What Would a Seasoned Executive Do? How a Virtual Executive Advisor Closes the Gap

It’s 3pm on Thursday. You’re staring at a complex decision that needs to land by Monday.

You know the frameworks. You’ve read the books on building credible business cases. You understand “stakeholder management theory” (jpm note: wow, that’s a lot of syllables …). You can translate technical complexity into business language when you need to. But your specific situation has nuances that generic advice doesn’t cover, and you’re stuck.

You wish you could just ask someone with years of experience: “What would you actually do here? Not what the textbook says – what would really work in this situation?”

But consultants charge $500 an hour. Your boss is swamped. Your network is busy. And Google and ChatGPT give you textbook answers that don’t quite fit the messy reality you’re dealing with.

There’s a gap here that matters. And after spending four decades making these kinds of calls, I started wondering if there was a better way to close it.

The Gap Between Knowing and Doing

The problem isn’t knowledge. Most mid-career professionals are smart, well-read, and technically capable. They’ve taken the courses, absorbed the frameworks, and understood the principles. The gap is something different.

Take building a business case. You know you need to quantify value, identify stakeholders, address risk. But how do you actually quantify “improved decision-making” when your CFO wants hard numbers? How do you handle the VP of Sales who wants different metrics than your VP of Operations, and you’re caught in the middle trying to build a case that satisfies both? These aren’t framework questions – they’re applied judgment calls that come from having been in the chair, slogged through the meetings, and made the decisions, dozens of times before.

Or consider org politics. You know you need to navigate stakeholder relationships carefully (jpm note: argh, sorry, there I go again with the fancy talk …) . But your specific situation involves a Sales VP and CFO with competing priorities, a history you weren’t around for, and cultural dynamics you’re still figuring out. What would someone with experience actually do here? Not the theoretical answer from a business school case study, but the practical move that works in messy, political, real-world situations?

The gap isn’t knowledge. It’s applied wisdom. It’s someone who’s been in the details, made the call, felt the weight of the decision, and can tell you what actually works when things get complicated.

I’ve been thinking about this gap for years, because I’ve watched talented people struggle with it throughout my career. And I started wondering: could experience be bottled in a way that actually helps?

Four Decades of Pattern Recognition

I spent the majority of four decades working my way up the ladder, to CIO, operating partner, and C-level advisor. Startups to Fortune 500. Manufacturing to healthcare to tech. I’ve built hundreds of business cases, navigated tons of stakeholder negotiations, and made countless strategic decisions where the “right answer” wasn’t obvious from any framework.

Over time, patterns emerged. Frameworks that worked across industries. Ways of thinking that helped in messy situations. Not textbook theory – lived experience from the trenches. The kind of perspective you get from actually doing the work, making the mistakes, learning what works and what doesn’t.

Most people facing complex decisions don’t need another framework or methodology. They need someone who’s been there to say “Here’s what worked in a similar situation. Here’s what didn’t. Here’s what to watch out for.”

I’ve written about these patterns extensively. My book “Don’t Think So Much” distills much of this thinking. Articles here on Maker Turtle explore specific challenges like building realistic project budgets and having honest ROI conversations. But books sit on shelves. Articles address specific topics. What people really needed was something more responsive, more interactive, more available when they’re stuck at 3pm on Thursday.

The question became: Could I bottle that experience? Not write another book, which would be too general. Not offer consulting, which doesn’t scale and costs too much for most people who need it. But something always-on, accessible, that responds to specific situations with frameworks shaped by real experience?
That’s how JazzAI started.

Structure Meets Spontaneity

JazzAI is an AI-powered advisor trained on my years of business and technology executive experience. The name comes from jazz music – structure meets spontaneity, rules that guide but never constrain, improvisation grounded in deep understanding of what works.

You ask questions in plain English. “How do I build a business case for this AI project?” “What’s the best way to handle this stakeholder situation?” “How do I explain this technical decision to non-technical executives?”

