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Productivity tips, calendar hacks, & product updates from the Reclaim team.

Clockwise vs. Reclaim.ai: 8 Key Differences in these Smart Calendar Tools
July 7, 2021

I’ll preface this post by saying that we’re big fans of Clockwise and what they’ve built. In many ways, the “calendar automation” or “smart calendar assistant” space is in extremely early innings, and ultimately, it’s going to take years for companies and professionals to embrace software as a means for solving their time management problems. The jury is still very much out on the “best way” to build a smart calendar assistant, and while we have strong opinions on the matter, we know that there’s room for many different approaches.

Nevertheless, we get asked nearly every day “So what’s the difference between Reclaim and Clockwise?”, or “Is Reclaim a Clockwise alternative?” and since we’re advocates for building a written culture, we decided the best way to answer this question was to write a post about it.

What is Clockwise?

Clockwise is a smart calendar assistant that frees up blocks of uninterrupted time in your calendar for focus work. At a very high level, perhaps the best way to put it is that Clockwise — from our perspective — was built for people who can block out their entire calendar (or most of it) for heads-down work without worrying about balancing meetings and other commitments. This doesn’t apply to the vast majority of managers across every role, and it increasingly doesn’t apply to even the “makers” who are finding themselves getting dragged into meetings every day.

What is Reclaim?

Reclaim is a smart calendar assistant that uses flexible time blocking for your calendar to make time for your important priorities, routines and tasks. Reclaim was built for people who have calendars that are slammed. If you’re competing with 50-60% of your calendar being taken up by meetings, or if you’re constantly having to context switch from one thing to another throughout the day, Reclaim is for you. Again, many of the people who have this problem tend to be in management positions, but we’re starting to see it more prevalently among individual contributors as well.

Clockwise and Reclaim have similar goals, but fundamentally different philosophies on how to get there. There are some things that Clockwise does that Reclaim doesn’t do (yet), some things that Reclaim does that Clockwise doesn’t do, and some things that we do similarly but with key differences. This post will go into detail on them so you can make the best decision for your unique schedule and needs.

TL;DR: 8 Key Differences Between Reclaim and Clockwise

We know you’re busy people, so for brevity's sake, here’s a quick summary of what we see as the 8 main differences between Reclaim and Clockwise. Click into the headers for more details, or feel free to skip this section and read on if you’re in it for the full story!

1. Flexible time blocking

Clockwise: Blocks generic “Focus Time” events as either entirely “free” or “busy”, which makes your calendar either totally open to interruptions, or not open enough for collaboration.

Reclaim: Blocks smart, flexible time for specific to-dos and routines, automatically toggling them between “free” and “busy” depending on how busy your schedule is to maximize availability while defending your time. 

2. Tasks and routines

Clockwise: Uses “Focus Time” or “busy” blocks to reserve time on your calendar, but lacks context around what you’re working on, making your events more interruptible by others.

Reclaim: Allows you to personalize your time blocks for Tasks and Habits with names and descriptions, so schedulers have insight into your priorities and are less likely to disrupt your working sessions.

3. Prioritized scheduling

Clockwise: Does not support prioritization or tradeoffs on time blocks.

Reclaim: Offers the ability to customize which Tasks and Habits you want to prioritize week-to-week, order them by importance, and completely reshuffle your schedule around your high-priority time blocks when plans change.

4. Integrations

Clockwise: Integrates with Google Calendar with a cool Chrome extension, Asana, and Slack where you can view your agenda and sync your Slack status to your calendar.

Reclaim: Integrates with Google Calendar, Google Tasks, Jira, ClickUp, Todoist, Linear (Asana and Trello coming soon), Zoom, Google Meet, as well as Slack where you can manage your agenda, create Tasks from Slack messages, check off todos, start and stop your Tasks and Habits, and sync your Slack status to your calendar.

5. Support for synced calendars

Clockwise: Supports basic personal calendar sync to your work calendar to block off personal events as “busy” blocks.

