Tech Productivity Issue #396 (A Playbook for Better 1:1s)

Issue #396 (A Playbook for Better 1:1s) 09/14/26

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A lot of things are now being automated in tech due to AI. But it's clear that many things are best to not fall under automation, or in some cases they're just impossible to automate.

One Substack creator recently posted a graphic displaying what he automates vs. what he doesn't.

Is this something you've personally thought about? Or do you consider whether to automate something only in the moment when it comes up. I can definitely see some benefits from planning things in this way, so maybe this graphic will help you too.

Now on to this week's hand-picked productivity links!

Tools & Apps

Viktor — An AI assistant for Slack and MS Teams that integrates with all your tools and works like a new hire to carry out tasks that you sign-off on.

Clockjumper — A world time zone converter and meeting planner that enables teams to convert time between cities, compare working-hour overlap, and find the best time for international meetings.

Shift — A new browser for Mac and Windows that you build piece by piece, with support for custom spaces and integrations with 4500+ apps that you work with every day.

The One Options Trade I Make Every Week — A single 0-day options trade, handed to you with the strike, the entry price, and the exit already mapped. Grab this week's free report to see how it works before the next signal drops. sponsor

Scratch — A minimalist, offline-first markdown note-taking app for macOS, Windows, and Linux, with keyboard shortcuts, syntax highlighting, preview mode, and lots more.

Portero — An open source app for monitoring ports on a Mac, giving you a clear view of everything running on your machine, so you always know what's using each port and can stop what you don't need.

Hndmark — A web tool that lets you annotate images with shapes and text but in a handwriting style that looks more human.

Articles & Resources

How to One-on-One — A 1:1 playbook of sorts that encourages leaders to stop using 1:1s for status updates but instead use them to prep async, focus on career growth, coaching, feedback, and human connection.

How to Ask For Help from People Who Don't Know You — The main thrust of this advice is to put yourself in the other person's mind in order to improve communication.

Turn AI into Your Income Engine — Ready to transform artificial intelligence from a buzzword into your personal revenue generator? Our ground-breaking guide "200+ AI-Powered Income Ideas" is your gateway to financial innovation in the digital age. sponsor

The Case for Not Responding to Every Little Work Message — "Companies tend to value hyper-responsiveness during the workday, but being constantly available pulls your focus away from real work, and it takes time to switch back."

Most Tech Revolutions Made Work Worse for Employees. AI Could Be the Exception. — In contrast to previous changes in the workplace, is AI going to allow us to use the saved time for more collaboration and improved creativity?

Can One Bad Apple Ruin Your Team? — An interesting anecdote about a former team member who brought a lot of energy to the workplace, but often made the office an unhappier place.

Reflections After 10 Years of Teaching Time Management and Productivity — From someone who has been writing newsletters, blog posts, and books, creating courses, coaching professionals, and publishing YouTube videos on these subjects for ten years.

Suggestions?

Have a suggestion for a productivity-related tool, article, or other resource? Send me a direct message via X or chat via Bluesky and I’ll consider including it in a future issue.

Stay productive!

Louis
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