Sam Liang is utterly baffled when I reveal the primitive way I record interviews: firing up the Voice Memos app on my iPhone, then painstakingly copying the transcript into a Google Doc by hand. The CEO of Otter, a transcription platform designed for dissecting meetings, watches me with the same bewilderment you’d show someone trying to join a video call with a rotary dialer. Deep down, he’s convinced I’d be far better off using Otter—and he’s almost certainly correct.
This mindset reflects an emerging persona both in professional settings and personal life: the AI native. A wave of time-saving productivity solutions—from next-generation note-capturing instruments to autonomous task-executing agents and conversational email helpers—is surging in popularity as it weaves itself through every corner of our digital existence. While remaining vigilant about security risks and fabricated responses when engaging with any AI capability is essential, early enthusiasts are cultivating a fluency that stands to reward them handsomely over the long haul.
Being AI native—or “agentic,” as those in the know describe it—means embracing flexibility in the face of new tools and workflows. Setting aside the occasional transcription hiccup, I’ve thrown myself into experimentation wholeheartedly, from using AI to generate podcasts to delegating desktop file organization to Claude. (I explored several of these experiments in my newsletter series last year, called AI Unlocked.) If you’re determined to master AI utilities to such a degree that your colleagues start wondering whether your veins carry blood or fiber-optic cables, here are my seven strategies for AI-driven advancement.
1. Retirement-Proof Your Chatbot Habits
ChatGPT feels like a relic from 2022. These days, the trendsetters have migrated to Codex. You might understandably roll your eyes at the term “AI agents,” but when stacked against what was available even twelve months ago, software automation platforms like Codex and Anthropic’s Cowork are in another league entirely—capable of genuinely seizing control of your machine and executing tasks on your behalf. There’s no reason to fuss with a single chatbot when you could be orchestrating an entire legion of them.
2. Switch to Voice-First
Still manually typing every single instruction you want your AI tools to follow, like some digital-era dinosaur? How charming. But take Otter’s Liang at his word: “Voice is on track to take the lead from here on out,” he tells me. “People detest typing things out.” (He adds the caveat that *I*, as a journalist, might be an exception—and he’s mostly right about that.) This shift is mainly about how you feed input to the system, not necessarily how you consume the results. I rarely lean on ChatGPT’s audio-only mode, for example, but I frequently dictate a prompt through my phone and then scan through the resulting text.
3. Establish a Playground Environment
Even though agents have genuinely leveled up, those mischievous troublemakers can still wreak absolute chaos if you don’t keep them on a leash. (Just this past year, a Claude-driven agent wiped out a fledgling company’s entire production database—plus every backup they had.) So before handing over the reins of your computer to an external force, carve out an afternoon to familiarize yourself with the full scope of what these platforms can do, then carve out designated folders stocked with the files you actually want them touching.
4. Feed It Your Entire Digital Life
Forgive the slight to the privacy champions covering cybersecurity, but the reality is blunt: the more data you funnel into AI, the sharper and more tailored the results become. Jo Barrow serves as chief of staff at Granola, one of Otter’s rivals, and she frames it plainly: “I’ve built what amounts to a personal operating system—a cluster of files stored on my PC where my AI essentially resides. Every time I pose a question, all that context sits right at its fingertips, and the agent can dig through it independently. I’m saved from having to spell things out repeatedly.” A friendly note of caution: intimate or classified conversations are still safest when kept off any permanent record.
5. Build Yourself a Digital Twin
Barrow explains that she exports all of her Slack messages into a single document so the AI can study how she communicates on that platform, and she replicates the method for her email inbox and social accounts. “People turn to AI to refine their tone of voice,” she says. “You can only repeat yourself so many times—’OK, warmer please. Now dial back the formality.’ That’s an enormous drain on your time.” Crafting these behavioral blueprints for your bots won’t perfectly clone your voice, but they can steer the AI toward producing text that actually resembles your natural rhythm and style.
6. Collaborate Across Teams
Data is a powerhouse, and bringing in more of it from the people around you can supercharge your AI tool’s performance. Think about your colleagues: “Plenty of folks have adopted a meeting note-taking assistant, but they’re still operating it one meeting at a time,” Liang points out. He champions the “knowledge engine” Otter can assemble when an entire workplace gets on board—from the engineers to the marketing folks. And this extends to your household, too: when family members feed their daily notes and observations into one shared AI platform, you’ll extract far more meaningful insights than if everyone kept their usage isolated.
7. Master the Art of Jailbreaking
Making AI tools work for you in 2026 doesn’t demand that you write—or rather, *speak*—flawless prompts. Even so, kick off more ambitious tasks with a thoughtfully crafted, creatively worded request and you’ll often gain an edge. Tinker with phrasing, particularly when you stumble into unexpected guardrails that block or filter the output. Recently, I tried getting an AI to hand over email addresses for a roster of niche experts, and it flat-out refused. But in a fresh conversation, I spelled out my reasoning (purely for journalistic purposes—not harassment, naturally)—and it coughed up a list.
Your Turn to Sound Off
Share your thoughts on this piece in the comments section below. Or, if you’d prefer, you can draft a letter to the editor and send it to [email protected].