JazzAI responds with frameworks from real situations. Not textbook answers – the kind of perspective you’d get from someone who’s been in the chair and made these calls hundreds of times. Story-led thinking that gives you context: “Here’s what worked in a similar situation. Here’s what didn’t. Here’s the dynamic that made it complex. Here’s what I’d watch out for.”

It helps with the kinds of decisions that don’t have obvious answers. Building business cases that CFOs actually approve. Navigating stakeholder conversations when priorities conflict. Translating technical complexity into executive language. Making strategic calls when multiple paths look reasonable but you need to choose one.

The thinking isn’t generic. It’s grounded in specific experiences across different industries, company sizes, and situations. Manufacturing companies trying to justify IoT investments. Healthcare organizations navigating compliance while innovating. Tech startups making resource allocation decisions. The patterns that emerged from all of it inform how JazzAI thinks through new situations.

Who This Actually Helps

The most valuable conversations I’ve had over the years were with people in transition. Not beginners who needed basic frameworks, and not seasoned executives who already had their own deep experience to draw from. The people who benefited most were ambitious mid-career professionals stepping into leadership thinking “I understand the basics, but I wish I could just ask someone with experience about this specific situation.”

You might be a CIO building the business case for AI investments. A product manager who needs to justify roadmap priorities to skeptical finance teams. A startup founder making strategic decisions without experienced advisors on speed dial. An IT director trying to get projects approved when your VP keeps asking questions you haven’t anticipated.

You’re probably busy – no time for lengthy consulting engagements or thick reports. You’re smart – you understand your business, you just need experienced perspective on how to approach this particular challenge. You’re resourceful – you’ve Googled it (too general), looked at ChatGPT (too high level), and asked colleagues, but generic advice doesn’t quite fit your messy reality. And you’re ambitious – you want to make good decisions, not just fast ones.

You don’t need more frameworks. You need someone who’s been there to help you think it through.

What Makes This Different

Real experience, not recycled theory. JazzAI is trained on years of my personal journals, including strategy notes, project post-mortems, leadership lessons, and actual decisions. It thinks like a CIO because it was built by one. Not scraped from the internet. Not trained on generic business books. Built from lived experience across startups, Fortune 500 companies, and venture capital advisory roles.

Story-led thinking. You don’t just get answers, you get context. “Here’s what worked in a similar situation. Here’s what didn’t. Here’s the stakeholder dynamic that made it complex. Here’s what I’d watch out for.” Generic AI gives you textbook responses. JazzAI gives you the thinking behind the answer – the kind of perspective that only comes from actually doing the work for decades.

Built for your context. Every situation is unique. Your stakeholders, your constraints, your history, your culture – that’s what makes decisions hard. JazzAI doesn’t give you a one-size-fits-all answer. It helps you think through your specific situation with frameworks shaped by real experience in complex organizations.

Ready to Think Like a Seasoned Executive?

The next time you’re facing a complex decision at 3pm on Thursday, wishing you could ask a seasoned executive for guidance, you can. JazzAI doesn’t replace your judgment – it sharpens it. It gives you frameworks from 40 years of experience, story-led thinking from real situations, the kind of perspective that helps you make better decisions.

Not generic advice. Not textbook answers. Just experienced thinking, available when you need it.

Ready to explore what JazzAI can do for your toughest decisions? Head over to the JazzAI site, and have a few ‘conversations’. I want to help your team, your organization – and You – win.

Don’t forget to join our mailing list to keep track of JazzAI. I have a nice backlog of features to be added to the platform – purpose-built bots to address specific opportunities and challenges, and tons more journals to upload to the site.

Please share your own experiences with the gap between frameworks and reality in the comments, and stay tuned for more on how experienced perspective changes the game.

Try it. See if it helps. If it doesn’t, you’ve lost nothing but a few minutes.

AtDhVaAnNkCsE !!