Reclaim: Allows you to sync unlimited calendars in multiple directions, and merge availability across all of them to give schedulers a unified picture.

6. Calendar privacy options

Clockwise: Events are either completely private or completely public, giving you no “in between” option to show context without sacrificing privacy.

Reclaim: Provides options to customize how your synced events and time blocks appear to others, with advanced options for privacy controls such as “Personal Commitment” time blocks to communicate additional context around your time.

7. Pricing & free tier

Clockwise: Limits free tier usage to only 75 schedule assists every week for your entire organization, which are “counted when Clockwise schedules or assists on behalf of a user”, making it hard to try out even in a small team. No ability to purchase individual or single team licenses.

Reclaim: Requires no organization-wide commitment or organization caps on free tier, and includes basic Calendar Sync, Habits, unlimited Task scheduling with limited customization, and full integration with Slack, Zoom, Google Meet, and Google Tasks.

8. Time blocking for teams

Clockwise: Supports “no-meeting days” and blocks time for meetings using Autopilot.

Reclaim: Supports "no-meeting days" and offers team plans with Smart 1:1 Meetings (Group Tasks coming soon), enabling your team to not only find the best times to meet, but also make intelligent decisions about your priorities for each week.

1. Reclaim was built for people who need flexibility

If you’re the kind of person who is constantly fighting for every scrap of time you can find on your calendar, you’ve probably tried blocking time for your priorities and heads-down work. You’ve also likely run into a variety of challenges around time blocking: it’s too time-consuming, too manual, and ultimately results in you spending a large percentage of your workweek just trying to keep your calendar in check.

Yet there’s another challenge that emerges when we think about time blocking, particularly if you’re someone who needs to stay available to meet with your team and other colleagues: flexibility

Let’s take a practical example: it’s Sunday night, and you’re getting prepped for the week ahead. You see a few hours of open slots on your calendar, so you decide to block them out to get some work done. Monday morning rolls around, and you wake up to a deluge of email and Slack messages -- many of which are from coworkers who looked at your calendar, hoping to meet with you that week, and couldn’t find any time slots available. “Your calendar looks nuts!” they say, prepping you for the negotiation ahead. “It looks like you’ve got a few hours blocked out here. Can I take 30m to sync up?”

And herein lies the problem with time blocking methods and tools: they don’t give you a sufficient balance between collaboration time and focus time, which in turn leads to you spending even more time trying to wrangle schedule negotiations like the example above. Because your schedule is changing all the time, and because you don’t have the luxury of blocking out your entire workweek to just go heads down, you have to maintain some flex in your schedule in order to make time blocking effective.

When we first started building Reclaim, we took this example very much to heart, having lived the experience for years as overwhelmed middle managers in a fast-growing company with too many meetings. We realized that we could build software that could make the calendar smart enough to know when to “lock things down” and defend your time, or when to “keep things flexible” and preserve some free time for people to meet with you. Not only is it a more intelligent way to block time, it’s also just much more realistic: let’s not pretend you’re going to have zero hours of meetings every week, or that your role doesn’t rely on collaborating with your coworkers.

You can see this experience most prominently in how we built Tasks and Habits. With Tasks, for example, you tell Reclaim when something is due and how much time you need, and Reclaim automatically finds time for your focus work on your calendar before the due date. 

But here’s where it gets interesting: Reclaim runs millions of simulations daily against the calendar, and looks ahead to try and predict how many other possible options you might have to get that work done before it’s due. If the answer is “lots of options”, then Reclaim puts the event down but marks it as free time, which means that it isn’t visible to your coworkers and can still be booked over. 

