A New AI Agent Wants to Schedule Your Life—Should You Let It?

Have you ever thought your working life would be easier with an executive assistant? A suite of new AI agents are cropping up, promising to take on the work and deliver all the benefits of having an EA without you actually having to hire anyone for the job. And, ostensibly, all for a far lower price tag. To find out if technology could do a better job than I could at making my schedule work for me, I tested out a free trial of Blockit, a new AI-powered agent that integrates with a user’s calendars and email. When signing up for the tool, Blockit promised me that in as little as five minutes it could learn the same amount of information about my schedule, habits, and preferences as a human EA might over the course of several months. Here’s how Blockit works: The AI agent learns your preferences for taking meetings, including when and where you like to conduct certain kinds of business. Then, you can copy the Blockit bot into emails or Slack messages with your contacts and give it instructions to set up a meeting at your chosen time and place. It sounded fantastically simple, but after using the tool, I realized that letting Blockit’s AI into my schedule required more than a little work on my part, too. Here are my three biggest takeaways from letting AI into my schedule for a week. You need to work to make it work for you Blockit’s onboarding process involves answering multiple questions about your habits and schedule, some of which got me thinking a little more about where, in fact, I like to work. So if you like to take certain meetings in a coffee shop near your office, you need to tell Blockit the exact address and the AI will make a note of it for future reference. Similarly, if you have an office or work from home on certain days, Blockit will log that, too. Doing this means that when you copy Blockit’s bot into an email with a contact that you want to get a coffee with, the bot will schedule a meeting at your preferred spot, invite the other person to it, and block off the time on your calendar that it will take you to get there from wherever you told it you would be working that day. That’s extremely helpful! But it also requires you to make some concrete decisions about where and when you will be working—and that’s not always totally obvious if you are in an industry that regularly puts you in many different locations on short notice. Blockit, to its credit, can keep up—it will even ask you to confirm if you are traveling if you tell it to set a meeting in an unfamiliar city. But if you are a busy CEO, keeping your AI agent up to date on your schedule might not always be top of mind. Another interesting Blockit feature is its codewords function. Users can teach the AI codewords that trigger certain actions: For example, say I sign off an email agreeing to a meeting with “best wishes” and copy Blockit to set something up. I could have already set “best wishes” as a codeword meaning that this meeting is not high priority, can be set sometime three or four weeks away, and can be canceled if I get another, higher priority request for the same time between now and then. It’s a clever idea, but again, I had to go through the work of teaching Blockit my codewords, a process that the desktop app doesn’t make particularly intuitive. Overall, I had to spend a solid chunk of time training Blockit—it definitely took more than five minutes of work to get value from this tool. If you’re already feeling stretched, taking those hours to invest in the AI might not be your top priority. But if you do, it may be worth it. Blockit needs access to everything An obstacle I ran into early with Blockit was that it didn’t want to work with just one Google calendar—it wanted access to every calendar app I had access to. That would be fine if the people who owned those other calendars were also Blockit users, which they were not. Blockit only works if you share all your calendar data with it, and if you are an entrepreneur or contractor who works regularly with other companies and are copied into their calendar, you likely don’t have the authority to give Blockit permission to see everything you can see. You might also have some personal privacy concerns that would prevent you from sharing certain information with Blockit. As a result, you might end up letting the app see only half the picture—which could make it less adept at sorting your schedule out for you. Another hurdle for the AI was the fact that I don’t schedule everything in my calendar. I don’t block time-off for certain kinds of work, or log when I’m taking free time. I also often block off a day in my calendar with reminders like “parents arriving today,” and it looks like I’m busy all day—but I’m not really. I tried to clean up my calendar and make it more faithful to what my days actually look like, but I gave up after spending an hour on planning out just two weeks into the future. In that sense, Blockit might be better suited to someone who is starting from scratch—say, joining a new company—or whose company has a calendar system that has become overwrought. Advantages of large-scale integration Blockit is supercharged when other people in your contacts list have Blockit too. Your AI agent can directly communicate with their AI agent and set a meeting up for you with minimal human engagement required. Unfortunately, none of my regular contacts have Blockit. The company behind it has put nothing into marketing it, so its customer base is word-of-mouth only. This brings me back to a realization I raised earlier: Blockit may work best on a company-wide scale rather than on an individual level. The app is genuinely helpful for individuals, but if it were integrated across a team or a company, I can see it taking on some of the core functions of a secretary or EA with little effort. (What the final pricing would be in my case, should I continue to use it past the free trial, is unclear.) That would also get over another potential hurdle with Blockit: Not everyone is used to having an AI agent ask them for their availability. If you’re trying to book a coffee date with your elderly relative, for example, or set up an intro call with a first-time contact, they might be a little skeptical. On a company-wide scale, however, Blockit may be just as intuitive as other AI-powered productivity tools, whether they be schedulers like Sunsama, Structured, or Todoist; note-takers like Fireflies.ai or Otter.ai; or management systems like Airtable or Jira. And, importantly, if your company invests in a tool like Blockit, it would likely become just as big a part of employee workflow as any other software-as-a-service product. BY CLAIRE CAMERON, FREELANCE WRITER