first day on the job at an elite strategy consultancy, fresh out of business school. Little did I know how gamechanging that day would be for me in my career.
My boss introduced me to the art and science of deep thinking - how to frame the problem, how to see patterns, how to synthesize ideas, and how to simplify the complex through storytelling.
Ever since, I developed the habit of daily "thinking" time with an hour of deliberate, structured, and uninterrupted focus on a specific topic. My best ideas and most creative solutions have emerged out of this practice - sometimes during that hour, and often throughout the day (or night).
In a world of information overload and distractions, deep thinking has been my competitive advantage. It’s helped me see around corners, anticipate challenges, and navigate uncertainty with confidence.
But here's what's changed: I now use AI as my deep thinking partner, not just a notepad (shhh...don't tell my former boss)!
When you don't have weeks or even days to make high-impact decisions, AI can be a powerful tool to enhance your thinking. With AI, you have an unbiased partner that helps you see patterns you might miss, pressure-test your ideas before you act, and make smarter, faster decisions.
Your decades of experience, strategic thinking, and ability to lead people? That’s irreplaceable. But knowing how to elevate your innately human skills - now that's priceless!
Let’s dive in.
This Week's Insights:
- Trends shaping leadership in the future of work
- Decision framework to filter the signal from the noise
- Best practices to get the most out of your favorite tool
TRENDS
Smart leaders are adopting AI as their thought partner. Here are some leadership trends shaping the future of work:
Cognitive Amplifier
80% of CEOs say they are overwhelmed by the speed of change in their industries. Leaders using AI as a cognitive amplifier are able to think deeper and faster by asking better questions.
Pattern-Recognition
AI can reveal trends and correlations that human intuition might miss. Leaders who use AI to stress-test their strategies and uncover blind spots are consistently making better decisions with lower risk.
Faster Insights
76% of executives say their biggest challenge is making high-quality decisions under time pressure. AI shortens the time from insight to action, giving leaders an edge in fast-moving markets.
TIPS
While AI cannot replace your instincts and judgment, nor make high-stakes leadership calls on your behalf, it can be a valuable partner in decision-making. Use this framework to filter the signal from the noise:
Frame Problems
- What is the problem we’re solving, and how has it evolved over time?
- What data or evidence suggests this is the right priority right now?
- What are the second- and third-order consequences of this decision
- What does success look like in 12 months? What about failure?
- If we had to explain this decision in one sentence, what would it be?
Model Scenarios
- What are the best-case, worst-case, and most likely scenarios if we move forward?
- How would this decision play out in different competitive conditions?
- What factors would make this decision a game-changer or a massive failure?
- What are the opportunity costs of choosing this path over others?
- If we succeed beyond expectations, what new risks or constraints will emerge?
Test Assumptions
- What assumptions are we making that could be flawed or outdated?
- What evidence would immediately prove this decision wrong?
- What are the hidden risks or unintended consequences we aren’t considering?
- Are we making this decision based on past success, or future relevance?
- What is the hidden downside of being right?
Prioritize Speed
- What is the ONE critical insight that makes this decision 80% clear right now?
- If we had to make this decision within 24 hours, what would we prioritize?
- Are we optimizing for certainty, or are we delaying out of fear?
- If we delay this decision by 6 months, what are the risks and missed opportunities?
- What’s the smallest action we can take to test this decision before fully committing?
Build Feedback Loops
- What are the top 3 leading indicators that will signal whether this decision is working?
- What biases might cause us to ignore early warning signs of failure?
- If this decision needs to be reversed, what’s the fastest and least costly way to do it?
- How will we ensure that feedback is acted upon, not just collected?
- What questions should we be asking 6 months from now to reassess this decision?
TOOLS
The effectiveness of AI depends on how thoughtfully you engage with it. Follow these best practices to get the most out of your favorite tool (ChatGPT, Perplexity, DeepSeek, Claude):
Be Specific and Contextual
- Provide relevant background information
- Clearly state constraints and requirements
- Share your current thinking and concerns
Maintain Critical Thinking
- Use AI as a thought partner, not a decision-maker
- Challenge AI-generated suggestions
- Cross-reference important insights with other sources
Iterate and Refine
- Break complex problems into smaller components
- Use follow-up questions to dig deeper
- Request alternative perspectives and approaches
How will you use AI as your thinking partner this week?
Until next time...stay curious!
Cheers,
Nikki
PS: Hit reply and share your feedback. I’d love to hear from you!