Conversely, if the answer is “you’re running out of time”, Reclaim locks the time down and marks it as busy, adding a description to the event that indicates to others that they’re competing for a more time-sensitive block:

Clockwise is a better fit for people who don’t need that flexibility in their workweek, and who can be reasonably confident that they won’t have a lot of inbound requests for their time. This is because, unlike Reclaim, Clockwise blocks “Focus Time” as either entirely free or entirely busy. That means that either your blocked times are totally invisible to schedulers -- which doesn’t help you much in defending your time -- or they’re completely visible, which means you’re back to negotiating for your time.

While it’s useful to have software block out your time automatically, it’s less useful if it doesn’t address a core challenge that’s prevented you from being successful at it in the first place. Reclaim takes advantage of a little-used feature in Google Calendar -- the concept of “free” and “busy” events -- and uses automation to manage those states in a way that gives you optimal balance between heads-down work and collaboration time.

2. Reclaim makes your calendar intentional

Another core issue that we heard from users in the early days of building Reclaim was that their time blocks were simply too interruptible. “I do block out time to focus,” they’d say, “But it doesn’t help, because people just book over it.”

Mike Monteiro, the co-founder of Mule Design, put this brilliantly in a post he wrote back in 2013

People rarely schedule working time. And when they do it’s viewed as second-tier time. It’s interruptible. Meetings trump working time. Why?

One thing we’ve found, time and time again, is that context matters when it comes to your calendar. A block of time that simply says “Focus Time” or -- even less helpfully -- “busy”, is inherently less useful to would-be schedulers than an event that has a named purpose and intention. In other words, if someone looks at your calendar and sees a block of time for four hours that simply says “busy”, they’re very likely to ping you on Slack and say “Are you really busy at that time, or can you meet?”

This, like flexibility in your schedule, creates even more pain. Rather than using your calendar as an external record of your priorities, which gives signals to people about whether or not they can ask for your time, it turns your calendar into a meaningless space where schedulers can’t determine if one “busy” block is more important than the other. That means more time negotiating, more time adjusting events, and less time for the good stuff.

When we built Reclaim, we felt it was critical to have a strong opinion about time blocks as intentional spaces. We didn’t want to recreate the problem that we knew all too well, and we really believed (and continue to believe) that a great calendar should be a reflection of your truest priorities. For that reason, features like Habits and Tasks purposefully push you to name your objectives and routines and to make specific choices about the relative importance of them. 

This, combined with the more flexible approach to time blocking that Reclaim takes, gives you a really powerful way to broadcast your true availability -- without the manual work. Beyond that, making your calendar intentional means that you get a roadmap for your day and week that you can follow, which is essential for staying focused. 

Again, Clockwise here is great if you don’t have a lot of fears about being interrupted or your calendar being run over by would-be schedulers. By filling up your calendar with blocks of time that either say “Focus Time” or just “busy”, you’re still in the situation where people feel empowered to interrupt your heads-down work.

If you’re someone who wants to get ahead of interruptions and schedule negotiations, it’s critical to make your time blocks intentional instead of generic. Reclaim was built with this philosophy in mind, and we believe strongly that as the future of work evolves, the calendar will need to become a more accurate representation of your priorities. 

3. Reclaim lets you make tradeoffs about your schedule

Speaking of priorities, let’s talk about how they affect time blocking. Instinctively, we know that not all the tasks on our to-do list are urgent and that some are inherently more important than others. Regardless of what time management methodology you adhere to, you inevitably have to make decisions about where you’ll spend your time, and to do that you have to push work off that is lower-priority.

We apply this kind of scrutiny to our backlog, but it never seems to translate to our schedules. It’s almost as if our to-do list is the “real” record of what we want to do with our time, but the thing that determines where our time actually goes (the calendar) often ends up being an obstacle course that we have to complete in order to get to the stuff we actually need to work on.

In order to manage your schedule effectively, you have to have some ability to frontload the work that is more important and push off the stuff that is less so. But doing this kind of “calendar surgery” comes with a lot of challenges: often, when you want to make even a small adjustment to the priorities of events on your calendar, it requires you to think through some tough bin packing problems manually.

