A few months ago, I met a senior executive—we’ll call him Sam Musk. He runs a $50 million-a-year business. Sharp operator. Respected leader. Surrounded by a loyal team and deep in the grind of daily decisions.
He reached out, curious about how AI might improve his leadership and streamline operations. So we talked. I shared examples from my personal AI operation system. We explored tools. I even ran a chemistry session with him to show exactly how he could:
- Automate routine work
- Improve how he tracked decisions
- Free up time to focus on higher-value opportunities and
- Role model success to coach his team to follow his lead
Together, we mapped out a five-week executive coaching program—customized, targeted, and designed to give him real ROI from day one.
Yet at the final step? He hesitated.
Not because the program didn’t deliver value.
Not because he lacked interest.
But because, in his words, “it might be too hard, too time-consuming, and too expensive.”
Let that sink in.
A leader with a $50M business.
Faced with the opportunity to unlock massive gains in productivity, performance, and peace of mind.
But still defaulted to the same system, the same approach, the same grind.
The Executive Who Waited
This story isn’t rare. It’s the norm.
Most executives are too busy to try, too proud to admit what they don’t know, and too trapped in old habits to Unlearn.
They say they want innovation, but they won’t change their own workflow.
They say they want to empower their team with AI, but they haven’t tried it themselves.
They say they want to move fast, but they’re still waiting for the next board meeting or strategy offsite.
That’s why I’m writing this blog.
To challenge you. To invite you.
To stop reading and start experimenting.
Let’s get one thing straight
Here’s the hard truth:
You will not learn to lead with AI by reading about it.
You can’t delegate your way out of this.
You will not learn how to lead with AI by waiting for your CTO to brief you.
You learn by doing it. And the longer you wait, the further behind you’ll fall.
Executives who hesitate aren’t just losing productivity—they’re ceding their competitive edge.
This is a defining leadership moment.
The Real Question: Where Do I Start?
That’s the question I get asked most.
Not why AI. Not should I use AI.
But where the hell do I start?
That’s what this blog is for. We’ll answer:
- Who needs to lead this?
- Where should you focus first?
- What tools should you try?
- How do you build momentum?
- And how do you keep unlearning, relearning, and breaking through?
You’ll also get:
- A downloadable AI Strategic Roadmap to get started
- A link to our AI strategy blog, worksheet and webinar on creating your AI strategy
- A free diagnostic tool to find your best starting point
WHO: This Starts With You
Executives often assume AI is a tech team problem.
It’s not. It’s a leadership problem—and a massive opportunity.
You need to start.
Not your assistant. Not your digital team. You.
If you don’t understand how AI can enhance your productivity, decision-making, and strategy, you can’t credibly guide your team or company.
Executives who delegate AI exploration are setting themselves up to be disrupted.
The leaders of the next decade are learning this tech now. Hands-on.
The transformation starts with you.
WHERE: Find Your Friction Points
The best place to start?
Right where you feel the most friction in your daily workflow.
Ask yourself:
- What do I do that’s repetitive or reactive?
- Where do I feel overwhelmed or avoidant?
- What slows me down every day?
- What tasks are my highest effort, lowest return for time invested?
Start with what you already do. Then layer in tools to amplify, automate, or accelerate those tasks.
For me, I’m dyslexic. Writing emails, and communications often took time, and twice that of others, especially if it was an email that mattered. Worrying about typos, grammar, and lack of clarity.
Today, those worries are almost eradicated, and I fly through concise replies with confidence using a set of the tools below.
That’s how you begin to build your personal AI productivity stack.
WHAT: Your First AI Stack
If you’re an executive new to AI, don’t start with coding or chatbot development.
Start with foundational tools that allow you to optimze your individual work experience, and scale from there.
For any person looking to improve their personal productivity, here’s my recommended starter stack:
- Otter.ai / Fireflies.ai Auto-transcribe meetings, generate action items, and follow up faster than your chief of staff.
