Summary
Users struggle with inefficient and error-prone scheduling, a lack of integration between tools, and the manual effort required to manage appointments and availability, leading to frustration and wasted time.

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1
Problems with Existing Solutions

Manual and Inefficient Scheduling Processes

Users spend excessive time manually inputting and managing appointments, availability, and schedules, leading to errors and overwhelm. This is particularly acute for businesses with multiple team members or complex appointment structures.

Quotes

Because our team has grown SO much over the past year or so, our simple system that has been working great is just no longer working. Our office manager now has to wade through a ton of “off” artists/stylists to figure out who is actually available. It can get overwhelming, and our office manager occasionally will give wrong availability causing obvious issues.

I’ve looked into When I Work (mainly geared towards the service industry), but it doesn’t look like our artists/stylists can add their own appointments which is very important.

I'm having issues organizing my hundred line App::new and I can only imagine that I'm going to add several hundred more lines of systems.

The problem is that we have to manually go to our calendar app (Calendly) and book all the appointments making sure we know exactly what session number it is for each day, then after that, send to the person via Whatsapp. The problem is that there is a high chance of making mistakes like I've done in the past but also, with the amount of clients growing, it's getting harder and more time consuming.

The current calendar/scheduling culture seems ineffective, time-consuming, and outdated. Why rely on 100 emails when we could just use tools to streamline the process and adjust as needed?

Frequency9
Intensity8
Specificity9
Solvability9
2
Problems with Existing Solutions

Lack of Tool Integration and Visibility

Users find it difficult to use multiple scheduling or organizational tools effectively due to poor integration. A lack of visibility into combined availability or event details across different platforms causes confusion and inefficiency.

Quotes

Ideally, what I’d like to find is a scheduling/calendar that our office manager can type in a date/time, and only those available show up rather than having to go through who all is off. I’d also like it to allow our artists/stylists to input their appointments themselves as they currently do.

I was thinking of using fantastical alone for task management but seems not good enough. Wondering why do you like Ticktick over any other app? What features you use most and like and how do you fully use it on macOS iOS and watchOS? I’m so confused trying to find perfect system

This is very slick. Exactly the when2meet/Doodle hybrid I've been hoping to find.

This is so great! One thing, if there are 2 Google calendars with overlapping events, it's difficult to see what the events are. Otherwise, huge fan.

I can integrate it to zapier but the only options are "create event" and "delete event" pretty much and I can't create custom events, so the way I think I should do is to create events on google calendar triggered by calendly and then integrate google calendar to calendly. But I've struggled with that and gave up for now.

Frequency8
Intensity7
Specificity8
Solvability8
3
Scheduling Challenges

Difficulty Managing Complex Schedules and Availability

Users struggle with coordinating schedules for multiple people, managing time-off requests, and accurately reflecting availability, especially in dynamic environments like freelance teams or event planning.

Quotes

Our artists/stylists are independent contractors that are free to schedule their own time off without needing approval from me.

I’ve looked into When I Work (mainly geared towards the service industry), but it doesn’t look like our artists/stylists can add their own appointments which is very important.

I’m a children’s librarian and I do children’s programming. I plan a variety of events for kids at the library that has a wide range of attendance. I have small scale events that are like storytimes, craft programs, and STEAM programs that usually has about 20 kids. Summer reading programs can have anywhere from 50-100 kids spending on the program/event.

My local salon uses Vagaro, which seems Very flexible.

Many business have moved to Google.

Frequency7
Intensity7
Specificity7
Solvability7
4
Communication Issues

Ineffective Communication and Coordination for Scheduling

Scheduling coordination often relies on fragmented email threads or outdated methods, leading to miscommunication, delays, and a lack of a clear audit trail.

Quotes

I’m receiving numerous emails from other executives and EAs with questions about availability that could easily be answered by simply checking the Scheduling Assistant and utilizing the “propose a new time” feature on calendar events.