Reclaim lets you express your priorities -- both in terms of where they stand in general as well as how they shift week-to-week -- and takes care of the hard scheduling math for you. You can tell Reclaim the order in which you want your tasks and routines to be scheduled, and you can click a single button to let Reclaim know if your plans have changed during the week. When you mark a task or routine as “prioritized”, Reclaim will automatically reshuffle your events to accommodate your changed plans and more aggressively defend your time:

Reclaim also lets you know when it hasn’t been able to schedule certain tasks or routines due to your schedule, and highlights them so you can decide whether to push them off to next week or move them up in scheduling priority:

Because Clockwise isn’t blocking time for intentional work, and instead opts to place general “Focus Time” blocks on your schedule, it can’t know if one “Focus Time” block is more important than another. That makes it much harder to make tradeoffs around your time, both in terms of moving particular time blocks up in scheduling priority as well as pushing off non-essential work to make more time for other priorities.

We believe strongly that your calendar has to be a reflection of your priorities. To do that, you need a system that is aware of what those priorities are. 

4. Reclaim meets you in more places where you already work

We didn’t build Reclaim with the intention of building a better calendar app. Talking with hundreds of early users, it wasn’t clear that the calendar itself was broken, it was just missing a lot of context, intelligence, and automation. Calendars are pretty decent at doing what they do: creating, visualizing, editing, and deleting events. What they lack is any sense of what matters to you, which is why they can’t offer you more powerful controls for managing your workweek.

To that end, we started Reclaim with the goal of stretching the existing calendar as far as we could take it. We wanted to meet people where they already worked, and not force them to adopt an entirely new platform in order to get control over their schedule.

In addition to integrating with Google Calendar, we built robust integrations with Slack, Zoom, ClickUpAsana, Jira, Todoist, Linear, and Google Tasks (Monday.com, Trello, and more coming soon). We wanted to make it possible for users to manage Reclaim events and make changes to their tasks and routines from anywhere, even if that meant they spent less time interacting with our own UI. With our Google Tasks integration, we enabled users to create tasks directly alongside their calendars that would automatically sync with Reclaim to block time out. Our project management integrations allow you to automatically sync your task list from your projects so you can fully integrate your calendar with your to-do list. With Slack, we went even further.

Reclaim’s Slack integration isn’t just a background tool that you can use to view your agenda and update your status (although we do that too). It’s a hub for you to create Tasks from Slack messages, make decisions about when to start your Habits and Tasks, as well as get deep control over how your week is structured. Again, this theme of intentionality and flexibility are embedded in how we built our integration: we recognize that stuff changes, and we want you to have maximum control over what kinds of things you decide to prioritize during the day.

Clockwise’s Slack integration provides an agenda view as well as a feature that automatically syncs your Slack status with your calendar events. But again, it lacks some of that control you’d find in Reclaim’s Slack integration: particularly around actually managing your schedule via Slack. Even where Reclaim and Clockwise have features in common, we’ve taken some very different approaches. For example, Clockwise will let you set Do Not Disturb based on “meetings” and “Focus Time”, but doesn’t offer any other customization beyond that. 

While it’s useful to be able to let people know when you’re in a meeting or heads down on work, it doesn’t cover the reality of your world. What if you want to really make sure you don’t get interrupted during family time? Or, what if you want to communicate Do Not Disturb for your one-on-ones, but no other meetings?

Reclaim gives you a lot more control here, and allows you to communicate the context of what you’re working on with as little or as much detail as you’d like:

In fairness, Clockwise does offer a pretty awesome Chrome extension that plugs into your calendar and sits alongside it -- but the central challenge with that approach is that it really doesn’t work for mobile use cases. The reason we built Reclaim to integrate natively with the calendar without having to add another app or add-on was because we wanted you to be able to get control over your calendar without having to worry about what channel you’re operating from.

5. Reclaim offers more coverage for syncing your calendars

The first feature we ever built and launched was Calendar Sync. Calendar Sync solves that age-old problem where events from other calendars never show as blocked on your work calendar, which means you get overbooked for a meeting during a doctor’s appointment.

