Friday, March 27, 2026
FRIDAY – AI FOR THE C SUITE
Read time: 9-10 min · Read online
Hi, it’s Chad. Every Friday, I serve as your AI guide to help you navigate a rapidly evolving landscape, discern signals from noise and transform cutting-edge insights into practical leadership wisdom. Here’s what you need to know:
1. Sound Waves: Podcast Highlights
This coming Monday, I’m sharing the full talk I recently delivered at the Technology Council of Central Pennsylvania. I make the case that reskilling the C-suite matters more than reskilling your operational teams. The middle management layer most executives depend on to interpret what’s happening in their organizations is about to get compressed, and if leadership isn’t evolving its capacity to match an exponentially advancing technology, you’re running a zombie organization.
Subscribe and listen wherever you get your pod on:
Apple · Spotify · iHeart · Amazon · YouTube
2. Algorithmic Musings: The Step Everyone Skips
Why Process Mapping Is the Real Starting Line for Your AI Journey
Every week, I talk to CEOs who want to “do AI.” They’ve seen the demos, sat through the vendor pitches, and almost every one of them wants to start with the technology. I understand the impulse. But after years of working with mid-market leadership teams through AI adoption, I keep landing on the same conclusion: the organizations that win with AI are the ones that understand their own processes first.
Not in the abstract. Not on a slide deck. I mean whether anyone in the building can walk you through, step by step, how a specific piece of work actually moves from trigger to completion. Who touches it. In what order. How long each step takes. Where it stalls. I ask executives to do this all the time. What I hear, nine times out of ten, is some version of: “Well, it comes in, and then it goes through our process, and then it gets handled.”
That’s not a process. That’s a prayer. And no AI tool on the planet is going to fix a prayer. You’ll just be automating chaos.
Process Mapping Is a Coaching Intervention, Not an Operations Exercise
Here’s where I part ways with most of the advice you’ll read on this topic. The conventional playbook says to bring in the process engineers, pull out the swim lane templates, and schedule a series of workshops. That approach works on paper. In practice, it dies. It dies because the people who need to own the transformation weren’t engaged when the process was documented. Someone mapped their process for them rather than with them. And that distinction makes all the difference.
The most effective process mapping I’ve done happens in a room with one executive. Not a team. Not a committee. The person who owns the outcome. I ask them to narrate the process, start to finish, while I listen, sketch, and interrogate. Walk me through what happens when a new order hits. When a position opens. When a customer complaint lands. Tell me the story.
Something shifts when the executive is the one narrating. They hear themselves describe the bottleneck. They hear themselves say “that step takes three hours because only Jason knows how to do it.” They hear the problem in their own voice, in their own words. By the time we get to “what should this look like instead,” they’re already bought in. Not because I sold them on a recommendation. Because they diagnosed the problem themselves.
That’s not a technical exercise. That’s a leadership development moment. And it’s the most overlooked step in every AI adoption playbook I’ve seen.
The Conversation Is the Artifact
There’s a practical dimension to this approach that goes beyond coaching. When you record that conversation and run it through transcription, you’ve just created the richest possible input for AI-powered deliverable generation. Not a static diagram that someone drew in Visio three years ago. Not a process map that lives in a shared drive nobody opens. A living narrative with context, reasoning, exceptions, emotional weight, and institutional knowledge embedded in every sentence.
From a single recorded conversation, AI can generate current-state process diagrams, future-state recommendations, friction point analysis, phased implementation plans, and executive briefing documents. I’ve done it, repeatedly. The transcript becomes the source of truth, and every downstream artifact traces back to what the operator actually said, not what a consultant assumed.
This flips the traditional model on its head. Most organizations start with the diagram and try to get buy-in after the fact. This approach starts with the conversation, gets buy-in during the mapping, and produces the diagram afterward. The executive was there for the whole thing. They said the words. The AI just organized them.
The “We’re Special” Defense
There’s a moment in nearly every process mapping session where the executive hits a messy part of the workflow and shifts in their chair. The pace of their narration slows. Their language turns hedgy and qualified. And then it comes: “You have to understand, our business is different. This process is too complex to simplify.”
I call this the “we’re special” defense, and I’ve heard it from transit agency directors, food distributors, construction company owners, and manufacturing executives. The industries are different, but the tell is always the same: the executive’s voice tightens around the one part of the process they know is broken but haven’t been able to fix. Complexity becomes a shield. If the process is too unique to standardize, then it can’t be their fault that it’s slow.
