Sam Liang is appalled as I confess my technique for recording an interview: running the Voice Memos app on an iPhone and transferring the transcript manually to a Google Doc. The CEO of Otter, a transcription service for analyzing meetings, looks at me as if I tried to call into our video chat using a rotary phone. He believes, naturally, that I should switch to Otter. He’s probably right.
It’s all part of a new identity at work (and maybe at home): the AI native. Time-saving productivity tools like next-gen note-takers, task-based agents, and chatty inbox assistants are exploding in popularity as they invade every nook and cranny of our digital lives. While it’s critical to keep concerns about security and hallucinations top of mind when using any AI feature, early adopters are developing a fluency that will likely pay dividends for years to come.
Being AI native—or “agentic,” as AI natives say—means staying adaptable to new experiences. Transcription failures aside, I’ve embraced experimentation, from generating AI podcasts to letting Claude organize my desktop files. (Some of this I talked about in my newsletter series last year, AI Unlocked.) If you want to get so good at using AI tools that your coworkers start questioning whether it’s blood or ribbon cables running beneath your skin, here are my seven tips for AI-powered ascendance.
1. Kill Your Chatbots
ChatGPT is so 2022. These days, the cool kids are all about Codex. Your eyes may glaze over, rightfully, at the mention of “AI agents,” but compared to anything on the market even a year ago, software automation tools like Codex and Anthropic’s Cowork are leagues better at actually taking over your computer and completing tasks. Don’t waste your time fiddling with a single chatbot when you could be commanding a whole army of them.
2. Go Voice Mode
Oh, you’re still typing up everything you want your AI tools to do, Boomer-style? That’s cute. But trust Otter’s Liang: “Voice will become more dominant moving forward,” he tells me. “People hate writing.” (He caveats that I, a journalist, probably don’t hate writing, which is, mostly, true.) This move is primarily for the input, not necessarily the output. I rarely use the voice-only mode on ChatGPT, for instance, but I often speak a prompt into my phone and then skim the written output.
3. Build a Sandbox
Even though agents are actually good now, the rascally little devils can still eff everything up without proper boundaries. (Earlier this year, a Claude-powered agent deleted a startup’s entire production database and backups.) So if you’re ready to have some external entity take control of your computer, you need to spend an afternoon researching everything these tools can do and set up some dedicated folders with the files you want them to access.
4. Give It Everything You’ve Got
With apologies to our privacy-minded security writers, it’s simply the case that the more data you share with AI, the more personalized the outputs can be. Jo Barrow is the chief of staff at Granola, one of Otter’s competitors, and she puts it this way: “I have a personal OS system, which is a series of files on my computer which my AI lives inside. Whenever I ask questions, all of that context is right there, and the agent can go and figure it out. I don’t need to repeat myself over and over again.” Fair warning: Sensitive conversations are still best had without a permanent record.
5. Create an Impersonator
Barrow tells me she dumps all of her Slack messages into a document to let bots know how she sounds on that platform, and she does the same for her email inbox and social media accounts. “People use AI for finessing their tone of voice,” she says. “There’s only so many times you can say, ‘OK, a little bit warmer. OK, a little less formal.’ That’s a big time sink.” Creating these guides for the agents to follow won’t fully replicate your voice, but they can nudge the bot to output something at least closer to your cadence and tone.
6. Think Across Teams
Data is powerful, and adding more of it from people around you can further enhance AI tools. Consider your coworkers: “Many people are using a meeting note-taker now, but they’re still using it at the individual meeting level,” Liang says. He touts the “knowledge engine” Otter can create when a whole workplace buys in, from the engineering team to the marketing department. You can even do this at home: If family members pour various notes from their day into a single, shared AI tool, that’s going to provide more insights than siloed usage.
7. Learn to Jailbreak
Successfully using AI tools in 2026 doesn’t require writing—I mean speaking—perfect prompts. Even so, starting off more complex tasks with a creative, well-calibrated request can be clutch. Experiment with the wording, especially if you’re hitting unexpected guardrails blocking the output. Recently, I attempted to convince a bot to send me email addresses for a variety of niche experts, and it refused to deliver. But when I started a new chat and shared details about why I wanted this info (for reporting purposes, of course, not stalking), it forked over a list.
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