In the beginning, Calendar Sync was simple: it let you sync one calendar to another, and specifically focused on syncing your personal calendar to your work one. As more and more use cases emerged, we evolved the feature to support much more complex setups that we were seeing in our users’ environments. 

For example, we found that a lot of people not only wanted their personal calendars to sync to their work calendars, but that they also wanted to sync back their work schedule to their personal calendars so that their family knew when they had work commitments. Similarly, we found that there were people who had more than just one additional calendar -- shared family calendars, side gig calendars, school calendars -- all of which were disconnected from one another. 

This prompted us to take a platform approach, where we rebuilt Calendar Sync from the ground up to support a broader array of use cases and setups. Today, users can sync as many calendars as they want in as many directions as they want, giving them true merged availability across all their schedules:

Clockwise has a calendar sync feature, but it’s not clear that it’s evolved beyond the original use case we targeted: personal to work. 

Beyond that, Clockwise doesn’t support syncing any other calendars to your work calendar. No shared calendars, no syncing in multiple directions, and no multiple accounts. That gives you some simple controls to keep your personal calendar defended on your work calendar, but it doesn’t cover the multitude of other calendars that you’re still struggling to balance.

6. Reclaim gives you more options for controlling your privacy

As we’ve mentioned several times now, context matters. But there’s a tension between offering context and preserving your privacy. On the one hand, exposing the details of your calendar to others is critical to keeping you from getting interrupted, but on the other hand, it can be anxiety-inducing to have your events on full display to your coworkers. Google Calendar doesn’t help this much. Google gives you two options: all or nothing. You can show everyone all the details of an event, or you can show them “Busy”.

Reclaim gives you nuance around these controls by offering privacy options that sit in-between “all details” and “just busy”. For example, if you sync your personal calendar to your work calendar using Reclaim, you can opt to show synced events to others in a variety of ways, including as “Personal Commitments”:

This is a seemingly simple thing, but it has powerful benefits. You can communicate to your coworkers that you’re busy for something personal -- thereby giving them a sense of its interruptibility -- without giving them all the details. Again, these kinds of features are what give you flexibility, and enable you to better defend your time.

Clockwise’s privacy settings essentially match Google’s: you can mark your events as “private” or “full details”, but nothing in between. While your time gets blocked and your events get synced, you might find yourself still getting interrupted often and playing a lot of Calendar Tetris because your coworkers can’t see any context around your calendar events.

7. Clockwise pricing makes it harder for teams to adopt

While we’re not charging for Reclaim until March 28th, we’ve had published pricing on our site since the very beginning. We’re strong believers in radical transparency, particularly around things like pricing models: we know that it’s hard to invest in a free product as a user if you aren’t sure what it’s going to cost in the future. 

One of the benefits of published pricing is that you get a lot of really good feedback from users, even when they’re not yet paying you a dime, which enables you to tweak the pricing model and really understand where your value comes from. We ultimately came away with the realization that it was to our benefit to give users a pretty generous free tier of the product: because Reclaim fundamentally changes how users manage their time and schedules, it’s imperative that they get a chance to really feel it out over several weeks before they decide to go deeper.

Our free tier includes personal Calendar Sync (essentially one additional calendar), up to 3 Habits, unlimited Task scheduling (with limited customization) as well as integrations with Slack, Zoom, Google Meet, and Google Tasks. We think -- and our users have validated -- that that’s more than enough for people to really sink their teeth into Reclaim before they decide to make a commitment.

Beyond the free tier, we don’t plan to ask anyone to make organization-level purchases if they’re not ready to. You can purchase Reclaim as an individual, a team, a department, or an organization -- it's up to you. That means that if you’re getting value out of Reclaim and want to purchase it for you and your team, expense it to the company, and move on, that’s a-ok with us. We believe that it’s our job to prove that Reclaim is worth it, not to force your hand.

