This Humble AI Makes You Focus Like a CEO
This Humble AI Makes You Focus Like a CEO
Reclaim is a priorities-first scheduling assistant that gets out of the way.
You’re reading the newsletter of Hear Me Out, a workplace culture strategy firm. We uncover your team’s biggest obstacles, then collaborate on a process that makes everyone feel motivated and heard. Learn how we help leaders make space for open dialogue.
There are two kinds of help.
The first is eager to impress. It tries to anticipate your needs without much guidance, but often ends up creating more work to steer back on course.
The second is more restrained, but also more effective. At first, it asks question after question to gain a precise understanding of how to support you. Rather than make assumptions, it relies on constraints and priorities, set clearly upfront.
Reclaim, a scheduling app with an evocative name and a devoted following, offers the latter kind. While less flashy than the generative AI startups that have captured headlines, Reclaim starts by recognizing people, not technology, as the experts on their own needs. And the company’s unassuming, customer-focused approach has lessons for business that go far beyond scheduling.
Freeing up space for priorities by handing over control
Despite an overall dip in AI funding, 2023 will likely be the year generative AI goes mainstream. In 2021 and 2022, over 500 generative AI startups raised a total of $9.3 billion, including 3 of the 5 companies that broke the billion-dollar valuation mark this year: Anthropic, Adept, and Character.ai. But while generative AI can feel magical, it’s not the only, or even the best, option for every product.
Reclaim’s take on AI is simple and direct. It doesn’t obscure its inner workings. Instead, it hands over control and gets out of the way. This philosophy mirrors the approach used to keep digital systems online. The app’s founders, Patrick Lightbody and Henry Shapiro, worked at New Relic, a software platform that keeps mission-critical services up and running. While there, Shapiro told me, they wondered why calendars weren’t also maintained through configurable, automated systems.
This rules-based approach means Reclaim takes time to set up, but the up-front investment pays off. The app can be configured to sync personal calendars, block out travel time, and add short decompression breaks after video calls. It also automatically reschedules 1:1 meetings as managers' schedules change.
Reclaim is designed to defend work-life balance, not just drive efficiency. The app’s default list of habits leads with fundamentals like an hour-long lunch, or short walking breaks. But the area where the app shines most is enabling time for deep work. It syncs with popular task management and collaboration apps for a seamless workflow from decisions to next steps. And unless a commitment is personal or confidential, the whole team can see why that time slot is unavailable.
Handing off the details of my schedule to a rules-based AI frees up mental space to focus on my priorities. By Monday at noon, all my week’s tasks are in the calendar and anyone I share it with can see where my time goes. (In line with Hear Me Out’s values, lunch and exercise come before everything else.) When events change or priorities shift, the app adjusts my calendar based on the rules I’ve set for my availability.
Products exist to serve people, not optimize them
Reclaim’s creators understand what many tech companies fail to grasp: the most important problems we need to solve in life are deeply personal. And few things impact our lives more than how we spend our time.
Since the 1950s, meetings have more than doubled, with many executives spending more than half of the week in them. That means less time to connect and recharge. And remote brought meeting overload to the rest of the org chart. After the pandemic, Shapiro saw users schedule six times more meetings, with managers in even more.
For many remote teams, meetings replaced hallway chats. Now, Shapiro said, CEOs and Chief People Officers have a new concern: managing complex, hybrid office schedules. How can they balance in-person meetings and still allow employees the flexibility and work-life balance they’ve grown used to?
The answer isn’t to hand off scheduling to a chatty virtual assistant. It’s to invest in the processes, the documentation, and the tools to enable complex scheduling across teams and locations. Even if generative AI becomes the main way people interact with software, Shapiro stressed that product teams “still have to be the keepers of customer problems,” understanding their needs and expectations.
Software’s power lies in the way it defines those problems—and redefines them—to benefit a specific user. While some companies have asked for productivity tracking, the founders are more interested in giving users back their time.
Efficiency gains are often framed as a win-win, but unless they result in a shorter workday, the company still benefits the most. Reclaim exemplifies the kinds of experiences employees ought to see more often: ones where people’s needs come first. Where even a scheduling app can enable creativity, connection, and joy.
Reclaim represents a vision that’s unfortunately rare in tech these days: a product that solves a clearly-defined problem and respects the needs of everyday people. In a world where work steadily encroaches on life, giving everyone the agency to “reclaim their time,” as Rep. Maxine Waters famously demanded, is radically empowering.
Rules, after all, are rules.
You’re reading the newsletter of Hear Me Out, a workplace culture strategy firm. We uncover your team’s biggest obstacles, then collaborate on a process that makes everyone feel motivated and heard. Learn how we help leaders make space for open dialogue.