Bots, polls, bookings and publishing – which is best for calendar scheduling

One of the most frustrating experiences in business these days is scheduling meetings with people over email. The more people you have; the harder it gets. Add in external people; even harder. Throw in multiple time zones; now you’re up for a challenge!

There are now multiple tools available for simplifying meeting scheduling. Some of these have been around for a while and are simply unknown, whereas others are more recent and change the way we book meetings.

The whole issue of booking meetings is such an issue I wrote several topics about it over at The Office 365 Good Etiquette Guide. (Look for topics starting with “Organising meetings”.)

The premise of this post is to focus on meetings with people outside of your organisation, and the tools available to make that easier.

What’s in the box

Before we look at third-party tools, let’s look at those already at our disposal within Office 365.

For those inside your organisation there is a feature known as the Scheduling Assistant, and it’s been there for a while. A long while; since Outlook 2007 in fact. If this is news to you stop right now and read the previous link about how it works – your colleagues will thank you.

Exchange Server as the back-end for Outlook has had the ability to share calendars with external organisations since the 2010 version – which meant it was also available in Office 365. In fact, I wrote a blog for the Microsoft site in mid-2011 (two months after Office 365 was released) explaining how to set it up. Effectively this meant an organisation could establish a relationship with another organisation (“federation”) that would allow users in each organisation to use the Scheduling Assistant and see each other’s availability. This is beneficial in a variety of scenarios, such as: a merger/acquisition, close partnership or joint venture, outsourcing, or any other close relationship where there might be a lot of meetings with people from both organisations.

I’ll show you mine if you show me yours

Outlook has the ability for individuals to share their calendar with other individuals, and to request the same access in return.

This is beneficial in short-term scenarios where you want to meet with someone as it gives you the ability to share for a date range, or just keep the sharing open.

In my case I have used this in scenarios where some of the partners I work with want to book me for workshops with their customers. By sharing my calendar with them, they are able to see when I am available as well as others in their organisation at the same time – while on the phone with the customer. To the partner, I appear as one of their own people.

Unlike Exchange calendar federation, sharing calendars is performed on an individual level which means that only the sharer’s calendar is accessible – not anyone else in the organisation.

More information here.

Share your calendar with the world

Well, not entirely – but you can publish your calendar so anyone with the link can access it at any time. This is useful for users who are often dealing with people outside of their organisation on a regular basis. As an independent consultant this is important for me as 100% of the people I deal with are external. When you publish your calendar, Exchange generates a HTML page that you can link to directly. In my case I put this link in my signature and invited people to click it if they wanted to book a meeting with me. This cut down the amount of calls and emails I received with people asking when I was available, as I’d simply direct them to that link which allowed them to see a live version of my calendar at any time.

More information here.

Just book it!

Recently made available in Office 365 is the Bookings service which publishes your calendar but offers significantly more features and controls. Having switched to this method myself recently, I wrote a piece recently explaining why you would use it and how it works.

This is generally aimed at cutting to the chase and booking people who are effectively resources or part of a team. This works well for me individually, as it also means my meetings have a purpose. Instead of people simply booking a meeting with me they can choose what type of meeting it is, and I can build some business rules around that. This cuts down the back and forth over meetings a bit further.

Let’s take a vote

FindTime originally began as a Microsoft Garage project (ie. where people hack together cool ideas that may or may not come to life). Effectively this allows you to create a meeting poll with any number of people, both internal and external. For internal folks, FindTime shows you their availability so you can find slots where you know that they are available. The meeting initiator nominates a bunch of days and times and sends out a meeting poll to all the recipients. When everyone completes voting, a meeting invite is automatically sent based on the first available nominated meeting slot that everyone agreed on. If for some reason you as a voter don’t see a suitable slot, you can nominate additional days/times and the voting begins again. This makes the whole process incredibly quick.

While it was still a Microsoft Garage project and not an official project, over time bits of FindTime found their way into Outlook on the web under the functionality of “find a time” which wasn’t as good. Microsoft then announced that FindTime would be shut down. We the users spoke, the product was saved, and is now full feature component of Office 365.

Rise of the machines

Also, inside of Office 365 is a preview service known as – also branded as Cortana for your calendar. This is not the first AI bot for scheduling, and won’t be the last, but it is included with of Office 365 at no extra cost.

