The Huddle: Issue 02

A biweekly look at what's changing in AI, ways to apply it today, resources you didn't know you had, and sharing wins and what's working.

Lost in Translation

Nobody wakes up one morning fluent in a new language. You stumble through it. You mispronounce things. You use the wrong word in front of someone important and feel dumb for the rest of the day. Then you do it again tomorrow, and the day after that, and eventually something clicks.

AI is a new language for most businesses. And like any language, you don't learn it by reading about it. You learn it by using it, getting it wrong, and having someone around who can translate when you're stuck. That's what this issue is about: meeting you wherever you are right now and giving you the next step forward.

HEADLINES THAT ACTUALLY MATTER

An Enterprise Reality Check

Aaron Levie, CEO of Box, posted a thread this week after sitting down with 20+ enterprise AI and IT leaders.

The short version: these leaders aren’t focused on chatbots, they are obsessed with developing and deploying agents. The word agent has meant a lot of things in the last couple years, but let’s simply define it as AI that goes beyond answering questions and starts doing the work itself. Think document processing, customer onboarding, operations that used to eat up someone's entire week. Some of these enterprises have dozens of agents running in production already, which is further along than most people realize.

The roadblocks to ramping at the speed they want are the unglamorous stuff (because the models are plenty good enough). Agents are struggling with data spread across systems that were never meant to talk to each other, no clear rules for what an agent should or shouldn't have access to, and years of document fragmentation that nobody cared about until AI needed to make sense of all of it at once. We work through these same issues with our clients every week. The technology is ready. The organizational translation usually isn't (yet).

Even Apple Needs a Translator

Apple's AI-powered Siri overhaul (first promised in June 2024) is still nowhere in sight. Apple is now partnering with Google's Gemini model because their own technology wasn't ready, and even with that partnership, they're behind schedule.

I share this not to pick on Apple, but because I think it's genuinely encouraging. If the most valuable company on Earth, with unlimited resources and the best engineers money can buy, is still struggling to get AI deployed reliably, then you have full permission to take a breath. You don't have to have this figured out yet. The companies that win will be the ones who took the time to learn the new language.

SHARING SOME WINS

Finance and Accounting: 3 Hours a Week, Back in the Budget

One of our clients was spending three-plus hours every week manually matching credit card charges to transactions. They use Ramp as their payment processor, and while Ramp's platform is solid, the reconciliation step was still a human staring at rows, matching numbers, and fixing discrepancies line by line. We built an AI-assisted workflow that handles the matching automatically and flags the exceptions for human review. Three hours a week is back on the table. Now reconciliations can happen weekly and month-end closing of the books got a little less painful. If your finance team is still reconciling by hand, this is one of the fastest ways to get time back. Reach out and we'll show you how it works.

Training Unlocked: Turning a Mountain of Documents into Training

We built a custom notebook (in NotebookLM) for a client to help their team navigate an enormous library of documentation and regulations. If you haven't tried NotebookLM yet, here's the short version: you upload your documents, and it creates an AI assistant that only answers based on what you've given it. No making things up or hallucinating. Just the stuff you told it, completely searchable.

But the part that got us excited was the multimedia output. NotebookLM can turn a 50-page regulation document into a podcast-style audio walkthrough, a video summary, a mind map, or a slide deck. All of these are generated directly from the source material. Imagine your newest team member listening to a 20-minute audio overview on their commute instead of dreading a binder full of policies they'll never finish reading. We're using this across several client engagements now, and if your team has a mountain of documentation people are expected to know but rarely have time to read, this might be the most practical tool in our whole playbook.

TRAINING TIPS OF THE WEEK

The Trailblaze Academy Is Live

I've been hinting at this for a while to anyone who will listen (apologies), but now it’s ready for primetime. The Trailblaze Academy is live with nine new training videos and a knowledgebase of articles, all available to our clients right now. We built these from the ground up based on the questions we hear most often in our 100+ training sessions. Each one is short, practical, and ends with a concrete exercise you can try the same day.

Here's why I'm so fired up about this. The gap between what AI can do and what most teams have been trained to do with it is the single biggest missed opportunity in business right now. Not because people aren't smart enough. Because nobody's translated it for them yet. That's what these videos are: translation.

Check them out at trailblazelabs.ai/academy. We’re already working with teams to get this content on their LMS platforms, but it’s hosted on our academy site for quick access to all clients. Just type in your email address and you’ve unlocked access.

You're Probably Using AI the Same Way for Everything

Here's something we see in almost every training session. Someone's been using ChatGPT or Claude for three months, and they're doing everything through the same chat window. Writing emails, analyzing spreadsheets, brainstorming strategy, building a proposal. Same tool, same approach, every time. And then they wonder why half the time it feels like magic and half the time it feels like arguing with a toddler (or an intern… or a toddler intern).

The problem usually isn't the AI, it's the setup. Take Claude as an example: most people don't realize there are now three completely different ways to use it, and they're built for different kinds of work. Claude Code is basically a developer on your team: you describe what you want built, and it builds it (far beyond code and applications, it’s a truly groundbreaking tool). Claude Cowork sits on your desktop, reads your actual files, and works alongside you in a way that starts to sound like you the longer you use it (the closest thing you have to an off-the-shelf agent right now). Claude Projects is where you set up a workspace with instructions that carry over between conversations, so you're not starting from scratch every Monday morning. Picking the right one matters more than most people think. We've watched people go from a frustrating half-hour chat to a five-minute polished result just by switching which mode they were working in. And while we are pointing this out in Claude, it translates well to ChatGPT (and mostly translates to Gemini).

THE BUZZER

Wherever you are with AI right now, it’s important to know you're not too late.

We all need translators - in medicine, law, finance, or technology. The people who pretend they've always understood this stuff are either lying or they've forgotten what it felt like to be new. Our team is still (voraciously) learning every day. Every week I find something I was doing wrong, or a tool I didn't know existed, or a better way to explain something I thought I already understood.

That's why Trailblaze exists. We translate AI to the language of your business. Not because you can't learn it yourself, but because you shouldn't have to do it alone.

Thanks for huddling with us before the weekend,

Bryce

ABOUT TRAILBLAZE LABS

We started Trailblaze Labs because we saw a gap forming between what AI could do and what most businesses knew how to do with it. Turns out, that gap is where we live now. We help business leaders set real AI strategy, train their teams to use these tools with confidence, and build the workflows that actually move the needle. Trailblaze translates AI to the language of your business.

If something in this newsletter sparked a question, gave you an idea, or made you want to push back on something I said, I want to hear about it. Seriously. Reply to this email, connect with me on LinkedIn, or just say hi. I read everything and I love a good friendly argument about where this is all headed.

Let's keep building.