How AI Can Supercharge Your Favorite Productivity Frameworks

AI is rewriting all of our standard productivity techniques. I’ve already written that it will spell the end of organizing, but what about applying it to other classic standbys, like the Eisenhower matrix and the Pomodoro technique? Read this guide from Stella Garber—former head of marketing at Trello—if you want to learn how to maximize your favorite productivity hack with AI. —Dan Shipper

NOTE: I’m speaking on a creator panel at New York Tech week this Wednesday afternoon, along with a16z’s Steph Smith, Gumroad’s Sahil Lavingia, and Numlock’s Walt Hickey. If you’re interested in attending, register here:

A few years ago, as the head of marketing at Trello, I found myself constantly “firefighting” at work. Even though I’d start each day with a clear set of priorities and tasks, invariably the pings would start rolling in from Slack. Why didn’t the contract get signed by the due date? Where are the adjusted budgets for next quarter’s campaign? Which audience are we targeting for the current enterprise campaign?

Answering all of these “urgent” questions required coordinating with multiple people and cross-referencing documents spread across different tools. Most frustrating of all, it yanked me out of whatever I had set as my goal for the day. I found myself being pulled into impromptu meetings and having to set aside quiet time in the evenings to do focused work. There wasn’t enough time in the workday to actually do my work.

It’s no surprise I began to feel the effects of burnout.

The modern workplace has become significantly more distracting and interruptive in recent years. If you sit in front of a computer each day, you likely endure an endless barrage of pings and dings from Slack, your email, and constant calendar invitations. Organizational researcher Rob Cross, who wrote the book Beyond Collaboration Overload, found that collaborative demands on time—such as brainstorming meetings, draft reviews, and momentary gut-checks—have increased more than 50 percent in the past two decades as barriers to collaboration have decreased (and even more so since the pandemic).

Artificial intelligence could ameliorate some of these problems. It could simplify the collaborative burden we put on others and help us get through our own to-do lists. That is, if only we actually knew how to use it.

I’ve spent more than a decade helping people be more productive at work—first, running marketing at Trello (which was bought by Atlassian), and now building my own artificial intelligence startup, Hoop. Through these experiences, I’ve found one overarching theme that pervades the thousands of conversations I’ve had with people about their work and time: Most of us want to manage our time better and be more productive at work, but that doesn’t mean we have all the answers, let alone a good system for ensuring productivity and efficiency.

As AI becomes impossible to ignore at work, tried-and-true organizational systems are begging for a refresh. We’ll go through four of the most popular—the GTD method, the Eisenhower matrix, time blocking, and the Pomodoro method—and consider how artificial intelligence could super-charge them both for their adherents and the millions of people who can never quite stick to one system to get them through the day. 

How to get things done

First published in 2001, David Allen’s book Getting Things Done quickly gained popularity for its promise to both eliminate stress and increase productivity. His method has one simple idea: Get everything out of your head and put it somewhere else where you can organize it. When I worked at Trello, I encountered tons of Getting Things Done, or GTD, acolytes who swore by this structured method. So how do you get started? There are five stages:

1. Capture: Write down everything in your head
2. Clarify: Expand on what each item means and how you want to approach it
3. Organize: Sort different tasks into projects and define subtasks
4. Reflect: Make sure what you’ve created reflects your intentions
5. Engage: Actually do the thing!

Like any good framework, GTD brings order to the chaos of work bouncing around in our brains. There are lots of great ways to implement it, as explained in the book and subsequent resources. It’s also somewhat tool-agnostic, so you can pick whichever system you prefer to make it work, be it pen and paper or your favorite project management software.

AI power-up: Use AI to capture information

AI-powered note-taking tools like Supernormal, Fathom, and Otter can eliminate step one by extracting summaries and action items from meeting recordings. In a previous era, you might have had a project manager or executive assistant sit in on a meeting and take notes. But now, these tools automate that job by having a bot attend meetings and send out notes afterward.

Other tools automatically capture data elsewhere. Hoop captures activity across Slack, your meetings, and soon email while Limitless uses a wearable pin-like device that’s present throughout all of your daily in-person activities. Arc, a web browser that launched in 2022, has also hinted that AI capture is part of its near-term product roadmap. These tools could allow workers to forgo the mental and physical energy needed to remember tasks and write them down, which can add up if you’re in a lot of meetings every single day.

