Quick note: These ARE NOT AI generated tips, these are lessons I have learned from other executives and have iterated to be effective for strategic executive tasks.
Most professionals I know are dabbling, asking ChatGPT to draft an email or LinkedIn post or using it like a search engine. These have their place and can provide value but the real value for executives comes when you turn ChatGPT into:
- A thought partner
- A personal advisory board
- A force multiplier on your productivity and decision-making
The key is NOT outsourcing tasks, it is using it as an extension of yourself.
Over the last 18 months, these three simple “hacks” have helped me save hundreds of hours, avoid costly mistakes, and sharpen how I lead and operate. And when you stack them together, the results compound.
You can use each one on its own but the magic is in the workflow at the end.
Beginner Tip #1: Use High-Quality Ingredients in Every Prompt
I call this a “Beginner Tip” because it is so foundational. Yet I’m surprised at the number of otherwise very intelligent professionals who are still using vague or lazy prompts.
You would never walk into a meeting, look at your VP of Sales, and say, “Can you make a strategy for xyz?”—and then walk out. You’d:
- Choose the right person who is capable of providing that specific strategic insight
- Outline the expected outcomes
- Give them context including why this is a priority
- Define the scope, budget, timeline, decision criteria, deliverable expectations, etc
ChatGPT is no different.
A simpler example:
If you ask ChatGPT to “make me a recipe book for next week,” without clarifying your tastes, nutritional goals, number of people for whom you are cooking, your budget, or how much prep time you have, you will technically get what you asked for but it will be entirely useless!
So, if you treat every prompt like a recipe, you will need high quality ingredients
- Persona – Who is answering (e.g., a CTO, an expert on retail marketing, etc.)
- Task – What you want it to do
- Context – What’s going on or why does this matter
- Limits/Requirements – Time, tone, format, deliverable expectations
Just like giving crystal clear expectations to a teammate or coworker, the more detail you give on the front end, the better the outcome will be!
Watch me walk through a “good prompt vs. great prompt” here:
Pro Tip #2: Interview Yourself Before You Outsource the Thinking
It is tempting to open ChatGPT and ask it a generic question or vague task when approaching a strategic topic and expect something brilliant. I admit I still do this from time to time! The output is almost guaranteed to be mediocre at best and likely entirely miss the mark of your main objective. To get the best possible outcome, you must ask ChatGPT to “interview me” before jumping to any conclusions.
This is so simple! If there’s only one thing you start doing differently when using ChatGPT to get the biggest impact, this would be it.
Instead of saying, “Write a board update about our missed targets,” I start with:
“Act as an expert in [insert field] and interview me one question at a time, up to [#] questions to help me clarify [insert challenge] so that I can [insert outcome]. ”
I’ve used this approach to:
- Shape keynote talks and conference presentations
- Build business plans and GTM experiments
- Prepare candid but constructive board updates
- Navigate complex leadership and org decisions
The magic is that you still do the thinking and ChatGPT just pulls it out of your head, organizes it, and reflects it back in a way that’s easier to refine and share.
Watch me demonstrate it here:
Pro Tip 3: Build a Personal Board of Advisors Inside ChatGPT
If you have used ChatGPT or any LLM enough, you are likely to start seeing the patterns of generic LLM advice. It lacks creativity and authenticity and probably most importantly, it doesn’t necessarily align with your personal values. I want targeted feedback from people I trust and respect. But that doesn’t always mean people I know (or would agree to give me feedback and guidance every day!).
So I built a custom GPT modeled after my personal board of advisors.
Mine includes voices like:
- Jim Collins for strategic focus and brutal clarity.
- Brené Brown, for trust, vulnerability, and courageous leadership
- Jeff Bezos, for operational intensity and customer obsession.
- Craig Groeschel for relational leadership and value focus.
- Alan Mulally for operational alignment and culture through systems.
- Patrick Lencioni for building cohesive teams through clarity and trust
- Me through uploading documents (frameworks, tools, annual plans, etc.) I have used over the years to represent how I think, lead, and want to grow
I trust some of these individuals’ character and leadership style while others I respect their business process and decision making. It is intentionally diverse in thought and approach to give me tough and constructive feedback on strategic topics that really matter. This GPT knows how I think and it since the individuals I selected have published so much publicly available content, knows how they think. So when I need advice I ask:
“What would my board say about this business opportunity…?”
or
“What blind spots might I be missing in this leadership move…?”
It gives me differentiated input from individuals I respect and trust that are often more challenging and more insightful than anything I’d get from a single person.
Watch me demo my advisor GPT here:
Bringing It All Together: This Is the Real Workflow
Used in isolation, each of these tools is helpful but used together (especially with strategic challenges) they can be a force multiplier!
- Interview yourself to get clarity on your own ideas
- Run it by your board GPT to challenge your perspective.
- Craft a structured prompt to get ChatGPT to do EXACTLY what you want the first time.
The best leaders in 5 years from now will be the ones that don’t outsource strategic thinking, they will be the ones that leverage technology to challenge themselves to think differently!
If you’ve found a smarter way to work with Generative AI, I’d love to hear it!