I’ve used Cortana a few times for scheduling and while it’s “ok”, from a usability perspective I found it a bit slow to begin the scheduling conversation. The main issue I have with Cortana is the name – people know it. So, when I CC Cortana and ask it to schedule a meeting, what I’m saying to the other person is that my time is more important than theirs. This made me feel uncomfortable as I try to treat everyone around me equally, and as such I’ve stopped using it.

All that is in Office 365!?

Yep, absolutely. There are a lot of features in Office 365 for scheduling meetings, many of which remain unused as people simply don’t know what they don’t know.

How they stack up against each other

Product Scheduling Assistant Calendar sharing Calendar publishing Bookings FindTime Cortana
Scenario You want to send a meeting invite to one or more people You want specific external people to be able to send you a meeting invite You want any external person to be able to send you a meeting invite You want clients to book meetings with you, but want to specify meeting types, conditions and rules You want to schedule a meeting with multiple external (and maybe internal) people, often across multiple timezones You don’t want to talk to the person you are organising a meeting with, until the meeting is booked
Audience Anyone inside the organisation, or externals who have shared their calendar with you External people who also use Outlook and need to see your availability External/anonymous people who need to see your availability and don’t necessarily use Outlook Clients who need to book specific meeting types Internal and external people who can’t necessarily see each others calendars External people
Where to you find it Inside Outlook Inside Outlook Inside Outlook Separate app Outlook add-in Email
Pros Visibility of people’s calendars People outside your organisation can see your calendar Not dependant on targeted sharing Separate web interface, set business rules, create groups of people, define meeting types and durations Vote on multiple meeting options Defer meeting scheduling to an “assistant”
Cons None None Anyone with the link can see your availability Calendar appointments go through the Bookings service, so any changes in your calendar are not reflected in Bookings or the person who booked the meeting People’s availability can change while voting is occurring Impersonal, no visibility of the process

For the sake of those who like visual representations, here’s a pinwheel for you:

What’s else is out there?

Outside of Office 365 we have similar solutions that in some instances go a step further.

Competing against Bookings we have services like and others which cost extra and have their own benefits.

Competing against Cortana/ we have services like and other AI-based scheduling services which also cost extra and have their own benefits.

Looking further at

One thing does well is makes the bot appear more human with the names of Amy Ingram and Andrew Ingram. It can also be set up to use your corporate domain (ie. unlike Cortana which only uses and gives away the fact that it’s a bot.

If you have regular meeting places for coffee, breakfast, lunch, dinner or the office – these can be defined as locations so when you say “Amy book a breakfast meeting with John at 8am” it will send a meeting invite with the address details.

One annoyance of is that at this point it doesn’t integrate with Skype for Business but does with Skype and other service that support static meeting URLs (ie. Zoom, GoToMeeting, etc.). This is where Cortana has an advantage in that you can request the meeting to be via Skype for Business and it will send a meeting invite with the relevant conference details.

A very small benefit of is that it recognises when you are scheduling a meeting with another user who is in a different time zone, so if your preference is only to meet between 8:30am to 5:30pm but the other person is in a different time zone where the business hours don’t cross over with yours – it will tell you straight away. That being said you can respond back and ask to stretch to meet the time specified.

A challenge of using is that as much as it uses natural language to communicate as best as possible (ie. you can talk to it like you would a real human assistant), it is still a bot that requires parameters to do its job. So, if you already deal with bots in your personal life such as Google Assistant, Siri, Alexa, or even Cortana (on Windows 10 and as a mobile app on Android and iOS, or the Invoke speaker) – this is another one to learn how to communicate with.

Which calendar helper to use when?

At the end of the day it comes down to personal choice and requirements, as well as knowing your audience.

If you were dealing with a prospective client, you would not be doing yourself any favours by deferring them to a bot, polling tool, or web page where they can find a free slot themselves. In that instance you’d get them on the phone and treat them with the attention and importance they deserve.

How I use them

I use the Scheduling Assistant when bookings meetings with anyone who has shared their calendar with me (ie. partners or clients I work with regularly).

Similarly, I share my calendar with partners and clients who regularly engage me and need to book me for meetings or workshops – so they don’t have to ask me when I’m free, they can just send meeting invites to me directly.

