← Techstars Blog

I don’t remember when, exactly, but there I was again: trying to schedule a phone call, going back and forth and back and forth.

“Do you have 11am, 3:30pm, on Monday or 3:15pm on Tuesday open?”

Simultaneously flipping between days on my Google calendar, collecting potential times.

“…but what about these times?”

And round and round. Dejavu.

I had to blow it up. 


When looking for a tool that could help me schedule meetings efficiently and with a little style – I started by identifying my key needs:

  • The chosen solution couldn’t make scheduling time impersonal or create more work for the other party. (Working with customers and partners, I definitely wanted to make things easier for both of us.)
  • It had to sync with the major calendar services and send nicely formatted invites (Google Calendar, iCal).
  • The solution had to keep itself in sync automatically with my calendar (I use Google Calendar).
  • It had to have room to represent ‘me’ – meaning, I wanted the communications to feel personal, not like booking time with some big company or dealing with a robotic, automated interface.

I preface this knowing that there are literally thousands of tools out there for scheduling/booking – especially getting into enterprise level tools and small business appointment scheduling platforms and the like – but I’m sticking to a more personal use case for this article. Below are the applications which work for me and the way I interact with people in my day to day. I’d love to hear tools or methods you use in the comments below.

1. Calendly

My number one calendar tool right now is Calendly. I use it to let people schedule times of their choosing in times that I have available. It syncs with my Google Calendar and never shows me available for times that are already taken. The recipient can choose our meeting length and it adds the event to both our calendars.

Why I like it so much:

  • It feels personal: It has a picture of my face and a short intro. I can also customize the colors and all the event descriptions.
  • Because it will show the scheduler all my open time slots, they can easily pick a day and time that works for them instead of wasting time going back and forth over email.

2. YouCanBook.Me

A close second is a tool I used for a long time (and still do on occasion) called YouCanBook.Me. It offers a really robust set of tools and customizations vs. Calendly and is just as easy for both parties to use. I ultimately chose Calendly as my main tool because I liked guiding people to select the right amount of time a little more explicitly and my Calendly page seemed more ‘me’.

Other than that, YouCanBookMe is a fantastic tool and will let you play with far more settings than Calendly. It also plays nice with Google Calendar and iCal and keeps in sync with both automatically.

Screen Shot 2014-07-21 at 4.07.58 PM

Take a look at all the features you can have with YouCanBookMe. The free option is great, but if you want to get your whole Organization on a service like this, YouCanBookMe could be a great option.

3. Assistant.to

For a new ‘old school’ approach – try Assistant.to. If you’re worried about sending people links or them struggling with the booking tools above, this could be perfect for you. Assitant.to works right in Gmail and adds an interface to pull open times of your choosing right from your Google Calendar. It then inserts a nicely formatted list of those times for the other party to peruse right in the email! (Watch their video here)

Pro Tip

Remember to always insert these into an email in a fun or personal way. I work to make sure I don’t just ‘link drop’, but preface it with something like:

‘Here is a link to my calendar, you can book anything that works best for you’.


‘I hope this will make it easier for us to connect’.

I always use language that doesn’t make it seem like a requirement or that I am too lazy to give you times, but that it is a potentially easier option and that I’m flexible to schedule in other ways.

In my experience, people have been thankful for the link and some have even adopted one of these tools themselves. With the right message, you can easily position this as an exciting way to be transparent about your availability. It’s especially great for people you will talk to on many occasions over time. They love that they can always get to your calendar and find time with you.

Bonus tip: Since I use these calendar links so much, I added them to a nifty tool called Text Expander for Chrome, so I just have to type @cal (or whatever I want to define as the shortcut) and it pops the link right in for me. This is useful for all your commonly typed phrases, even credit card numbers, URLs, addresses, or for those words you can never seem to spell right.

How do you hack your day for better productivity?  I’d love to hear about the tools that make your day easier.

Mitchell Cuevas
(@mcuevasm) I am the Sr. Marketing Director here at Techstars, am passionate about helping entrepreneurs, and am obsessed with finding, playing with, and implementing all the best new marketing (and other) technology I can get my hands on.

  • Pedro Sorrentino

    Great post @mcuevasm! Really helpful. I use Assistant.to but Tony (Brazil CM) talked to me about Calendly

  • Anupe Diaz

    Would be great to see what your reboot in 2016 may look like as the market has changed – Calendly has evolved, x.ai is on the horizon, and my tool http://Appointment.one has a unique angle as well (auto populate your calendar invite with rich data on all attendees for those blind meetings we all get).