It’s our job to investigate solo when able and minimize unnecessary touchpoints, IMO. There don’t seem to be any consistent recurring rhythms for alignment. There is seemingly limited usage of outlook tools, and scheduling feels disorganized, akin to messy Tetris, with extensive back and forth emails before a final decision is reached.

I find it so annoying when people throw things on my SVP’s calendar without consulting me first. That is one of the reasons I am there, for calendar support.

It takes a lot of time to form a stable group. You have to keep advertising and replacing characters. You cannot have an "open door" policy. In or out 90% of sessions or OUT.

I’ve been GMing various systems for a while now for a wide rotation of players that always seem to drop after the first session. I've tried all the methods and advice from both this subreddit and general scheduling tips— fixed time schedule and schedule coordination apps, delegating scheduling to another player, everything.

Frequency7
Intensity8
Specificity8
Solvability8
5
Group Dynamics

Frustration with Player Commitments in Group Activities

Users involved in group activities like TTRPGs experience frustration when players are inconsistent, frequently cancel, or fail to commit to scheduled sessions, leading to a loss of passion and momentum.

Quotes

I've been GMing various systems for a while now for a wide rotation of players that always seem to drop after the first session. I've tried all the methods and advice from both this subreddit and general scheduling tips— fixed time schedule and schedule coordination apps, delegating scheduling to another player, everything. Regardless of the tools and tips I use or employ, it seems all the games that I organize seem to either never come to fruition or end after the first session of play due to scheduling issues. Given the amount of times this has happened, I'm really just tired of having to go through this cycle.

Yes, all the time. I guess I'm just more into the game than my players. They are having fun, and after the session, they send memes and are more energetic, I also ask for feedback and they say nice things, but then the day we planned to play they ask to reschedule (or just move the session to the later hour and then everyone is sleepy and tired) because they suddenly want to do "an activity" (like a gym class or spontaneously went running and will be late etc). And it makes me feel so irrelevant, like, I prepared for the game, I stressed out the whole day about that, I could have also planned "an activity" if they could only tell me in advance!

We’ve been playing weekly since 1994. Always a week day, same time, same place. Even shift workers have been able to play by reserving that evening to not be on their rota.

I am in 2 campaigns currently as a player. 1. Campaign - not a dedicated weekday/weekend/time. Get's moved around frequently. Some players seem to now abuse this fact and the "i'ts my GFs birthday" or "theres a party I am going to" or whatever has become the norm, to the point we are meeting once ever 3 weeks. Awesome campaign, but it's frusterating as a player. Often we are missing a player even still, which makes the campaign weird mechanically.

Yes, all the time. I guess I'm just more into the game than my players. They are having fun, and after the session, they send memes and are more energetic, I also ask for feedback and they say nice things, but then the day we planned to play they ask to reschedule (or just move the session to the later hour and then everyone is sleepy and tired) because they suddenly want to do "an activity" (like a gym class or spontaneously went running and will be late etc).

Frequency7
Intensity8
Specificity8
Solvability6
6
Industry Needs

Need for Specialized Business Scheduling Solutions

Users in specific industries (hair salons, event planning, volunteer management) require specialized features like recurring appointment management, cancellation policies, and volunteer roster management that general calendar apps do not offer.

Quotes

I own a hair and makeup company that primarily services weddings, but we also provide services for a variety of events at our studio. We have about 20 artists/stylists on our team. Our artists/stylists are independent contractors that are free to schedule their own time off without needing approval from me. They also handle their own bookings through our contracting system, HoneyBook.

I’m looking for something open source, or with a fixed cost per month not exceeding €50. What I would like the system to be able to do is * Keep track of volunteer information (contact details, profession, volunteer group) * Schedule volunteers on specific days (does not need anything fancy, just this person is working on this day etc) * Volunteers should be able to login and see their schedule or the complete schedule of their group * Adding custom pages for general information (optional)

I have a hair treatment clinic and I'm struggling with scheduling our patient's next appointments. When they start working with us, we book 6 weekly appointments and then the next 4 every other week. The problem is that we have to manually go to our calendar app (Calendly) and book all the appointments making sure we know exactly what session number it is for each day, then after that, send to the person via Whatsapp.

