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We’re Asking AI the Wrong Questions

The problem usually isn’t the tool. Recently, I received a message on Teams after a customer demo.  The technology worked and the demo went well, but the feedback was telling: “Finance and sales feel like they wouldn’t know how to prompt… and they’re worried they won’t use it.” I’ve heard some version of that concern more times than I can count. On the surface, it sounds reasonable. If people don’t know how to interact with the system, adoption is going to be a challenge. So the natural reaction is to think in terms of training, or user experience, or simplifying the interface. But that framing misses something important. These are not inexperienced users. They understand their business. They work with data every day. They’ve been using systems like Salesforce, ERP platforms, and reporting tools for years. Asking them to “learn how to prompt” shouldn’t be the barrier it’s often made out to be. Which raises a different question:  if the technology works and the users are capabl...
Recent posts

Most AI Strategies Fail Before the First Prompt

I’ve been thinking a lot about AI strategy lately.  Not the tools nor the models - the strategy itself. Specifically, I wondered why so many companies seem to be making progress on paper but are not getting the kind of results they expected.  From the outside, it all looks pretty good. Pilots are running. Outputs are being generated. There’s a lot of activity.  But something about it doesn’t quite add up. And the more I think about it, the more I’ve come to believe that a lot of these efforts are running into trouble much earlier than people realize, often before anything that really looks like AI is even in place. The Myth: “Every Company Needs an AI Strategy” I was reminded of this recently when I came across a post on LinkedIn from a venture capitalist that said, plainly: Looks like progress. Still needs the right formula. Every private equity-backed company needs an AI strategy. It wasn’t a surprising take. In fact, I’ve seen variations of this sentiment repeatedly ...

AI Raises the Bar, But It Doesn’t Remove the Builders

Every week, there’s a new headline suggesting that AI is about to make large portions of the workforce obsolete. Development cycles are collapsing. Models are writing code. Systems are improving themselves. It’s not unreasonable to ask whether the role of the human professional is shrinking. But that framing misses something important. AI is not simply reducing labor costs - it is raising expectations. And when expectations rise, the need for human judgment doesn’t disappear. It shifts. Acceleration Without Elimination Recently, while preparing a business demo, I leaned heavily on AI to troubleshoot and refine parts of the workflow. It generated SQL, suggested configuration changes, and dramatically accelerated the iteration cycle. But it also produced malformed SQL queries and confidently recommended an incorrect fix for a configuration issue. Each time, the system moved me forward faster, but it didn’t actually solve the problem. I still had to diagnose the root cause, constrain th...

Invisible Mastery: Making the Difficult Feel Inevitable

Some time ago at a previous job, my manager performed a 360 review of my performance. If you’re unfamiliar with the term, a 360 review is one where your manager, peers, direct reports, and sometimes even customers are given an opportunity to discuss how well you perform your job. After the interviews had concluded, I was told that someone had commented:  " Larry is incredibly technical, but you'd never know it from talking to him. " Initially, I wasn’t sure how to interpret that comment. After all, I spent the first half of my career in highly technical roles and prided myself on my technical acumen. Was this a criticism or a compliment? And what was that person actually saying about my expertise and how I communicated it? After sitting with it for a while, I came to an unexpected conclusion: mastery, in its highest form, is invisible . Put another way, true expertise simplifies experience without sacrificing substance. It’s like a perfectly baked apple pie fresh out o...

Finding Clarity in the Chaos of a Job Search

Job searches are humbling. They test your confidence, your patience, and your ability to stay motivated when things don’t move as quickly as you’d like. But they also teach you things about yourself that you might not have learned any other way. For me, the past few months have been a crash course in rediscovering what really matters: not just in a résumé, but in relationships, self-perception, and how we use technology to help tell our stories. Here are three lessons that stood out. Reach Out to Your Network (Long Before You Need It) Your network is a living thing. It requires upkeep, time, and attention, just like a flower garden. You can’t ignore it for years and expect it to bloom the moment you need it. Start planting early. Stay in touch with people whose paths you’ve crossed - colleagues, mentors, partners, even those you only worked with briefly. Drop a note once in a while. Comment on their posts. Share something that made you think of them. These small gestures are the sunl...

The Assistant You Didn’t Know You Had

Everywhere you look, someone is debating AI:  is it useful, ethical, or even trustworthy? After all the noise, the verdict is still the same: inconclusive.  I’m not here to settle that debate. Instead, I want to show how AI can be used effectively without turning it from a tool into a crutch. Why the Bad Rap? First let's acknowledge something.  AI has an entirely different reputation depending on the context in which it is used.  In the corporate world, AI is often seen as a force multiplier while at the same time is derided as potentially displacing several thousand jobs.  The latter has most recently been seen in the elimination of 4,000 jobs at Salesforce all under the guise of AI being used to do mundane jobs that used to be filled by people.  (Whether this is true or not is a topic for a future discussion.) We've been trying to reach you about your automobile warranty. On a personal level, AI often gets dismissed, whether it’s in academics , fake Amazo...

Time to Level Up!

With the recent news out of Salesforce and Oracle, it’s easy to understand why folks affected by layoffs might feel discouraged. Not only are they leaving companies they may have called home for years, but they’re also facing the daunting prospect of job hunting while headlines scream about “AI taking over human jobs.” Not long ago, another company I follow - let’s call it Acme  - went through a similar round of layoffs. Two employees in particular (we’ll call them Jim and John) showed how mindset can make all the difference. Jim had been at Acme for over 20 years. He was reliable, steady, and well-liked, but not exactly the standout type. When he was laid off, he decided to take some time off before even thinking about his next move. After all, he had a severance package. Didn’t he deserve a break after two decades of hard work? John’s story was different. Though he hadn’t been at Acme as long, he’d built a strong reputation and had both technical and leadership skills. Instead of...