- ChatGPT (Pro Mode) Draft content, analyze text, write emails, summarize reports. Your thinking partner, research assistant, and writing coach in one.
- Grammarly / Wordtune For execs with dyslexia or just a busy brain—write clearly, get feedback in real time, and speak with confidence.
- Superhuman or Fyxer.AI For email optimization, templated replies and speed.
- Perplexity.ai AI-powered web search that summarizes what you need without the noise.
- Notion AI / Mem.ai Turn scattered thoughts into structured knowledge—great for vision planning, briefing docs, and strategic memos.
You don’t need to implement all of these on day one. In fact, for most people it’s better to trial a new tool for a few days, or a week and work it into your AI stack over time. However, regardless of how many you begin with,, the most important step is to pick one and get started.
HOW: Create Your AI Strategy
This is where you link to our Create an AI Strategy for Your Business, which I wrote about last month, and also create an AI Strategy Worksheet to get you started).
(Read it here if you missed it, watch my 25-minute webinar on how to do it here if you didn’t see it. And, download our AI Strategy Worksheet.)
There, we walk you through how to build AI into your business model, not just your inbox.
That’s the playbook for scaling AI.
But before you scale, you need to start. Which brings us to…
[FREE Diagnostic Tool] Where Should You Start With AI?
We’ve been inundated with so many requests on how to do this, and after helping tens of Executives get started with our Coaching Program we’ve set up a quiz to help leaders understand where they are, what outcomes they are aiming for, what’s missing and where to start with AI.
We’ve created a simple diagnostic to help you find the best starting point for your AI journey.
It takes 5 minutes.
Answer 20 questions.
Get clear on where to focus:
- Personal productivity
- Departmental optimization
- Product and service innovation opportunities and
- Benchmark both your own and businesses AI-readiness
Take the AI Diagnostic and Discovery Your AI-Readiness Score Now
The Roadmap: From Day 1 to Day 90
Now you’re in motion, how do you continue to build momentum? No surprise, you need a roadmap to scale up, and out across the organization.
For me, whether it’s teaching leaders to unlearn, launching new products or transforming their business, I always like to ask the questions; what can you do in a day, in a week, in a month, in three months.
Mapping this as, as below, gives both your and your team a vision of where you’re trying to get to, with milestones and metrics along the way. This is never a one and done. It’s a rolling wave of adaptation.
Here’s a simple to guide your next 90 days:
Day 1: Activate
- Set up ChatGPT and one AI assistant (e.g. Otter)
- Identify 1–2 friction points in your daily work
- Use AI to solve one of them today
Week 1: Experiment
- Use AI tools daily: write, summarize, analyze
- Capture wins and frustrations
- Begin building your personal AI stack
Month 1: Integrate
- Identify one team or function where AI could help
- Pilot a tool like Jasper (marketing), Supernormal (HR), or DataRobot (finance)
- Start thinking cross-functionally
Day 90: Scale
- Revisit our strategy blog
- Draft your AI vision
- Define next 3 AI pilots
- Set AI literacy goals for your team
- Share what you’ve learned—lead by doing
Final Thought: AI Doesn’t Replace You—It Reveals You
AI isn’t here to take your job. It’s here to reveal how you work, how you lead, and how fast you adapt.
This is your opportunity to learn in public, to lead with humility, and to get curious—fast.
The only way to learn AI is by using it.
If you hear yourself saying the words, “it might be too hard, too time consuming, and too expensive” ask yourself this.
How much is a day of high productivity worth to you, your business or portfolio? And what if you could start stacking days, compounding over time, and scaling across everything you do… What would that be worth to you and your business over time?
The only way to lead with it is by starting now.
Don’t wait. Think BIG. Start small. Learn fast.
We’re here to help.
Make Sure You Don’t Miss
→ Take the Executive AI Diagnostic
→ Fill out the AI Strategy Worksheet
→ Download our AI Strategic Roadmap
→ Book a call to Create Your AI Strategy