Capture is just the first step of the GTD framework. Eventually, AI might also help with all five steps: auto-tagging and grouping tasks, analyzing your workload and suggesting how to prioritize tasks, and—finally—doing the tasks for you.

Working the Eisenhower way

In 1954, President Dwight D. Eisenhower said, “I have two kinds of problems: the urgent and the important. The urgent are not important, and the important are never urgent.” As president and during his storied military tenure, Eisenhower was known for being ruthless with his time management.

The Eisenhower matrix, codified by Stephen Covey in his book The 7 Habits of Highly Effective People, teaches us to distinguish between the important and the urgent. Unfortunately, we often get off track because we prioritize things that are urgent yet unimportant rather than those tasks that are important but less urgent.

We can borrow from Eisenhower’s work ethic by thinking of our own work as a matrix with urgency and importance on the two axes. Therefore work can be:

• Important and urgent → Do these first
• Important but not urgent → Consider scheduling these
• Not important but urgent → Delegate
• Not important and not urgent → Most likely this is a distraction

Once we start sorting tasks according to this framework, we can begin to reconsider what we’re really spending our time and energy doing, and start to course-correct.

The Eisenhower matrix helps us prioritize longer-term projects that require our focus but don’t release the short-term dopamine hits that often come from checking urgent but unimportant tasks off our to-do list.

AI power-up: Use ChatGPT to categorize your to-do list

ChatGPT is well acquainted with the matrix and can help us identify how to categorize our lists with some simple context sharing. When you write your prompt, be explicit about what’s most important to you to accomplish. A prompt might look like this:

“You are a project manager helping me organize my tasks using the Eisenhower matrix. My most important goals this week are related to marketing my startup. Other tasks that are more operational aren’t as urgent; for example, anything related to public relations activities. Categorize this task list [paste task list].”

(Bonus tip: If you’re a visual thinker, ChatGPT can also visually categorize your to-do lists for you, plotting them on the Eisenhower matrix.)

As AI tools become more robust and feature-rich, you can imagine them suggesting which tasks you should prioritize on an ongoing basis by knowing exactly what’s relevant to you at any given moment and applying the matrix accordingly. And eventually, the AI will be able to do some of the work for us.

An Eisenhower matrix representation of my task list as I was writing this piece as rendered by ChatGPT. Source: the author.

Blocking out time

If I’ve learned anything from seeing how thousands of people manage their work, it’s that everyone does things their own way. At Trello, we talked to people every day that were figuring out how to best manage their work and, at Hoop, I’m doing user research figuring out how AI can help people be more effective with task management. I’ve yet to have two identical conversations about how people manage their work. It’s the beautiful messiness of humanity—we’re all individuals with different organizational preferences, workplace skills, and processing styles.

Still, there’s a temptation to categorize people to better understand how people handle their work. At Trello, we often grouped people into three distinct categories: list people, visual people, and calendar people.

The list people were happiest with a giant, never-ending list of items to accomplish. Some preferred Apple’s Notes app, others Google Docs, but the most important thing was that a consolidated list of tasks existed for them to tackle—wherever it was. The visual people, meanwhile, needed to see their tasks in some sort of schematic representation to understand what to do. And then there were the calendar people, who scheduled tasks as events in their calendar and lived by the adage, if it’s not in my calendar, it’s not getting done.

I happen to be a mix between a visual person and a list person. I need to see tasks visually represented, but something about crossing items off a list is extremely satisfying.

Time blocking is a productivity framework for that final class of thinkers—the calendar people. The key is to make sure your calendar reflects your priorities. People will block periods on their calendars either to reflect the task that they’ll be working on during that time, or to do different types of focused work, like writing or coding. In a meeting-heavy work culture, you might block out time to merely focus on a project or have a scheduled moment of open-ended, unstructured thinking.

Time blocking is effective because it forces people to focus on a finite resource: time. Calendars are the most honest representation of what work needs to get done, how, and, of course, when. Tasks and projects should be limited to the number of hours set aside in the day to work. If a task spills over, then it’s taking time away from another task.

Of course, the challenge is that work is dynamic, and calendars can feel inflexible. People may constantly need to update their calendars if work does spill over, they miss a deadline, or a personal matter pops up that sidetracks them from specially allotted time.

