Preparing Your Team for a Cloud Migration

Your boss reaches out and informs you that it’s time to prepare your team for a cloud migration. You are responsible as the leader of your department to manage the change that is coming. What steps should you take?

We’ve noticed that many people underestimate the work required to prepare, support, and help their team in making organizational change. In this blog, we’ll outline some of the steps you can take to prepare yourself to prepare your team for the transition.  

Understand the Why

It’s your job to be the leader and help calm the inevitable fear, uncertainty, and doubt that change brings. Someone on your team is going to ask, “Why is this happening to us?!” Do your research and reach out to your organization’s leadership team for information about the purpose of the migration. They may have a Migration Guiding Principles document already prepared and will be able to provide you with an understanding of the reasons (and benefits!) behind the move.

To be prepared to answer questions from your team, you should know:

  • Why are we making the move?
  • How does this align with our strategic initiatives?
  • What are the corporate goals of this move?
  • What are we losing? Will there be pushback?
  • What are we gaining? What doors will this open?

Create a Migration Dream Team

Choose a business champion for the migration project. This person will be responsible for liaising with the migration team. They will also be responsible for communicating information and updates about the migration to your team. You want someone you can trust to own this task and treat it as a priority, instead of something they’re doing off the side of their desk. Be prepared to delegate their current workload for at least 1-2 months.

Choose at least two cloud champions. These people should be confident using technology. They don’t have to be savvy or proficient, but they should be curious, eager to learn, and good with understanding new technology. These will become the go-to people for your team to reach out to with questions about how to use the new cloud tools. You want to choose folks that are helpful and approachable. Create a plan with your business champion about how your team will reach out to the cloud champions for help (such as a form, Teams channel, or directly via email).

Make Time for Your Team to Adapt

Your team is going to experience some discomfort and frustration during this transition. However, you do have some control over keeping these waves of discomfort from getting out of control and transforming into a storm of overwhelming anxiety or burn out. The stress that comes from change and the unfamiliar is inevitable. Help your team by creating space for the migration. Reprioritize deliverables and shift deadlines. It’s extremely rare that an entire department can hit the ground running at the same speed and proficiency after switching to a new environment to store, share, and work on files.

Your team needs to know they should not book any important meetings or work deliverables in the first three days after the migration takes place. (Yes, you heard that right. We’re serious.) They need that time to orientate themselves with how to access your files and familiarize themselves with how to use the new tools in their digital toolkit.

If certain people whiz through the change with zero issues, fantastic! Identify who they are by planning for frequent check-ins with your team members to “take their temperature” and assess where they are at. What do you do when you find people who are thriving? Have them share examples of tips and tricks or productivity strategies at team meetings. Also, ask those that are willing to work with coworkers who are struggling to offer extra support. Suggest they book a 15-minute one-on-one meeting to touch base, screen share, and walk-through tasks they may be frustrated with.

And for those that are struggling? Have them share their pain points in a safe space that fits your corporate culture. You don’t want to have a team meeting devolve into a rant session, so have frustrations funneled into a central place to figure out the key challenges people are facing. Ask your cloud coach or in-house cloud champions to brainstorm solutions and present them at team meetings.

What about those that are really, really struggling? That’s where post-support comes in. We’ll discuss that later on.

Communicate Early and Often

Communicate to your team that change is coming. Do this verbally at team meetings as well as through email. Reach out to key people in your team to prepare them ahead of time. Certain people take change poorly and a one-on-one heads-up chat can make a world of difference so that they don’t react (get angry, panic, give their notice) during a team meeting. Let your team know that you will announce any changes that will affect them to give time for people to prepare and point out potential outcomes that can be avoided.

Share small updates as you receive them. Provide small, snackable bites of information that are easy to digest to reduce the risk of overwhelming people. People will read small, one-page memos every day for 50 days with ease. They will find any excuse to avoid reading a 50-page PDF that says the exact same thing. A few examples of what to break into separate conversations include:

  • Why the change is happening (“We are switching to the cloud to eliminate all physical servers. This benefits you because…”)
  • What will change (“Our old data will be read only; our current data will reside in SharePoint”)
  • When the change will occur (“The X week of X month; data will be inaccessible from X date to X date”)
  • Who your cloud dream team are (“X and Y will be here to support us through the migration”)
  • What will be affected (“Process to edit a PDF will change, and we will provide training on how to…”)
  • Where to get help (“Please review the Cloud Migration communication site for updates about…”)

Prepare and send out a What You Need to Know document explaining important dates and deadlines. Some migration teams may prepare these for your department, so have your business champion ask the migration team who should own this task. Include key dates and critical deadlines such as when there will be a hard stop on working in the old environment and when they can start working in the new environment.