You have two choices: either create a branded scheduling website where customers can book appointments online while you manage everything through an admin panel, or develop a branded app with the same capabilities. You can also opt for both for added flexibility.

I would start by looking into an automation tool like Zapier to see if Calendly has any integrations where you can add some automation to your workflow process.

Frequency6
Intensity7
Specificity8
Solvability8
7
Problems with Existing Solutions

Reliance on Outdated or Limited Tools

Users are often forced to use outdated or limited tools (like Google Calendar for complex team scheduling or When2Meet for its limitations) because better-integrated or more feature-rich solutions are too expensive or not a good fit.

Quotes

Currently, we are using Google calendar to show appointment times and their availability for each day. One calendar is for them to mark themselves off on, and another calendar is to input appointments.

I was frustrated with When2meet so my friends and I made a cool tool called Schej. It's basically When2meet with better UI and the ability to see your Google Calendar events while adding your availability.

This was so much better than both When2Meet (only allows a month out) and Doodle (charges for more than 20 options). So appreciate you!

My current company is also experiencing this, and it’s a huge pain. I was wondering if there’s an alternative to When2Meet that’s free, has a simple UI, and doesn’t charge for more than 20 options. But there doesn’t seem to be anything.

Our current intranet is a very old custom-built PHP/HTML/MySQL solution that is in need of replacement.

Frequency6
Intensity6
Specificity7
Solvability7
8
Unmet Needs

Seeking Universal Scheduling and Planning Tools

Users are actively searching for a single, integrated platform or tool that can handle various aspects of scheduling, task management, and organization, rather than juggling multiple disparate applications.

Quotes

I’m looking for a scheduler/calendar app that can make our team more efficient. I would consider our business needs pretty niche, so I’m having a hard time finding something that would help.

I’m looking for a good organizational / calendar app to keep my life on track LOL will take any and all suggestions <3

I use Google Calendar for events + Todoist for task-managing. The only issue with Todoist is there's a limit of 5 projects in the free plan, so not sure if that will be enough depending on your categorisation

I’m using Google Calendar (for scheduling), Todoist (for my projects and tasks), and Spark (for mail).

I built https://to-day.app while I was a student back in 2020 (after having used Notion and needing something more streamlined), and I’ve been using it ever since, even now that I’ve entered the work force.

Frequency5
Intensity6
Specificity7
Solvability8
9
Workplace Culture

Differing Calendaring Cultures in Professional Settings

Professionals, particularly Executive Assistants, encounter challenges due to varied calendaring cultures across companies, with some prioritizing tool-based efficiency and others relying on email-heavy coordination, causing frustration and adaptation difficulties.

Quotes

My new executive is technically more senior than my previous VP, but she isn’t the “top dog” in our region, and as an HR exec is more limited by other exec’s needs, meaning about 80% of her calendar must be coordinated around L1, L2, and L3 scheduling needs, leaving me with control over about 20%.

I’m receiving numerous emails from other executives and EAs with questions about availability that could easily be answered by simply checking the Scheduling Assistant and utilizing the “propose a new time” feature on calendar events. I understand executives/directors may not do this, but I find it frustrating when EAs don’t attempt to find answers independently before reaching out to me.

The current calendar/scheduling culture seems ineffective, time-consuming, and outdated. Why rely on 100 emails when we could just use tools to streamline the process and adjust as needed?

I worry that I may have to lower my standards and scheduling practices to align with this more non-strategic level of calendar management, as it seems they all (execs and EAs alike) utilize email threads for questions and confirmations before decisions are made.

I excel when EA calendar management culture promotes tool usage and independence for sorting scheduling challenges, with direct email communications as a last resort. As someone with ADHD, I’ve utilized these tool-based methodologies to leverage my strengths rather than let my condition hinder me. Relying on tracking numerous email threads for various items will be a daily challenge for me, especially knowing there’s a more efficient way to manage scheduling without excessive emails.

Frequency5
Intensity8
Specificity9
Solvability7

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