Bandwidth – You need decent bandwidth before you think about moving some or all of your services to the cloud. If the bandwidth is not sufficient you and the rest of your staff will have a poor user experience, be that with something as simple as checking your office 365 email or using an RDP session to connect to your shiny new virtual server up there in AWS or Azure. So poor broadband plus user demand equals poor experience.
What are you actually trying to move? Just email to office 365, or perhaps file data to onedrive/Sharepoint or Google drive. Do you have applications that need to be moved or migrated to the cloud. You need to have a plan and strategy in place to make sure you have either verified your applications are cloud ready or there is a SAAS version of them available for migration. Alternatively you may need to create a full virtual environment running Remote desktop services of Citrix to allow for a more traditional working environment.
Security –With great power comes great responsibility, Office 365s email platform now has 180 million users (As is usual in Microsoft’s April quarterly report (for Q3 FY19), they gave a new number for Office 365 users. In the earnings call, CEO Satya Nadella said that “Office 365 commercial now has 180 million users.” ).So as you can imagine this makes these type of SAAS and IAAS providers accounts a prime target, for hackers and spammers etc, looking for an easy way in. So two factor authentication and complex passwords are really an essential at this point, unless you want to end up with the GDPR commissioner knocking on your door asking where your adequate security measures are, after the fact!.
Compliance –As part of your move to the cloud you need to consider the compliance burden that all businesses face from GDPR, HIPPA to SOX etc. Whilst security and encryption tools go a long way towards helping achieve compliance with some of these standards, depending on your industry vertical you may also be governed by data location rules with regards to the data you keep and its type and security.
Hybrid –Most small business operate on a hybrid type setup moving some services to the cloud and operating some in house, for either compatibility or compliance reasons or a mixture of the two. Often starting with the Microsoft office 365 email migrations first and then Office 365 SharePoint combined with Onedrive for the local file data, finally the customer CRM and accounts applications are usually either migrated to a compatible provider Life Salesforce or Xero, or put into a virtual server (Amazon AWS or Microsoft Azure) with access over VPN or https+RDP etc.