What it actually signals is one of two things. Either the process has calcified around a specific person’s habits rather than around business logic, or no one has ever challenged the assumptions baked into the workflow. Both are fixable. But only if you have the map in front of you. When you lay out eight steps with timing and ownership, and the executive can see that 60 percent of the cycle time is consumed by a single manual step, the “we’re special” argument doesn’t survive the evidence. And that’s usually the moment the real conversation begins.
Where AI Actually Fits
Once you have a validated process map with friction points surfaced, the AI conversation changes completely. The question stops being “what AI tool should we buy” and becomes “which of these specific friction points can AI address, and in what sequence?” You’re matching solutions to diagnosed problems. You can phase the work. You can set measurable targets. You can calculate ROI against real time savings instead of projections.
I’ve watched this play out sitting with a transit CEO mapping rider complaint resolution and again with a distributor mapping order fulfillment and again with a staffing firm mapping their recruiting pipeline. Different industries, different processes, same human dynamic. Once the executive can see the full workflow laid out with timing and ownership, the path forward stops being a debate and starts being a decision.
And the path forward often surprises them. A significant portion of the improvement typically doesn’t require AI at all. It requires eliminating steps that shouldn’t exist, fixing handoffs that stall for no structural reason, or building templates where people have been starting from scratch every time. AI accelerates what remains. But the process map is what tells you where to aim.
The Starting Line
If your organization is serious about AI adoption, don’t start with the technology. Pick the process that keeps you up at night. The one where you know there’s waste but you can’t quantify it. Sit down with the person who owns it. Record the conversation. Let them narrate while you listen, question, and push. Don’t map their process for them. Map it with them.
That conversation is your AI strategy’s real starting line. Not the vendor demo. Not the pilot program. The conversation. Everything else is noise.
3. Research Roundup: What the Data Tells Us
Your Most Empathetic Leaders Might Be Your Worst Empathic Communicators
Last week we talked about AI coaching with respect to goal-setting. This week we dig in to the idea of cultivating greater empathy with AI coaching as Northwestern and Stanford researchers just exposed a gap most CEOs don’t know exists. In a study of nearly 1,000 people across 3,000 conversations, self-reported empathy had virtually zero correlation with actual communication skill. Three out of four participants rated themselves as strong empathic communicators. Independent evaluators? Fewer than one in five actually were.
The numbers that matter: Participants who received personalized AI coaching improved by nearly a full standard deviation across all six communication dimensions measured. More than one in five showed individually meaningful skill change, compared to fewer than one in thirty without coaching. Cost per person: about four dollars.
What this means for your Monday morning: You probably have managers who genuinely care about their teams but consistently make people feel unheard. They default to giving advice when someone needs validation. They think they’re helping. They’re not. And telling them to “be more empathic” won’t work because they already believe they are.
The catch: Video training alone actually made one problem worse. Participants who watched instructional content without personalized coaching increased their unsolicited advice-giving. Generic soft skills content without behavioral feedback can reinforce the patterns you’re trying to fix.
Action item: Pick one leadership cohort and run a 90-day pilot with an AI-powered empathic communication tool. Measure before and after using behavioral assessment, not self-reports. The researchers’ six-dimension framework gives you a ready-made scorecard.
Read our full analysis of this research at AI for the C Suite.
4. Radar Hits: What’s Worth Your Attention
EY survey finds 52% of corporate AI projects are running without formal oversight. Nearly half of tech executives surveyed reported confirmed or suspected data leaks from employees using unauthorized AI tools in the past year. Even at large tech companies with dedicated governance teams, adoption is outrunning controls. If that’s happening at 5,000+ employee tech firms, it’s almost certainly happening at yours. This week’s move: ask your IT lead how many unsanctioned AI tools your teams are actually using.
a16z’s latest Top 100 AI Apps report reveals a platform war that matters for your AI vendor decisions. The big AI platforms are diverging fast. ChatGPT is building a consumer super-app with shopping, travel, and lifestyle integrations. Claude is going deep on professional tools: financial data terminals, developer infrastructure, and enterprise connectors. Once your team wires an AI assistant into your CRM and email, switching costs get real. If you’re standardizing on a platform, this split should inform your evaluation now, not after you’re locked in.
5. Elevate Your Leadership with AI for the C Suite
This week’s piece came from a pattern I see every time I sit down with an executive. The process they thought they understood turns out to be the process nobody’s actually mapped. If that hit close to home, you’re not alone, and that’s the exact conversation I have with leadership teams every week.
My Q2 calendar is filled but Q3 is just around the corner. If you’ve got a process that keeps you up at night and you want to map it before you buy anything, let’s talk.
And if this newsletter is useful to you, forward it to one person on your leadership team who’s about to make an AI decision without a process map in hand. They’ll thank you later.
Stay safe. Stay healthy. Be strong. Lead well.
Chad