In my email signature I have a link to my Microsoft Bookings page to make it easier for anyone I email to schedule me in for a meetings, chats, or workshops. Previously I had a link to my web-based published calendar however have switched recently to Bookings, and I may end up switching back.

I generally only use FindTime when scheduling meetings with people from multiple organisations and/or in different time zones.

I personally found the bot approach unprofessional and am starting to think similar of Bookings – but this is subjective as others would be fine with them.

My recommendation would be to try each one for a bit and see what works for you and in what scenario.

Microsoft Bookings – a hidden time-saving tool in the Office 365 toolkit

Microsoft Bookings is customer-facing online booking & scheduling system for users of Office 365. It is part of the value-add tools targeted at small businesses such as Invoicing MileIQ, Listings, Connections, and Outlook Customer Manager.

Originally, Bookings was only available to customers of Business plans however is now available to Enterprise customers as well – while the others are yet to cross the licensing bridge.

What is it, and why would you use it?

Bookings competes with online scheduling systems such as which are gaining in popularity as they cut down on the back and forth of setting appointments by simply publishing your calendar and allowing external people to find available slots.

Apart from being included in the Office 365 suite I’m not sure what the differentiator is for Bookings, but as I was considering using it made sense for me to use Bookings instead.

There are a number of different ways people can schedule meetings and appointments in the corporate world (I’ll be writing a comparison piece on those options soon), whereas Bookings is aimed more at the ‘customer off the street’ market – in that the calendar is made available publicly and anyone can come along and book an appointment.

While I don’t normally focus on small business customers, I think in this new era of customer-centric business approaches this particular tool can serve even enterprises – and not just in retail or small businesses.

How it works

Bookings allows multiple businesses to be set up within a single tenant. This means that external-facing teams can have their own setup, and different users assigned.

Each booking calendar can have different options set such as time increments, lead time (aka notice period) for bookings or cancellations, whether customers can choose specific team members for the booking, language and time zone, business hours, as well as logo and theme.

Once the basics are done staff can be assigned to the booking calendar by selecting their profile from Office 365. Options can be set such as selecting business hours, but also to allow events in their Office 365 calendar to affect availability.

Each calendar can also have different appointments or services set, which can be customised. For myself I don’t expect people to come to me from Facebook or the general web, however have defined a number of different meetings types available for my clients and partners to choose from. In my instance I chose not to put prices in to any of the services as the prices may vary depending on engagement, but also there are plenty of meetings I have with prospective clients or partners where I don’t charge.

When a calendar is published a URL is generated which can be placed on a website, or in my case – added as a link in my email signature:

This has allowed me, my clients and partners to significantly reduce the amount of time we spend trying to organise meetings. It has also allowed them to continue accessing my availability and booking meetings in without even consulting me – which removes myself as a bottleneck.

Who can use this?

If Bookings is enabled in Office 365 – anyone can use it. This page explains how users can access it, and then configure the calendars.

While it is aimed at small businesses I feel that it can be better targeted at small teams. Many organisations will have teams that can benefit this that are not necessarily external or public facing.

What are the shortcomings?

While this tool cuts down time, it also removes human interactions. Some may say in particular scenarios this is not ideal, however if the expectation is set then nobody’s feathers should be ruffled. When directing someone to use the Bookings page – simply explain in one line how this will help.

My two biggest shortcomings are that there is no integration with Skype for Business, and the bookings are not direct. What I mean by the latter is that when appointments are scheduled in Bookings, it is from the system itself – not between the two people. This means that when the booking appears in my calendar, if I move or delete it there is no effect on the actual booking, nor is anything sent to the user. If I want to go back to the person and change the time, I need to do this via the Bookings app or communicate directly.

The fact it doesn’t integrate with Skype for Business is disappointing, as it would save further time if upon the booking creation a Skype for Business meeting was included so people on both sides of the fence could simply connect straight in at the scheduled time – instead of having to send a separate meeting.

Why use this over other methods?

I will be publishing a piece in the coming week comparing a variety of different scheduling tools available to us from Office 365, however why use Bookings specifically:

Bookings vs. Reasons
Publishing or sharing your calendar Individual-based only

Can’t apply rules to the appointment

FindTime Requires a human to initiate the poll
Cortana / Requires a human to initiate the conversation or others Separate tools that add costs