Which Email?

Choosing between Google and Microsoft
Google and Microsoft branded keys
Last updated:
July 16, 2020

The Key to Your Online LIfe

If you've been using email since the 90's (or earlier) choosing a new email for your small business isn't simple today. You've likely accumulated several accounts over time for different work and personal situations. While it would feel great to consolidate everything into one inbox, that's a lot of work and not good idea.

Email accounts and associated passwords are keys into your online life. It's important to compartmentalize them correctly into different personal and professional silos balancing convenience, security, and compliance with new privacy guidelines.

Gmail vs Outlook Servers

To be clear, I'm talking about email servers not the client apps on your computer or phone. For most people in the English-speaking world that means choosing between Google Gmail (part of G Suite US$ 72/year) and Microsoft Outlook 365 (Business Premium US$ 150/year).

Branded Paid Email Account

In the past you may have used a free email product from Google, Microsoft, Apple, or your telecom company for business communications. In 2019 it looks pennywise and pound foolish. Also, when everyone is highly sensitive to data privacy issues using a free email can look like you store client data in the equivalent of a shoebox.

Email – Not Just Email Anymore

Google and Microsoft Products with Email account linked devices and external services

Which one do you choose for your branded company email? The complicating factor is that Email has evolved from a simple tool for asynchronous communication into a:

  1. Archive (of communications and attached documents)
  2. Key to access online accounts and services
  3. Identifier shared across different service providers
  4. Identifier across several devices

I'll walk through a few personal examples.

1 - Email as an Archive

My browser-based Hotmail account from the mid 90's is an archive of receipts, invoices and conversations. My personal Gmail account took over that role after 2005. I recall collecting PDF attachments at that time too.

2 - SaaS Login

Google changed the paradigm in 2012 with introduction of Google Drive and associated services Docs, Sheets, and Slides. They aren't complete substitutes for the stand-alone word processor, spreadsheet, or presentation tools available then (or now) but for someone who rarely printed anything they were good enough.

Others followed a similar SaaS (software as a service) subscription model where access required an email to receive a license key for a downloaded app or to login into your service.

Needless to say, I have a lot of logins and passwords.

3 - Shared Credentials & Privacy

As Google, Facebook, Twitter and other services became more popular, sharing credentials or a single sign-in across multiple services started appearing.

It's convenient to click "Signin with Google" or Facebook or Twitter instead of setting up a separate email password combination each time. But this requires some faith that the parties involved are completely honest and transparent about how your information is shared and used by them. If you've been following the news that faith in the big tech companies has been misplaced.

Consequently, new regulations like CCPA (California Consumer Privacy Act) or GDPR are forcing more privacy disclosures and restrictions around the collection and usage of user data. It used to be that only people working in finance or dealing with patient data needed premium services that were compliant with SOX or HIPAA regulations about data.

More businesses of every size are exposed to compliance issues now. Balancing security and convenience, you want to silo where your business email is used as a login.

4 - Browser Logins

A further blow to consumer confidence came in a September 2018 Chrome browser update. By default, the web browser now logged you into a user profile when you signed in to a google account. There are privacy implications that for some people that outweigh the convenience to share browser settings and bookmarks between devices. The feedback pushed Google to add a control to turn off this default behavior in an October 2018 update (Version 70).

A simple workaround is to use a different browser like Firefox or Safari when logging in to your business G Suite account.

Security Disclaimer

First, nothing I mention here will prevent someone with state actor level resources from accessing your email account. Even if you use a service from another country not that most have reciprocal agreements to share data if there's a legal proceeding against you. The countries that don't share aren't exactly champions of privacy either.

Second, useable email needs good search. This means your email is scanned by the provider. It goes without saying that using that content to target you is uncomfortable but it's only starting to be regulated.


Word Processor

Gmail vs Outlook

Brief history lesson aside, either Gmail or Outlook are reasonable choices as a work email that uses your domain name. Microsoft offers company branding at double the price of Google ($150 vs $72) but many people absolutely need the Office Suite and want to stick with one provider. Telecom companies will charge you more for a company branded email that's less functional than the current Google and Microsoft products. Apple doesn't do business email from your own domain.

Some other considerations include:

  • Search - Gmail is better at searching my email.
  • Folders - Outlook organizes emails into discrete folders.
  • Tags - Gmail allows overlapping categories.
  • Nesting - Some hate Gmail's approach to nesting conversations.
  • Security -Both can be setup with 2 factor authentication


Microsoft Office is the current leader for word processing, spreadsheet and presentation software. Google and Apple offer productivity suites that are good enough in some circumstances.


Online storage is available through Google Drive or Microsoft OneDrive and are roughly comparable in features. They are not usable without an email account with their respective company, so it makes sense to stick with the same company for your storage as your business email


GDPR and the upcoming CCPA should be easily manageable for small business or consultancy using either Office or G Suite unless they are in finance or handle medical data.

The basic G Suite and Office 365 products are not explicitly compliant with SOX and HIPAA out of the box. To give an idea of the scope of the issues the HIPAA implementation guide from Google run to 26 pages. Both Microsoft and Google offer enterprise level versions that are compliant and can accommodate e-discovery requirements.

Client Communications

Video Conf
File Hosting

Both companies' tools offer similar features for communicating with client and sharing files. Quite often, you might find it easiest to use a client's favorite video conferencing or file sharing tool. If you need to create a new account use your business email if convenience is the priority,or use a new free gmail account for that access if security is the priority.


Google Hangouts is accessible through the Gmail interface, so it requires a Google email account. You can use a non-Gmail account as an alternate signin but your branding won't carry over.

Skype is a standalone product that can be accessed by an existing Microsoft email or a new account. Choose your Skype ID carefully as it cannot be changed once set.

Whatsapp has some of the same functionality as Hangouts and Skype through its desktop app. It requires a mobile phone number as an identifier instead of an email so that might affect how you silo access to private information.


Choosing which service to sharing files with clients is straightforward choice between Google and Microsoft. Apple's iCloud is not accessible to anyone outside your family so it's useless in this context. Google Drive and Microsoft OneDrive have similar features and are good enough for basic use cases.

If you need more granular control for client facing storage across different operating systems, Dropbox is the most popular solution. Google offers shared sign-in to Dropbox. Dropbox also has an integration with Microsoft Office that lets you collaborate on Office Documents saved on Dropbox.

Online Marketing

Email Marketing (1)

If you are committing time to marketing yourself online keep your primary business with Google for convenience. Google's single sign-in allows you to easily access several tools like website builders and email marketing tools. Google dominates search, PPC (pay per click) ads and video (Youtube). Google Analytics is a free product that's much better than the analytics data provided by most website providers and integrates with reasonably well with the other Google products. Microsoft is not a player in this space. Adobe has many products in that area, but they are priced for marketing agencies not small businesses.


It's clear that many people need accounts from both Microsoft and Google. The choice of which company to use as your branded email boils down to how much time you will spend using Office products compared to Google products for Client Communications and Marketing.

Granular Control with Google

If your work is mostly online and you want to manage it tightly use a business G Suite account and basic Office 365 account just for the productivity tools. Use the business account login for accessing other Google services.

You can silo your browser usage by logging into your G Suite account on Safari or Firefox instead of Chrome.

Use a different Google account on Chrome for personal email, Youtube-ing and search.

Focused Office Work

Setup Outlook as your primary work email if you need to focus on delivering work in Excel and Powerpoint, and plan to outsource your online marketing. Your marketing partner can provide access to their Google accounts with a free gmail account.