Why I switched between apps too many times
The first time I tried running a team on Google Calendar, everything felt oddly clean and simple. I could drop in repeating meetings, color code them, and people with Gmail accounts just clicked once to RSVP. The catch was when I had clients who lived in Outlook all day — suddenly those invites either vanished into limbo or showed up as text blobs that nobody could open. I remember sending a test invite to myself at a hotmail address and it literally showed as raw ICS file text in the email body. That was a facepalm.
Then I moved to Outlook calendars because I thought maybe it would play better for corporate folks. Honestly it felt more like driving a bus than a car. Every option is hidden under another ribbon or dropdown. The single biggest issue I hit was double booking. On Outlook, my recurring meetings sometimes reset their own time zone to UTC after a system update. I only noticed because a client asked why our meeting suddenly said 2 am. On Google Calendar the issue was different — it shifted daylight savings wrong for one team member. Both platforms had these weird silent resets that you would never expect until they bite you. ¯\\_(ツ)_/¯
So it was not a case of one being better universally. It was usually me picking which set of problems I was willing to tolerate that week.
Handling shared calendars without arguments
Real truth is nobody talks about calendar permission hell. In Google Calendar, if you try to share with someone outside your org, their screen just shows free or busy by default. If you forget to flip the detail setting, you get constant pings like “I see the block but what is it.” In Outlook it swings the opposite way. If IT has locked sharing down, you cannot open someone’s calendar even if they sent you a link. I had to email our IT guy, wait for a ticket, and then suddenly I had ten calendars layered on my screen like a mess of spaghetti.
What finally saved me was making two separate calendars. One public with no detail except appointment labels like “team call” and another private calendar where I kept all the personal notes. In Google Calendar switching between those was a single checkbox. In Outlook you have to juggle calendar groups but once set it works. It just took me opening way too many help forums and missing one call because the event wouldn’t display.
Trying to book clients without back and forth
Calendly is supposed to fix this dance but it behaves differently depending on which base calendar you hook it into. When linked to Google, it picked up my personal blocks immediately. If I blocked lunch, Calendly didn’t offer those times. With Outlook it kept offering slots that were technically blocked until I dug into the advanced settings for “event classification.” Apparently Outlook flags some meetings as “working elsewhere” and Calendly ignores them. My test client booked during my commute and I just stared at my phone saying nope. 😛
So if you want less drama, hook a booking tool into Google first. But if your corporate policy forces Outlook, you really need to test with a fake client before trusting it. I learned that the hard way with a double scheduled intro call.
Keeping mobile and desktop in sync
My iPhone calendar showing up blank during a busy morning almost made me throw it across the room. Google Calendar sync usually takes seconds. I update on desktop, check my phone, and it is just there. Outlook app though… you tap refresh and nothing happens. Ten minutes later events finally appear. The catch is Outlook mobile app actually caches old event times, so even if you fix something on laptop, your phone might be lying to you for hours. That’s why I stopped trusting it for same day updates. Instead, I keep Google Calendar app pinned in the first row on my phone. If a meeting is updated, I know the app will push it correctly.
And yes I tried using the iOS native calendar linked to my Outlook account. It sort of works, but recurring meetings sometimes skip a week. It made me miss one standup because my phone said the series ended when it didn’t.
Notifications that either nag or stay silent
Notifications sound small but they actually decide if you show up on time. Google Calendar lets me easily set multiple reminders like email one day before and popup ten minutes before. It always worked. On Outlook I’d set separate reminders and half of them default back to “15 minutes” after restarting the app. Which means I got spammed with too many dings clustered together.
One afternoon I sat down thinking I had an hour. Outlook calendar suddenly pinged me five times in a row for different things because they all reset. Meanwhile Google’s email reminder is excellent if you live in Gmail all day. The one thing I wish: Outlook had no option for SMS reminders the last time I checked, while Google killed off SMS alerts but at least the push notifications are reliable.
Offline access when WiFi dies
On a train trip I actually realized the biggest differentiator. Google Calendar offline mode works in Chrome. You open the calendar tab before losing WiFi, and you can still see everything. You cannot create new invites offline though. Outlook however had no visible offline access through the web portal when I tried. Its desktop app can show cached items but you better hope you opened it recently. I saw an empty screen once because my cache cleaned itself after update. That made me abandon responsibility for train meetings. Honestly if I know I’ll be offline I print the schedule now, which feels ancient but avoids the chaos.
Integrations that really decide the winner
The choice for me came down to hooks. Google Calendar easily connects into Zapier, Notion, project boards — it is easy to push and pull events. Outlook has integrations but half the time you need admin approval. Once I tried to connect Outlook to Trello and a permissions dialog popped up that I could not bypass. My admin later told me he denied it without asking because he thought it looked suspicious. With Google I usually just click approve and done.
For heavier enterprise use though, Outlook ties into Teams better than Google ever will. If you schedule a meeting in Outlook, a Teams link appears instantly. Google requires me to choose Meet separately. It saved a few steps but honestly caused some false links when a colleague expected Zoom instead.
The choice I settled for temporarily
After bouncing back and forth too many times, I sort of landed on using Google Calendar as my master and then syncing Outlook as a secondary. That way I meet clients where they live but I still trust my own base calendar. The downside is sync sometimes lags and duplicates appear, but at least I do not miss time zones or silent resets anymore. It is like having a messy drawer — not pretty but gets the job done 🙂