It is also handy to give instructions on what they should do if they need help, what training will be offered to them, and actions required of them before the migration happens. This can include things like:

  • Clean up your files – Organize all those messy, loose files into their correct folders; restructure/move things around and delete or archive ancient files.
  • Upgrade your files – Look for legacy Microsoft Office files and convert them to the modern format (docx).

Commit to Custom Coaching

Attend the training and encourage all of your staff to participate. People are used to attending large, in-person, multi-day classroom training sessions, which are often time consuming and boring. Let your team know that you are bringing in a cloud coach from the migration team to work with your business champion and Cloud champions to create custom coaching sessions tailored to their specific needs. Coaching is meant to create space for informal, participant-driven discussion where your team can share feedback and engage in real-time dialogue about their needs. Live demos are used wherever possible to show cause and effect of actions, as well as demonstrate the “art of the possible” with the new environment. Encourage your team to submit as many questions as they come up with to help the coach understand where their concerns lie and where they want to focus.

Schedule a “Pre-Migration: What’s Coming” coaching session a week before the migration begins. Your migration team cloud coach will cover concepts like the migration schedule, what to expect before, during, and after the migration, governance policies, naming convention protocol, and most importantly, where to access your data and how to navigate in the new environment.

Schedule a “Post-Migration: Now What” coaching session a day or two after the migration is completed. Your migration team cloud coach will cover concepts like file management, searching for files, editing files, and communicating about files. There is often a sizeable amount of time set aside to “ask anything”, so team members can mention situations they’ve run into or expect to run into where they will need assistance.

Prepare for Post-Support

Ensure a method of communication is set up to address post-migration support requests. We recommend that staff do not directly email the support team if possible, and suggest the following as alternatives:

  • A Microsoft Teams channel to capture and address questions and issues in message threads.
  • A process around your organization’s internal IT ticketing system.
  • A Microsoft Form to capture issues, display trends in data, and deliver messages to the support team (via email or Microsoft Teams).

This allows you to collect submissions and direct requests to your internal Cloud champions first. If they can’t figure it out, you can prioritize if the team member’s request should be escalated to your internal IT department’s Support Desk (if it’s a technical issue) or directed to one of the migration team’s Cloud coaches. Encourage your in-house Cloud champions to stay involved so they learn and can take that knowledge with them to support others.

Prepare to have the Cloud coach from the migration team work one-on-one with members that need more assistance. Remember those people that are really, really struggling? Everyone learns differently. Some people need a slower, more personalized learning experience where they can be hands-on in their real environment and driving the conversation with their coach. The coach acts as their co-pilot, guiding them on how to perform a task or find something they need. Work with your team’s cloud coaches to identify which team members are a good fit for a one-on-one session. Sessions can be recorded to capture the knowledge and share with the team, and coaches often produce a written step-by-step summary of the solution with annotated screenshots that can be shared with your team to ensure everyone is on the same page.

Show Your Commitment

Be an example for your team. Don’t ghost after the migration kick-off. It’s crucial that your team believes you are excited about the change. (Wait…you’re not excited? Here are some reasons why switching to the Cloud is awesome…and here are a few for the business owners reading this). Show your investment in making the move a success by being the first person to sign up for coaching and adopt the tools wholeheartedly. This may require you to invest a little more time than others to learn, practice, and become a champion that others can come to for help.

Don’t shy away from real talk. Be transparent that things aren’t going to be easy at first. Be clear that some things will be different forever. Be frank that change is hard and will take time. Here is a little pep talk we find that works well, and even includes a few direct quotes from some of our clients:

The day after the migration will not be a normal work day.
I need to highlight how challenging the first couple of weeks post-migrations can be as we get used to the “new world” and a new way of working. Migrations are hard. It’s like learning a new hobby or sport. Your muscles will hurt. You will feel clumsy. You will fumble through using Teams at first. You will want to say “OMG, this is frustrating!” but remember the bigger picture. It’s such a better tool! And you will get the hang of it. It will take some time to get used to going back and forth between environments, but it is super easy once you have it figured out. What you need to know is that the positives will outweigh the annoyances. We will be up front with you about changes that will have the biggest impact on the way we do things today. We will support you as you learn. We will treat mistakes as learning opportunities. We are here to guide you. The time is now to learn and figure this out. It’s your adoption that will define how the system is used. And we’re not going back. Onwards and forwards!


Preparing for a migration takes time, patience, and persistence. There are numerous things you can do to manage the change occurring within your team, including understanding why your company is making the move, creating a migration dream team, communicating the migration plan early, making time for your team to adapt, committing to coaching, providing post-support, and generally displaying your commitment and excitement about the possibilities once you’re in the Cloud. You may not be able to apply all of the techniques we discussed, and these are far from all of the recommendations we have, but know that any action is better than inaction.

Looking for assistance in planning your move to the cloud? Get in touch with us at!

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