Clockwise has some pretty big differences with Reclaim when it comes to pricing. The free tier at Clockwise offers all its core features, but limits usage based on a metric called “schedule assists”. Schedule assists, in Clockwise’s words, are “counted when Clockwise schedules or reschedules on behalf of a user”, and on the free tier of the product, companies are restricted to 75 schedule assists per week. 

That limitation makes it practically hard to really utilize the product. For example, imagine that you have 10 people inside of an organization who all use it, and they want to block a total of 15 hours every week per user for Focus Time. In Clockwise’s model, you’d burn through all your schedule assists within the first 5 days -- and that’s assuming that Focus Time blocks don’t get rescheduled or adjusted once they’ve been scheduled.

By offering a transparent pricing model and a broad free tier, we think Reclaim gives you more opportunities to really see if it’s right for you before committing to a purchase.

8. Both Reclaim and Clockwise block time for teams

Similar to our Tasks and Habits feature, we also take the same approach to scheduling your one-on-one meetings at Reclaim -- with flexibility based on your actual availability. Let me start saying if you've felt like your one-on-ones have evolved from maybe once a week to every single day, you're not going crazy. Before the pandemic, the professionals only averaged 0.9 one-on-one meetings a week -- as of October 2021, this average increased over 500% to 5.6 one-on-one meetings a week. This has been the major driver in the overall 69.7% increase in meetings since February 2020, and was clearly the place we needed to start in our journey to optimizing meetings for our users busy calendars.

So, we decided to build Smart 1:1s which allow you to automatically schedule your recurring one-on-one meetings across two peoples calendars, considering both parties availability. Instead of locking in a rigid meeting time where ultimately 42% of one-on-ones gets rescheduled and 30% are cancelled, Reclaim allows you to automatically find the best time for your one-on-ones every time, and auto-reschedules for you when conflicts come up or either party requests a new time. You can even convert your existing one-on-ones to Smart 1:1s using your current meeting details as the ideal time, and it will auto-schedule within your working hours.

Clockwise also offers scheduling for teams through Flexible Meetings which allows their users to enable flexible scheduling for meetings they are open to moving around on their calendar. The goal behind Clockwise's Flexible Meetings is to try to group them together in meetings blocks to free up fragmented time in a users calendars to they can block that off for Focus Time.

One the of limitations of Clockwise's Flexible Meetings is they are only available for internal meetings, where Reclaim works with internal and external one-on-ones so you can keep up with clients, partners, and contractors, in addition to your team. Another challenge that we've heard from many users is that Clockwise's Flexible Meetings feature is a bit too aggressive -- it doesn't let the other party opt in or get control over how the meetings get scheduled according to their preferences, and it can result in people burning out on the feature quickly. However, Clockwise does support group meetings in addition to one-on-ones, which is a feature we're launching at Reclaim later this year.

We are also planning a Group Task feature that will allow you to pull even more value out of the project management integrations we've seen such incredible demand for since starting Reclaim. We believe that we’re extremely well-positioned to build team features that can be smarter about how people block their time. Because we’ve built a system that is aware of priorities, keeps your schedule flexible, and thinks of time blocking as an intentional process, we have the power to think of meetings and projects in the same way that we think of other time blocks: they’re part of your prioritized plan, and we intend for them to fit neatly into the model we’ve already built around how we block time for you.

Over the next several months, we’ll be rolling out features that will empower teams to take advantage of Reclaim, and we’re excited to share them with you.

Clockwise vs. Reclaim: which should you choose?

This may seem like a silly question given the bias of this article’s author, but as we mentioned at the beginning, we do believe that we’re in the early innings of this space and there is a lot of room for different approaches. We’re believers in what we’ve created, and we think it better addresses the needs of people with busy calendars who need a lot of flexibility and intentionality in how they block time. 

But ultimately, it comes down to what fits your workflows best. Try them both and decide for yourself!

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