5 Reasons why Calendar Management tools are vitamin pills

Dario De Santis
7 min readOct 14, 2021
Photo by Michele Blackwell on Unsplash

Many years of product management experience taught me that one of the most effective analogies to categorize a product consists of determining whether it’s a painkiller, meaning it solves a real problem that is affecting a significant user base, or a vitamin pill, which means it’s an incremental improvement that does not have a radical impact in terms of value.

Recently, a new wave of intelligent calendaring tools are heating up the productivity market by promising huge time savings and a more efficient time allocation, mostly based on scheduling automation and proactive suggestions on when to take a break or book focus time. Some of these tools simply offer improved workflows, while others go one step further and implement proactive AI-based calendar management.

Although, there is no doubt that automating tedious tasks and proactively addressing user needs deliver value in terms of time savings, there are a few limitations that prevent such solutions to solve fundamental problems and revolutionize the industry.

1. Workflow tools transfer coordination cost to the invitees

You contact Frank and you both decide you need to have a meeting to discuss a specific topic, so Frank offers to organize the meeting. You think: “how nice of him to take care of the scheduling!”.

However, you receive an invitation from him through a tool that shows his availability and asks you to pick a slot. At that point, you are a bit frustrated because you have to open your calendaring app and go back and forth between Frank’s calendaring tool and your calendar to figure out which of Frank’s available slots would also work for you.

This is definitely a really good experience for Frank who uses the tool, but it does not solve your problem, especially if you (likely) don’t use the same tool and you can’t have your availability information readily available.

Imagine you are a salesperson approaching an important decision maker. Do you want to start with the wrong foot and have her do extra scheduling work while she thinks you are a crafty egoist?

2. AI tools can’t do much for you

Throughout the years, you have perfected a routine to maximize the outcome of your day. You are so rooted in your habits, that changing isn’t easy: it comes with a new learning curve and the cognitive cost of destabilizing your daily balance with the hope to find an uncertain more effective setup.

Unless you are merely a victim of your calendar, I am sure you, busy person, have recurrent activities that you perform at specific times of the day. E.g., workout at 3pm, lunch at 12pm, etc.

In addition to those activities spread throughout your calendar, you, an enterprise worker, have a series of must-attend recurrent meetings with 5–10 invitees.

Start putting all those constraints in the AI tool and suddenly there isn’t much wiggle room to move events around. Hence, the AI contribution is limited to saving you some time for scheduling and rescheduling events every once in a while.

3. Calendar management AI may push you to work overtime

One of the promises AI-based calendar management tools make is solving the problem of having multiple bookings for the same time slot. This is a typical issue in the calendar of a large enterprise manager, who, on average, spends almost 30 hours/week in meetings.

Imagine you have a double booking to solve. The AI looks at the relative priorities of the overlapping events, makes a decision based on your and the other participant availability, and ends up rescheduling one of the two events in one of your free slots automatically.

Sounds awesome, no?

Yes, until you realize the meetings that get rescheduled “eat” into the free slots you need to accomplish your solo tasks; in other words, it reduces the time for you to focus on the work that matters.

As a consequence, you are forced to work overtime to complete your tasks, thus negatively affecting your health and personal relationships.

4. Task-based prioritization is flawed for most people

The reality is few people use tasks, and most of those people aren’t diligent enough to keep track of everything in just one tool. I am definitely one of those people. I tend to keep my todo list items scattered across cloud note-taking tools, physical post-its, mark-up in various documents, flagged emails / instant messages and applications left open on purpose on a specific screen to act as a reminder.

You can’t change the way you work overnight; therefore, when you start using smart todo lists, chances are, you’ll almost immediately get a couple of bad calendar reshuffles and end up uninstalling the tool.

5. They make it easier to book your entire day, limiting your productivity

In your ideal world, would you prefer to feel the pressure of following a tight schedule or doing whatever you like without looking at the calendar, at all?

Calendar management tools make it easier for you to put new events and reshuffle existing ones in your calendar, which saves you coordination cost but results in a calendar that is more full than ever!

Do you remember that day when your calendar was miraculously empty and you’ve been able to close your day by exceeding your productivity expectations, with spare time for leisure?

Photo by S Migaj on Unsplash

Well, with an AI that reshuffles and spreads appointments throughout your day, you can forget that sensation. Any open slot is a good candidate for a reschedule, and your days will suffer from a more constrained pace.

The more the events in your calendar, the more your day is divided into chunks with a minimum size of 30 min each. And those chunks are limited in number (just 16 for an 8-hour day), which means your overall productivity is limited: there is only so much you can accomplish in a day made of back-to-back events.

Following the wrong North Star

If you have been paying attention to the 5 reasons why calendar management tools are vitamin pills, you may have noticed that the main limitation of calendar-based productivity tools is determined by the fact that the calendar is not an efficient tool to break down your day.

Photo by Estée Janssens on Unsplash

Yes, the issue is the calendar itself, which is an old concept unable to accommodate demanding modern workflows. Over time, our society evolved with technologies towards new levels of productivity, however, the basic function of the calendar stayed pretty much the same since Julius Cesar.

Based on your day divided into chunks - the wrong playground - Calendar management tools provide moderate time savings and, when not perfectly designed, come with the risk of generating overtime work or schedules that you don’t like.

Resolving scheduling through AI is a very hard problem; accuracy and effectiveness of reorganizing someone’s calendar depend greatly on fundamental variables outside the reach of calendar management tools. For instance: user implicit intentions, preferences, external factors affecting priorities, and more.

So, why keep wasting increasingly greater resources trying to play with someone’s schedule, only to provide marginal improvements towards the intrinsic limitations imposed by the outdated calendar?

A new painkiller is coming soon!

Photo by Hal Gatewood on Unsplash

Wouldn’t it be amazing to have a new way of working that allows you to do anything you want or should do at any moment, without constraints dictating the pace of your day?

A day that becomes fluid, where the right interactions with the right people happen at the right moment, for the right amount of time, in a magical way.

You might think: “ok, dreaming is nice, but what’s available today to make me more productive?”

Instead of making it easier to clutter your calendar, constrain your day and force you to work overtime, Tweelin allows you to remove 1:1 events from your life by transforming them into impromptu conversations presented at the right time, hence, giving you precious time back to focus on what matters.

Photo by Pablo Heimplatz on Unsplash

Tweelin makes you less dependent on your overcrowded calendar, until, one day, it will completely free you from it, thus, removing the biggest factor that limits your ability to reach unprecedented levels of productivity with a better work-life balance.

How does it do that?

Tweelin observes, learns the way you work and communicate, understands your preferences, collects your explicit intentions (or wishes), and is able to predict the right moment for you to get in contact with someone. All in a fluid manner, without creating any event in your calendar.

Learn more at www.tweelin.com and join the waitlist to access exclusive offers!

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Dario De Santis

Long-termist visionary technology Entrepreneur and Product Leader, with a strong passion for improving people's productivity through innovative solutions.