Time blocking is nothing new. In fact, it’s been around for centuries. Benjamin Franklin, one of the most productive and prolific humans of all time, famously time-blocked his day into six appointments:

• Start—shower, personal study, prep for the day: 3 hours
• Morning work: 4 hours
• Lunch and current product review: 2 hours
• Afternoon work: 4 hours
• Dinner and evening activities: 4 hours
• Sleep: 7 hours

In Franklin’s autobiography, he complained about people constantly interrupting his day and taking him off track…something each of us can relate to.

AI power-up: AI can manage your calendar into task-size blocks depending on your priorities

For the modern-day worker managing tasks, AI can help with how dynamic the workday can be. Lots of AI-powered tools, including Reclaim and Sunsama, have popped up to help the time blockers manage their schedules more efficiently and effectively using AI. Reclaim will shuffle meeting times on teams to account for individual preferences for focus time, and Sunsama lets people match their priorities to their calendars.

Time blocking can be a great exercise in helping you understand whether your time actually matches your priorities. And if they don’t, you can course-correct.

The kitchen timer that changed productivity

What does a tomato-shaped timer have to do with productivity? If you’re a devotee of the Pomodoro technique, the answer is, well, everything.

The Pomodoro method was developed in the 1980s by a graduate student in Italy who was having a hard time staying focused. He was inspired to use a simple kitchen timer to help him create periods of intense focus—about 20 or 25 minutes often on one task at a time, followed by a five-minute break. What’s interesting about this technique is that it mirrors how our brains work: We’re not great at focusing for long stretches of time, but we can force ourselves to focus intensely for short bursts.

Followers of this technique break their day up into Pomodoro-sized chunks. For example, I might budget two hours to write the first draft of this piece, but to help me not feel overwhelmed by such a large task, I might plan to give myself six Pomodoros with breaks in between. It’s much less daunting to plan for 20 minutes of intense focus than two hours.

In this way, the Pomorodo method plays into the psychology of breaking up a big, seemingly insurmountable task into smaller, bite-size chunks with the reward of a break at the end. Some people will incentivize themselves by indulging in small luxuries at the end of a Pomodoro session such as coffee, a snack, or even a walk. Others may allow themselves a short social media break, check their email, or catch up on the news at the end of a Pomodoro to satisfy a specific urge.

There are apps, browser extensions, and plugins that make it easy to incorporate the Pomodoro method into your workflow, such as the Pomodoro Power-Up for Trello.

AI power-up: Integrate Pomodoro with ChatGPT

If AI helps us get rid of the rote and repetitive tasks in our workflow, AI paired with the Pomodoro technique can increase our creative velocity. Here are a few ideas how:

• ChatGPT as a creative sidekick: I’ve written many blog posts and newsletters by allowing myself one or two Pomodoros to produce a first draft and then having ChatGPT help by writing headlines, making suggestions to my drafts, and even being my first editor. A piece of writing that might’ve taken me a week of procrastination and back-and-forth revisions can now take me a few hours by dialing in my focus, and outsourcing some of the initial requests to AI to help me think more deeply.
• Creating Pomodoro-sized blocks of work: Give ChatGPT your task list along with a prompt describing the Pomodoro method, and you’ll get suggestions for which tasks to prioritize in blocks of time.
• AI prompts for down time: ChatGPT can even give you ideas for ways to use your break time depending on your mood and goals. For example, it might suggest a five-minute meditation exercise if you’re feeling stressed or a quick stretch to get rejuvenated.

Regaining control over time

While AI in its current iteration still feels fresh and novel, most of the issues plaguing the human condition are not.

In his book about the philosophy of time and mortality, Four Thousand Weeks, Oliver Burkeman writes about how modern appliances were promised to give housewives of the 1950s more time for recreation and leisure. The reality was that the mainstream adoption of this technology simply shifted people’s expectations for a clean home, and women never got more free time.

Generative AI is already helping people be more productive by automating rote and repetitive tasks, which, in turn, should help us have more time for creativity and focus on our priorities. That is, unless AI ups the standard on creative output in a way that leaves us like the housewives of the 1950s: tricked into believing a new technology would give them more free time.

It’s up to us to make sure we can use AI to benefit our day-to-day lives instead of getting swept away in some unsuspecting trend like those aforementioned housewives. Burkeman’s book laments how even trying to control our time to be more productive is an illusion and distraction from our own coming mortality.

Artificial intelligence won’t save us from those feelings, but, if used correctly, it can make our work lives easier and let us focus on the important things in work and life—so we can spend more time on the stuff we want to be doing.

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