Charter Work Tech: The best AI time-blocking tools

Our process

We evaluated five tools—SkedPal, Timehero, TrevorAI, Motion, and Reclaim—on flexibility, ease of use, integrations, price, and level of customization. Each received a score from one to five, with five as the highest; because we judged ease of use and flexibility to be the two most critical factors, those two categories were weighted twice as heavily as the rest. We then chose our picks based on the highest total score.

Because one primary purpose of time-blocking is to create space for focus and deep work, for the purposes of our review, we focused on each program as a productivity tool for individuals rather than groups. To that end, we did not evaluate their ability to coordinate calendars across teams, though Reclaim, Motion, and TimeHero have varying built-in functionalities for cross-team scheduling and collaboration. (We’ll be separately reviewing more outwardly focused calendar-management tools in an upcoming edition of Work Tech.)

For the most accurate comparison, we tested all five programs on the same single week, syncing a Charter staffer’s Google calendar that included any personal obligations scheduled during or near working hours. We then populated each tool with the same real to-do list for that week, coding tasks by the larger project they support—for example, “Charter Work Tech” was one to-do list category, with tasks for each test, drafting, and producing—and adding new tasks as the week progressed.

Our recommendations

Our top two picks are TrevorAI, which offers a free plan and a Pro plan for $3.99 per month or $29.99 per year, and Reclaim, which offers a free option for single users and multiple paid tiers depending on team size, starting at $8 per user per month.

Here’s how each of our picks stacks up on key features:

Flexibility: New meetings, last-minute requests, and unforeseen hiccups can disrupt a carefully time-blocked schedule. Reclaim responds in real time to updates in your synced calendar, automatically moving tasks to new time blocks. Its ability to set a minimum and maximum duration is also useful if you’re unsure how long a task will take, or if you want to dedicate time to something more open-ended, such as a walk break or an inbox clean-out. While TrevorAI doesn’t share Reclaim’s responsiveness to conflicts, its drag-and-drop functionality makes it simple enough to manually move tasks to a new time block as needed. Its “quick reschedule” option also makes it easy to bump a task to a later day or week; if you’re not ready to commit to a new time block for a task, the “unschedule” function sends it from your calendar back to your to-do list. When a new task is created, TrevorAI also shows it in multiple possible spots on your calendar, allowing you to choose by clicking the option you prefer.

Customization: Both of our picks allow tasks to be grouped for more effective management. TrevorAI uses a simple sorting mechanism, with color-coded lists that organize tasks by project or type. Reclaim’s system gets more granular and therefore requires a few more steps when adding new tasks, but with the payoff of a highly organized and clear calendar: Its color-coding system sorts tasks according to context, including solo work, personal, travel and logistics, and various types of meetings; users can also include emojis in task titles, which could function as another type of coding system for an additional layer of detail.

Reclaim may be more effective for those who want an app’s help in drawing clear boundaries between work and life, allowing users to customize working hours by day of the week, as well as the time windows in which meetings and personal tasks can fall. Both picks make it easy to set up recurring tasks. Reclaim has templates for daily to quarterly habits, such as lunch, morning catch-up, and budget planning; while TrevorAI doesn’t distinguish between habits and ordinary tasks, it’s straightforward enough to create a separate list for recurring habits and set each one to repeat at your desired cadence.

Ease of use: Trevor’s biggest strength may be the simplicity of its user experience. Adding new tasks is a quick one-step process that doesn’t require clicking through multiple fields, and adding a new task directly to a list requires simply typing “#[listname]” at the end of the task title. When scheduling, shorthand buttons for specific time windows (ie today, this week, this weekend) provide a quick way to create a narrower window for a task’s time block. Reclaim is a bit more detailed, though by no means overly complicated, with additional parameters for more fine-tuned auto-scheduling: To add new tasks, users type out the duration and earliest and latest points it can be scheduled, and select work or personal hours. The option to split an item into multiple time blocks is a helpful feature for lengthier tasks or those with more cluttered schedules.

For accountability, both our picks provide helpful safety nets to prevent tasks from languishing past their assigned due dates. TrevorAI clearly highlights due dates on unscheduled tasks for easy scannability, while Reclaim’s task dashboard sorts tasks into “open” (those that haven’t been scheduled, and those that have been scheduled but not completed), “scheduled,” “done scheduling” (those that have already passed on the calendar have already passed, but have not been manually marked complete) and “completed” (those that have been confirmed as done). Both have all-in-one views that show your to-do list of tasks on one side and your calendar on the other, making it easy to toggle back and forth between the two with a full picture of your schedule while adding tasks and assigning due dates.

Both also have a section in each task card for notes. TrevorAI a has an “AI action plan” in beta, which ostensibly generates detailed steps for accomplishing a task, but in practice the steps are too obvious as to be helpful—for a task titled “Edit newsletter draft,” it included such suggestions as “review the draft for errors and inconsistencies” and, amusingly, “edit the draft.”

Integrations: For Google Calendar users, Reclaim has the clear upper hand: Its paid plans support integration with multiple task-management apps, including Google Tasks, ToDoist, Asana, ClickUp, Jira, and Linear. Outlook users, however, will likely find it cumbersome to sync their calendars, as doing so requires first creating a Google calendar to import your main calendar into, per Reclaim’s guide. While TrevorAI allows users to directly connect either a Google or an Outlook calendar, integrations are a relative weak spot, as it connects only with ToDoist.

Pricing deep dive

TrevorAI offers two pricing tiers: Free and Pro.

• Free supports syncing with a single calendar and includes unlimited task scheduling.
• Pro is $3.99 per month or $29.99 per year and supports syncing with multiple calendars. It also includes a dashboard that provides users with insights on how their time breaks down across categories and how they’re progressing toward their goals, and adapts to users’ scheduling habits to estimate how long tasks will take and fine-tune suggestions for time blocks.

Reclaim offers four pricing tiers: Lite, Starter, Business, and Enterprise.

• Lite is free for a single user, supporting two connected calendars and allowing schedule blocking up to three weeks out. Notably, this tier is the only one that does not come with access to Reclaim’s support team for troubleshooting any issues that may arise, though users can take their questions to Reclaim’s Slack community. It’s also the only one that limits the number of recurring habits users can add to their schedules (a maximum of three) and integrations (only Google Tasks).
• Starter is $8 per user per month, providing eight weeks of scheduling at a time for up to 10 users. It syncs with unlimited calendars and allows users to customize how others see the time blocks on their calendar.
• Business is $12 per user per month, with 12 weeks of scheduling for up to 100 users. In addition to all the features of the Starter tier, it also comes with company-wide onboarding and priority support from Reclaim’s team.
• Enterprise is $18 per user per month for 100-plus users. It includes all the features of the Business tier, plus enhanced control over user permissions company-wide.

How we chose what to review

The landscape of time-blocking apps is a crowded one, but many programs offer time-blocking as a secondary feature while focusing on a related productivity or team-coordination aim as their primary purpose. We excluded AI tools that did not identify individual time-blocking as a main function, which eliminated software programs built for cross-team calendar management (such as Clockwise) and cross-team task management and time tracking (such as Timely). We also excluded those that exist solely as mobile apps (such as TimeBloc). Within the field of remaining tools, we focused on those with auto-scheduling capabilities that can be synced with Google Calendar and Outlook, either directly or through connective programs such as Zapier.